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naphthoquinones

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Description

Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID4227422
MeSH IDM0014463

Synonyms (6)

Synonym
naphthoquinones
acetamide, n-[1,4-dihydro-3-(methylamino)-1,4-dioxo-2-naphthalenyl]-
1676-56-8
DTXSID50401028
2-acetylamino-3-methylamino-1,4-naphthoquinone
n-(3-(methylamino)-1,4-dioxo-1,4-dihydronaphthalen-2-yl)acetamide

Research Excerpts

Overview

Naphthoquinones are a group of highly reactive organic chemical species that interact with biological systems owing to their prooxidants nature. 1,4-naphthaquinones have been known for decades as a privileged scaffold in medicinal chemistry regarding their many biological properties.

ExcerptReferenceRelevance
"Naphthoquinones are a class of aromatic compounds relevant for their chemical characteristics, structural properties, and biological activity. "( Natural and Synthetic Naphthoquinones as Potential Anti-Infective Agents.
Hernandez-Soberanis, L; Ortiz-Pérez, E; Perales-Flores, JD; Rivera, G; Salas, CO; Trofymchuk, OS; Vázquez, K; Zarate-Ramos, JJ, 2021
)
2.38
"Naphthoquinones are a group of highly reactive organic chemical species that interact with biological systems owing to their prooxidants nature."( Redox ticklers and beyond: Naphthoquinone repository in the spotlight against inflammation and associated maladies.
Gambhir, L; Kandwal, P; Kapoor, N; Sharma, G, 2021
)
1.34
"Naphthoquinones are a type of quinone that is found in nature and has vital biological roles."( Naphthoquinones and derivatives as potential anticancer agents: An updated review.
Ahmed, L; Akash, S; Al Abdulmonem, W; Aljohani, ASM; Islam, MR; Khalil, AA; Rahman, MM; Rauf, A; Sharma, R; Shohag, S; Supti, FA; Thiruvengadam, M, 2022
)
2.89
"1,4-naphthoquinones are an important class of natural products and have been known for decades as a privileged scaffold in medicinal chemistry regarding their many biological properties."( An overview on the antibacterial properties of juglone, naphthazarin, plumbagin and lawsone derivatives and their metal complexes.
Benfodda, Z; Duvauchelle, V; Majdi, C; Meffre, P, 2023
)
1.39
"Naphthoquinones are a valuable source of secondary metabolites that are well known for their dye properties since ancient times. "( Biological Activity of Naphthoquinones Derivatives in the Search of Anticancer Lead Compounds.
Bolívar, J; Chinchilla, N; Durán, AG; Gutiérrez, MT; Macías, FA; Molinillo, JMG; Simonet, AM; Valdivia, MM, 2023
)
2.66
"Naphthoquinones are an important class of natural products or synthetic compounds with cytotoxic effect demonstrated on different cancer types."( Molecular mechanism of action of new 1,4-naphthoquinones tethered to 1,2,3-1H-triazoles with cytotoxic and selective effect against oral squamous cell carcinoma.
Alvarez Abreu, P; Cardozo Paes de Almeida, E; Carolina Carvalho da Fonseca, A; Cavalcanti Chipoline, I; de Carvalho da Silva, F; de Queiroz, LN; Francisco Ferreira, V; Luiz Ferraz de Souza, T; Pereira de Souza, M; Pontes, B; Ribeiro Machado da Costa, G; Robbs, BK; Won-Held Rabelo, V, 2020
)
1.55
"Naphthoquinones are a group of phytochemicals, which have a wide range of pharmacological potential, including antidiabetic activity."( Antidiabetic Naphthoquinones and Their Plant Resources in Thailand.
Keach, JE; Panichayupakaranant, P; Shah, MA, 2018
)
1.57

Effects

Naphthoquinones have been found to have a wide range of biological activities, including cytotoxicity to cancer cells. They are considered privileged structures and useful templates in the design of hybrids.

ExcerptReferenceRelevance
"Naphthoquinones have been shown to inhibit cancer cell growth and are considered privileged structures and useful templates in the design of hybrids."( Hybrid Molecules Containing Naphthoquinone and Quinolinedione Scaffolds as Antineoplastic Agents.
Defant, A; Mancini, I; Sighel, D; Vigna, J, 2022
)
1.44
"Naphthoquinones have been described with antitumor activity."( Chemoselective Synthesis of Mannich Adducts from 1,4-Naphthoquinones and Profile as Autophagic Inducers in Oral Squamous Cell Carcinoma.
Abreu, LS; Abreu, PA; Amaral, AAP; Borges, AA; da Fonseca, ACC; da Silva, FC; de Almeida, ECP; de Carvalho, CJC; de Queiroz, LN; de Souza, MP; Ferreira, VF; Forezi, LDSM; Pontes, B; Rabelo, VW; Ribeiro, RCB; Robbs, BK; Wermelinger, GF, 2022
)
1.69
"Naphthoquinones have been identified as potential growth inhibitors produced by Impatiens glandulifera, an exotic annual plant that recently invaded temperate forests in Europe."( Inhibitory potential of naphthoquinones leached from leaves and exuded from roots of the invasive plant Impatiens glandulifera.
Baur, B; Glauser, G; Hesse, K; Ruckli, R; Rusterholz, HP, 2014
)
1.43
"Naphthoquinones have been studied extensively due to their activity as topoisomerase inhibitors. "( Toxicological assessment of beta-lapachone on organs from pregnant and non-pregnant rats.
Cavalcanti, JB; Couto, GB; da Mota, DL; da Silva Costa-Junior, W; da Silva, AC; da Silva, LL; da Silveira, AB; de Almeida, ER; de Sousa Filho, SD; Lucena, FR; Silva, CV, 2009
)
1.8
"Naphthoquinones have been found to have a wide range of biological activities, including cytotoxicity to cancer cells. "( Cytotoxicity of lapachol, β-lapachone and related synthetic 1,4-naphthoquinones against oesophageal cancer cells.
Caira, MR; da Silva Júnior, EN; Davies-Coleman, MT; de la Mare, JA; Edkins, AL; Hendricks, DT; Osoniyi, O; Pinto, AV; Shunmoogam-Gounden, N; Sunassee, SN; Veale, CG, 2013
)
2.07
"Naphthoquinones have been reported to be toxic to liver cells in vitro. "( Development of polyclonal antibodies for detection of protein modification by 1,2-naphthoquinone.
Hammock, BD; Zheng, J,
)
1.57

Actions

Naphthoquinones are known to inhibit 5-lipoxygenase. They may cause oxidative stress in exposed cells and, therefore, affect redox signaling.

ExcerptReferenceRelevance
"Naphthoquinones may cause oxidative stress in exposed cells and, therefore, affect redox signaling. "( 1,4-naphthoquinones: from oxidative damage to cellular and inter-cellular signaling.
Hou, X; Jacob, C; Klotz, LO, 2014
)
2.4
"Naphthoquinones are known to inhibit 5-lipoxygenase. "( Leukotriene biosynthesis inhibition by aryl and aroyl substituted naphthoquinones.
Grim, KS; Kimble, EF; Kowalski, TJ; Macchia, WM; Roland, DM; White, DH, 1991
)
1.96
"1,4-Naphthoquinones inhibit feeding of Periplaneta americana by complexing with sulfhydryl groups of receptor protein in sensory neurons, by oxidizing the sulfhydryl groups, and by being reduced."( Energy transduction: inhibition of cockroach feeding by naphthoquinone.
Baker, JE; Borg, TK; Ferkovich, SM; Norris, DM; Rozental, JM, 1970
)
0.81

Toxicity

ExcerptReferenceRelevance
"The toxic effect of lapachol, beta-lapachone and several 1,2-naphthoquinone derivatives on the growth, viability and infectivity of Trypanosoma cruzi were compared."( In vitro and in vivo evaluation of the toxicity of 1,4-naphthoquinone and 1,2-naphthoquinone derivatives against Trypanosoma cruzi.
Cruz, FS; Docampo, R; Gilbert, B; Lopes, JN; Pinto, AV; Sampaio, MC; Vasconcellos, ME, 1978
)
0.26
" The only drug-related adverse effect was a maculopapular rash in one patient that resolved without discontinuation of the drug."( Safety and pharmacokinetics of 566C80, a hydroxynaphthoquinone with anti-Pneumocystis carinii activity: a phase I study in human immunodeficiency virus (HIV)-infected men.
Flynn, PM; Fullen, G; Hetherington, SV; Hughes, WT; Kennedy, W; Lancaster, DJ; Palte, S; Rosenbaum, D; Shenep, JL; Stein, DS, 1991
)
0.28
" Haemolysis was the only toxic change identified in rats dosed with 2-methyl-1,4-naphthoquinone."( Haemolytic activity and nephrotoxicity of 2-hydroxy-1,4-naphthoquinone in rats.
Fowke, EA; Munday, R; Smith, BL, 1991
)
0.28
" 1,4-NQ was more toxic than 2-Me-1,4-NQ whereas 2,3-diMe-1,4-NQ did not cause cell death at the solubility-limited concentrations used."( Mechanisms of toxicity of naphthoquinones to isolated hepatocytes.
Cohen, GM; Miller, MG; Rodgers, A, 1986
)
0.57
" Dicumarol was toxic to cultured non-induced rat hepatocytes and produced little or no increase in quinoneimine toxicity."( Quinoneimines as substrates for quinone reductase (NAD(P)H: (quinone-acceptor)oxidoreductase) and the effect of dicumarol on their cytotoxicity.
Hodnett, EM; Melder, DC; Powis, G; Santone, KS; See, KL, 1987
)
0.27
"Quinones are believed to be toxic by a mechanism involving redox cycling and oxidative stress."( Redox cycling and sulphydryl arylation; their relative importance in the mechanism of quinone cytotoxicity to isolated hepatocytes.
Cohen, GM; Gant, TW; Mason, RP; Rao, DN, 1988
)
0.27
" The two analogs, unlike menadione, cannot alkylate nucleophiles directly and were considerably less toxic than menadione."( The role of oxidative processes in the cytotoxicity of substituted 1,4-naphthoquinones in isolated hepatocytes.
Moldéus, P; Orrenius, S; Ross, D; Sandy, MS; Smith, MT; Thor, H; Threadgill, MD, 1986
)
0.5
" The latter was significantly toxic to mice, by itself."( Influence of in vitro ubiquinone antagonists on doxorubicin toxicity in vivo.
Combs, AB; Lewandowski, E; Tábora, O, 1986
)
0.27
"1-Naphthol was selectively toxic to human colorectal tumours compared to corresponding normal colonic tissue removed at surgery and maintained in short-term organ culture."( Selective toxicity of 1-naphthol to human colorectal tumour tissue.
Cohen, GM; d'Arcy Doherty, M; Wilson, GD, 1985
)
0.27
" sanguis, O2- can exert a toxic effect independent of the production of OH."( Oxygen toxicity in Streptococcus sanguis. The relative importance of superoxide and hydroxyl radicals.
DiGuiseppi, J; Fridovich, I, 1982
)
0.26
" We examined several biochemical parameters that may contribute to the differential sensitivity of the cell lines used in our laboratory to the toxic effects of antitumor compounds."( Detoxification ability and toxicity of quinones in mouse and human tumor cell lines used for anticancer drug screening.
Baker, LH; Corbett, TH; Djuric, Z; Heilbrun, LK; Valeriote, FA, 1995
)
0.29
"Atovaquone was compared to trimethoprim-sulfamethoxazole (TMP-SMZ) for the relationship of time receiving therapy, plasma drug concentrations, and incidence of adverse reactions in patients with AIDS-associated Pneumocystis carinii pneumonia."( Adverse events associated with trimethoprim-sulfamethoxazole and atovaquone during the treatment of AIDS-related Pneumocystis carinii pneumonia.
Hughes, WT; LaFon, SW; Masur, H; Scott, JD, 1995
)
0.29
" Juglone was more toxic toward bacterial cells under hypoxia than under air."( Effects of nitroxide stable radicals on juglone cytotoxicity.
Hirsch, O; Mohsen, M; Samuni, A; Zhang, R, 1994
)
0.29
" This toxic effect is believed to result from oxidative damage to erythrocytes by "active oxygen" species formed via one-electron reduction of the naphthoquinone by oxyhaemoglobin."( Comparative toxicity of alkyl-1,4-naphthoquinones in rats: relationship to free radical production in vitro.
Fowke, EA; Munday, CM; Munday, R; Smith, BL, 1994
)
0.57
" In order to establish if such toxic effects are common to other 2-hydroxynaphthoquinone derivatives, the short-term toxicity of a number of 2-hydroxy-3-alkyl-1,4-naphthoquinones has been compared in rats."( Comparative toxicity of 2-hydroxy-3-alkyl-1,4-naphthoquinones in rats.
Munday, CM; Munday, R; Smith, BL, 1995
)
0.75
" Niosome-encapsulated plumbagin was less toxic than free drug."( Niosomal plumbagin with reduced toxicity and improved anticancer activity in BALB/C mice.
Devi, PU; Naresh, RA; Udupa, N, 1996
)
0.29
" The results showed m-atovaquone to be safe and well tolerated."( Phase I safety and pharmacokinetics study of micronized atovaquone in human immunodeficiency virus-infected infants and children. Pediatric AIDS Clinical Trials Group.
Beauchamp, B; Dorenbaum, A; Hughes, W; McNamara, J; Moye, J; Purdue, L; Rogers, M; Sadler, B; van Dyke, R; Xu, J; Yogev, R, 1998
)
0.3
" BQ was more toxic to rat platelets than menadione, while DMNQ did not cause LDH leakage at all."( The relative importance of oxidative stress versus arylation in the mechanism of quinone-induced cytotoxicity to platelets.
Chung, JH; Lee, JY; Lee, MY; Park, JS; Seung, SA, 1998
)
0.3
"Currently recommended prophylactic regimens for Plasmodium falciparum malaria are associated with a high incidence of adverse events and/or suboptimal efficacy."( Efficacy and safety of atovaquone/proguanil as suppressive prophylaxis for Plasmodium falciparum malaria.
Aleman, GM; Gordon, DM; Klotz, FW; Oloo, AJ; Sadie, D; Scott, TR; Shanks, GD, 1998
)
0.3
" The Caco-2 cell line was particularly vulnerable to NQ and MEN and displayed moderate toxic effects of DIM."( Quinone toxicity in DT-diaphorase-efficient and -deficient colon carcinoma cell lines.
Karczewski, JM; Noordhoek, J; Peters, JG, 1999
)
0.3
" In the present study, rats were dosed with BHA and then challenged with a toxic dose of 2-hydroxy-1,4-naphthoquinone, a substance that causes haemolytic anaemia and renal damage in vivo."( Effect of butylated hydroxyanisole on the toxicity of 2-hydroxy-1,4-naphthoquinone to rats.
Munday, CM; Munday, R; Smith, BL, 1999
)
0.3
" Malaria blood smears were prepared on a weekly basis and a failure of chemoprophylaxis was defined as any subject who had a positive blood smear, or who withdrew from the study due to a treatment-related adverse event."( A randomized, double-blind, placebo-controlled field trial to determine the efficacy and safety of Malarone (atovaquone/proguanil) for the prophylaxis of malaria in Zambia.
Chisdaka, N; Mulenga, M; Roskell, NS; Scott, TR; Sukwa, TY, 1999
)
0.3
" Adverse events were generally typical of malaria symptoms and each occurred in < 10% of the patients in either group, with the exception of increased vomiting found in the atovaquone/proguanil group."( Efficacy and safety of atovaquone/proguanil compared with mefloquine for treatment of acute Plasmodium falciparum malaria in Thailand.
Canfield, CJ; Chalermarut, K; Hutchinson, DB; Looareesuwan, S; Rattanapong, Y; Wilairatana, P, 1999
)
0.3
" Prophylactic success was summarized using a 95% confidence interval for the proportion of subjects who did not develop parasitemia or who withdrew due to a treatment-related adverse event."( Safety and efficacy of atovaquone and proguanil hydrochloride for the prophylaxis of Plasmodium falciparum malaria in South Africa.
Duvenage, CS; Roskell, NS; Scott, TR; van der Berg, JD, 1999
)
0.3
" None of the 16 patients treated with atovaquone experienced treatment-associated adverse effects."( A prospective randomized trial comparing the toxicity and safety of atovaquone with trimethoprim/sulfamethoxazole as Pneumocystis carinii pneumonia prophylaxis following autologous peripheral blood stem cell transplantation.
Colby, C; Finkelstein, D; Fishman, J; McAfee, S; Sackstein, R; Spitzer, T, 1999
)
0.3
"It has previously been shown that rats pre-treated with butylated hydroxyanisole (BHA), a well-known inducer of the enzyme DT-diaphorase, are protected against the toxic effects of 2-methyl-1,4-naphthoquinone but are made more susceptible to the harmful action of 2-hydroxy-1,4-naphthoquinone."( Effect of inducers of DT-diaphorase on the toxicity of 2-methyl- and 2-hydroxy-1,4-naphthoquinone to rats.
Munday, CM; Munday, R; Smith, BL, 1999
)
0.3
" Modulation of DT-diaphorase activity in animals may therefore not only alter the severity of naphthoquinone toxicity, but also cause pronounced changes in the site of toxic action of these substances."( Effects of modulation of tissue activities of DT-diaphorase on the toxicity of 2,3-dimethyl-1,4-naphthoquinone to rats.
Munday, CM; Munday, R; Smith, BL, 2001
)
0.31
"54 ppm), differently from the potassium salt of lapachol that can be considered non toxic (LC90=176."( Toxicity of lapachol and isolapachol and their potassium salts against Biomphalaria glabrata, Schistosoma mansoni cercariae, Artemia salina and Tilapia nilotica.
dos Santos, AF; Goulart, MO; Lima, NM; Porfírio, Z; Sant'Ana, AE, 2002
)
0.31
"We performed a prospective, double-blind, randomized study to compare the occurrence of neuropsychiatric adverse events and concentration impairment during prophylactic use of either mefloquine or atovaquone plus chloroguanide (INN, proguanil)."( Atovaquone plus chloroguanide versus mefloquine for malaria prophylaxis: a focus on neuropsychiatric adverse events.
Ditters, JM; Ligthelm, RJ; Overbosch, D; Stricker, BH; Sturkenboom, MC; van Riemsdijk, MM, 2002
)
0.31
" Toxic pathway discrimination is needed to group chemicals for potency predictions and identification of structural parameters associated with distinct types of reactive toxicity, a necessary step for development of mechanistically based quantitative structure-activity relationships (QSARs) to predict chemical toxic potential."( Discriminating redox cycling and arylation pathways of reactive chemical toxicity in trout hepatocytes.
Denny, JS; Hammermeister, DE; Kolanczyk, RC; Schmieder, PK; Sheedy, BR; Tapper, MA, 2003
)
0.32
"No serious adverse events occurred."( The safety of atovaquone/proguanil in long-term malaria prophylaxis of nonimmune adults.
Petersen, E, 2003
)
0.32
"Atovaquone/proguanil was safe and well tolerated in this group of long-term nonimmune travelers."( The safety of atovaquone/proguanil in long-term malaria prophylaxis of nonimmune adults.
Petersen, E, 2003
)
0.32
"We prospectively studied adverse reactions reported by long-term travelers using atovaquone/proguanil among a population intolerant to mefloquine."( Post-marketing surveillance: adverse events during long-term use of atovaquone/proguanil for travelers to malaria-endemic countries.
Overbosch, D, 2003
)
0.32
" Comparison with data from previous, larger atovaquone/proguanil studies shows that the adverse events reported by the long-term atovaquone/proguanil users are no different in type and frequency of occurrence to those travel-related health problems normally encountered in the Tropics."( Post-marketing surveillance: adverse events during long-term use of atovaquone/proguanil for travelers to malaria-endemic countries.
Overbosch, D, 2003
)
0.32
" The outcome measures were parasite clearance time, fever clearance time, efficacy, and adverse events profile."( A randomized open label clinical trial to compare the efficacy and safety of intravenous quinine followed by oral malarone vs. intravenous quinine followed by oral quinine in the treatment of severe malaria.
Ayuo, PO; Esamai, F; Jakait, B; Obala, A; Ong'or, WO; Tenge, CN, 2005
)
0.33
" Toxic activity was retained by a cyano solid phase extraction cartridge and the toxin was isolated by elution from the cartridge in acetonitrile and Si-gel thin layer chromatography of the eluate."( Chickpea wilt: identification and toxicity of 8-O-methyl-fusarubin from Fusarium acutatum.
Beale, MH; Gopalakrishnan, S; Strange, RN; Ward, JL, 2005
)
0.33
" It is not possible to generalize with regard to the effects of modulation of tissue levels of DT-diaphorase on naphthoquinone toxicity in vivo, since this may change not only the severity of the toxic effects, but also the target organ specificity."( Effect of inducers of DT-diaphorase on the haemolytic activity and nephrotoxicity of 2-amino-1,4-naphthoquinone in rats.
Munday, CM; Munday, R; Smith, BL, 2005
)
0.33
" An effective and safe prophylactic antimalarial drug is needed."( Malaria prophylaxis for aircrew: safety of atovaquone/proguanil in healthy volunteers under aircraft cabin pressure conditions.
Krul, AJ; Simons, R; Valk, PJ,
)
0.13
" No significant differences were found between the effects of placebo and A/P on vigilance, alertness, complex information processing, sleep duration and quality, and the occurrence of adverse effects."( Malaria prophylaxis for aircrew: safety of atovaquone/proguanil in healthy volunteers under aircraft cabin pressure conditions.
Krul, AJ; Simons, R; Valk, PJ,
)
0.13
" Some such compounds are known, however, to be toxic to both animals and humans."( Structure-activity relationships in the haemolytic activity and nephrotoxicity of derivatives of 1,2- and 1,4-naphthoquinone.
Munday, CM; Munday, R; Smith, BL,
)
0.13
" High removal rates for biota require broad spectrum biocides that are safe to transport and handle and pose no corrosion problems for ships' structure."( Naphthoquinones as broad spectrum biocides for treatment of ship's ballast water: toxicity to phytoplankton and bacteria.
Cutler, HG; Cutler, SJ; Dawson, R; Graneli, E; Orano-Dawson, CE; Wright, DA, 2007
)
1.78
"Temporary henna tattoos have become increasingly popular as a safe alternative to permanent tattoos among American and European children and teenagers during the summer holidays."( Temporary henna tattoo is unsafe in atopic children.
Chianca, M; Chini, L; Corrente, S; Graziani, S; Iannini, R; La Rocca, M; Moschese, V, 2007
)
0.34
" Natural henna leaves did not show toxic effects, whereas two out of four samples of marketed henna products were shown toxicity effects."( Cytotoxicity of lawsone and cytoprotective activity of antioxidants in catalase mutant Escherichia coli.
Horita, M; Masuoka, N; Ogino, K; Sano, K; Sauriasari, R; Takemura, Y; Tsutsui, K; Wang, BL; Wang, DH, 2007
)
0.34
" These results suggest that a gender-specific 1,4-naphthoquinone metabolic pathway may exist, which gives rise to unknown toxic metabolites."( In vitro toxicity of naphthalene, 1-naphthol, 2-naphthol and 1,4-naphthoquinone on human CFU-GM from female and male cord blood donors.
Croera, C; Ferrario, D; Gribaldo, L, 2008
)
0.35
" However, the results showed that, even by different pathways, both drugs were capable of generating oxidative stress through their toxic effects."( Cytotoxicity mechanism of two naphthoquinones (menadione and plumbagin) in Saccharomyces cerevisiae.
Castro, FA; Eleutherio, EC; Mariani, D; Panek, AD; Pereira, MD, 2008
)
0.63
" Data on natural toxic chemicals could be used for extrapolation methods such as read-across."( The comparative toxicity to soil invertebrates of natural chemicals and their synthetic analogues.
Chaplow, JS; Harman, M; Hopkin, S; Potter, E; Scott, WA; Sims, I; Sorokin, N; Whitaker, J, 2009
)
0.35
" In a range of concentration from 0 to 10 microg/ml C(1) and C(3) were non toxic against TLT cells, while compound C(2) killed about 50% of cells by necrosis."( Part 2: influence of 2-euryfuryl-1,4-naphthoquinone and its peri-hydroxy derivatives on both cell death and metabolism of TLT cells, a murine hepatoma cell line. modulation of cytotoxicity by vitamin C.
Benites, J; Buc Calderon, P; Taper, H; Valderrama, JA, 2009
)
0.35
" The main outcome measures for safety were incidences of post-treatment clinical and laboratory adverse events."( Artemisinin-naphthoquine combination (ARCO) therapy for uncomplicated falciparum malaria in adults of Papua New Guinea: a preliminary report on safety and efficacy.
Geita, J; Hiawalyer, G; Hombhanje, FW; Jones, R; Kevau, I; Kuanch, C; Linge, D; Masta, A; Sapuri, M; Saweri, A; Toraso, S, 2009
)
0.35
" Both regimens were well tolerated with no serious adverse events."( Artemisinin-naphthoquine combination (ARCO) therapy for uncomplicated falciparum malaria in adults of Papua New Guinea: a preliminary report on safety and efficacy.
Geita, J; Hiawalyer, G; Hombhanje, FW; Jones, R; Kevau, I; Kuanch, C; Linge, D; Masta, A; Sapuri, M; Saweri, A; Toraso, S, 2009
)
0.35
" In vitro cytotoxicity studies against melanoma cells indicated that liposomal juglone was more toxic than free juglone."( Evaluation of pharmacokinetic, biodistribution, pharmacodynamic, and toxicity profile of free juglone and its sterically stabilized liposomes.
Aithal, BK; Arumugam, K; Prabhu, V; Rao, BN; Sajankila, SP; Satish Rao, BS; Satyamoorthy, K; Shavi, G; Sunil Kumar, MR; Udupa, N; Upadhya, R, 2011
)
0.37
" All regimens were well tolerated, with no serious adverse events."( Artemisinin-naphthoquine combination therapy for uncomplicated pediatric malaria: a tolerability, safety, and preliminary efficacy study.
Benjamin, J; Davis, TM; Griffin, S; Lautu, D; Lee, ST; Moore, B; Mueller, I; Salman, S; Senn, M; Siba, P, 2012
)
0.38
" Few and mild adverse events were reported."( Efficacy and safety of artemisinin-naphthoquine versus dihydroartemisinin-piperaquine in adult patients with uncomplicated malaria: a multi-centre study in Indonesia.
Amansyah, F; Dedang, TA; Driyah, S; Ekowatiningsih, R; Hasugian, AR; Januar, L; Labora, J; Prasetyorini, B; Purnama, A; Purnamasari, T; Salwati, E; Siswantoro, H; Tjitra, E; Wijayanto, B; Yusnita, EA; Yuwarni, E, 2012
)
0.38
"AN and DHP are confirmed very effective, safe and tolerate for treatment of any malaria."( Efficacy and safety of artemisinin-naphthoquine versus dihydroartemisinin-piperaquine in adult patients with uncomplicated malaria: a multi-centre study in Indonesia.
Amansyah, F; Dedang, TA; Driyah, S; Ekowatiningsih, R; Hasugian, AR; Januar, L; Labora, J; Prasetyorini, B; Purnama, A; Purnamasari, T; Salwati, E; Siswantoro, H; Tjitra, E; Wijayanto, B; Yusnita, EA; Yuwarni, E, 2012
)
0.38
" The combined toxic effects of 1-NP and 1,2-naphthoquinone (1,2-NQ) on A549 were also evaluated."( [Combined effects of 1-nitropyrene and 1,2-naphthoquinone on cytotoxicity and DNA damage in A549 cells].
Jiang, YT; Li, Y; Shang, Y; Zhang, L, 2014
)
0.4
" However, plumbagin crude extract found to be highly toxic to normal cells when compared to plumbagin nanoformulation, thus confirming nano plumbagin cytocompatibility with normal cells and dose dependent toxicity to prostate cells."( Plumbagin Nanoparticles Induce Dose and pH Dependent Toxicity on Prostate Cancer Cells.
Kamath, RC; Lakshmanan, VK; Nair, HA; Nair, SV; Snima, KS, 2015
)
0.42
" Furthermore, we show that the induction of cellular NAD(+) levels using dunnione, which targets intracellular NQO1, prevents the toxic effects of cisplatin through the regulation of PARP-1 and SIRT1 activity."( Dunnione ameliorates cisplatin ototoxicity through modulation of NAD(+) metabolism.
Cho, EY; Choe, SK; Khadka, D; Kim, HJ; Kwak, TH; Lee, S; Lee, SB; Oh, GS; Pandit, A; Park, R; Shen, A; Shim, H; So, HS; Yang, SH, 2016
)
0.43
"Amyloid-β, one of the hallmarks of Alzheimer's disease, is toxic to neurons and causes cell death in the brain."( Cratoxylum formosum Extract Protects against Amyloid-Beta Toxicity in a Caenorhabditis elegans Model of Alzheimer's Disease.
Keowkase, R; Weerapreeyakul, N, 2016
)
0.43
" All three treatments showed good tolerance and safety with scarce adverse events observed."( Efficacy, safety and tolerance of imidocarb dipropionate versus atovaquone or buparvaquone plus azithromycin used to treat sick dogs naturally infected with the Babesia microti-like piroplasm.
Bartolomé, A; Checa, R; Gálvez, R; González-Fraga, JL; Marino, V; Miró, G; Montoya, A; Ortega, N, 2017
)
0.46
"In previous studies, naphthoquinone (NQ) compounds have been shown to be effective, selective, and ecologically safe algicides for controlling harmful algal blooming species (HABs) or winter bloom species, such as Stephanodiscus hantzschii."( Improvement of cyanobacterial-killing biologically derived substances (BDSs) using an ecologically safe and cost-effective naphthoquinone derivative.
Byun, JH; Choi, HJ; Han, MS; Joo, JH; Kim, SH; Park, BS; Wang, P, 2017
)
0.46
"Adverse side effects of cancer agents are of great concern in the context of childhood tumors where they can reduce the quality of life in young patients and cause life-long adverse effects."( Lapatinib potentiates cytotoxicity of  YM155 in neuroblastoma via inhibition of the ABCB1 efflux transporter.
Brunak, S; Halasz, M; Huber, KVM; Kolch, W; Papamarkou, T; Radic-Sarikas, B; Superti-Furga, G; Tsafou, KP; Winter, GE, 2017
)
0.46
" The toxic mode of action of Basic Blue 99 seems to be the induction of cell death, without genotoxic effects, but while the necrotic pathway is observed in HaCaT monolayer cell culture, was apoptosis seen in the Equivalent Human Epidermis (EHE) model."( Immortalized equivalent human epidermis as a platform to evaluation hair dyes toxicity: Efficiency comparison between 3D and monolayer culture.
Dorta, DJ; Maria-Engler, SS; Mini, CA; Oliveira, DP, 2020
)
0.56
" However, only a few studies have reported the adverse effects of acetylshikonin, with respect to reproductive toxicity and genotoxicity."( Pharmacology, toxicity and pharmacokinetics of acetylshikonin: a review.
Bai, J; Cai, M; Dong, X; Ni, J; Wu, H; Yao, Y; You, L; Zeng, Y; Zhang, Z, 2020
)
0.56
" Our previous research found its toxic effects on oocytes maturation."( Vitamin C protects early mouse embryos against juglone toxicity.
Cheng, W; Liu, H; Tao, R; Xu, H; Zhang, X; Zhou, C, 2020
)
0.56
" No serious adverse events/deaths were reported."( Napabucasin Drug-Drug Interaction Potential, Safety, Tolerability, and Pharmacokinetics Following Oral Dosing in Healthy Adult Volunteers.
Brantley, SJ; Dai, X; Goulet, MT; Hard, ML; Hitron, M; Karol, MD; McLaughlin, CF, 2021
)
0.62
" Napabucasin was well-tolerated across the study (n = 70), and no serious adverse events or significant safety issues were reported when administered with or without food."( Effects of a reactive oxygen species generator, napabucasin (BBI608), on tolerability, safety, pharmacokinetics, and QT/QTc interval in healthy volunteers.
Horibuchi, Y; Iino, S; Kakuyama, H; Matsuki, S; Noda, N; Ogama, Y; Takagaki, T; Yodo, Y, 2021
)
0.62
" The most frequently reported adverse events were diarrhea (83."( A Phase I Study to Investigate the Safety, Tolerability and Pharmacokinetics of Napabucasin Combined with Sorafenib in Japanese Patients with Unresectable Hepatocellular Carcinoma.
Eguchi, Y; Iino, S; Kageyama, R; Morimoto, M; Nakamura, S; Okusaka, T, 2023
)
0.91

Pharmacokinetics

ExcerptReferenceRelevance
" For all drugs studied, the proposed techniques are specific, reliable and sensitive enough and can be used to perform pharmacokinetic studies in human or in animal after administration of doses in the therapeutic range."( [Quantitative determination of drugs by in situ spectrophotometry of chromatograms for pharmacokinetic studies. I. Sulpiride and other benzamides, vincamine, naftazone (author's transl)].
Bres, J; Bressolle, F; Brun, S; Rechencq, E, 1979
)
0.26
"1 microM) of 5-lipoxygenase, but its therapeutic potential is compromised by a short plasma half-life (22 min) and extremely poor oral bioavailability (less than 2%)."( Pharmacokinetic screening of o-naphthoquinone 5-lipoxygenase inhibitors.
Douglas, FL; Jones, DR; Kotake, AN; Kuwahara, SK; Oglesby, TD; Rakhit, A; Soliman, VF; Tripp, SL; Wasley, JW, 1990
)
0.28
" Pharmacokinetic parameters were determined by noncompartmental methods, and statistical comparison of parameters for single doses was performed by analysis of variance."( Single-dose and steady-state pharmacokinetics of a novel microfluidized suspension of atovaquone in human immunodeficiency virus-seropositive patients.
Dixon, R; Posner, J; Pozniak, AL; Rolan, P; Watt, HM, 1996
)
0.29
"The potential pharmacokinetic interaction between atovaquone and phenytoin was investigated in 12 healthy male volunteers."( Atovaquone has no effect on the pharmacokinetics of phenytoin in healthy male volunteers.
Davis, JD; Dixon, R; Khan, AZ; Posner, J; Rolan, PE; Toon, S, 1996
)
0.29
"05) in the area under the plasma drug concentration-time curve (AUC), apparent oral clearance (CL/F) and elimination half-life (t1/2) of PROG between patients given PROG alone and PROG/ ATQ."( Pharmacokinetics of proguanil in malaria patients treated with proguanil plus atovaquone.
Edstein, MD; Kyle, DE; Looareesuwan, S; Viravan, C, 1996
)
0.29
" The pharmacokinetic parameters of the drug are shown."( [Pharmacokinetics and clinical efficacy of histochrome in patients with acute myocardial infarction].
Fedoreev, SA; Golubiatnikov, VB; Ivanova, MV; Kol'tsova, EA; Krasnovid, NI; Lebedev, AV; Mishchenko, NP; Zakirova, AN,
)
0.13
"A phase I dose-escalating safety and pharmacokinetic study evaluated an oral suspension of micronized atovaquone (m-atovaquone) in infants and children stratified into age groups from 1 month to 12 years of age."( Phase I safety and pharmacokinetics study of micronized atovaquone in human immunodeficiency virus-infected infants and children. Pediatric AIDS Clinical Trials Group.
Beauchamp, B; Dorenbaum, A; Hughes, W; McNamara, J; Moye, J; Purdue, L; Rogers, M; Sadler, B; van Dyke, R; Xu, J; Yogev, R, 1998
)
0.3
" Factors such as inter- and intraindividual pharmacokinetic variability and changes in AZT intracellular concentrations should be considered as other mechanisms responsible for changes in AZT pharmacokinetics with concomitant therapies."( Glucuronidation of 3'-azido-3'-deoxythymidine (zidovudine) by human liver microsomes: relevance to clinical pharmacokinetic interactions with atovaquone, fluconazole, methadone, and valproic acid.
Collins, JM; Jamis-Dow, C; Klecker, RW; Trapnell, CB, 1998
)
0.3
" Despite a lack of significant difference in the mean AZ pharmacokinetic parameters, the steady-state values of AZ's area under the concentration-time curve from 0 to 24 h and maximum concentration in serum were consistently lower (n = 7 of 7) for the SIM regimen than they were for the ALONE regimen."( Pharmacokinetics of azithromycin administered alone and with atovaquone in human immunodeficiency virus-infected children. The ACTG 254 Team.
Burchett, S; Dankner, WM; Hughes, WT; Ngo, LY; Sadler, B; Unadkat, JD; Xu, J; Yogev, R, 1999
)
0.3
" The geometric mean elimination half-life (t1/2) of atovaquone was 57."( Lack of a pharmacokinetic interaction between atovaquone and proguanil.
Gillotin, C; Mamet, JP; Veronese, L, 1999
)
0.3
"To determine the pharmacokinetic profiles of atovaquone (ATO), proguanil (PROG) and its active metabolite cycloguanil (CYCLO) with respect to possible accumulation and kinetic interaction upon repeated dosing with Malarone."( Time-dependent pharmacokinetics and drug metabolism of atovaquone plus proguanil (Malarone) when taken as chemoprophylaxis.
Ashton, M; Bergqvist, Y; Björkman, A; Johansson, I; Lindegårdh, N; Nivelius, S; Thapar, MM, 2002
)
0.31
" Single-dose and steady-state pharmacokinetic parameters were determined for each individual."( Time-dependent pharmacokinetics and drug metabolism of atovaquone plus proguanil (Malarone) when taken as chemoprophylaxis.
Ashton, M; Bergqvist, Y; Björkman, A; Johansson, I; Lindegårdh, N; Nivelius, S; Thapar, MM, 2002
)
0.31
"To determine the pharmacokinetic properties of atovaquone, proguanil, and the triazine metabolite cycloguanil in women with recrudescent multi-drug resistant falciparum malaria during the second and third trimesters of pregnancy treated by artesunate-atovaquone-proguanil."( The pharmacokinetics of atovaquone and proguanil in pregnant women with acute falciparum malaria.
Cho, T; Edstein, MD; Gilveray, G; Looareesuwan, S; McGready, R; Nosten, F; Stepniewska, K; White, NJ, 2003
)
0.32
" Using conventional and population pharmacokinetic analyses, Cl/F and Vd/F estimates for both drugs were approximately twice, and plasma concentrations less than half those reported previously in healthy subjects and patients with acute malaria."( The pharmacokinetics of atovaquone and proguanil in pregnant women with acute falciparum malaria.
Cho, T; Edstein, MD; Gilveray, G; Looareesuwan, S; McGready, R; Nosten, F; Stepniewska, K; White, NJ, 2003
)
0.32
" The pharmacodynamic interactions among atovaquone, proguanil and its metabolite cycloguanil were investigated in 4 Plasmodium falciparum parasite strains by culture assays in vitro."( Pharmacodynamic interactions among atovaquone, proguanil and cycloguanil against Plasmodium falciparum in vitro.
Björkman, A; Gupta, S; Spindler, C; Thapar, MM; Wernsdorfer, WH,
)
0.13
" Blood samples were taken for pharmacokinetic investigations of atovaquone, proguanil, and cycloguanil up to 288 h (day 14) after the last dose."( The pharmacokinetics and pharmacodynamics of atovaquone and proguanil for the treatment of uncomplicated falciparum malaria in third-trimester pregnant women.
Kioy, D; Konsil, J; Manyando, C; Miller, GB; Mulenga, M; Na-Bangchang, K; Ruengweerayut, R, 2005
)
0.33
" There were no significant differences in any of the pharmacokinetic parameters of atovaquone, proguanil or cycloguanil between patients from Thailand and Zambia."( The pharmacokinetics and pharmacodynamics of atovaquone and proguanil for the treatment of uncomplicated falciparum malaria in third-trimester pregnant women.
Kioy, D; Konsil, J; Manyando, C; Miller, GB; Mulenga, M; Na-Bangchang, K; Ruengweerayut, R, 2005
)
0.33
"The pharmacokinetics of atovaquone and cycloguanil appeared to be influenced by the pregnancy status, resulting in an decrease in the Cmax and AUC of approximately twofold."( The pharmacokinetics and pharmacodynamics of atovaquone and proguanil for the treatment of uncomplicated falciparum malaria in third-trimester pregnant women.
Kioy, D; Konsil, J; Manyando, C; Miller, GB; Mulenga, M; Na-Bangchang, K; Ruengweerayut, R, 2005
)
0.33
" The method was successfully applied to pharmacokinetic study of chimaphilin in rat plasma following oral administration of a 30-mg/kg dose of chimaphilin in Lu xian cao decoction to male Wistar rats."( LC-MS method for determination and pharmacokinetic study of chimaphilin in rat plasma after oral administration of the traditional Chinese medicinal preparation Lu xian cao decoction.
Bi, K; Chen, X; Kim, C; Qin, S; Tebayashi, S; Zhang, Y, 2006
)
0.33
" This assay was demonstrated to be applicable for clinical pharmacokinetic studies."( HPLC method for the determination of fluvoxamine in human plasma and urine for application to pharmacokinetic studies.
Ulu, ST, 2007
)
0.34
" This method is simple, reliable and can be routinely used for preclinical pharmacokinetic studies for BPQ."( Optimization and validation of RP-HPLC-UV method with solid-phase extraction for determination of buparvaquone in human and rabbit plasma: application to pharmacokinetic study.
Croft, SL; Majid, MI; Mansor, SM; Nair, NK; Navaratnam, V; Ramanathan, S; Venkatesh, G, 2008
)
0.35
" Plasma and urine samples were assayed to determine pharmacokinetic parameters and excretion."( Phase I and pharmacokinetic study of YM155, a small-molecule inhibitor of survivin.
Antonia, S; Bartels, P; Daud, AI; Garrett, CR; Keating, A; Lewis, LD; Mita, A; Papadopoulos, K; Patnaik, A; Takimoto, C; Till, E; Tolcher, AW, 2008
)
0.35
" The validated LC-MS/MS method was successfully applied to the preliminary pharmacokinetic study in rats."( Quantitative determination of beta,beta-dimethylacrylshikonin (DASK) in rat whole blood by liquid chromatography-tandem mass spectrometry with pre-column derivation and its pharmacokinetic application.
Dou, G; Meng, Z; Sun, D; Tian, H; Yuan, D, 2009
)
0.35
" Pharmacokinetic studies showed a 22."( Preparation, in vitro characterization, pharmacokinetic, and pharmacodynamic evaluation of chitosan-based plumbagin microspheres in mice bearing B16F1 melanoma.
Aithal, K; Anandam, A; Arumugam, K; Bhat, K; Bola Sadashiva, SR; Mandala Rayabandla, SK; Musmade, P; Nayanabhirama, U; Shavi, G, 2010
)
0.36
" The half-life of naphthoquine phosphate was approximately 255 hours."( Single-dose safety, pharmacokinetics, and food effects studies of compound naphthoquine phosphate tablets in healthy volunteers.
Gao, HZ; Hao, GT; Hu, JC; Li, HY; Li, YY; Liu, WL; Liu, ZY; Qu, HY; Wang, XF, 2010
)
0.36
" Free juglone had short plasma half-life of about 2 h, whereas liposomal juglone exhibited significantly improved pharmacokinetics with a 12-fold increase in plasma half-life."( Evaluation of pharmacokinetic, biodistribution, pharmacodynamic, and toxicity profile of free juglone and its sterically stabilized liposomes.
Aithal, BK; Arumugam, K; Prabhu, V; Rao, BN; Sajankila, SP; Satish Rao, BS; Satyamoorthy, K; Shavi, G; Sunil Kumar, MR; Udupa, N; Upadhya, R, 2011
)
0.37
" To build on limited knowledge of the pharmacokinetic properties of the components, especially the tetra-aminoquinoline NQ, we studied ART-NQ disposition in Papua New Guinea children aged 5 to 12 years with uncomplicated malaria, comparing a single dose (15 and 6 mg/kg of body weight) administered with water (group 1; n = 13), a single dose (22 and 9 mg/kg) with milk (group 2) (n = 17), and two daily doses of 22 and 9 mg/kg with water (group 3; n = 16)."( Artemisinin-naphthoquine combination therapy for uncomplicated pediatric malaria: a pharmacokinetic study.
Batty, KT; Benjamin, J; Davis, TM; Hombhanje, FW; Ilett, KF; Lee, ST; Moore, BR; Mueller, I; Page-Sharp, M; Pitus, N; Salman, S; Siba, P, 2012
)
0.38
" performed the first pharmacokinetic study of ART-NQ combination therapy for uncomplicated pediatric malaria, and the authors' results are described and discussed below."( A pharmacokinetic approach to assess artemisinin-naphthoquine combination therapy for uncomplicated pediatric malaria.
Dong, HF; Jiang, MS; Liu, R, 2012
)
0.38
" This method was successfully applied to a pharmacokinetic study of biflorin after the intravenous and oral administration of biflorin to rats."( A sensitive LC-MS/MS method for the quantitative determination of biflorin in rat plasma and its application to pharmacokinetic studies.
Han, HK; Jang, DS; Ryu, JH; Yang, L; Yang, SJ, 2015
)
0.42
" The aim of the study was to investigate the pharmacokinetic profile following a single oral dosing to explain inconsistency of results of the in vitro and in vivo antimalarial activities."( Pharmacokinetics, toxicity, and cytochrome P450 modulatory activity of plumbagin.
Na-Bangchang, K; Plengsuriyakarn, T; Sumsakul, W, 2016
)
0.43
" The pharmacokinetic profile of plumbagin following a single oral dose of 100 mg/kg body weight suggests that delayed absorption and short residence time (median values of time to maximal concentration and elimination half-life = 9."( Pharmacokinetics, toxicity, and cytochrome P450 modulatory activity of plumbagin.
Na-Bangchang, K; Plengsuriyakarn, T; Sumsakul, W, 2016
)
0.43
" Pharmacokinetic property of this compound may be a limiting factor that explains the weak antimalarial activity of plumbagin observed in animal models."( Pharmacokinetics, toxicity, and cytochrome P450 modulatory activity of plumbagin.
Na-Bangchang, K; Plengsuriyakarn, T; Sumsakul, W, 2016
)
0.43
" To better understand the pharmacokinetic properties of juglone, the protein binding rate of juglone was determined by ultrafiltration method, and the binding affinity and mechanism between JL and human serum albumin (HSA) was investigated in vitro through multi-spectroscopic, thermodynamic, and molecular modeling methods."( Drug-protein binding mechanism of juglone for early pharmacokinetic profiling: Insights from ultrafiltration, multi-spectroscopic and molecular docking methods.
Cai, Q; Cheng, L; Gao, G; Hou, X; Li, S; Lu, N; Zhang, L; Zhao, P, 2017
)
0.46
" In assessing the pharmacokinetic aspects of the new drug, the authors draw at- tention of researchers to profound study of histochrome administration schemes and dosing regime in the context of improving its therapeutic applications."( [SPECIFIC FEATURES AND PROSPECTS OF THE PHARMACOKINETIC STUDY OF HISTOCHROME.]
Bryukhanov, VM; Mishchenko, NR; Talalaeval, OS; Zverev, YF,
)
0.13
" Pharmacokinetic studies demonstrate that acetylshikonin is associated with a wide distribution and poor absorption."( Pharmacology, toxicity and pharmacokinetics of acetylshikonin: a review.
Bai, J; Cai, M; Dong, X; Ni, J; Wu, H; Yao, Y; You, L; Zeng, Y; Zhang, Z, 2020
)
0.56
" The validated analytical method was successfully applied to a pharmacokinetic study of a single, oral dose of 100 mg MB12066 (a clinical form of β-lapachone) in healthy volunteers."( Rapid Interference-free Analysis of β-Lapachone in Clinical Samples Using Liquid Chromatography-Mass Spectrometry for a Pharmacokinetic Study in Humans.
Cho, S; Gwon, MR; Kang, WY; Kim, BK; Lee, HW; Lee, IK; Seong, SJ; Yoon, YR, 2021
)
0.62
" A pharmacokinetic study was conducted in adults and children over 5 years of age (6 to 10, 11 to 17, and ≥18 years of age) with uncomplicated malaria in Tanzania."( Population Pharmacokinetics of Antimalarial Naphthoquine in Combination with Artemisinin in Tanzanian Children and Adults: Dose Optimization.
Abdulla, S; Ali, AM; Bakari, BM; Denti, P; Gausi, K; Gwandu, CH; Hamad, A; Jongo, SA; Juma, OA; Kassim, KR; Lweno, ON; Mbaga, TA; Milando, FA; Mkindi, C; Mtoro, AT; Penny, MA; Shekalaghe, SA; Simon, B, 2022
)
0.72
" Here, we aimed to investigate the physicochemical properties and metabolic profiles of echinochrome A and establish a physiologically-based pharmacokinetic (PBPK) model as a useful tool to support its clinical applications."( Physicochemical characterization and phase II metabolic profiling of echinochrome A, a bioactive constituent from sea urchin, and its physiologically based pharmacokinetic modeling in rats and humans.
Byun, JH; Choi, E; Fedoreyev, SA; Han, DG; Han, J; Jung, IH; Kim, HK; Kwak, J; Mishchenko, NP; Seo, SW; Stonik, VA; Vasileva, EA; Yoon, IS; Yun, H, 2023
)
0.91
" The pharmacokinetic results for napabucasin were consistent with prior publications."( A Phase I Study to Investigate the Safety, Tolerability and Pharmacokinetics of Napabucasin Combined with Sorafenib in Japanese Patients with Unresectable Hepatocellular Carcinoma.
Eguchi, Y; Iino, S; Kageyama, R; Morimoto, M; Nakamura, S; Okusaka, T, 2023
)
0.91

Compound-Compound Interactions

ExcerptReferenceRelevance
"The prophylactic efficacies of atovaquone (ATQ) alone and in combination with azithromycin, clarithromycin, rifabutin, proguanil, PS-15, trimethoprim, co-trimoxazole, or dapsone were investigated in a SCID mouse model of Pneumocystis carinii pneumonia (PCP)."( Effect of atovaquone and atovaquone drug combinations on prophylaxis of Pneumocystis carinii pneumonia in SCID mice.
Comley, JC; Sterling, AM, 1995
)
0.29
"The efficacy of atovaquone alone or combined with pyrimethamine, sulfadiazine, clarithromycin, and minocycline was examined in vitro and in a murine model of acute toxoplasmosis."( In vitro and in vivo activities of the hydroxynaphthoquinone atovaquone alone or combined with pyrimethamine, sulfadiazine, clarithromycin, or minocycline against Toxoplasma gondii.
Derouin, F; Pudney, M; Romand, S, 1993
)
0.29
"The activity of atovaquone in the treatment of murine toxoplasmosis was greatly enhanced when administered in combination with pyrimethamine or sulfadiazine."( The activity of atovaquone (566C80) in murine toxoplasmosis is markedly augmented when used in combination with pyrimethamine or sulfadiazine.
Araujo, FG; Lin, T; Remington, JS, 1993
)
0.29
" To improve cure rates, atovaquone was administered in combination with other drugs with antimalarial activity."( Clinical studies of atovaquone, alone or in combination with other antimalarial drugs, for treatment of acute uncomplicated malaria in Thailand.
Canfield, CJ; Hutchinson, DB; Kyle, DE; Looareesuwan, S; Viravan, C; Webster, HK, 1996
)
0.29
" Doses of each drug that were not effective in reducing inflammation in the brain of mice with toxoplasmic encephalitis when used alone were used in combination with a dose of rifabutin which was minimally effective."( Use of rifabutin in combination with atovaquone, clindamycin, pyrimethamine, or sulfadiazine for treatment of toxoplasmic encephalitis in mice.
Araujo, FG; Remington, JS; Suzuki, Y, 1996
)
0.29
"The efficacy of rifabutin (RIFA) alone or in combination with atovaquone (ATO) was examined in vitro and in a murine model of acute toxoplasmosis."( In vitro and in vivo effects of rifabutin alone or combined with atovaquone against Toxoplasma gondii.
Della Bruna, C; Derouin, F; Farinotti, R; Romand, S, 1996
)
0.29
"Clinical studies have shown proguanil (PROG) combined with atovaquone (ATQ) to be an effective and safe antimalarial combination for the treatment of multidrug-resistant falciparum malaria."( Proguanil polymorphism does not affect the antimalarial activity of proguanil combined with atovaquone in vitro.
Edstein, MD; Kyle, DE; Looareesuwan, S; Rieckmann, KH; Wilairatana, P; Yeo, AE,
)
0.13
"The anticryptosporidial activity of four macrolides alone and in combination with other antimicrobial agents was investigated against ten clinical isolates of Cryptosporidium parvum recovered from stools of AIDS patients."( In-vitro activity of macrolides alone and in combination with artemisin, atovaquone, dapsone, minocycline or pyrimethamine against Cryptosporidium parvum.
Cirioni, O; Giacometti, A; Scalise, G, 1996
)
0.29
" Trovafloxacin, a new fluoroquinolone with potent activity against Toxoplasma gondii, was examined for potential synergistic activity when combined with other drugs used for treatment of human toxoplasmosis."( Activity of trovafloxacin in combination with other drugs for treatment of acute murine toxoplasmosis.
Araujo, FG; Khan, AA; Polzer, RJ; Remington, JS; Slifer, T, 1997
)
0.3
" The same dose protected 100% of infected mice when administered in combination with non-protective doses of atovaquone, clindamycin or sulphadiazine."( Use of ketolides in combination with other drugs to treat experimental toxoplasmosis.
Araujo, FG; Bryskier, A; Khan, AA; Remington, JS, 1998
)
0.3
"To investigate whether ascorbic acid could enhance the efficacy of arsenic trioxide (As(2)O(3)) combined with 2, 3-dimethoxy-1, 4-naphthoquinone (DMNQ) in inducing the apoptosis of leukemia cell line U937 and its possible mechanism."( [Ascorbic acid enhances the apoptosis of U937 cells induced by arsenic trioxide in combination with DMNQ and its mechanism].
Gao, F; Li, H; Shi, G; Shi, X; Tang, X; Wang, Z; Yi, J, 2002
)
0.31
"The efficacy of atovaquone (ATO) combined with clindamycin (CLI) against Toxoplasma gondii was examined in murine models of infection with a mouse-non-virulent (Me49) strain."( Efficacy of atovaquone combined with clindamycin against murine infection with a cystogenic (Me49) strain of Toxoplasma gondii.
Bobić, B; Djurković-Djaković, O; Grujić, J; Milenković, V; Nikolić, A, 2002
)
0.31
" After the onset of ECF clinical signs, the animals in the first two groups were treated with buparvaquone in combination with either dexamethasone (group I) or promethazine (group II), and the third group was treated with buparvaquone alone."( The effect of dexamethasone and promethazine in combination with buparvaquone in the management of East Coast fever.
Boniphace, S; Gwamaka, M; Maselle, RM; Matovelo, JA; Mbassa, GK; Mtambo, MM, 2004
)
0.32
" We conclude that atovaquone-proguanil shows no evidence of cardiotoxicity either alone or when combined with artesunate."( Short report: no evidence of cardiotoxicity of atovaquone-proguanil alone or in combination with artesunate.
Gupta, RK; Looareesuwan, S; Nosten, F; Paiphun, L; Slight, T; Van Vugt, M; White, NJ, 2005
)
0.33
"The compound 2-hydroxy-3-(1'-propen-3-phenyl)-1,4-naphthoquinone (PHNQ6) was evaluated for activity against Toxoplasma gondii, alone or combined with sulfadiazine."( Toxoplasma gondii: in vitro and in vivo activities of the hydroxynaphthoquinone 2-hydroxy-3-(1'-propen-3-phenyl)-1,4-naphthoquinone alone or combined with sulfadiazine.
Ferreira, RA; Oliveira, AB; Ribeiro, MF; Tafuri, WL; Vitor, RW, 2006
)
0.33
"To study the antimalarial activity of naphthoquine phosphate combined with artemisinine against Plasmodium knowlesi in rhesus monkey."( [Therapeutic efficacy of naphthoquine phosphate combined with artemisinine against Plasmodium knowlesi].
Ding, DB; Li, GF; Wang, JY; Zhao, JH, 2008
)
0.35
" Here, we evaluated the therapeutic potential of YM155, a selective survivin suppressant, alone and in combination with docetaxel using human melanoma models."( Antitumor activity of YM155, a selective small-molecule survivin suppressant, alone and in combination with docetaxel in human malignant melanoma models.
Kaneko, N; Kita, A; Kiyonaga, F; Nakahara, T; Sasamata, M; Takeuchi, M; Yamanaka, K; Yamauchi, T, 2011
)
0.37
" Furthermore, the efficacy of YM155 combined with docetaxel was further examined in established xenograft models."( Antitumor activity of YM155, a selective small-molecule survivin suppressant, alone and in combination with docetaxel in human malignant melanoma models.
Kaneko, N; Kita, A; Kiyonaga, F; Nakahara, T; Sasamata, M; Takeuchi, M; Yamanaka, K; Yamauchi, T, 2011
)
0.37
" YM155 in combination with docetaxel is well tolerated and shows greater efficacy than either agent alone in mouse xenograft models."( Antitumor activity of YM155, a selective small-molecule survivin suppressant, alone and in combination with docetaxel in human malignant melanoma models.
Kaneko, N; Kita, A; Kiyonaga, F; Nakahara, T; Sasamata, M; Takeuchi, M; Yamanaka, K; Yamauchi, T, 2011
)
0.37
" In this study, we investigated erlotinib in combination with shikonin and 14 shikonin derivatives in parental U87MG and transfected U87MG."( Shikonin and its derivatives inhibit the epidermal growth factor receptor signaling and synergistically kill glioblastoma cells in combination with erlotinib.
Bauer, R; Efferth, T; Kretschmer, N; Zhao, Q, 2015
)
0.42
" Naphthoquinones, combined with ascorbate, caused phosphorylation of H2AX and inhibited pAkt."( DNA damage and inhibition of akt pathway in mcf-7 cells and ehrlich tumor in mice treated with 1,4-naphthoquinones in combination with ascorbate.
Benites, J; Calderon, PB; Castro, LS; Correia, JF; Farias, MS; Felipe, KB; Grinevicius, VM; Kviecinski, MR; Ourique, F; Pedrosa, RC; Rios, D; Valderrama, J, 2015
)
1.54
" In vitro and in vivo models were used to examine the anticancer efficacy of YM155, either as a monotherapy or in combination with CDDP to identify more effective therapeutics against hepatoblastoma."( Antitumor activity of YM155, a selective survivin suppressant, in combination with cisplatin in hepatoblastoma.
Kang, Y; Liu, Y; Wang, J; Yu, Y; Zhang, Y; Zhao, X, 2015
)
0.42
"The aim of the present study was to investigate the protective effect exerted by bone marrow mesenchymal stem cells (BMSCs) in combination with plumbagin on spinal cord injury (SCI) and explore the mechanism behind this protective effect."( Treatment with bone marrow mesenchymal stem cells combined with plumbagin alleviates spinal cord injury by affecting oxidative stress, inflammation, apoptotis and the activation of the Nrf2 pathway.
Liang, M; Song, J; Yang, JY; Yang, W; Yang, Y, 2016
)
0.43
"The purpose of the study was to obtain further in vivo data of antitumor effects and mechanisms triggered by juglone and Q7 in combination with ascorbate."( In vivo inhibition of tumor progression by 5 hydroxy-1,4-naphthoquinone (juglone) and 2-(4-hydroxyanilino)-1,4-naphthoquinone (Q7) in combination with ascorbate.
Benites, J; Calderon, PB; Castro, LSEPW; Gomes Castro, AJ; Kviecinski, MR; Mena Barreto Silva, FR; Ourique, F; Pedrosa, RC; Rios, D; Valderrama, JA; Zirbel, G, 2016
)
0.43
" This study aimed at screening synthetic aminonathoquinone derivatives (Rau 008, Rau 010, Rau 015 and Rau 018) alone and in combination with curcumin for anti-breast cancer activity."( Evaluation of the Effects of Aminonaphthoquinone Derivatives in Combination with Curcumin Against ER-positive Breast Cancer and Related Tumours.
Davids, H; DE Koning, CB; Mohammed, R; Pereira, MC; VAN Otterlo, WAL, 2017
)
0.46
"We report on the potential of Rau 015 or Rau 018 as anti-breast cancer agents when combined with curcumin."( Evaluation of the Effects of Aminonaphthoquinone Derivatives in Combination with Curcumin Against ER-positive Breast Cancer and Related Tumours.
Davids, H; DE Koning, CB; Mohammed, R; Pereira, MC; VAN Otterlo, WAL, 2017
)
0.46
"Objective To investigate the effect and molecular mechanism of β-lapachone combined with NVP-BEZ235 on the proliferation and migration of BGC-823 human gastric cancer cells."( [β-Lapachone combined with NVP-BEZ235 inhibit proliferation and migration of BGC-823 gastric cancer cells].
Chen, L; Cui, X; Lin, Z; Sun, J; Wang, Y, 2018
)
0.48
" The aim of this study was to evaluate the anti-Mycobacterium tuberculosis activity of nine naphthoimidazoles, alone and combined with isoniazid (INH) and rifampicin (RIF)."( Anti-Mycobacterium tuberculosis activity of naphthoimidazoles combined with isoniazid and rifampicin.
Carvalho, TDSC; Corrêa Barros, LP; da Silva, PEA; de Moura, KCG; Del Rio, KP; Halicki, PCB; Pinto, MDCFR; Ramos, DF, 2018
)
0.48
" In our research, the effect of naphthazarin (DHNQ) combined with 2-hydroxy-1,4-naphthoquinone (NQ-2-OH) or 1,4-naphthoquinone (1,4-NQ) on the elongation growth, pH changes of the incubation medium, oxidative stress and redox activity of maize coleoptile cells were investigated."( Effects of Naphthazarin (DHNQ) Combined with Lawsone (NQ-2-OH) or 1,4-Naphthoquinone (NQ) on the Auxin-Induced Growth of
Karcz, W; Ludynia, M; Rudnicka, M, 2019
)
0.51
"This phase I study was conducted to evaluate the safety and pharmacokinetics of YM155, a potent, selective survivin inhibitor, in combination with erlotinib in patients with EGFR TKI refractory advanced non-small cell lung cancer (NSCLC)."( Phase I safety and pharmacokinetic study of YM155, a potent selective survivin inhibitor, in combination with erlotinib in patients with EGFR TKI refractory advanced non-small cell lung cancer.
Morishita, M; Nakagawa, K; Nishio, K; Okamoto, I; Okamoto, K; Sakai, K; Shimizu, T; Takeda, M, 2020
)
0.56
"To observe the clinical effect of platelet rich plasma (PRP) combined with β tricalcium phosphate bioceramic bone in the treatment of non traumatic necrosis of the femoral head in ARCO stageⅡ."( [Platelet-rich plasma combined with core decompression and bone grafting in the treatment of non traumatic necrosis of femoral head in ARCO stageⅡ].
Chen, DD; Hao, YQ; Li, HH; Lu, C; Wang, QX; Yuan, XC; Yuwen, X, 2020
)
0.56
"9) months, underwent core decompression and bone grafting combined with PRP implantation."( [Platelet-rich plasma combined with core decompression and bone grafting in the treatment of non traumatic necrosis of femoral head in ARCO stageⅡ].
Chen, DD; Hao, YQ; Li, HH; Lu, C; Wang, QX; Yuan, XC; Yuwen, X, 2020
)
0.56
"Platelet-rich plasma(PRP) combined with artificialbone for core decompression and bone grafting can change the situation of simple artificial bone implantation and uncertain curative effect, improve the success rate of this operation, effectively reduce the collapse rate of femoral head necrosis in the early and middle stage, delay or even avoid hip replacement."( [Platelet-rich plasma combined with core decompression and bone grafting in the treatment of non traumatic necrosis of femoral head in ARCO stageⅡ].
Chen, DD; Hao, YQ; Li, HH; Lu, C; Wang, QX; Yuan, XC; Yuwen, X, 2020
)
0.56
"Napabucasin 240 mg BID in combination with FOLFIRI and bevacizumab was tolerated, with a manageable safety profile in Japanese patients with metastatic CRC."( Phase I study of napabucasin in combination with FOLFIRI + bevacizumab in Japanese patients with metastatic colorectal cancer.
Bando, H; Iino, S; Kadowaki, S; Kageyama, R; Kawazoe, A; Masuishi, T; Muro, K; Taniguchi, H; Yoshino, T, 2021
)
0.62
" Probe A was selectively and efficiently sensitive to NQO1 with good safety profile and plasma stability, enabling its combination with NQO1 substrates in vivo for NQO1-overexpressing cancer theranostics for the first time."( Rational designed highly sensitive NQO1-activated near-infrared fluorescent probe combined with NQO1 substrates in vivo: An innovative strategy for NQO1-overexpressing cancer theranostics.
Gong, Q; Hu, J; Li, T; Li, X; Wang, P; Yang, F; Zhang, X, 2021
)
0.62

Bioavailability

ExcerptReferenceRelevance
" Initial studies in humans indicate that 566C80 is safe and has adequate bioavailability after oral administration."( A preliminary evaluation of 566C80 for the treatment of Pneumocystis pneumonia in patients with the acquired immunodeficiency syndrome.
Davey, RT; Falloon, J; Feuerstein, I; Hughes, W; Kovacs, J; LaFon, S; Lancaster, D; O'Neill, D; Polis, M; Rogers, M, 1991
)
0.28
"1 microM) of 5-lipoxygenase, but its therapeutic potential is compromised by a short plasma half-life (22 min) and extremely poor oral bioavailability (less than 2%)."( Pharmacokinetic screening of o-naphthoquinone 5-lipoxygenase inhibitors.
Douglas, FL; Jones, DR; Kotake, AN; Kuwahara, SK; Oglesby, TD; Rakhit, A; Soliman, VF; Tripp, SL; Wasley, JW, 1990
)
0.28
" It was found that the antibiotic was well absorbed topically so that topical LD50 was approximately the same as intravenous LD50 in mice."( [The therapeutic effect of nanaomycin A against experimental Trichophyton mentagrophytes infection in guinea pigs (author's transl)].
Araki, Y; Kitaura, K; Marumo, H, 1980
)
0.26
" The bioavailability of the high and low doses of atovaquone was similar."( Population pharmacokinetics of atovaquone in patients with acute malaria caused by Plasmodium falciparum.
Canfield, CJ; Eaves, J; Hussein, Z; Hutchinson, DB, 1997
)
0.3
"To compare the relative bioavailability of a single atovaquone 750 mg suspension oral dose when administered in the fasting state, after a normal breakfast, and after an enteral nutrition supplement."( Relative bioavailability of atovaquone suspension when administered with an enteral nutrition supplement.
Dall, LH; Freeman, CD; Klutman, NE; Lamp, KC; Strayer, AH, 1998
)
0.3
"This study has shown that the new atovaquone oral suspension also has significantly greater bioavailability when administered after food or a nutrition supplement that has a moderate fat content."( Relative bioavailability of atovaquone suspension when administered with an enteral nutrition supplement.
Dall, LH; Freeman, CD; Klutman, NE; Lamp, KC; Strayer, AH, 1998
)
0.3
" In the case of BCS class II drugs dissolution is rate-limiting to absorption, so the use of biorelevant dissolution tests can be used to predict differences in bioavailability among different formulations and dosing conditions."( In vitro-in vivo correlations for lipophilic, poorly water-soluble drugs.
Dressman, JB; Reppas, C, 2000
)
0.31
" The bioavailability of bupravaquone is limited when given orally."( Production and characterisation of mucoadhesive nanosuspensions for the formulation of bupravaquone.
Jacobs, C; Kayser, O; Müller, RH, 2001
)
0.31
" While atovaquone has potent in vitro activity against Toxoplasma gondii, it is poorly absorbed after oral administration and shows poor therapeutic efficacy against TE."( Atovaquone nanosuspensions show excellent therapeutic effect in a new murine model of reactivated toxoplasmosis.
Borner, K; Hahn, H; Kayser, O; Krause, K; Liesenfeld, O; Müller, RH; Schöler, N, 2001
)
0.31
" The liquid form offers better bioavailability and convenient dosing."( FDA approves new PCP drug. Food and Drug Administration.
, 1995
)
0.29
"Although prediction of the plasma profile of lipophilic drugs solely on the basis of in vitro data remains an ambitious target, this study shows that the plasma profile of a lipophilic drug can be predicted with appropriate in vitro dissolution data, provided that the absolute bioavailability of the drug is known and the drug has dissolution limited absorption."( Biorelevant dissolution testing to predict the plasma profile of lipophilic drugs after oral administration.
Dressman, JB; Nicolaides, E; Reppas, C; Symillides, M, 2001
)
0.31
" Main advantages of nanosuspensions (amongst others) are their increase of saturation solubility and dissolution velocity, improving the bioavailability of drugs."( Buparvaquone mucoadhesive nanosuspension: preparation, optimisation and long-term stability.
Jacobs, C; Müller, RH, 2002
)
0.31
"To explore the use of cyclodextrins (CD) to form inclusion complexes with beta-lapachone (beta-lap) to overcome solubility and bioavailability problems previously noted with this drug."( Enhancement of solubility and bioavailability of beta-lapachone using cyclodextrin inclusion complexes.
Beman, M; Boothman, DA; Bornmann, WG; Bruening, A; Gao, J; Nasongkla, N; Ray, D; Wiedmann, AF, 2003
)
0.32
" Biologic activity and bioavailability of beta-lap inclusion complexes were investigated by in vitro cytotoxicity studies with MCF-7 cells and by in vivo lethality studies with C57Blk/6 mice (18-20 g)."( Enhancement of solubility and bioavailability of beta-lapachone using cyclodextrin inclusion complexes.
Beman, M; Boothman, DA; Bornmann, WG; Bruening, A; Gao, J; Nasongkla, N; Ray, D; Wiedmann, AF, 2003
)
0.32
" Bioisosteric replacement of the carboxylic function by tetrazole to increase bioavailability and to maintain comparable acidity led to improved antimalarial properties as well, but only with the cyanoethyl-protected tetrazoles."( 5-substituted tetrazoles as bioisosteres of carboxylic acids. Bioisosterism and mechanistic studies on glutathione reductase inhibitors as antimalarials.
Bauer, H; Biot, C; Davioud-Charvet, E; Schirmer, RH, 2004
)
0.32
"Exogenous surfactants are increasingly used to enhance the dispersion properties of lipid-based formulations of poorly water-soluble drugs, yet their possible effects on formulation digestion and oral bioavailability in-vivo are not well documented."( Examination of the impact of a range of Pluronic surfactants on the in-vitro solubilisation behaviour and oral bioavailability of lipidic formulations of atovaquone.
Boyd, BJ; Charman, WN; Porter, CJ; Sek, L, 2006
)
0.33
"The aim of the present study is to develop an automated blood sampling (ABS) method coupled to a liquid chromatography-tandem mass spectroscopy (LC-MS/MS) method to evaluate the oral bioavailability of plumbagin in a conscious freely moving rat."( Measurement and pharmacokinetic study of plumbagin in a conscious freely moving rat using liquid chromatography/tandem mass spectrometry.
Hsieh, YJ; Lin, LC; Tsai, TH, 2006
)
0.33
" However, poor aqueous solubility and low bioavailability hinder its therapeutic applications."( Modulating beta-lapachone release from polymer millirods through cyclodextrin complexation.
Ai, H; Blanco, E; Boothman, DA; Gao, J; Wang, F, 2006
)
0.33
"The aim of this study was to prepare a lipid-based self-microemulsifying drug delivery system (SMEDDS) to increase the solubility and oral bioavailability of a poorly water-soluble compound, buparvaquone (BPQ)."( In vitro and in vivo evaluation of self-microemulsifying drug delivery system of buparvaquone.
Croft, SL; Majid, MI; Mansor, SM; Nair, NK; Navaratnam, V; Venkatesh, G, 2010
)
0.36
" The calculated absolute oral bioavailability for BPQ was found to be 40."( In vitro and in vivo evaluation of self-microemulsifying drug delivery system of buparvaquone.
Croft, SL; Majid, MI; Mansor, SM; Nair, NK; Navaratnam, V; Venkatesh, G, 2010
)
0.36
"Various shortcomings of the available methods of extraction of plumbagin from Plumbago zeylanica using non-edible organic solvents coupled with the poor aqueous solubility and low bioavailability called for extracting plumbagin in a water soluble form via a single step technique using hydrophilic lipid Gelucire 44/14."( Novel solvent-free gelucire extract of Plumbago zeylanica using non-everted rat intestinal sac method for improved therapeutic efficacy of plumbagin.
Bothiraja, C; Dama, GY; Joshi, PP; Pawar, AP; Shaikh, KS, 2012
)
0.38
" In vitro intestinal absorption and bioavailability of plumbagin from GPZ in comparison with that of aqueous (APZ), ethanolic extract (EPZ) and standard plumbagin studied using non-everted rat intestinal sac model."( Novel solvent-free gelucire extract of Plumbago zeylanica using non-everted rat intestinal sac method for improved therapeutic efficacy of plumbagin.
Bothiraja, C; Dama, GY; Joshi, PP; Pawar, AP; Shaikh, KS, 2012
)
0.38
" We also included in the analysis several β-lap derivatives expected to modify drug bioavailability and activity."( Yeast cytotoxic sensitivity to the antitumour agent β-lapachone depends mainly on oxidative stress and is largely independent of microtubule- or topoisomerase-mediated DNA damage.
Estévez-Braun, A; García-Luis, J; Lorenzo-Castrillejo, I; Machín, F; Matos-Perdomo, E; Medina-Coello, C; Quevedo, O; Ramos-Pérez, C, 2014
)
0.4
" Despite ex vivo activity, none of the compounds tested was active in vivo, suggesting that the limited bioavailability may compromise compound activity."( Synthesis and evaluation of 1,4-naphthoquinone ether derivatives as SmTGR inhibitors and new anti-schistosomal drugs.
Becker, K; Belorgey, D; Chessé, M; Davioud-Charvet, E; Day, L; Huang, HH; Johann, L; Williams, DL, 2015
)
0.42
" βLAP (and its combinations with CDs) absorption rate coefficients and effective permeability values have been determined in vitro in MDCK or MDCK-Mdr1 monolayers and in situ in rat by a closed loop perfusion technique."( Intestinal Permeability of β-Lapachone and Its Cyclodextrin Complexes and Physical Mixtures.
Bermejo, M; Casabó, VG; Echezarreta-López, M; González-Álvarez, I; González-Álvarez, M; Gutiérrez-Nieto, J; Landin, M; Mangas-Sanjuan, V, 2016
)
0.43
" Complexing shikonin with β-lactoglobulin reduced its toxicity while preserving the inhibitory effect on NLRP3 inflammasome activation, suggesting that shikonin with improved bioavailability might be interesting for therapeutic applications in inflammasome-mediated conditions."( Shikonin Suppresses NLRP3 and AIM2 Inflammasomes by Direct Inhibition of Caspase-1.
Hafner-Bratkovič, I; Sušjan, P; Zorman, J, 2016
)
0.43
" However, this approach is frequently limited by the bioavailability and toxicity of the combined agents and delivery at ratios to specific locations that synergistically kill cancer cells."( Nanoparticle-Based Celecoxib and Plumbagin for the Synergistic Treatment of Melanoma.
Gowda, R; Kardos, G; Robertson, GP; Sharma, A; Singh, S, 2017
)
0.46
" Atovaquone is a drug that inhibits the respiratory chain of Plasmodium falciparum, but with serious limitations like known resistance, low bioavailability and high plasma protein binding."( Insights into cytochrome bc1 complex binding mode of antimalarial 2-hydroxy-1,4-naphthoquinones through molecular modelling.
Abrahim-Vieira, B; Ferreira, SB; Ferreira, VF; Garcia, CR; Pascutti, PG; Rocha, DR; Silva, FP; Sodero, AC; Torres, PH, 2017
)
0.68
" However, its lower bioavailability limits biopharmaceutical properties due to insolubility in water."( Plumbagin-loaded aptamer-targeted poly D,L-lactic-co-glycolic acid-b-polyethylene glycol nanoparticles for prostate cancer therapy.
Ju, W; Li, W; Li, Z; Pan, M; Xiao, Y; Xing, Y; Yang, J; Zhang, X; Zhao, J, 2017
)
0.46
"A structure-activity relationship to evaluate the effect of bioavailability was performed."( Influence of lipophilicity in O-acyl and O-alkyl derivatives of juglone and lawsone: a structure-activity relationship study in the search for natural herbicide models.
Chinchilla, N; Durán, AG; Macías, FA; Molinillo, JM, 2018
)
0.48
"The aim of this paper was to compare the in vitro dissolution and in vivo bioavailability of three solubility enhancement technologies for β-lapachone (LPC), a poorly water soluble compound with extremely high crystallization propensity."( Oral bioavailability enhancement of β-lapachone, a poorly soluble fast crystallizer, by cocrystal, amorphous solid dispersion, and crystalline solid dispersion.
Chen, H; Chen, Y; Chen, Z; Liu, C; Liu, Z; Pui, Y; Qian, F, 2018
)
0.48
" However, poor water solubility and low bioavailability limit its wide application in clinical practice."( Anticancer Efficacy of Targeted Shikonin Liposomes Modified with RGD in Breast Cancer Cells.
Cai, D; Fan, L; Li, J; Sun, J; Wang, Q; Wen, X; Wu, Y; Yue, L; Zhou, L, 2018
)
0.48
" Buparvaquone (BPQ), a hydroxynapthoquinone with in vitro activity in the nanomolar range, failed to clinically translate as a viable treatment for visceral leishmaniasis due to its poor oral bioavailability limited by its poor aqueous solubility (BCS Class II drug)."( Orally Bioavailable and Effective Buparvaquone Lipid-Based Nanomedicines for Visceral Leishmaniasis.
Bolás-Fernández, F; Dea-Ayuela, MA; Lalatsa, A; Mauger, M; Serrano, DR; Smith, L, 2018
)
0.48
" Nano encapsulation of plumbagin overcomes the poor water solubility and bioavailability obstacles, enhancing the pharmaceutical relevance with better therapeutic efficacy."( Emerging role of plumbagin: Cytotoxic potential and pharmaceutical relevance towards cancer therapy.
Biswal, BK; Panda, M; Tripathi, SK, 2019
)
0.51
" A brief history of these compounds is reviewed along with their potential effects and mechanisms of action and the most recent attempts to improve their bioavailability and potency against different types of cancer."( Anticancer Potential of Resveratrol, β-Lapachone and Their Analogues.
Ferraz da Costa, DC; Ferreira, VF; Ferretti, GDDS; Martins-Dinis, MMDDC; Pereira Rangel, L; Silva, JL, 2020
)
0.56
" Nanoemulsions are drug delivery systems that can assist in the administration of hydrophobic drugs, increasing their bioavailability and protecting from degradation."( Enhanced antitumor efficacy of lapachol-loaded nanoemulsion in breast cancer tumor model.
Alcântara Lemos, J; Alves, RJ; Cassali, GD; de Barros, ALB; Fernandes, RS; Ferreira, LAM; Mendes Miranda, SE; Ottoni, FM; Rubello, D; Silva, JO; Townsend, DM, 2021
)
0.62
" β-Lapachone (BLPC) was selected for its anticancer activity and its limited bioavailability due to very low aqueous solubility, with the aim to improve this by using LAP/Tetronic nano-hybrid systems."( Nanocomposite gels of poloxamine and Laponite for β-Lapachone release in anticancer therapy.
Almeida Júnior, RF; Barbosa, RM; Câmara, CA; Câmara, GBM; de Lima E Moura, TFA; Dreiss, CA; Farias, KJS; García-Villén, F; Machado, PRL; Raffin, FN; Viseras, C, 2021
)
0.62
"This study aimed to improve the potency and bioavailability of BiQ compounds and investigate antileukemic activity of the lead compound in vitro and a human AML xenograft mouse model."( Pre-Clinical Activity of Amino-Alcohol Dimeric Naphthoquinones as Potential Therapeutics for Acute Myeloid Leukemia.
Ambulos, N; Bollino, D; Carter-Cooper, B; Chang, E; Choi, EY; Dash, S; Emadi, A; Ferraris, D; Gartenhaus, R; Jing, Y; Kamangar, F; Kapadia, B; Kipe, O; Lam, V; Lapidus, R; LaRossa-Garcia, M; Lee, M; Mason, K; Palmer, R; Truong, P; Williams, E; Zhang, Y, 2022
)
0.98
" Biphasic bigels consisting of solid and liquid components represent suitable formulations improving diffusion and bioavailability of NQs into the skin."( In Vitro and In Silico Studies of Two 1,4-Naphthoquinones and Their Topical Formulation in Bigels.
Bouajila, J; Efferth, T; Hayouni, EA; Khelifi, D; Khelifi, I; Ksouri, R; Tourrette, A, 2021
)
0.89
" Buparvaquone is a potential drug against the leishmaniases, but it is highly hydrophobic resulting in poor bioavailability and low therapeutic efficacy."( Biogenic nanoporous silicon carrier improves the efficacy of buparvaquone against resistant visceral leishmaniasis.
Lehto, VP; Mondal, S; Näkki, S; Närvänen, A; Nissinen, T; Rantanen, J; Riikonen, J; Thapa, R, 2021
)
0.62
" The drug of choice to treat this disease is albendazole; however, the bioavailability and efficacy of the drug are variable."( Cysticidal effect of a pure naphthoquinone on Taenia crassiceps cysticerci.
Aranda-López, Y; Becerril-Villanueva, LE; Castro, KEN; Del Río-Araiza, VH; Girón-Pérez, MI; López-López, L; Morales-Montor, J; Ponce-Regalado, MD, 2021
)
0.62
" An overview of attempts to design novel formulations which could enhance its bioavailability is also presented."( Plumbagin: A Potential Candidate for Future Research and Development.
Janathia, B; Thakor, N, 2022
)
0.72
" To estimate the bioavailability of Ech A as an oral administration drug, small intestinal and colonic epithelial organoids were developed from mice and humans."( Implication of Echinochrome A in the Plasticity and Damage of Intestinal Epithelium.
Ahn, JS; Fedoreyev, SA; Han, J; Kang, MJ; Kim, HK; Kim, HS; Lee, BC; Mishchenko, NP; Nguyen, DK; Nguyen, PT; Oh, SJ; Park, SY; Seo, Y; Shin, YY; Song, MH; Stonik, VA; Vasileva, EA, 2022
)
0.72

Dosage Studied

Toxicity of the hydroxy-alkylnaphthoquinones decreased with increasing size of the alkyl substituent. No toxic changes were recorded in animals dosed with 2-hydroxy-3-butyl- or 2-Hydroxy- 3-pentyl-1,4-naphThoquinone.

ExcerptRelevanceReference
" parva, menoctone cured all of 7 cattle at a total dosage of 10 mg/kg injected intravenously (i."( Experimental therapy of theileriosis.
McHardy, N, 1979
)
0.26
" 6,7-Bis(bromomethyl)quinoline-5,8-dione had moderate inhibitory activity against Sarcoma 180 at its optimal daily dosage level of 15 mg/kg."( Potential bioreductive alkylating agents. 5. Antineoplastic activity of quinoline-5,8-diones, naphthazarins, and naphthoquinones.
Lillis, BJ; Lin, AJ; Sartorelli, AC, 1975
)
0.47
" Buparvaquone, at the dosage evaluated, had transitory therapeutic efficacy against acute B equi infection in splenectomized horses, but was unable alone to clear carrier infection."( Efficacy of buparvaquone as a therapeutic and clearing agent of Babesia equi of European origin in horses.
Lane, VM; Zaugg, JL, 1992
)
0.28
" Pretreatment of the cells with an inhibitor of the 5-lipoxygenase pathway, U-70344A, shifted the dose-response curve to the right; pretreatment with indomethacin, an inhibitor of the cyclooxygenase pathway, had no effect."( Arachidonic acid and lipoxygenase metabolites uncouple neonatal rat cardiac myocyte pairs.
Burt, JM; Massey, KD; Minnich, BN, 1992
)
0.28
" Haemolysis was the only toxic change identified in rats dosed with 2-methyl-1,4-naphthoquinone."( Haemolytic activity and nephrotoxicity of 2-hydroxy-1,4-naphthoquinone in rats.
Fowke, EA; Munday, R; Smith, BL, 1991
)
0.28
" The most active compounds, benzenesulfonate 4, p-toluenesulfonate 5, p-methoxybenzenesulfonate 7,8-quinolinesulfonate 17, and 2-thiophenesulfonate 20, in the aromatic sulfonate series, at their optimum daily dosage level of 25 mg/kg X 6, produced 100%, 90%, 75%, 80%, and 100% 50-day survivors, respectively, of L1210 tumor-bearing mice."( Synthesis of 2,3-diaziridinyl-1,4-naphthoquinone sulfonate derivatives as potential antineoplastic agents.
Cosby, LA; Lin, TS; Sartorelli, AC; Xu, SP; Zhu, LY, 1989
)
0.28
"The chitin synthetase inhibitor plumbagin and its 2-demethyl derivative juglone were found to inhibit in a dose-response fashion the cytochrome P-450 dependent ecdysone 20-monooxygenase activity associated with adult female Aedes aegypti, wandering stage larvae of Drosophila melanogaster, and fat body and midgut from last instar larvae of Manduca sexta."( Effects of the chitin synthetase inhibitor plumbagin and its 2-demethyl derivative juglone on insect ecdysone 20-monooxygenase activity.
Mitchell, MJ; Smith, SL, 1988
)
0.27
"Kidneys from male and female Wistar rats dosed with 1 of 3 chemically unrelated pharmacological agents, a pyrazoline BW540C, a naphthoquinone BW58C and the levoisomer of tetramisole, levamisole or the light hydrocarbon Decalin, were examined by light and electron microscopy."( Induction and exacerbation of hyaline droplet formation in the proximal tubular cells of the kidneys from male rats receiving a variety of pharmacological agents.
Astbury, PJ; Morgan, RJ; Parsons, DN; Port, CJ; Read, NG, 1988
)
0.27
" Imidocarb, at a dosage of 4 mg/kg of body weight, given IM at 72-hour intervals 4 times, was ineffective in eliminating B equi-carrier infection in 9 mature geldings."( Imidocarb and parvaquone in the treatment of piroplasmosis (Babesia equi) in equids.
Gipson, CA; Kuttler, KL; Zaugg, JL, 1987
)
0.27
" In patients with mild to moderate PCP, a dosage of 750mg 3 times daily (administered in tablet form) has similar overall therapeutic efficacy (defined as clinical response without a treatment-limiting adverse event) to the conventional therapies oral cotrimoxazole (trimethoprim-sulfamethoxazole) and intravenous pentamidine, respectively."( Atovaquone. A review of its pharmacological properties and therapeutic efficacy in opportunistic infections.
Goa, KL; Spencer, CM, 1995
)
0.29
" The recurrences were successfully treated by increasing the dosage of Atovaquone to 4 x 750 mg/d and the addition of Trimethoprime/Sulfamethoxazol and Clindamycine/Pyrimethamine respectively."( [Treatment of toxoplasmosis retinochoroiditis with atovaquone in an AIDS patient].
Althaus, C; Armbrecht, C; Jablonowski, H; Schimkat, M; Sundmacher, R, 1995
)
0.29
" ATQ drug combinations affected the prophylactic efficacy of a subcurative dosage of ATQ (50 mg/kg/day given orally) in the following ways: dapsone (25 mg/kg/day) or co-trimoxazole (25 mg of sulfamethoxazole plus 5 mg of trimethoprim per kg/day) had no significant effect on ATQ, azithromycin (200 mg/kg/day) or clarithromycin (200 mg/kg/day) had a slight additive effect with ATQ, trimethoprim (100 mg/kg/day) or PS-15 (5 mg/kg/day) had an additive effect with ATQ, and proguanil (25 mg/kg/day) or rifabutin (200 mg/kg/day) had a marked synergistic effect on ATQ."( Effect of atovaquone and atovaquone drug combinations on prophylaxis of Pneumocystis carinii pneumonia in SCID mice.
Comley, JC; Sterling, AM, 1995
)
0.29
" These data can be used to develop a stable oral liquid dosage form of the drug."( Isoxazoles. 8. Preformulation studies of an isoxazolylnaphthoquinone derivative.
de Bertorello, MM; Granero, GE; Longhi, MR, 1994
)
0.29
"The mechanism of action, pharmacokinetics and pharmacodynamics, clinical efficacy, adverse effects, and dosage of atovaquone in the management of mild to moderate Pneumocystis carinii pneumonia (PCP) are reviewed."( Atovaquone: a new antipneumocystis agent.
Artymowicz, RJ; James, VE, 1993
)
0.29
"Plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) isolated from Plumbago zeylanica Linn, when administered orally, at a dosage of 4 mg/kg body weight induces tumour regression in 3-methyl-4-dimethyl aminoazobenzene (3MeDAB) induced hepatoma in Wistar male rats."( Effect of Plumbagin on some glucose metabolising enzymes studied in rats in experimental hepatoma.
Parimala, R; Sachdanandam, P, 1993
)
0.29
" Furthermore, the toxicity of the hydroxy-alkylnaphthoquinones decreased with increasing size of the alkyl substituent and no toxic changes were recorded in animals dosed with 2-hydroxy-3-butyl- or 2-hydroxy-3-pentyl-1,4-naphthoquinone."( Comparative toxicity of 2-hydroxy-3-alkyl-1,4-naphthoquinones in rats.
Munday, CM; Munday, R; Smith, BL, 1995
)
0.81
" At an oral dosage equivalent to 100 mg of ATQ per kg of body weight per day, 17C91 protected 9 of 10 mice from PCP and had a prophylactic efficacy comparable to that of co-trimoxazole (at 250 mg of sulfamethoxazole plus 50 mg of trimethoprim per kg per day orally)."( Antipneumocystis activity of 17C91, a prodrug of atovaquone.
Comley, JC; Frend, TJ; Yeates, CL, 1995
)
0.29
" These results suggest that combining rifabutin with certain drugs that are active against Toxoplasma gondii may be useful for the treatment of toxoplasmic encephalitis in humans and may allow for a reduction in dosage of either or both drugs with a resulting reduction in untoward side effects."( Use of rifabutin in combination with atovaquone, clindamycin, pyrimethamine, or sulfadiazine for treatment of toxoplasmic encephalitis in mice.
Araujo, FG; Remington, JS; Suzuki, Y, 1996
)
0.29
"The single- and multiple-dose pharmacokinetics of and tolerability to a new microfluidized suspension of atovaquone were studied in human immunodeficiency virus-seropositive patients with CD4 counts of < or = 200 cells per mm3 in order to define a dosing regimen for the treatment of Pneumocystis carinii pneumonia."( Single-dose and steady-state pharmacokinetics of a novel microfluidized suspension of atovaquone in human immunodeficiency virus-seropositive patients.
Dixon, R; Posner, J; Pozniak, AL; Rolan, P; Watt, HM, 1996
)
0.29
" The results of this preliminary study suggest that ATQ is unlikely to affect the pharmacokinetics of PROG to a clinically important extent at an ATQ dosage of 500 mg twice a day for 3 days in malaria infected patients."( Pharmacokinetics of proguanil in malaria patients treated with proguanil plus atovaquone.
Edstein, MD; Kyle, DE; Looareesuwan, S; Viravan, C, 1996
)
0.29
" Dosages of 30 mg/kg/day were adequate to achieve an average steady-state concentration of greater than 15 micrograms/ml in children ages 1 to 3 months and 2 to 12 years, but a dosage of 45 mg/kg/day was needed to reach this concentration in infants 3 to 24 months of age."( Phase I safety and pharmacokinetics study of micronized atovaquone in human immunodeficiency virus-infected infants and children. Pediatric AIDS Clinical Trials Group.
Beauchamp, B; Dorenbaum, A; Hughes, W; McNamara, J; Moye, J; Purdue, L; Rogers, M; Sadler, B; van Dyke, R; Xu, J; Yogev, R, 1998
)
0.3
" beta-lapachone produced DNA strand breaks as determined by alkaline elution assay; alkaline elution profiles from treated cells showed a bimodal dose-response pattern, with a threshold dose above which a massive dose-independent DNA degradation was observed."( DNA damage and cytotoxicity induced by beta-lapachone: relation to poly(ADP-ribose) polymerase inhibition.
Ceccarelli, R; Cundari, E; De Salvia, R; Degrassi, F; Fiore, M; Ricordy, R; Vanni, A, 1998
)
0.3
" Dosing or frequency of TMP-SMX did not seem to influence risk of chemoprophylaxis failure."( Pneumocystis carinii pneumonia incidence and chemoprophylaxis failure in ambulatory HIV-infected patients. HIV Outpatient Study (HOPS) Investigators.
Holmberg, SD; Moorman, AC; Palella, FJ; Von Bargen, JC, 1998
)
0.3
" Nanocapsules were chosen as the oral dosage form of administration."( Assessment of the activity of atovaquone-loaded nanocapsules in the treatment of acute and chronic murine toxoplasmosis.
Aumjaud, Y; Derouin, F; Fessi, H; Sordet, F, 1998
)
0.3
" In the present study, rats were dosed with BHA and then challenged with a toxic dose of 2-hydroxy-1,4-naphthoquinone, a substance that causes haemolytic anaemia and renal damage in vivo."( Effect of butylated hydroxyanisole on the toxicity of 2-hydroxy-1,4-naphthoquinone to rats.
Munday, CM; Munday, R; Smith, BL, 1999
)
0.3
" For the assay of proguanil, cycloguanil and atovaquone, blood was sampled before dosing and at regular intervals over 8 days when proguanil was given, and over 17 days when atovaquone was given."( Lack of a pharmacokinetic interaction between atovaquone and proguanil.
Gillotin, C; Mamet, JP; Veronese, L, 1999
)
0.3
" During a long-term dosing phase, a subset of subjects were evaluated for an interaction between atovaquone and trimethoprim-sulfamethoxazole (TMP-SMX)."( Atovaquone suspension in HIV-infected volunteers: pharmacokinetics, pharmacodynamics, and TMP-SMX interaction study.
Bechtel, C; Davey, RT; Falloon, J; Kovacs, JA; LaFon, SW; Lane, HC; Masur, H; Piscitelli, SC; Polis, MA; Sadler, B; Sargent, S; Walker, RE, 1999
)
0.3
" Differences between products (both in vitro or in vivo) were less pronounced than differences due to media composition (in vitro) or dosing conditions (in vivo)."( Forecasting the in vivo performance of four low solubility drugs from their in vitro dissolution data.
Dressman, JB; Efthymiopoulos, C; Galia, E; Nicolaides, E; Reppas, C, 1999
)
0.3
" Rats were dosed with BHA, butylated hydroxytoluene (BHT), ethoxyquin (EQ), dimethyl fumarate (DMF) or disulfiram (DIS) and then challenged with a toxic dose of the naphthoquinones."( Effect of inducers of DT-diaphorase on the toxicity of 2-methyl- and 2-hydroxy-1,4-naphthoquinone to rats.
Munday, CM; Munday, R; Smith, BL, 1999
)
0.5
" The dosing regimen was well tolerated."( Atovaquone and proguanil hydrochloride followed by primaquine for treatment of Plasmodium vivax malaria in Thailand.
Chinnapha, S; Chulay, JD; Glanarongran, R; Indravijit, KA; Looareesuwan, S; Scott, TR; Supeeranontha, L; Wilairatana, P,
)
0.13
" It was not possible to obtain the ED(50) for free ATV because the dose-response curve reached a plateau around 33% of parasite suppression."( Therapeutic evaluation of free and liposome-encapsulated atovaquone in the treatment of murine leishmaniasis.
Astier, A; Cauchetier, E; Deniau, M; Fessi, H; Paul, M; Rivollet, D, 2000
)
0.31
" Groups of female Sprague-Dawley rats were dosed by oral intubation on 5 consecutive days with either juglone or plumbagin at 12."( Induction of quinone reductase and glutathione transferase in rat tissues by juglone and plumbagin.
Munday, CM; Munday, R, 2000
)
0.31
" In the case of BCS class II drugs dissolution is rate-limiting to absorption, so the use of biorelevant dissolution tests can be used to predict differences in bioavailability among different formulations and dosing conditions."( In vitro-in vivo correlations for lipophilic, poorly water-soluble drugs.
Dressman, JB; Reppas, C, 2000
)
0.31
" Overall results from these studies indicate patients who are eligible for PCP prophylaxis should be advised to take double-strength trimethoprim/sulfamethoxazole (TMP/SMX) on a daily basis, a dosage found more effective than thrice-weekly."( Optimizing PCP therapy.
Cadman, J; Torres, G, 1997
)
0.3
" The latter is defined as regular intake of antimalarial drugs in subtherapeutic dosage in order to suppress the development of clinical disease."( [Malaria--chemoprophylaxis 2001].
Beck, B; Blum, J; Funk, M; Furrer, H; Genton, B; Hatz, FR; Holzer, B; Loutan, L; Markwalder, K; Raeber, PA; Schlagenhauf, P; Siegl, G; Steffen, R; Stürchler, D; Wyss, R, 2001
)
0.31
" Good safety, tolerance, and efficacy, along with key advantages in dosing requirements, make primaquine an excellent drug for preventing malaria in nonpregnant, G6PD-normal travelers."( Randomized, parallel placebo-controlled trial of primaquine for malaria prophylaxis in Papua, Indonesia.
Baird, JK; Bangs, MJ; Barcus, MJ; Basri, H; Fryauff, DJ; Gramzinski, R; Hoffman, SL; Jones, TR; Kusumaningsih, M; Lacy, MD; Ling, J; Maguire, JD; Sismadi, P; Wiady, I, 2001
)
0.31
" In dose-response studies, induced thermotolerance paralleled the induced increase in life expectancy, which is consistent with a common origin."( Multiple stressors in Caenorhabditis elegans induce stress hormesis and extended longevity.
Cypser, JR; Johnson, TE, 2002
)
0.31
"To determine the pharmacokinetic profiles of atovaquone (ATO), proguanil (PROG) and its active metabolite cycloguanil (CYCLO) with respect to possible accumulation and kinetic interaction upon repeated dosing with Malarone."( Time-dependent pharmacokinetics and drug metabolism of atovaquone plus proguanil (Malarone) when taken as chemoprophylaxis.
Ashton, M; Bergqvist, Y; Björkman, A; Johansson, I; Lindegårdh, N; Nivelius, S; Thapar, MM, 2002
)
0.31
" We measured cysteinyl adducts of these metabolites in hemoglobin (Hb) and albumin (Alb) from F344 rats dosed with 100-800 mg naphthalene per kg body weight."( Measurement of hemoglobin and albumin adducts of naphthalene-1,2-oxide, 1,2-naphthoquinone and 1,4-naphthoquinone after administration of naphthalene to F344 rats.
Lindstrom, AB; Rappaport, SM; Troester, MA; Waidyanatha, S, 2002
)
0.31
" falciparum malaria in nonimmune adults, adolescents and children (>/=11 kg) visiting malaria-endemic regions for ( Atovaquone/proguanil: a review of its use for the prophylaxis of Plasmodium falciparum malaria.
McKeage, K; Scott, L, 2003
)
0.32
" falciparum malaria and compared with other commonly used antimalarial agents has an improved tolerability profile, and, overall, a more convenient dosage regimen, particularly in the post-travel period."( Atovaquone/proguanil: a review of its use for the prophylaxis of Plasmodium falciparum malaria.
McKeage, K; Scott, L, 2003
)
0.32
"The patient was given chloroquine by his captain in a dosage regimen appropriate for quinine (2 tablets 3 times daily for 7 d)."( Toxicity related to chloroquine treatment of resistant vivax malaria.
Barrett, PH; Davis, TM; Ilett, KF; Syed, DA, 2003
)
0.32
" For drugs with a narrow therapeutic index such as chloroquine, recommended dosing regimens should be respected, and adequate information sources must be available where such drugs are dispensed by untrained personnel."( Toxicity related to chloroquine treatment of resistant vivax malaria.
Barrett, PH; Davis, TM; Ilett, KF; Syed, DA, 2003
)
0.32
" The dose-response data indicated that livers would have been cleared of parasites if the nanocapsule preparation had been given as three doses each equivalent to 3 mg ATV/kg, whereas the maximum suppression possible with the free drug would have been about 61%, whatever the dose."( Therapeutic evaluation of free and nanocapsule-encapsulated atovaquone in the treatment of murine visceral leishmaniasis.
Astier, A; Cauchetier, E; Deniau, M; Fessi, H; Paul, M; Rivollet, D, 2003
)
0.32
" Both have the advantage of providing causal prophylaxis and therefore require continued dosing for only 1 wk after departure from a malaria endemic area."( The impact of Malarone and primaquine on psychomotor performance.
Cook, T; Gibson, N; Gray, G; Kenny, G; McCarthy, AE; Paul, MA, 2003
)
0.32
"Twenty-eight subjects (20 men and 8 women) ranging from 21 to 52 yr of age were assessed for psychomotor performance on 2 psychomotor test batteries at the end of a 7-d dosing protocol for each of placebo, Malarone, and primaquine treatment, in a double-blind crossover design with counterbalanced treatment order."( The impact of Malarone and primaquine on psychomotor performance.
Cook, T; Gibson, N; Gray, G; Kenny, G; McCarthy, AE; Paul, MA, 2003
)
0.32
" The cells were dosed with these complexes at varying concentrations, and cell viability was measured by a sulforhodamine B (SRB) method."( The cytotoxicity and mechanisms of 1,2-naphthoquinone thiosemicarbazone and its metal derivatives against MCF-7 human breast cancer cells.
Afrasiabi, Z; Chen, J; Huang, YW; Liu, G; Ma, Y; Padhye, S; Sinn, E, 2004
)
0.32
"Three simple and sensitive spectrophotometric methods were developed and validated for determination of the hydrochloride salts of fluoxetine, sertraline, and paroxetine in their pharmaceutical dosage forms."( Development and validation of spectrophotometric methods for determination of fluoxetine, sertraline, and paroxetine in pharmaceutical dosage forms.
Darwish, IA,
)
0.13
"A randomized, double-blind crossover study was conducted in which 24 subjects were enrolled to use A/P and placebo, each in a 14-day prophylactic dosing regimen with a 21-day washout phase."( Malaria prophylaxis for aircrew: safety of atovaquone/proguanil in healthy volunteers under aircraft cabin pressure conditions.
Krul, AJ; Simons, R; Valk, PJ,
)
0.13
" High concentrations of juglone-derived radioactivity were found in kidney for all three dosing routes."( Metabolism and disposition of juglone in male F344 rats.
Burka, LT; Chen, LJ; Lebetkin, EH,
)
0.13
"The application of microcapsule for pharmaceutical dosage form for various drugs has received considerable attention in recent years due to its multiple advantages."( Microencapsulation of extract containing shikonin using gelatin-acacia coacervation method: a formaldehyde-free approach.
Cham, TM; Cheng, YH; Huang, YI; Tsai, TR; Yu, CC, 2007
)
0.34
" Those excipients should be avoided in the development of solid dosage forms."( Compatibility of the antitumoral beta-lapachone with different solid dosage forms excipients.
Cunha-Filho, MS; Landín, M; Martínez-Pacheco, R, 2007
)
0.34
" The observed responses varied according to dosage and mite species."( Acaricidal activity and function of mite indicator using plumbagin and its derivatives isolated from Diospyros kaki Thunb. roots (Ebenaceae).
Lee, CH; Lee, HS, 2008
)
0.35
" The electrostatic particulate dosage and exposure system (EPDExS) operates on the principle of electrostatic precipitation and is shown to deposit fine and ultrafine aerosol particles directly to cells with 100% efficiency for particle diameters in the range of 40-530nm."( A new method for quantifiable and controlled dosage of particulate matter for in vitro studies: the electrostatic particulate dosage and exposure system (EPDExS).
MacPherson, M; Mossman, BT; Petrucci, GA; Stevens, JP; Zahardis, J, 2008
)
0.35
" Plasma pharmacokinetic data of ARQ 501 in mouse from intraperitoneal (IP) dosing at 60 mg/kg obtained using this validated method is presented along with tumor concentration data."( Development and validation of a liquid chromatography-tandem mass spectrometry method for the determination of ARQ 501 (beta-lapachone) in plasma and tumors from nu/nu mouse xenografts.
Bailey, J; Bresciano, K; Chan, TC; Hall, T; Savage, RE; Starace, M, 2008
)
0.35
" This color-developing reaction was successfully employed in the development of simple and rapid spectrophotometric method for determination of FXM in its pharmaceutical dosage forms."( Spectrophotometric study for the reaction between fluvoxamine and 1,2-naphthoquinone-4-sulphonate: Kinetic, mechanism and use for determination of fluvoxamine in its dosage forms.
Abdine, HH; Al-Rayes, LI; Amer, SM; Darwish, IA, 2009
)
0.35
"92 µmol/kg), dosed intraperitoneally (i."( A new naphthoquinone isolated from the bulbs of Cipura paludosa and pharmacological activity of two main constituents.
Cechinel Filho, V; da Silva, GF; Delle Monache, F; Ferreira, VM; Lucena, GM; Prediger, RD; Quintão, NL; Rocha, LW; Tessele, PB, 2011
)
0.37
" Animals received a 7-day continuous infusion of YM155, 2 mg/kg, and/or three bolus doses of docetaxel, 20 mg/kg, according to three dosing schedules: YM155 administered concomitantly with docetaxel, before docetaxel, and after docetaxel."( YM155, a novel survivin suppressant, enhances taxane-induced apoptosis and tumor regression in a human Calu 6 lung cancer xenograft model.
Hatakeyama, S; Kinoyama, I; Kita, A; Koutoku, H; Matsuhisa, A; Nakahara, T; Nakano, K; Sasamata, M; Shishido, T; Takeuchi, M; Yamanaka, K, 2011
)
0.37
"This study provides useful information for the development of βLAP dosage forms, their storage, manipulation and quality control."( Light effect on the stability of β-lapachone in solution: pathways and kinetics of degradation.
Cunha-Filho, MS; Echezarreta-López, MM; Estévez-Braun, A; Landín, M; Martínez-Pacheco, R; Pérez-Sacau, E, 2011
)
0.37
" The developed method was successfully applied for selective determination of CFP in pure form and in pharmaceutical dosage forms as well as CFA in human urine after single dose of CFP without prior need for separation."( An efficient one-pot reaction for selective fluorimetric determination of cefpodoxime and its prodrug.
Abdel-Wadood, HM; Ahmed, S; Mohamed, NA, 2011
)
0.37
" The effective dosage of GST in enhancement of cell proliferation was 10-50 nM, and the cell migration could be significantly enhanced after 6 hours in the presence of 2-50 nM GST."( Glutathione-S-transferase enhances proliferation-migration and protects against shikonin-induced cell death in breast cancer cells.
Chen, YT; He, S; Kuo, HM; Liao, TT; Lin, YL, 2011
)
0.37
" Low water solubility and large therapeutic doses constitute the main problems to overcome in the development of dosage forms of this drug."( Fast dissolving β-lapachone particles and tablets: an approach using surface adsorption technique.
Cunha-Filho, MS; Landin, M; Martínez-Pacheco, R, 2012
)
0.38
" The cells were dosed with these ortho-naphthoquinone derivatives at varying concentrations, and cell viability was measured by a 3-(4,5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assay with doxorubicin as positive control."( Synthesis, characterization and antiproliferative activity of 1,2-naphthoquinone and its derivatives.
Kumar, P; Shrivastava, SK; Shukla, S; Sodhi, A; Srivastava, RS, 2012
)
0.38
"1 h after dosing to male rats."( Pharmacokinetics, distribution and excretion of YM155 monobromide, a novel small-molecule survivin suppressant, in male and pregnant or lactating female rats.
Felder, L; Hashimoto, T; Iwai, M; Minematsu, T; Miyashita, A; Oppeneer, T; Shirai, N; Sonoda, T; Usui, T, 2012
)
0.38
" These drugs were incorporated in conventional dosage forms or loaded in lipid nanocarries, which have been used mainly for improved skin delivery and antileishmanial activity."( Drug delivery systems for the topical treatment of cutaneous leishmaniasis.
Aguiar, MG; Carneiro, G; Fernandes, AP; Ferreira, LA, 2012
)
0.38
" Insights into the most promising delivery strategies to improve treatment of CL with PA and AmB using conventional dosage forms, lipid nanocarriers, and combined therapy are presented and discussed."( Drug delivery systems for the topical treatment of cutaneous leishmaniasis.
Aguiar, MG; Carneiro, G; Fernandes, AP; Ferreira, LA, 2012
)
0.38
" The data showed a strong dose-response relationship between Shikonin exposure and the characteristics of HL-60 differentiation in terms of morphology changes, nitroblue tetrazolium (NBT) reductive activity, and the expression level of surface antigens CD11b/CD14."( The critical role of redox homeostasis in shikonin-induced HL-60 cell differentiation via unique modulation of the Nrf2/ARE pathway.
Chen, H; Chen, N; Wang, Z; Zhang, B; Zheng, Q, 2012
)
0.38
" The aim of the study was to assess the therapeutic efficacy, safety and tolerability of three dosage schedules of fixed-dose combination of artemisinin (125 mg) and naphthoquine (50 mg) for treating uncomplicated Plasmodium falciparum malaria among adolescents and adults in Calabar, South-east Nigeria."( Open-label trial of three dosage regimens of fixed-dose combination of artemisinin and naphthoquine for treating uncomplicated falciparum malaria in Calabar, Nigeria.
Alaribe, A; Asiegbu, V; Effa, E; Esu, EB; Eyam, E; Ezedinachi, EN; Meremikwu, MM; Odey, F; Oduwole, O; Oringanje, C; Oyo-Ita, A, 2012
)
0.38
" falciparum malaria were enrolled and randomly assigned to three dosage schedules: (A) 700 mg (four tablets) single dose; (B) 700 mg 12-hourly x two doses; and (C) 1,400 mg (eight tablets) single dose."( Open-label trial of three dosage regimens of fixed-dose combination of artemisinin and naphthoquine for treating uncomplicated falciparum malaria in Calabar, Nigeria.
Alaribe, A; Asiegbu, V; Effa, E; Esu, EB; Eyam, E; Ezedinachi, EN; Meremikwu, MM; Odey, F; Oduwole, O; Oringanje, C; Oyo-Ita, A, 2012
)
0.38
" Day 28-cure rates of the three dosage schedules were 85."( Open-label trial of three dosage regimens of fixed-dose combination of artemisinin and naphthoquine for treating uncomplicated falciparum malaria in Calabar, Nigeria.
Alaribe, A; Asiegbu, V; Effa, E; Esu, EB; Eyam, E; Ezedinachi, EN; Meremikwu, MM; Odey, F; Oduwole, O; Oringanje, C; Oyo-Ita, A, 2012
)
0.38
" The 50% cytotoxic concentration (CC(50)) was determined by the dose-response curve."( New biological activities of Rhinacanthins from the root of Rhinacanthus nasutus.
Horii, H; Sakagami, H; Shirataki, Y; Suzuki, R; Tomomura, A; Tomomura, M, 2013
)
0.39
" The methods were validated in terms of accuracy and precision and were successfully applied to the determination of MOX in its pharmaceutical dosage form."( New spectrophotometric methods for the determination of moxifloxacin in pharmaceutical formulations.
Aboul-Enein, HY; Ebraheem, SA; Elbashir, AA; Elwagee, AH, 2013
)
0.39
" Shikonin (10 and 25 mg/kg) was administered by gavage once a day for 3 days before surgery and another dosage after operation."( Protective effect of shikonin in experimental ischemic stroke: attenuated TLR4, p-p38MAPK, NF-κB, TNF-α and MMP-9 expression, up-regulated claudin-5 expression, ameliorated BBB permeability.
Chen, L; Cui, L; Li, Z; Miao, J; Qiao, H; Wang, L; Wang, S; Zhang, X; Zhu, C, 2014
)
0.4
" One MCV-positive MCC xenograft (MS-1) failed to significantly respond to YM155, which corresponds with in vitro dose-response activity."( Response of Merkel cell polyomavirus-positive merkel cell carcinoma xenografts to a survivin inhibitor.
Arora, R; Chang, Y; Dresang, LR; Guastafierro, A; Moore, PS; Normolle, D, 2013
)
0.39
"5-100 ng/mL dosage of shikonin treatment on AGS cancer cell line with the incubation time of 6h."( Shikonin induces cell cycle arrest in human gastric cancer (AGS) by early growth response 1 (Egr1)-mediated p21 gene expression.
Chang, HI; Kim, JM; Kim, SJ; Shim, SH, 2014
)
0.4
" Therefore, this liposomal formulation can be a new dosage form of YM155 that achieves sufficient efficacy and safety and is a more convenient administration regimen for users."( Antitumor efficacy and biodistribution of liposomal sepantronium bromide (YM155), a novel small-molecule survivin suppressant.
Kawano, H; Kita, A; Maeda, A; Nakata, M; Oku, N; Sako, K; Shakushiro, K; Watanabe, S, 2014
)
0.4
"4) or in 1 M sodium salicylate, which agrees with the desired dosing sequence of the two drugs to exert synergistic pharmacologic effect at different cell checkpoints."( β-Lapachone and Paclitaxel Combination Micelles with Improved Drug Encapsulation and Therapeutic Synergy as Novel Nanotherapeutics for NQO1-Targeted Cancer Therapy.
Chen, Z; Gao, J; Liu, C; Qian, F; Yang, K; Zhang, L, 2015
)
0.42
" The proposed methods were successfully applied to the assay of sodium valproate in tablets and oral solution dosage forms with good accuracy and precision."( Validated spectrophotometric methods for determination of sodium valproate based on charge transfer complexation reactions.
Abdel-Khalek, MM; Abo-Gharam, AH; Belal, TS; El-Kafrawy, DS; Mahrous, MS, 2016
)
0.43
" The aim of the study was to investigate the pharmacokinetic profile following a single oral dosing to explain inconsistency of results of the in vitro and in vivo antimalarial activities."( Pharmacokinetics, toxicity, and cytochrome P450 modulatory activity of plumbagin.
Na-Bangchang, K; Plengsuriyakarn, T; Sumsakul, W, 2016
)
0.43
" More severe adverse events required reduced or discontinued dosing of napabucasin or medication to reverse or manage symptoms."( Napabucasin: An Update on the First-in-Class Cancer Stemness Inhibitor.
Grothey, A; Hubbard, JM, 2017
)
0.46
" The absence of synergy in vivo highlighted the need to further optimize the dosing schedules of YM155 and sorafenib, as well as their routes of administration."( Action of YM155 on clear cell renal cell carcinoma does not depend on survivin expression levels.
Go, ML; Huynh, H; Sim, MY; Yuen, JSP, 2017
)
0.46
" Synergistic drug combinations can lessen potential toxic side effects through lower dosing and simultaneously help to overcome drug resistance."( Lapatinib potentiates cytotoxicity of  YM155 in neuroblastoma via inhibition of the ABCB1 efflux transporter.
Brunak, S; Halasz, M; Huber, KVM; Kolch, W; Papamarkou, T; Radic-Sarikas, B; Superti-Furga, G; Tsafou, KP; Winter, GE, 2017
)
0.46
" For potential clinical application, DC vaccine preparations treated with tumor cells that were already pretreated with chloroquine and shikonin further enhanced the antimetastatic activity of 4T1 tumors and reduced the effective dosage of doxorubicin."( Necroptosis promotes autophagy-dependent upregulation of DAMP and results in immunosurveillance.
Fan, YT; Hsiao, PW; Hsieh, SY; Lin, SY; Tsai, DH; Wei, WC; Wu, TS; Yang, NS, 2018
)
0.48
" In fat tissues, the key genes Lep, Nmb and Nmbr were altered in high dosed offspring, and were differentially expressed between sexes."( Effects on metabolic parameters in young rats born with low birth weight after exposure to a mixture of pesticides.
Axelstad, M; Christiansen, S; Hass, U; Mandrup, K; Ramhøj, L; Svingen, T; Vinggaard, AM, 2018
)
0.48
" Mechanistic studies showed that these inhibitors could release Nrf2 in H9c2 cells and LPS-inflammatory mouse models and translocate into the nucleus in a dose-response manner, which significantly increased the downstream genes (HO-1, NQO-1) and the pro-inflammatory cytokines (TNF-α, IL-1β, IL-6), while ROS production dramatically decreased."( Fragment-growing guided design of Keap1-Nrf2 protein-protein interaction inhibitors for targeting myocarditis.
Jiang, C; Meng, N; Miao, Z; Min, X; Su, L; Tang, H; Zhang, H; Zhang, W; Zhuang, C, 2018
)
0.48
" In assessing the pharmacokinetic aspects of the new drug, the authors draw at- tention of researchers to profound study of histochrome administration schemes and dosing regime in the context of improving its therapeutic applications."( [SPECIFIC FEATURES AND PROSPECTS OF THE PHARMACOKINETIC STUDY OF HISTOCHROME.]
Bryukhanov, VM; Mishchenko, NR; Talalaeval, OS; Zverev, YF,
)
0.13
" Downregulation of Pin1 gene dosage attenuated premature cranial suture closure and other phenotypes of AS in Fgfr2S252W/+ mutant mice."( PIN1 is a new therapeutic target of craniosynostosis.
Bae, HS; Baek, JH; Cho, YD; Choi, KY; Kim, BS; Kim, WJ; Lee, YS; Ryoo, HM; Shin, HR; Woo, KM; Yoon, HI, 2018
)
0.48
" Electron microscopy analysis showed that beta-lapachone caused the development of the autophagosomes, and the frequency of the autophagosomes increased with increased dosage of beta-lapachone."( Inhibition of Nasopharyngeal Carcinoma by Beta-Lapachone Occurs by Targeting the Mammalian Target of Rapamycin (mTOR)/PI3K/AKT Pathway, Reactive Oxygen Species (ROS) Production, and Autophagy Induction.
Han, Y; Li, J; Shi, D, 2019
)
0.51
" However, the effective ICD requires a high dosage of ICD stimulus, which could be associated to a dose-dependent toxicity."( Low dose shikonin and anthracyclines coloaded liposomes induce robust immunogenetic cell death for synergistic chemo-immunotherapy.
Cai, W; He, Z; Kuang, X; Li, J; Liu, H; Wang, Y; Yang, Y; Yu, J; Zhou, S, 2021
)
0.62
" Our proposed PBPK model of echinochrome A could be a valuable tool for predicting drug interactions in previously unexplored scenarios and for optimizing dosage regimens and drug formulations."( Physicochemical characterization and phase II metabolic profiling of echinochrome A, a bioactive constituent from sea urchin, and its physiologically based pharmacokinetic modeling in rats and humans.
Byun, JH; Choi, E; Fedoreyev, SA; Han, DG; Han, J; Jung, IH; Kim, HK; Kwak, J; Mishchenko, NP; Seo, SW; Stonik, VA; Vasileva, EA; Yoon, IS; Yun, H, 2023
)
0.91
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6,783)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901445 (21.30)18.7374
1990's721 (10.63)18.2507
2000's1518 (22.38)29.6817
2010's2367 (34.90)24.3611
2020's732 (10.79)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 53.89

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index53.89 (24.57)
Research Supply Index8.89 (2.92)
Research Growth Index4.76 (4.65)
Search Engine Demand Index94.13 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (53.89)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials149 (2.10%)5.53%
Reviews294 (4.14%)6.00%
Case Studies189 (2.66%)4.05%
Observational3 (0.04%)0.25%
Other6,475 (91.07%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]