adriamycinol profile

Adriamycinol is a synthetic analog of the antitumor antibiotic adriamycin. It is a potent inhibitor of topoisomerase II, an enzyme that plays a role in DNA replication and repair. Adriamycinol has been shown to have antitumor activity in vitro and in vivo, and it is currently being investigated as a potential therapeutic agent for the treatment of cancer. The synthesis of adriamycinol involves a multi-step process that begins with the reduction of adriamycin to its corresponding hydroquinone. The hydroquinone is then reacted with a suitable alkylating agent to introduce the desired alkyl group. Adriamycinol is studied for its potential anti-cancer properties due to its ability to inhibit topoisomerase II and induce apoptosis in cancer cells. Research into adriamycinol aims to develop new and more effective anticancer drugs with improved therapeutic index and reduced side effects.'

doxorubicinol : A member of the class of tetracenequinones that is the major metabolite of the anthracycline doxorubicin, a chemotherapeutic agent effective against a broad range of malignant neoplasms. It is thought to exhibit cardiotoxic properties. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	83970
CHEMBL ID	3277946
CHEBI ID	133817
MeSH ID	M0055229

Synonym
rp 27706
13-dihydrodoxorubicin
doxorubicinol
adriamycinol
antibiotic 27706rp
5,12-naphthacenedione, 7,8,9,10-tetrahydro-10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-8-(1,2-dihydroxyethyl)-1-methoxy-6,8,11-trihydroxy-, (8s-(8-alpha,8(r*),10-alpha))-
5,12-naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranosyl)oxy)-8-((1s)-1,2-dihydroxyethyl)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-, (8s,10s)-
13-dihydroadriamycin hydrochloride
(1s,3s)-3-[(1s)-1,2-dihydroxyethyl]-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-l-lyxo-hexopyranoside
CHEBI:133817
54193-28-1
(7s,9s)-7-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-9-[(1s)-1,2-dihydroxyethyl]-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione
unii-huh05ki4cf
huh05ki4cf ,
rp-27706
CHEMBL3277946
(8s,10s)-10-{[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-[(1s)-1,2-dihydroxyethyl]-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
(8s)-10-((2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)-8-((s)-1,2-dihydroxyethyl)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
DTXSID70920620
5,12-naphthacenedione,10-[(3-amino-2,3,6-trideoxy-a-l-lyxo-hexopyranosyl)oxy]-8-[(1s)-1,2-dihydroxyethyl]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-,(8s,10s)-
doxorubicinol (hydrochloride)
Q27280114
(8s,10s)-10-(((2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-8-((s)-1,2-dihydroxyethyl)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione
AKOS040746779
CS-0081325
HY-121259

Excerpt	Reference	Relevance
"One adriamycinol-treated rat and two adriamycin-treated ones died during the experiment."	( General and cardiac toxicity of adriamycinol in rats. Bernardini, C; Danesi, R; Del Tacca, M; Della Torre, P, )	0.9

Excerpt	Reference	Relevance
" Our finding that this highly toxic metabolite was produced by cardiac tissue exposed to doxorubicin suggests that doxorubicinol could accumulate in the heart and contribute significantly to the chronic cumulative cardiotoxicity of doxorubicin therapy."	( Doxorubicin cardiotoxicity may be caused by its metabolite, doxorubicinol. Boucek, RJ; Brenner, DE; Chang, BK; Cusack, BJ; Fleischer, S; Mushlin, PS; Olson, RD, 1988)	0.27
" Overall results indicate that doxorubicinol induces a doxorubicin-like toxic syndrome mainly affecting the heart, although to a lower degree of severity than that caused by the parent drug."	( Exogenous doxorubicinol induces cardiotoxic effects in rats. Bernardini, C; Danesi, R; del Tacca, M; Penco, S, 1987)	0.27
" We conclude that aglycones are not toxic to human marrow erythroid and myeloid progenitors in vitro and do not have a role in the development of doxorubicin-induced myelotoxicity."	( Toxicity of doxorubicin metabolites to human marrow erythroid and myeloid progenitors in vitro. Brenner, DE; Dessypris, EN; Hande, KR, 1986)	0.27
"The toxic effects of adriamycinol, the main metabolite of adriamycin, were studied during repeated treatment in rats, by evaluating survival, body growth, electrocardiographic parameters and cardiac histopathology."	( General and cardiac toxicity of adriamycinol in rats. Bernardini, C; Danesi, R; Del Tacca, M; Della Torre, P, )	0.73
" Demonstration that inhibition of carbonyl reductase blocks the toxic effects on the heart has important implications for improving the use of doxorubicin in chemotherapy."	( Protection from doxorubicin-induced cardiac toxicity in mice with a null allele of carbonyl reductase 1. Alvey, SJ; Bedja, D; Cardounel, AJ; Gabrielson, KL; Olson, LE; Reeves, RH, 2003)	0.32
" Previous limited studies with isolated human heart cytosol showed that paclitaxel was able to stimulate an NADPH-dependent reduction of doxorubicin to its toxic secondary alcohol metabolite doxorubicinol."	( Paclitaxel and docetaxel stimulation of doxorubicinol formation in the human heart: implications for cardiotoxicity of doxorubicin-taxane chemotherapies. Calafiore, AM; Cascegna, S; Gianni, L; Liberi, G; Menna, P; Minotti, G; Salvatorelli, E, 2006)	0.33
" Common adverse events included fatigue, nausea and skin rash."	( A phase I study of the safety and pharmacokinetics of the hypoxia-activated prodrug TH-302 in combination with doxorubicin in patients with advanced soft tissue sarcoma. Adkins, D; Butrynski, JE; Chawla, SP; Cranmer, LD; Ganjoo, KN; Kroll, S; Langmuir, VK; Lorente, G; Okuno, SH; Rushing, D, 2011)	0.37
" Redox inactivity in the face of high cardiac uptake suggests that pixantrone might also be safe in doxorubicin-naïve patients."	( The novel anthracenedione, pixantrone, lacks redox activity and inhibits doxorubicinol formation in human myocardium: insight to explain the cardiac safety of pixantrone in doxorubicin-treated patients. Chello, M; Covino, E; Menna, P; Minotti, G; Paz, OG; Salvatorelli, E; Singer, JW, 2013)	0.39
"The role of metabolism in daunorubicin (DAUN)- and doxorubicin (DOX)-associated toxicity in cancer patients is dependent on whether the parent drugs or major metabolites, doxorubicinol (DOXol) and daunorubicinol (DAUNol), are the more toxic species."	( A correlation between cytotoxicity and reductase-mediated metabolism in cell lines treated with doxorubicin and daunorubicin. Bains, OS; Cragg, GE; Grigliatti, TA; Lubieniecka, JM; Reid, RE; Riggs, KW; Szeitz, A, 2013)	0.39
" Although toxicity was greater on cycle 1, the adverse effects were managed safely."	( Doxorubicin pharmacokinetics and toxicity in patients with aggressive lymphoma and hepatic impairment. Balis, F; Cole, DE; Dombi, E; Lai, C; Lucas, N; Melani, C; Roschewski, M; Steinberg, SM; Widemann, BC; Wilson, WH, 2023)	0.91

Excerpt	Reference	Relevance
" Pharmacokinetic parameters for the parent drug and its metabolite were calculated for each course of treatment."	( Doxorubicin and doxorubicinol: intra- and inter-individual variations of pharmacokinetic parameters. Bourrier, M; Bressolle, F; Donadio, D; Galtier, M; Jacquet, JM; Jourdan, J; Rossi, JF, 1990)	0.28
" The demonstration of this pharmacodynamic relationship highlights the potential importance of pharmacologic data collection in ongoing attempts to predict the clinical effects of anticancer drugs."	( Pharmacokinetics and pharmacodynamics of long-term continuous-infusion doxorubicin. Ackland, SP; Choi, KE; Ratain, MJ; Ruane, M; Sinkule, JA; Vogelzang, NJ, 1989)	0.28
" This study characterized the pharmacokinetic behaviour of WLD-dox with particular attention to the effect of treatment duration on the variability of individual pharmacokinetic parameters."	( Pharmacokinetics of weekly low dose doxorubicin. François, E; Frenay, M; Khater, R; Milano, G; Namer, M; Pons, D; Renee, N; Thyss, A, 1989)	0.28
" Doxorubicin single-dose pharmacokinetic studies were performed in 10 New Zealand White rabbits after pretreatment with phenytoin or phenytoin vehicle (control) infusions in crossover fashion with 4-6 weeks between studies."	( Effect of phenytoin on the pharmacokinetics of doxorubicin and doxorubicinol in the rabbit. Brenner, DE; Cusack, BJ; Loseke, VL; Olson, RD; Tesnohlidek, DA; Vestal, RE, 1988)	0.27
"001) and elimination half-life (r = ."	( Doxorubicin clearance in the obese. Rodvold, KA; Rushing, DA; Tewksbury, DA, 1988)	0.27
" A pharmacokinetic analysis indicated an increase in the central volume of distribution, which is interpreted as an increase in tissue permeability in the alkaline state, due to the acid-base properties of the doxorubicin molecule."	( Pharmacokinetics of doxorubicin and its metabolite doxorubicinol in rabbits with induced acid and alkaline urine. Dalmark, M; Jensen, SE; Johansen, PB; Rasmussen, SN, 1984)	0.27
" The disappearance kinetics of Adriamycin could adequately be described by a biexponential equation with an initial half-life of 8-min and a terminal half-life of 30 hr."	( Plasma pharmacokinetics of adriamycin and adriamycinol: implications for the design of in vitro experiments and treatment protocols. Collins, JM; Greene, RF; Jenkins, JF; Myers, CE; Speyer, JL, 1983)	0.53
" In this study two administration regimens of DOX were compared in terms of area under the time concentration curve (AUC) in plasma."	( Pharmacokinetics of two different delivery regimens of doxorubicin in isolated hyperthermic limb perfusion. Krause, U; Pfeiffer, T; Scheulen, ME; Skorzek, M; Thome, U, 1995)	0.29
" Wide interpatient variability was observed for all pharmacokinetic parameters with coefficients of variation for apparent volume of distribution, clearance, and area under the curve (AUC) of 62%, 65%, and 65%, respectively."	( Pharmacokinetics and pharmacodynamics of doxorubicin in patients with small cell lung cancer. Piscitelli, SC; Rodvold, KA; Rushing, DA; Tewksbury, DA, 1993)	0.29
" In addition, elimination half-life of doxorubicinol was increased following infusion."	( Doxorubicin and doxorubicinol pharmacokinetics and tissue concentrations following bolus injection and continuous infusion of doxorubicin in the rabbit. Cusack, BJ; Driskell, J; Olson, RD; Young, SP, 1993)	0.29
"The pharmacokinetic and tissue distribution changes of adriamycin (ADM) were investigated after intravenous (i."	( Pharmacokinetic and tissue distribution changes of adriamycin and adriamycinol after intravenous administration of adriamycin to alloxan-induced diabetes mellitus rats. Lee, HJ; Lee, MG; Paik, WH, 1995)	0.53
"The pharmacokinetic and tissue distribution changes of adriamycin (ADM) and adriamycinol were investigated after intravenous (i."	( Pharmacokinetic and tissue distribution changes of adriamycin and adriamycinol after intravenous administration of adriamycin to uranyl nitrate-induced acute renal failure rats. Lee, HJ; Lee, MG; Paik, WH, 1996)	0.76
"The purpose of our investigation was to evaluate the pharmacokinetic profile of doxorubicin administered by a new schedule."	( [Pharmacokinetic profile of high-dose doxorubicin administered during a 6 h intravenous infusion in breast cancer patients]. Bergerat, JP; Duclos, B; Dufour, P; Levêque, D; Limacher, JM; Methlin, G; Wihlm, J, 1997)	0.3
" The pharmacokinetic characteristics of doxorubicin in the presence or absence of GF120918 indicate a very minor overall effect of the modulator, except at the highest combined dose level (i."	( Clinical pharmacokinetics of doxorubicin in combination with GF120918, a potent inhibitor of MDR1 P-glycoprotein. Chandler, LH; de Bruijn, P; Jewell, RC; Loos, WJ; Nooter, K; Paul, EM; Planting, AS; Sparreboom, A; van der Burg, ME; van der Gaast, A; Verweij, J; Wissel, PS, 1999)	0.3
"To develop a population pharmacokinetic model for doxorubicin and doxorubicinol in the presence of zosuquidar."	( A population pharmacokinetic model for doxorubicin and doxorubicinol in the presence of a novel MDR modulator, zosuquidar trihydrochloride (LY335979). Aarons, L; Burgess, M; Callies, S; de Alwis, DP; Sandler, A; Wright, JG, 2003)	0.32
"The population approach was used (implemented with NONMEM) to analyse doxorubicin-doxorubicinol pharmacokinetic data from 40 patients who had received zosuquidar."	( A population pharmacokinetic model for doxorubicin and doxorubicinol in the presence of a novel MDR modulator, zosuquidar trihydrochloride (LY335979). Aarons, L; Burgess, M; Callies, S; de Alwis, DP; Sandler, A; Wright, JG, 2003)	0.32
"A five-compartment pharmacokinetic model (including three compartments for doxorubicin pharmacokinetics with two pathways for doxorubicinol formation) best described the doxorubicin-doxorubicinol pharmacokinetics in the presence of zosuquidar."	( A population pharmacokinetic model for doxorubicin and doxorubicinol in the presence of a novel MDR modulator, zosuquidar trihydrochloride (LY335979). Aarons, L; Burgess, M; Callies, S; de Alwis, DP; Sandler, A; Wright, JG, 2003)	0.32
"This integrated parent-metabolite population pharmacokinetic model accurately characterized the increase in doxorubicin and doxorubicinol exposure (1."	( A population pharmacokinetic model for doxorubicin and doxorubicinol in the presence of a novel MDR modulator, zosuquidar trihydrochloride (LY335979). Aarons, L; Burgess, M; Callies, S; de Alwis, DP; Sandler, A; Wright, JG, 2003)	0.32
" The aim of the present study was to determine whether there is a pharmacokinetic interaction between monoHER and doxorubicin which may be involved in monoHER cardioprotection."	( The cardioprotector monoHER does not interfere with the pharmacokinetics or the metabolism of the cardiotoxic agent doxorubicin in mice. Abou El Hassan, MA; Bast, A; Kedde, MA; van der Vijgh, WJ; Zwiers, UT, 2003)	0.32
" No changes were observed in pharmacokinetic parameters such as initial and final half-lives, mean residence time, clearance and volume of distribution of monoHER and doxorubicin(ol) after single or combined administration."	( The cardioprotector monoHER does not interfere with the pharmacokinetics or the metabolism of the cardiotoxic agent doxorubicin in mice. Abou El Hassan, MA; Bast, A; Kedde, MA; van der Vijgh, WJ; Zwiers, UT, 2003)	0.32
"The cardioprotection of monoHER in mice is not caused by a pharmacokinetic interaction between monoHER and doxorubicin."	( The cardioprotector monoHER does not interfere with the pharmacokinetics or the metabolism of the cardiotoxic agent doxorubicin in mice. Abou El Hassan, MA; Bast, A; Kedde, MA; van der Vijgh, WJ; Zwiers, UT, 2003)	0.32
" Pharmacokinetic parameters of doxorubicin and doxorubicinol were estimated in Asian breast cancer patients undergoing adjuvant chemotherapy to investigate genotype-phenotype correlations."	( Novel SLC22A16 polymorphisms and influence on doxorubicin pharmacokinetics in Asian breast cancer patients. Ang, PC; Chen Shu, X; Chowbay, B; Figg, WD; Jada, SR; Lal, S; Lee, EJ; Wong, ZW; Xiang, X, 2007)	0.34
" This method was applied to study the pharmacokinetic profiles of doxorubicin and doxorubicinol in rats after a single dose administration of Stealth-49 liposomal doxorubicin HCl."	( Quantification of pegylated liposomal doxorubicin and doxorubicinol in rat plasma by liquid chromatography/electrospray tandem mass spectroscopy: Application to preclinical pharmacokinetic studies. Jiang, T; Liu, X; Liu, Y; Yang, Y, 2008)	0.35
" NONMEM was used to perform pharmacokinetic model fitting and S-PLUS was used to perform a post hoc analysis to examine the effect of body composition on pharmacokinetic parameters."	( Impact of body composition on pharmacokinetics of doxorubicin in children: a Glaser Pediatric Research Network study. Berg, SL; Bomgaars, LR; Ellis, KJ; Matthay, KK; Moore, TB; Renbarger, J; Rosner, GL; Thompson, PA, 2009)	0.35
" There was no evidence of pharmacokinetic interaction between TH-302 and doxorubicin."	( A phase I study of the safety and pharmacokinetics of the hypoxia-activated prodrug TH-302 in combination with doxorubicin in patients with advanced soft tissue sarcoma. Adkins, D; Butrynski, JE; Chawla, SP; Cranmer, LD; Ganjoo, KN; Kroll, S; Langmuir, VK; Lorente, G; Okuno, SH; Rushing, D, 2011)	0.37
" We then assessed the degree of over-representation of doxorubicin pharmacokinetic and pharmacodynamic genes in the dataset of doxorubicin resistance genes."	( Role of aldo-keto reductases and other doxorubicin pharmacokinetic genes in doxorubicin resistance, DNA binding, and subcellular localization. Guo, B; Heibein, AD; Maclean, DA; Parissenti, AM; Sprowl, JA, 2012)	0.38
" Seventeen and 43 per cent of doxorubicin pharmacokinetic genes were over-represented in the hit list, depending upon whether the gene name was identical or within the same gene family, respectively."	( Role of aldo-keto reductases and other doxorubicin pharmacokinetic genes in doxorubicin resistance, DNA binding, and subcellular localization. Guo, B; Heibein, AD; Maclean, DA; Parissenti, AM; Sprowl, JA, 2012)	0.38
"These findings demonstrate the utility of using curated pharmacokinetic and pharmacodynamic knowledge bases to identify highly relevant genes associated with doxorubicin resistance."	( Role of aldo-keto reductases and other doxorubicin pharmacokinetic genes in doxorubicin resistance, DNA binding, and subcellular localization. Guo, B; Heibein, AD; Maclean, DA; Parissenti, AM; Sprowl, JA, 2012)	0.38
" In patients presenting with elevated serum bilirubin, doxorubicin is commonly dose reduced or delayed based on limited pharmacokinetic data."	( Doxorubicin pharmacokinetics and toxicity in patients with aggressive lymphoma and hepatic impairment. Balis, F; Cole, DE; Dombi, E; Lai, C; Lucas, N; Melani, C; Roschewski, M; Steinberg, SM; Widemann, BC; Wilson, WH, 2023)	0.91

Excerpt	Reference	Relevance
"The purpose of this study was to determine the dose-limiting toxicities (DLT), maximum tolerated dose (MTD), safety, pharmacokinetics and preliminary activity of TH-302, a hypoxia-activated prodrug, in combination with doxorubicin in patients with advanced soft tissue sarcoma."	( A phase I study of the safety and pharmacokinetics of the hypoxia-activated prodrug TH-302 in combination with doxorubicin in patients with advanced soft tissue sarcoma. Adkins, D; Butrynski, JE; Chawla, SP; Cranmer, LD; Ganjoo, KN; Kroll, S; Langmuir, VK; Lorente, G; Okuno, SH; Rushing, D, 2011)	0.37
"The hematologic toxicity of doxorubicin is increased when combined with TH-302."	( A phase I study of the safety and pharmacokinetics of the hypoxia-activated prodrug TH-302 in combination with doxorubicin in patients with advanced soft tissue sarcoma. Adkins, D; Butrynski, JE; Chawla, SP; Cranmer, LD; Ganjoo, KN; Kroll, S; Langmuir, VK; Lorente, G; Okuno, SH; Rushing, D, 2011)	0.37

Excerpt	Reference	Relevance
" The approximated intracellular bioavailability of DOX during 6 h appeared to be lower for DEB than DLIP."	( Investigation of hepatobiliary disposition of doxorubicin following intrahepatic delivery of different dosage forms. Axén, N; Bondesson, U; Ebeling Barbier, C; Hedeland, M; Lennernäs, H; Lilienberg, E; Nyman, R, 2014)	0.4

Excerpt	Relevance	Reference
" In contrast, the heart accumulated DXR slowly, attaining levels after multiple dosing in excess of those found in the liver."	( Tissue distribution of doxorubicin and doxorubicinol in rats receiving multiple doses of doxorubicin. Acton, EM; Gordon, GR; Kashiwase, D; Peters, JH, 1981)	0.26
"Hepatic artery infusion (HAI) has been used to take advantage of the steep dose-response relationship characteristic of chemotherapeutic agents."	( Hepatic artery infusion of doxorubicin with hepatic venous drug extraction. Andrews, JC; August, DA; Brenner, DE; Vaerten, MA; Verma, N, 1994)	0.29
"The PK of DOX and DOXol were well characterized by the model developed, which could be used as a helpful tool to optimize the dosage of this drug."	( Population pharmacokinetics of doxorubicin and doxorubicinol in patients diagnosed with non-Hodgkin's lymphoma. Fernández de Gatta, MD; García, MJ; Hernández-Rivas, JM; Martín, A; Pérez-Blanco, JS; Santos-Buelga, D, 2016)	0.43

Role	Description
drug metabolite	null
cardiotoxic agent	A role played by a chemical compound exihibiting itself through the ability to induce damage to the heart and cardiomyocytes.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
p-quinones	A quinone in which the two oxo groups of the quinone are located para to each other on the 6-membered quinonoid ring.
anthracycline antibiotic	An organic compound that has a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine and which exhibits antibiotic activity.
deoxy hexoside
aminoglycoside
tetracenequinones
phenols	Organic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
aromatic ether	Any ether in which the oxygen is attached to at least one aryl substituent.
polyol	A compound that contains two or more hydroxy groups.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathway	Proteins	Compounds
Metabolism	1496	1108
Biological oxidations	150	276
Phase I - Functionalization of compounds	69	175
Doxorubicin Pathway, Pharmacokinetics	19	1
Doxorubicin Metabolism Pathway	17	14

Assay ID	Title	Year	Journal	Article
AID1145423	Inhibition of DNA synthesis in mouse L1210 cells assessed as inhibition of [3H]-thymidine incorporation measured per 10'6 cells at 3 uM pretreated for 1 hr followed by radiotracer addition measured after 1 hr by scintillation spectrometric analysis relati	1976	Journal of medicinal chemistry, May, Volume: 19, Issue:5	Cellular pharmocodynamics of several anthrocycline antibiotics.
AID1145424	Inhibition of DNA synthesis in mouse L1210 cells assessed as inhibition of [3H]-thymidine incorporation measured per 10'6 cells at 5 uM pretreated for 1 hr followed by radiotracer addition measured after 1 hr by scintillation spectrometric analysis relati	1976	Journal of medicinal chemistry, May, Volume: 19, Issue:5	Cellular pharmocodynamics of several anthrocycline antibiotics.
AID1145429	Ratio of inhibition of [3H]-thymidine incorporation into DNA in mouse L1210 cells to cellular uptake in mouse L1210 cells	1976	Journal of medicinal chemistry, May, Volume: 19, Issue:5	Cellular pharmocodynamics of several anthrocycline antibiotics.
AID1145422	Inhibition of DNA synthesis in mouse L1210 cells assessed as inhibition of [3H]-thymidine incorporation measured per 10'6 cells at 1 uM pretreated for 1 hr followed by radiotracer addition measured after 1 hr by scintillation spectrometric analysis relati	1976	Journal of medicinal chemistry, May, Volume: 19, Issue:5	Cellular pharmocodynamics of several anthrocycline antibiotics.
AID1145426	Inhibition of RNA synthesis in mouse L1210 cells assessed as inhibition of [14C]-uridine incorporation measured per 10'6 cells at 3 uM pretreated for 1 hr followed by radiotracer addition measured after 1 hr by scintillation spectrometric analysis relativ	1976	Journal of medicinal chemistry, May, Volume: 19, Issue:5	Cellular pharmocodynamics of several anthrocycline antibiotics.
AID1145425	Inhibition of RNA synthesis in mouse L1210 cells assessed as inhibition of [14C]-uridine incorporation measured per 10'6 cells at 1 uM pretreated for 1 hr followed by radiotracer addition measured after 1 hr by scintillation spectrometric analysis relativ	1976	Journal of medicinal chemistry, May, Volume: 19, Issue:5	Cellular pharmocodynamics of several anthrocycline antibiotics.
AID1145428	Cellular uptake in mouse L1210 cells assessed per 10'6 cells at 3 uM up to 120 mins	1976	Journal of medicinal chemistry, May, Volume: 19, Issue:5	Cellular pharmocodynamics of several anthrocycline antibiotics.
AID1145427	Inhibition of RNA synthesis in mouse L1210 cells assessed as inhibition of [14C]-uridine incorporation measured per 10'6 cells at 5 uM pretreated for 1 hr followed by radiotracer addition measured after 1 hr by scintillation spectrometric analysis relativ	1976	Journal of medicinal chemistry, May, Volume: 19, Issue:5	Cellular pharmocodynamics of several anthrocycline antibiotics.
AID1145430	Ratio of inhibition of [14C]-uridine incorporation into RNA in mouse L1210 cells to cellular uptake in mouse L1210 cells	1976	Journal of medicinal chemistry, May, Volume: 19, Issue:5	Cellular pharmocodynamics of several anthrocycline antibiotics.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	55 (34.38)	18.7374
1990's	38 (23.75)	18.2507
2000's	33 (20.63)	29.6817
2010's	28 (17.50)	24.3611
2020's	6 (3.75)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	11 (6.43%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	3 (1.75%)	4.05%
Observational	1 (0.58%)	0.25%
Other	156 (91.23%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
aconitic acid Aconitic Acid: A tricarboxylic acid with the formula (COOH)-CH2-C(COOH)=CH-COOH.. aconitic acid : A tricarboxylic acid that is prop-1-ene substituted by carboxy groups at positions 1, 2 and 3.	2.01	1	0	tricarboxylic acid
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	1.99	1	0	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	3.78	2	1	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
hydrogen carbonate Bicarbonates: Inorganic salts that contain the -HCO3 radical. They are an important factor in determining the pH of the blood and the concentration of bicarbonate ions is regulated by the kidney. Levels in the blood are an index of the alkali reserve or buffering capacity.. hydrogencarbonate : The carbon oxoanion resulting from the removal of a proton from carbonic acid.	1.96	1	0	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
hydroquinone [no description available]	2.08	1	0	benzenediol; hydroquinones	antioxidant; carcinogenic agent; cofactor; Escherichia coli metabolite; human xenobiotic metabolite; mouse metabolite; skin lightening agent
1-propanol 1-Propanol: A colorless liquid made by oxidation of aliphatic hydrocarbons that is used as a solvent and chemical intermediate.. propan-1-ol : The parent member of the class of propan-1-ols that is propane in which a hydrogen of one of the methyl groups is replaced by a hydroxy group.	1.97	1	0	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
1,10-phenanthroline 1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases	1.96	1	0	phenanthroline	EC 2.7.1.1 (hexokinase) inhibitor; EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor
phenytoin [no description available]	1.97	1	0	imidazolidine-2,4-dione	anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent
antipyrine Antipyrine: An analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29). antipyrine : A pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2.	7.37	2	0	pyrazolone	antipyretic; cyclooxygenase 3 inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
deferoxamine Deferoxamine: Natural product isolated from Streptomyces pilosus. It forms iron complexes and is used as a chelating agent, particularly in the mesylate form.. desferrioxamine B : An acyclic desferrioxamine that is butanedioic acid in which one of the carboxy groups undergoes formal condensation with the primary amino group of N-(5-aminopentyl)-N-hydroxyacetamide and the second carboxy group undergoes formal condensation with the hydroxyamino group of N(1)-(5-aminopentyl)-N(1)-hydroxy-N(4)-[5-(hydroxyamino)pentyl]butanediamide. It is a siderophore native to Streptomyces pilosus biosynthesised by the DesABCD enzyme cluster as a high affinity Fe(III) chelator.	1.96	1	0	acyclic desferrioxamine	bacterial metabolite; ferroptosis inhibitor; iron chelator; siderophore
ebselen ebselen : A benzoselenazole that is 1,2-benzoselenazol-3-one carrying an additional phenyl substituent at position 2. Acts as a mimic of glutathione peroxidase.	2.11	1	0	benzoselenazole	anti-inflammatory drug; antibacterial agent; anticoronaviral agent; antifungal agent; antineoplastic agent; antioxidant; apoptosis inducer; EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor; EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor; EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor; EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor; EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; EC 3.1.3.25 (inositol-phosphate phosphatase) inhibitor; EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor; EC 3.5.4.1 (cytosine deaminase) inhibitor; EC 5.1.3.2 (UDP-glucose 4-epimerase) inhibitor; enzyme mimic; ferroptosis inhibitor; genotoxin; hepatoprotective agent; neuroprotective agent; radical scavenger
mitoxantrone Mitoxantrone: An anthracenedione-derived antineoplastic agent.. mitoxantrone : A dihydroxyanthraquinone that is 1,4-dihydroxy-9,10-anthraquinone which is substituted by 6-hydroxy-1,4-diazahexyl groups at positions 5 and 8.	2.08	1	0	dihydroxyanthraquinone	analgesic; antineoplastic agent
primaquine Primaquine: An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404). primaquine : An N-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at the N(4) position. It is a drug used in the treatment of malaria and Pneumocystis pneumonia.	1.99	1	0	aminoquinoline; aromatic ether; N-substituted diamine	antimalarial
prednisone Prednisone: A synthetic anti-inflammatory glucocorticoid derived from CORTISONE. It is biologically inert and converted to PREDNISOLONE in the liver.. prednisone : A synthetic glucocorticoid drug that is particularly effective as an immunosuppressant, and affects virtually all of the immune system. Prednisone is a prodrug that is converted by the liver into prednisolone (a beta-hydroxy group instead of the oxo group at position 11), which is the active drug and also a steroid.	2.21	1	0	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; immunosuppressive agent; prodrug
aminopyrine Aminopyrine: A pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of AGRANULOCYTOSIS. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of CYTOCHROME P-450 metabolic activity in LIVER FUNCTION TESTS.. aminophenazone : A pyrazolone that is 1,2-dihydro-3H-pyrazol-3-one substituted by a dimethylamino group at position 4, methyl groups at positions 1 and 5 and a phenyl group at position 2. It exhibits analgesic, anti-inflammatory, and antipyretic properties.	1.97	1	0	pyrazolone; tertiary amino compound	antipyretic; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
egtazic acid Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.	1.97	1	0	diether; tertiary amino compound; tetracarboxylic acid	chelator
allyl alcohol allyl alcohol: structure. allylic alcohol : An alcohol where the hydroxy group is attached to a saturated carbon atom adjacent to a double bond (R groups may be H, organyl, etc.).. allyl alcohol : A propenol in which the C=C bond connects C-2 and C-3. It is has been found in garlic (Allium sativum). Formerly used as a herbicide for the control of various grass and weed seeds.	1.97	1	0	primary allylic alcohol; propenol	antibacterial agent; fungicide; herbicide; insecticide; plant metabolite
acridines Acridines: Compounds that include the structure of acridine.. acridine : A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.	3.79	2	1	acridines; mancude organic heterotricyclic parent; polycyclic heteroarene	genotoxin
luminol Luminol: 5-Amino-2,3-dihydro-1,4-phthalazinedione. Substance that emits light on oxidation. It is used in chemical determinations.	1.96	1	0
azomycin azomycin: RN given refers to parent cpd with specified locant; structure	3.45	1	1	C-nitro compound; imidazoles	antitubercular agent
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	1.96	1	0	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
deoxycytidine [no description available]	2.21	1	0	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	1.97	1	0	elemental platinum; nickel group element atom; platinum group metal atom
ammonium chloride Ammonium Chloride: An acidifying agent that has expectorant and diuretic effects. Also used in etching and batteries and as a flux in electroplating.. ammonium chloride : An inorganic chloride having ammonium as the counterion.	1.96	1	0	ammonium salt; inorganic chloride	ferroptosis inhibitor
daunorubicin Daunorubicin: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.. anthracycline : Anthracyclines are polyketides that have a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine.. daunorubicin : A natural product found in Actinomadura roseola.	3.92	13	0	aminoglycoside antibiotic; anthracycline; p-quinones; tetracenequinones	antineoplastic agent; bacterial metabolite
razoxane Razoxane: An antimitotic agent with immunosuppressive properties.	2.4	2	0	N-alkylpiperazine
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	9.27	10	7	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
etoposide [no description available]	2.6	1	0	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
epirubicin Epirubicin: An anthracycline which is the 4'-epi-isomer of doxorubicin. The compound exerts its antitumor effects by interference with the synthesis and function of DNA.	2.9	4	0	aminoglycoside; anthracycline antibiotic; anthracycline; deoxy hexoside; monosaccharide derivative; p-quinones; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	antimicrobial agent; antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
idarubicin Idarubicin: An orally administered anthracycline antineoplastic. The compound has shown activity against BREAST NEOPLASMS; LYMPHOMA; and LEUKEMIA.	1.98	1	0	anthracycline antibiotic; deoxy hexoside; monosaccharide derivative
gemcitabine gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.	2.72	2	0	organofluorine compound; pyrimidine 2'-deoxyribonucleoside	antimetabolite; antineoplastic agent; antiviral drug; DNA synthesis inhibitor; EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor; environmental contaminant; immunosuppressive agent; photosensitizing agent; prodrug; radiosensitizing agent; xenobiotic
irinotecan [no description available]	2.6	1	0	carbamate ester; delta-lactone; N-acylpiperidine; pyranoindolizinoquinoline; ring assembly; tertiary alcohol; tertiary amino compound	antineoplastic agent; apoptosis inducer; EC 5.99.1.2 (DNA topoisomerase) inhibitor; prodrug
1,7-phenanthroline [no description available]	1.96	1	0	phenanthroline
7-deoxyadriamycin aglycone 7-deoxyadriamycin aglycone: adriamycin metabolite; RN given refers to (R)-isomer	4.62	6	1
cremophor el cremophor EL: solvent for Althesin & Propanidid implicated as possible cause of similar adverse effects polyethoxylated castor oil; RN given refers to cpd with unknown MF; see also records for cremophor & cremophor A	3.78	2	1
fluorocitrate fluorocitrate: competitve inhibitor of aconitase; effects morphology of kidney tubules in fluorocitrate poisoning; RN given refers to cpd with unspecified isomeric designation	1.99	1	0	carbonyl compound
4'-deoxy-4'-iododoxorubicin 4'-deoxy-4'-iododoxorubicin: lipophilic derivative of doxorubicin which differs from the parent compound in substitution of hydroxyl group on the daunosamine sugar moiety	1.97	1	0	organoiodine compound; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone
elacridar Elacridar: inhibitor of MDR1 PROTEIN; structure given in first source	3.79	2	1
pixantrone pixantrone: an immunosuppressant; structure given in first source	2.08	1	0	isoquinolines
docetaxel anhydrous Docetaxel: A semisynthetic analog of PACLITAXEL used in the treatment of locally advanced or metastatic BREAST NEOPLASMS and NON-SMALL CELL LUNG CANCER.. docetaxel anhydrous : A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group.	2.03	1	0	secondary alpha-hydroxy ketone; tetracyclic diterpenoid	antimalarial; antineoplastic agent; photosensitizing agent
oracine oracine: structure in first source; 11-dihydrooracin is the enantiomer	2.46	2	0
7-deoxyadriamycinol aglycone 7-deoxyadriamycinol aglycone: adriamycin metabolite	2.37	2	0
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	2.04	1	0
leupeptins Leupeptins: A group of acylated oligopeptides produced by Actinomycetes that function as protease inhibitors. They have been known to inhibit to varying degrees trypsin, plasmin, KALLIKREINS, papain and the cathepsins.	2.1	1	0
quinidine Quinidine: An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.. quinidine : A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.	1.99	1	0	cinchona alkaloid	alpha-adrenergic antagonist; anti-arrhythmia drug; antimalarial; drug allergen; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; muscarinic antagonist; P450 inhibitor; potassium channel blocker; sodium channel blocker
ryanodine Ryanodine: A methylpyrrole-carboxylate from RYANIA that disrupts the RYANODINE RECEPTOR CALCIUM RELEASE CHANNEL to modify CALCIUM release from SARCOPLASMIC RETICULUM resulting in alteration of MUSCLE CONTRACTION. It was previously used in INSECTICIDES. It is used experimentally in conjunction with THAPSIGARGIN and other inhibitors of CALCIUM ATPASE uptake of calcium into SARCOPLASMIC RETICULUM.. ryanodine : An insecticide alkaloid isolated from South American plant Ryania speciosa.	1.98	1	0
daunorubicinol daunorubicinol: main metabolite of daunomycin. (13S)-13-dihydrodaunorubicin : The (13S)-diastereomer of 13-dihydrodaunorubicin.	3.49	8	0	13-dihydrodaunorubicin
resveratrol trans-resveratrol : A resveratrol in which the double bond has E configuration.	2.49	2	0	resveratrol	antioxidant; phytoalexin; plant metabolite; quorum sensing inhibitor; radical scavenger
dactinomycin Dactinomycin: A compound composed of a two CYCLIC PEPTIDES attached to a phenoxazine that is derived from STREPTOMYCES parvullus. It binds to DNA and inhibits RNA synthesis (transcription), with chain elongation more sensitive than initiation, termination, or release. As a result of impaired mRNA production, protein synthesis also declines after dactinomycin therapy. (From AMA Drug Evaluations Annual, 1993, p2015)	1.96	1	0	actinomycin	mutagen
benzyloxycarbonylleucyl-leucyl-leucine aldehyde benzyloxycarbonylleucyl-leucyl-leucine aldehyde: proteasome inhibitor. N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal : A tripeptide that is L-leucyl-L-leucyl-L-leucine in which the C-terminal carboxy group has been reduced to the corresponding aldehyde and the N-terminal amino group is protected as its benzyloxycarbonyl derivative.	2.1	1	0	amino aldehyde; carbamate ester; tripeptide	proteasome inhibitor
sodium bicarbonate Sodium Bicarbonate: A white, crystalline powder that is commonly used as a pH buffering agent, an electrolyte replenisher, systemic alkalizer and in topical cleansing solutions.	1.96	1	0	one-carbon compound; organic sodium salt	antacid; food anticaking agent
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	2.49	2	0	stilbene
rhodanine 2-mercaptothiazolinone: metabolite in urine from persons exposed to CS2; structure	2.6	1	0	thiazolidinone
epalrestat epalrestat : A monocarboxylic acid that is 1,3-thiazolidine which is substituted on the nitrogen by a carboxymethyl group, at positions 2 and 4 by thioxo and oxo groups, respectively, and at position 5 by a 2-methyl-3-phenylprop-2-en-1-ylidene group. It is an inhibitor of aldose reductase (which catalyses the conversion of glucose to sorbitol) and is used for the treatment of some diabetic complications, including neuropathy.	2.6	1	0	monocarboxylic acid; thiazolidines	EC 1.1.1.21 (aldehyde reductase) inhibitor
nadp [no description available]	2.42	2	0
ly335979 [no description available]	2.01	1	0	carbopolycyclic compound
7-deoxy-13-dihydroadriamycinone 7-deoxy-13-dihydroadriamycinone: a metabolite of epidoxorubicin	2.42	2	0
quercetin [no description available]	2.44	2	0	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
bilirubin [no description available]	4.08	3	1	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
quercitrin [no description available]	2.04	1	0	alpha-L-rhamnoside; monosaccharide derivative; quercetin O-glycoside; tetrahydroxyflavone	antileishmanial agent; antioxidant; EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.14.18.1 (tyrosinase) inhibitor; plant metabolite
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	2.01	1	0	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
aurone [no description available]	2.04	1	0	aurones; cyclic ketone
cholanic acid cholanic acid: RN given refers to parent cpd without isomer designation. cholanic acid : A steroid acid that consists of cholane having a carboxy group in place of the methyl group at position 24.. colanic acid : A polyanionic heteropolysaccharide containing a repeat unit with D-glucose, L-fucose, D-galactose, and D-glucuronic acid sugars that are non-stoichiometrically decorated with O-acetyl and pyruvate side-chains	2.07	1	0	cholanic acids
4'-iodo-4'-deoxydoxorubicinol 4'-iodo-4'-deoxydoxorubicinol: structure given in first source	1.97	1	0
pirarubicin [no description available]	1.97	1	0	anthracycline
calcimycin Calcimycin: An ionophorous, polyether antibiotic from Streptomyces chartreusensis. It binds and transports CALCIUM and other divalent cations across membranes and uncouples oxidative phosphorylation while inhibiting ATPase of rat liver mitochondria. The substance is used mostly as a biochemical tool to study the role of divalent cations in various biological systems.	1.96	1	0	benzoxazole
th 302 TH 302: an hypoxia-activated prodrug of bromo-isophosphoramide mustard; an antineoplastic agent	3.45	1	1
adriamycin aglycone adriamycin aglycone: RN given refers to (8S-cis)-isomer	3.99	14	0
idarubicinol idarubicinol: RN given refers to (7S-(7alpha,9alpha,9(R*))-isomer	2.38	2	0	anthracycline
23-hydroxybetulinic acid 23-hydroxybetulinic acid: structure in first source	2.11	1	0	triterpenoid	metabolite
chitosan [no description available]	2.03	1	0
natriuretic peptide, brain Natriuretic Peptide, Brain: A PEPTIDE that is secreted by the BRAIN and the HEART ATRIA, stored mainly in cardiac ventricular MYOCARDIUM. It can cause NATRIURESIS; DIURESIS; VASODILATION; and inhibits secretion of RENIN and ALDOSTERONE. It improves heart function. It contains 32 AMINO ACIDS.	3.51	1	1	polypeptide
cyclosporine Cyclosporine: A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).	4.12	3	1
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	2.21	1	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger

Condition	Relationship Strength	Studies	Trials
Leukemia L 1210 [description not available]	1.95	1	0
Liver Dysfunction [description not available]	3.99	1	1
Germinoblastoma [description not available]	4.41	2	2
Liver Diseases Pathological processes of the LIVER.	3.99	1	1
Lymphoma A general term for various neoplastic diseases of the lymphoid tissue.	4.41	2	2
Cardiac Toxicity [description not available]	2.61	2	0
Cardiotoxicity Damage to the HEART or its function secondary to exposure to toxic substances such as drugs used in CHEMOTHERAPY; IMMUNOTHERAPY; or RADIATION.	2.61	2	0
Complications, Neoplastic Pregnancy [description not available]	2.21	1	0
Diffuse Large B-Cell Lymphoma [description not available]	2.21	1	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	3.7	3	0
Lymphoma, Large B-Cell, Diffuse Malignant lymphoma composed of large B lymphoid cells whose nuclear size can exceed normal macrophage nuclei, or more than twice the size of a normal lymphocyte. The pattern is predominantly diffuse. Most of these lymphomas represent the malignant counterpart of B-lymphocytes at midstage in the process of differentiation.	2.21	1	0
Breast Cancer [description not available]	14.88	65	51
Cardiomyopathies, Primary [description not available]	2.44	2	0
Breast Neoplasms Tumors or cancer of the human BREAST.	14.88	65	51
Cardiomyopathies A group of diseases in which the dominant feature is the involvement of the CARDIAC MUSCLE itself. Cardiomyopathies are classified according to their predominant pathophysiological features (DILATED CARDIOMYOPATHY; HYPERTROPHIC CARDIOMYOPATHY; RESTRICTIVE CARDIOMYOPATHY) or their etiological/pathological factors (CARDIOMYOPATHY, ALCOHOLIC; ENDOCARDIAL FIBROELASTOSIS).	2.44	2	0
Bone Cancer [description not available]	2.17	1	0
Granuloma, Hodgkin [description not available]	2.17	1	0
Benign Neoplasms [description not available]	6.37	15	3
Ewing Sarcoma [description not available]	2.17	1	0
Bone Neoplasms Tumors or cancer located in bone tissue or specific BONES.	2.17	1	0
Hodgkin Disease A malignant disease characterized by progressive enlargement of the lymph nodes, spleen, and general lymphoid tissue. In the classical variant, giant usually multinucleate Hodgkin's and REED-STERNBERG CELLS are present; in the nodular lymphocyte predominant variant, lymphocytic and histiocytic cells are seen.	2.17	1	0
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	6.37	15	3
Sarcoma, Ewing A malignant tumor of the bone which always arises in the medullary tissue, occurring more often in cylindrical bones. The tumor occurs usually before the age of 20, about twice as frequently in males as in females.	2.17	1	0
Canine Diseases [description not available]	2.21	1	0
Neutropenia A decrease in the number of NEUTROPHILS found in the blood.	3.9	2	1
Hepatocellular Carcinoma [description not available]	2.92	4	0
Cancer of Liver [description not available]	3.09	5	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.92	4	0
Liver Neoplasms Tumors or cancer of the LIVER.	3.09	5	0
Carcinoma, Ehrlich Tumor A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.	2.08	1	0
Hematologic Malignancies [description not available]	2.1	1	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.94	4	0
Hematologic Neoplasms Neoplasms located in the blood and blood-forming tissue (the bone marrow and lymphatic tissue). The commonest forms are the various types of LEUKEMIA, of LYMPHOMA, and of the progressive, life-threatening forms of the MYELODYSPLASTIC SYNDROMES.	2.1	1	0
Anoxemia [description not available]	2.1	1	0
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	2.1	1	0
Diffuse Mixed Small and Large Cell Lymphoma [description not available]	2.13	1	0
Lymphoma, Non-Hodgkin Any of a group of malignant tumors of lymphoid tissue that differ from HODGKIN DISEASE, being more heterogeneous with respect to malignant cell lineage, clinical course, prognosis, and therapy. The only common feature among these tumors is the absence of giant REED-STERNBERG CELLS, a characteristic of Hodgkin's disease.	2.13	1	0
Experimental Hepatoma [description not available]	3.35	2	0
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	2.4	2	0
Phlegmon [description not available]	3.45	1	1
Dermatitis Medicamentosa [description not available]	3.45	1	1
Lymphocytopenia [description not available]	3.45	1	1
Sarcoma, Epithelioid [description not available]	3.45	1	1
Mucositis, Oral [description not available]	3.79	2	1
Abscess Accumulation of purulent material in tissues, organs, or circumscribed spaces, usually associated with signs of infection.	3.45	1	1
Anemia A reduction in the number of circulating ERYTHROCYTES or in the quantity of HEMOGLOBIN.	3.45	1	1
Cellulitis An acute, diffuse, and suppurative inflammation of loose connective tissue, particularly the deep subcutaneous tissues, and sometimes muscle, which is most commonly seen as a result of infection of a wound, ulcer, or other skin lesions.	3.45	1	1
Lymphopenia Reduction in the number of lymphocytes.	3.45	1	1
Sarcoma A connective tissue neoplasm formed by proliferation of mesodermal cells; it is usually highly malignant.	3.45	1	1
Stomatitis INFLAMMATION of the soft tissues of the MOUTH, such as MUCOSA; PALATE; GINGIVA; and LIP.	3.79	2	1
Animal Mammary Carcinoma [description not available]	2.07	1	0
Metastase [description not available]	4.7	2	1
Neoplasm Metastasis The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.	4.7	2	1
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.01	1	0
Cardiac Diseases [description not available]	14.64	53	49
Weight Reduction [description not available]	2.93	1	0
Heart Diseases Pathological conditions involving the HEART including its structural and functional abnormalities.	14.64	53	49
Weight Loss Decrease in existing BODY WEIGHT.	2.93	1	0
Recrudescence [description not available]	14.55	49	49
47,XX,+21 [description not available]	2.03	1	0
Acute Myelogenous Leukemia [description not available]	2.03	1	0
Down Syndrome A chromosome disorder associated either with an extra chromosome 21 or an effective trisomy for chromosome 21. Clinical manifestations include hypotonia, short stature, brachycephaly, upslanting palpebral fissures, epicanthus, Brushfield spots on the iris, protruding tongue, small ears, short, broad hands, fifth finger clinodactyly, Simian crease, and moderate to severe INTELLECTUAL DISABILITY. Cardiac and gastrointestinal malformations, a marked increase in the incidence of LEUKEMIA, and the early onset of ALZHEIMER DISEASE are also associated with this condition. Pathologic features include the development of NEUROFIBRILLARY TANGLES in neurons and the deposition of AMYLOID BETA-PROTEIN, similar to the pathology of ALZHEIMER DISEASE. (Menkes, Textbook of Child Neurology, 5th ed, p213)	2.03	1	0
Leukemia, Myeloid, Acute Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.	2.03	1	0
Disease Exacerbation [description not available]	2.03	1	0
Cancer of Ovary [description not available]	3.07	5	0
Ascites Accumulation or retention of free fluid within the peritoneal cavity.	2.03	1	0
Ovarian Neoplasms Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.	3.07	5	0
Cirrhosis, Liver [description not available]	1.95	1	0
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	1.95	1	0
Leucocythaemia [description not available]	1.96	1	0
Acute Disease Disease having a short and relatively severe course.	1.96	1	0
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)	1.96	1	0
Experimental Neoplasms [description not available]	1.95	1	0
Carcinoma, Oat Cell [description not available]	1.98	1	0
Cancer of Lung [description not available]	1.98	1	0
Lung Neoplasms Tumors or cancer of the LUNG.	1.98	1	0
Carcinoma, Small Cell An anaplastic, highly malignant, and usually bronchogenic carcinoma composed of small ovoid cells with scanty neoplasm. It is characterized by a dominant, deeply basophilic nucleus, and absent or indistinct nucleoli. (From Stedman, 25th ed; Holland et al., Cancer Medicine, 3d ed, p1286-7)	1.98	1	0
Alloxan Diabetes [description not available]	1.98	1	0
Deficiency of Glucose-6-Phosphate Dehydrogenase [description not available]	1.99	1	0
Glucosephosphate Dehydrogenase Deficiency A disease-producing enzyme deficiency subject to many variants, some of which cause a deficiency of GLUCOSE-6-PHOSPHATE DEHYDROGENASE activity in erythrocytes, leading to hemolytic anemia.	1.99	1	0
Acute Kidney Failure [description not available]	1.99	1	0
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	1.99	1	0
Dehydration The condition that results from excessive loss of water from a living organism.	1.99	1	0
Colorectal Cancer [description not available]	3.38	1	1
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	3.38	1	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.39	2	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.66	3	0
Acute Lymphoid Leukemia [description not available]	2.38	2	0
Bile Duct Obstruction [description not available]	1.97	1	0
Cholestasis Impairment of bile flow due to obstruction in small bile ducts (INTRAHEPATIC CHOLESTASIS) or obstruction in large bile ducts (EXTRAHEPATIC CHOLESTASIS).	1.97	1	0
Precursor Cell Lymphoblastic Leukemia-Lymphoma A neoplasm characterized by abnormalities of the lymphoid cell precursors leading to excessive lymphoblasts in the marrow and other organs. It is the most common cancer in children and accounts for the vast majority of all childhood leukemias.	2.38	2	0
Acquired Immune Deficiency Syndrome [description not available]	1.97	1	0
Acquired Immunodeficiency Syndrome An acquired defect of cellular immunity associated with infection by the human immunodeficiency virus (HIV), a CD4-positive T-lymphocyte count under 200 cells/microliter or less than 14% of total lymphocytes, and increased susceptibility to opportunistic infections and malignant neoplasms. Clinical manifestations also include emaciation (wasting) and dementia. These elements reflect criteria for AIDS as defined by the CDC in 1993.	1.97	1	0
Glial Cell Tumors [description not available]	1.97	1	0
Glioma Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)	1.97	1	0
Leukocytopenia [description not available]	1.97	1	0
Leukopenia A decrease in the number of LEUKOCYTES in a blood sample below the normal range (LEUKOCYTE COUNT less than 4000).	1.97	1	0
Cancer of Head [description not available]	1.97	1	0
Cancer of the Uterus [description not available]	1.97	1	0
Head and Neck Neoplasms Soft tissue tumors or cancer arising from the mucosal surfaces of the LIP; oral cavity; PHARYNX; LARYNX; and cervical esophagus. Other sites included are the NOSE and PARANASAL SINUSES; SALIVARY GLANDS; THYROID GLAND and PARATHYROID GLANDS; and MELANOMA and non-melanoma skin cancers of the head and neck. (from Holland et al., Cancer Medicine, 4th ed, p1651)	1.97	1	0
Uterine Neoplasms Tumors or cancer of the UTERUS.	1.97	1	0
Leukemia, Lymphocytic [description not available]	1.97	1	0
Leukemia, Lymphoid Leukemia associated with HYPERPLASIA of the lymphoid tissues and increased numbers of circulating malignant LYMPHOCYTES and lymphoblasts.	1.97	1	0
Arrhythmia [description not available]	1.97	1	0
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	1.97	1	0
Osteogenic Sarcoma [description not available]	6.96	1	0
Osteosarcoma A sarcoma originating in bone-forming cells, affecting the ends of long bones. It is the most common and most malignant of sarcomas of the bones, and occurs chiefly among 10- to 25-year-old youths. (From Stedman, 25th ed)	1.96	1	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	1.97	1	0
Cystadenocarcinoma A malignant neoplasm derived from glandular epithelium, in which cystic accumulations of retained secretions are formed. The neoplastic cells manifest varying degrees of anaplasia and invasiveness, and local extension and metastases occur. Cystadenocarcinomas develop frequently in the ovaries, where pseudomucinous and serous types are recognized. (Stedman, 25th ed)	1.96	1	0
Pleural Effusion Presence of fluid in the pleural cavity resulting from excessive transudation or exudation from the pleural surfaces. It is a sign of disease and not a diagnosis in itself.	1.96	1	0

adriamycinol

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