Page last updated: 2024-11-07

bifendate

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Description

Bifendate is a synthetic compound with the chemical name 2-(diethylamino)ethyl 2,2-diphenylvalerate. It has been studied for its potential therapeutic effects in a variety of areas, including anti-inflammatory, anti-allergic, and anti-tumor activities. However, it has not been widely used clinically and its exact mechanism of action remains unclear. Research suggests that bifendate may exert its effects by interfering with the release of histamine and other inflammatory mediators. Bifendate is primarily synthesized through a multi-step chemical process involving the reaction of 2,2-diphenylvaleric acid with diethylamine.'

7,7'-dimethoxy-(4,4'-bi-1,3-benzodioxole)-5,5'-dicarboxylic acid dimethyl ester: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID108213
CHEMBL ID105184
SCHEMBL ID896166
MeSH IDM0438944

Synonyms (48)

Synonym
biphenyl dimethyl-dicarboxylate
ccris 7767
(4,4'-bi-1,3-benzodioxole)-5,5'-dicarboxylic acid, 7,7'-dimethoxy-, dimethyl ester
bifendate
dimethyl-4,4'-dimethoxyl-5,6,5',6'-dimethylenedioxybiphenyl-2,2'-dicarboxylate
brn 5461320
alpha-diphenyldicarboxylate
dimethyl 4,4'-dimethoxy-5,6,5',6'-bis(methylenedioxy)biphenyl-2,2'-dicarboxylate
7,7'-dimethoxy-(4,4'-bi-1,3-benzodioxole)-5,5'-dicarboxylic acid dimethyl ester
dimethyl 7,7'-dimethoxy-(4,4'-bi-1,3-benzodioxole)-5,5'-dicarboxylate
diphenyl dimethyl dicarboxylate
methyl 7-methoxy-4-(7-methoxy-5-methoxycarbonyl-1,3-benzodioxol-4-yl)-1,3-benzodioxole-5-carboxylate
2,2'-dimethoxycarbonyl-4,4'-dimethoxy-5,6,5',6'-bismethylenedioxybiphenyl
diphenyl dimethyl bicarboxylate
.alpha.-ddb
dimethyl dicarboxylate biphenyl
CHEMBL105184
73536-69-3
bdbm50289527
dimethyl diphenyl bicarboxylate
bifendatatum
0g32e321w1 ,
unii-0g32e321w1
dimethyl 7,7'-dimethoxy-[4,4'-bibenzo[d][1,3]dioxole]-5,5'-dicarboxylate
FT-0602821
AKOS015895317
S4890
(4,4'-bi-1,3-benzodioxole)-5,5'-dicarboxylic acid, 7,7'-dimethoxy-, 5,5'-dimethyl ester
bifendate [who-dd]
dimethyl-4,4'-dimethoxy-5,6,5',6'-dimethylenedioxybiphenyl-2,2'-dicarboxylate
SCHEMBL896166
DTXSID40223736
bifendate,(s)
CS-W019577
B6112
mfcd01751431
dimethyl 7,7'-dimethoxy-4,4'-bibenzo[d][1,3]dioxole-5,5'-dicarboxylate
dimethyl 7,7 inverted exclamation mark -dimethoxy-[4,4 inverted exclamation mark -bi-1,3-benzodioxole]-5,5 inverted exclamation mark -dicarboxylate
SY021274
AS-13115
BCP12613
CCG-268865
[4,4'-bi-1,3-benzodioxole]-5,5'-dicarboxylic acid, 7,7'-dimethoxy-,dimethyl ester
Q27236735
SB67338
HY-W018791
A866077
dimethyl7,7'-dimethoxy-[4,4'-bibenzo[d][1,3]dioxole]-5,5'-dicarboxylate

Research Excerpts

Treatment

ExcerptReferenceRelevance
"Both bifendate and alkaloid treatment decreased the increase in liver enzymes and cell damage caused by CCl(4)."( Hepatoprotection in a rat model of acute liver damage through inhibition of CY2E1 activity by total alkaloids extracted from Rubus alceifolius Poir.
Hong, Z; Hu, J; Li, T; Lin, J; Zhao, J; Zhou, J, 2011
)
0.82

Toxicity

ExcerptReferenceRelevance
" Pretreatment with DDB was shown to slightly increase the level of AFM1, the less toxic metabolite."( Effects of dimethyl diphenyl bicarboxylate on the metabolism and hepatotoxicity of aflatoxin B1 in rats.
Li, Y; Lu, H, 2002
)
0.31
"The toxic effect of THA on mice liver was significantly reduced by DDB."( [Effect of dimethyl diphenyl bicarboxylate (DDB) on 9-amino-1,2,3,4-tetrahydroacridine-induced hepatotoxicity in mice].
Li, Y, 2001
)
0.31
" Oral daily administration of toxic dose of erythromycin stearate (EE, 100 mg/kg body weight) was given to male rats for fourteen days to induce hepatotoxicity."( Protective role of dimethyl diphenyl bicarboxylate (DDB) against erythromycin induced hepatotoxicity in male rats.
Abdel-Hameid, NA, 2007
)
0.34
" The secondary endpoints were changes in AST, liver stiffness, and the incidence of adverse events."( [Comparison on the efficacy and safety of biphenyl dimethyl dicarboxylate and ursodeoxycholic acid in patients with abnormal alanine aminotransferase: multicenter, double-blinded, randomized, active-controlled clinical trial].
Cheon, GJ; Jang, JY; Jeong, SW; Kim, BS; Kim, HS; Kim, SG; Kim, YD; Kim, YS; Lee, SH, 2014
)
0.4
" Severe adverse drug reaction occurred in 1 patient in DDB group but the subject continued therapy during the study period."( [Comparison on the efficacy and safety of biphenyl dimethyl dicarboxylate and ursodeoxycholic acid in patients with abnormal alanine aminotransferase: multicenter, double-blinded, randomized, active-controlled clinical trial].
Cheon, GJ; Jang, JY; Jeong, SW; Kim, BS; Kim, HS; Kim, SG; Kim, YD; Kim, YS; Lee, SH, 2014
)
0.4
" Furthermore it was safe and well tolerated by patients with abnormal ALT."( [Comparison on the efficacy and safety of biphenyl dimethyl dicarboxylate and ursodeoxycholic acid in patients with abnormal alanine aminotransferase: multicenter, double-blinded, randomized, active-controlled clinical trial].
Cheon, GJ; Jang, JY; Jeong, SW; Kim, BS; Kim, HS; Kim, SG; Kim, YD; Kim, YS; Lee, SH, 2014
)
0.4

Pharmacokinetics

The present method has been successfully applied to the pharmacokinetic study of bifendate liposome in rats.

ExcerptReferenceRelevance
" The present method has been successfully applied to the pharmacokinetic study of bifendate liposome in rats."( A simple HPLC method for the determination of bifendate: application to a pharmacokinetic study of bifendate liposome.
Chen, HX; Chen, ZP; Xiao, YY; Zhu, JB, 2007
)
0.82
"Although pharmacokinetic alternations by hepatic injury have been extensively studied, little is known about the potential influence of hepatoprotective agent's treatment."( Integral pharmacokinetics of multiple lignan components in normal, CCl4-induced hepatic injury and hepatoprotective agents pretreated rats and correlations with hepatic injury biomarkers.
Dai, C; Hao, H; Kang, A; Li, J; Liang, Y; Sun, S; Wang, G; Xie, L; Xie, T; Xie, Y; Zheng, X, 2010
)
0.36
" Compared with DDB-Sol, DDB-NSP exhibited a markedly different pharmacokinetic property with a 17."( Studies on pharmacokinetics and tissue distribution of bifendate nanosuspensions for intravenous delivery.
Duan, C; Hao, L; Jia, L; Liu, G; Liu, Y; Wang, F; Xie, P; Zhang, D; Zhang, Q; Zhang, X; Zheng, D, 2012
)
0.63
"In order to evaluate the pharmacokinetic characteristics of a new formulation of a bifendate solid dispersion in beagle dogs, a novel, sensitive and rapid supercritical fluid chromatography-tandem mass spectrometry (SFC-MS/MS) method was established and validated."( Preclinical pharmacokinetic evaluation of a new formulation of a bifendate solid dispersion using a supercritical fluid chromatography-tandem mass spectrometry method.
Liu, M; Ma, J; Wang, X; Yang, D; Zhang, T; Zhao, L, 2014
)
0.87

Compound-Compound Interactions

ExcerptReferenceRelevance
"The present study was designed to evaluate the effects of dimethyl-4,4'-dimethoxy-5,6,5',6'-dimethylene dioxybiphenyl-2,2'-dicarboxylate (PMC) in combination with garlic oil against chemical-induced hepatic injury in rats and mice."( Enhanced effectiveness of dimethyl-4,4'-dimethoxy-5,6,5',6'-dimethylene dioxybiphenyl-2,2'-dicarboxylate in combination with garlic oil against experimental hepatic injury in rats and mice.
Chung, HC; Hong, SY; Jung, KH; Kim, SG; Nam, SY, 1995
)
0.29
"6 and 30% decrease in ALT and AST, while DDB (75 mg/kg) combined with silymarin (22 mg/kg) resulted in 58."( Effects of biphenyldimethyl-dicarboxylate administration alone or combined with silymarin in the CCL4 model of liver fibrosis in rats.
Abdel-Salam, OM; Morsy, FA; Sleem, AA, 2007
)
0.34

Bioavailability

The bioavailability of water-insoluble bifendate was markedly enhanced by dispersing the drug in the polymer carrier Kollidon(®) VA 64 employing HME technology.

ExcerptReferenceRelevance
"Since the bioavailability of the suspension and the tablet of DDB given orally is only 20-30%, we have prepared four kinds of DDB solid dispersion preparations (DDB pilule I with polyethylene glycol 6000 as the vehicle, DDB pilule II with polyethylene glycol 6000 and absorption accelerator as the vehicle, capsule of DDB-urea fusing mixture and DDB-polyvinyl pyrrolidone coprecipitate), and the bioavailability of these preparations were studied in rabbits, rats and human volunteers by HPLC method."( [Bioavailability studies on the preparations of biphenyl dimethyl dicarboxylate(DDB)].
Gao, WW; Gu, SJ; Qiang, ZY; Qiao, PX; Song, ZY; Wang, AG; Wang, XL, 1990
)
0.28
" However, its oral preparations have been known to have limited bioavailability due to its extremely low solubility in water, and its solubility problem also limits preparation of its parenteral dosage forms."( Solubilization of biphenyl dimethyl dicarboxylate by cosolvency.
Han, SK; Kim, GY; Park, YH, 1999
)
0.3
"To improve the solubility and bioavailability of poorly water-soluble biphenyl dimethyl dicarboxylate (BDD), a drug used in treating liver diseases, a premicroemulsion concentrate composed of oil, surfactant, and cosurfactant for oral administration of BDD was prepared, and its physicochemical properties and the pharmacokinetic parameters of BDD were evaluated."( Preparation and evaluation of biphenyl dimethyl dicarboxylate microemulsions for oral delivery.
Cho, YJ; Gao, ZG; Kim, CK, 2001
)
0.31
" The method was sensitive and repeatable enough to be used in pharmacokinetic and bioavailability studies."( Determination of bifendate in human plasma by HPLC-MS and bioequivalence on bifendate pills in healthy volunteers.
Gu, L; Liang, J; Wang, Y; Zhou, L, 2006
)
0.67
"Biphenyl Dimethyl Dicarboxylate (BDD) is insoluble in aqueous solution and the bioavailability after oral administration is low."( Self-nanoemulsifying drug delivery system for enhanced bioavailability and improved hepatoprotective activity of biphenyl dimethyl dicarboxylate.
El-Laithy, HM, 2008
)
0.35
"The aim of this study was to evaluate several polymer carriers with regard to the bioavailability enhancement of bifendate solid dispersions (SD) prepared by hot-melt extrusion (HME) and select the most appropriate polymer carrier."( Evaluation of polymer carriers with regard to the bioavailability enhancement of bifendate solid dispersions prepared by hot-melt extrusion.
Feng, J; Gao, R; Luo, Y; Tang, X; Xu, L, 2012
)
0.82
" Finally, the oral bioavailability of bifendate dosage forms with bifendate-Plasdone(®) S-630 (1/9), bifendate-Eudragit(®) EPO (1/4) and bifendate-Kollidon(®) VA 64 (1/9) SD in beagle dogs was compared with that of commercially available benfidate pills."( Evaluation of polymer carriers with regard to the bioavailability enhancement of bifendate solid dispersions prepared by hot-melt extrusion.
Feng, J; Gao, R; Luo, Y; Tang, X; Xu, L, 2012
)
0.88
"2 simulated gastric fluid as the dissolution medium, while the relative bioavailability was just 87."( Evaluation of polymer carriers with regard to the bioavailability enhancement of bifendate solid dispersions prepared by hot-melt extrusion.
Feng, J; Gao, R; Luo, Y; Tang, X; Xu, L, 2012
)
0.61
"The bioavailability of water-insoluble bifendate was markedly enhanced by dispersing the drug in the polymer carrier Kollidon(®) VA 64 employing HME technology."( Evaluation of polymer carriers with regard to the bioavailability enhancement of bifendate solid dispersions prepared by hot-melt extrusion.
Feng, J; Gao, R; Luo, Y; Tang, X; Xu, L, 2012
)
0.87
" However, DDB therapeutic effectiveness is restricted by its low oral bioavailability that arises from its poor solubility and dissolution."( Novel diphenyl dimethyl bicarboxylate provesicular powders with enhanced hepatocurative activity: preparation, optimization, in vitro/in vivo evaluation.
Abdelbary, GA; Aburahma, MH, 2012
)
0.38
"It is reported that nano-sizing is one of the promising methods for improving the dissolution rate and oral bioavailability of poorly water-soluble drugs."( Development and in vitro characterizations of bifendate nanosuspensions.
Duan, C; Feng, F; Jia, L; Liu, Y; Wang, F; Wang, Y; Xie, P; Zhang, D; Zhang, Q; Zhang, X; Zou, D, 2011
)
0.63
"In this study, a self-emulsifying pellet (SEP) was prepared in order to improve the bioavailability of bifendate (DDB)."( Self-emulsifying bifendate pellets: preparation, characterization and oral bioavailability in rats.
Chen, Y; Ping, Q; Wang, S; Xiao, Y, 2013
)
0.94
" However, due to its impermeability across the gastrointestinal mucosa, oral bioavailability of the drug was relatively low."( Improvement of oral bioavailability of glycyrrhizin by sodium deoxycholate/phospholipid-mixed nanomicelles.
Fu, S; Han, J; Jin, S; Lu, Y; Lv, Q; Qi, J; Wu, W; Yuan, H, 2012
)
0.38
"In this study, to enhance the dissolution rate and oral bioavailability of bifendate, a silica-supported solid dispersion (SD) of bifendate was prepared using supercritical carbon dioxide (ScCO2) technology."( A silica-supported solid dispersion of bifendate using supercritical carbon dioxide method with enhanced dissolution rate and oral bioavailability.
Cai, C; Chang, H; Guo, B; Li, Y; Liu, M; Yang, X; Zhang, T; Zhang, X, 2016
)
0.93

Dosage Studied

ExcerptRelevanceReference
" However, its oral preparations have been known to have limited bioavailability due to its extremely low solubility in water, and its solubility problem also limits preparation of its parenteral dosage forms."( Solubilization of biphenyl dimethyl dicarboxylate by cosolvency.
Han, SK; Kim, GY; Park, YH, 1999
)
0.3
" Thus, this system may provide a useful dosage form for oral intake of a water-insoluble drug, BDD."( Preparation and evaluation of biphenyl dimethyl dicarboxylate microemulsions for oral delivery.
Cho, YJ; Gao, ZG; Kim, CK, 2001
)
0.31
" Finally, the oral bioavailability of bifendate dosage forms with bifendate-Plasdone(®) S-630 (1/9), bifendate-Eudragit(®) EPO (1/4) and bifendate-Kollidon(®) VA 64 (1/9) SD in beagle dogs was compared with that of commercially available benfidate pills."( Evaluation of polymer carriers with regard to the bioavailability enhancement of bifendate solid dispersions prepared by hot-melt extrusion.
Feng, J; Gao, R; Luo, Y; Tang, X; Xu, L, 2012
)
0.88
" However, little is known about the possible reversing effects of hepatoprotective agents, the understanding of which is of great importance in guiding clinical dosage adjustment for patients with liver injury."( Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
Hao, H; Jiang, S; Kang, A; Wang, G; Wang, H; Xie, T; Xie, Y; Yao, X; Zhou, F, 2012
)
0.38
"034), suggesting a dose-response effect of DDB plus GO on the decrease of ALT levels."( Efficacy and tolerability of diphenyl-dimethyl-dicarboxylate plus garlic oil in patients with chronic hepatitis.
Kim, SG; Kim, YM; Lee, MH, 2012
)
0.38
" Also, there might be potential interactions between SLE or DDB and co-administered medicines and it is necessary to adjust the dosage of co-administrated medicines in clinical medication of liver disease."( Reversing effects of lignans on CCl4-induced hepatic CYP450 down regulation by attenuating oxidative stress.
Guo, C; Hao, H; Kang, A; Wang, G; Wang, H; Xie, Y, 2014
)
0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AcetylcholinesteraseElectrophorus electricus (electric eel)IC50 (µMol)50.00000.00000.94539.9400AID1351113
CholinesteraseEquus caballus (horse)IC50 (µMol)50.00000.00002.22149.4000AID1351114
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (60)

Assay IDTitleYearJournalArticle
AID1351124Cytotoxicity against human HepG2 cells assessed as inhibition of cell viability at 10 uM by MTT assay relative to control2018European journal of medicinal chemistry, Jan-20, Volume: 144Development of tacrine-bifendate conjugates with improved cholinesterase inhibitory and pro-cognitive efficacy and reduced hepatotoxicity.
AID1351125Cytotoxicity against human HepG2 cells assessed as inhibition of cell viability at 50 uM by MTT assay relative to control2018European journal of medicinal chemistry, Jan-20, Volume: 144Development of tacrine-bifendate conjugates with improved cholinesterase inhibitory and pro-cognitive efficacy and reduced hepatotoxicity.
AID656816Cytotoxicity against human K562 cells after 72 hrs by MTS assay2012Bioorganic & medicinal chemistry, Apr-15, Volume: 20, Issue:8
Synthesis and biological evaluation of bifendate-chalcone hybrids as a new class of potential P-glycoprotein inhibitors.
AID629524Antiinflammatory activity in ICR mouse assessed as reduction in carrageenan-induced paw edema at 50 mg/kg, po administered 30 mins before carrageenan challenge measured at 3 hr post challenge2011European journal of medicinal chemistry, Dec, Volume: 46, Issue:12
Synthesis and biological evaluation of novel dimethyl[1,1'-biphenyl]-2,2'-dicarboxylate derivatives containing thiazolidine-2,4-dione for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID629520Hepatoprotective activity in BALB/c mouse hepatitis model assessed as reduction in concanavalin A-induced increase in serum AST level at 50 mg/kg, po administered 20 hrs before concanavalin A challenge relative to control2011European journal of medicinal chemistry, Dec, Volume: 46, Issue:12
Synthesis and biological evaluation of novel dimethyl[1,1'-biphenyl]-2,2'-dicarboxylate derivatives containing thiazolidine-2,4-dione for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID1211899Hepatoprotective activity in thioacetamide-induced Sprague-Dawley rat liver cirrhosis model assessed as downregulation of CYP3A2 protein level at 200 mg/kg administered intragastrically qd for 2 weeks by Western blotting analysis relative to control2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1351145Hepatotoxicity in Kunming mouse assessed as serum ALT level at 106 mg/kg, ig cotreated with THA after 48 hrs by colorimetric method (Rvb = 42.7 +/- 6.3 U/L)2018European journal of medicinal chemistry, Jan-20, Volume: 144Development of tacrine-bifendate conjugates with improved cholinesterase inhibitory and pro-cognitive efficacy and reduced hepatotoxicity.
AID1211892Reversal of thioacetamide-induced CYP2C6 inactivation in rat liver microsomes at 0.2 to 5 mM in presence of NADPH2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1211900Hepatoprotective activity in thioacetamide-induced Sprague-Dawley rat liver cirrhosis model assessed as downregulation of CYP2E1 protein level at 200 mg/kg administered intragastrically qd for 2 weeks by Western blotting analysis relative to control2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID78757Anti-HIV activity was evaluated by measuring the growth inhibition of acutely infected H9 lymphocytes as EC50.1995Journal of medicinal chemistry, Aug-04, Volume: 38, Issue:16
Anti-AIDS (acquired immune deficiency syndrome) agents. 17. New brominated hexahydroxybiphenyl derivatives as potent anti-HIV agents.
AID1211893Reversal of thioacetamide-induced CYP1A2 inactivation in rat liver microsomes at 2 to 50 uM in presence of NADPH2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1351114Inhibition of equine serum BuChE using butyrylthiocholine chloride as substrate preincubated for 15 mins followed by substrate addition measured every minute by Ellman's method2018European journal of medicinal chemistry, Jan-20, Volume: 144Development of tacrine-bifendate conjugates with improved cholinesterase inhibitory and pro-cognitive efficacy and reduced hepatotoxicity.
AID1211902Activity of CYP2C6 in thioacetamide-induced Sprague-Dawley rat liver cirrhosis model assessed as intrinsic clearance for enzyme-mediated diclofenac 4-hydroxylation in liver microsomes per mg protein at 200 mg/kg administered intragastrically qd for 2 week2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1211891Reversal of thioacetamide-induced CYP2C6 inactivation in rat liver microsomes at 2 to 50 uM in presence of NADPH2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1426655Anti-proliferative activity against P-gp overexpressing/drug resistant human K562/A02 cells measured after 72 hrs by MTS assay2017Journal of medicinal chemistry, 02-09, Volume: 60, Issue:3
Potent Inhibition of Nitric Oxide-Releasing Bifendate Derivatives against Drug-Resistant K562/A02 Cells in Vitro and in Vivo.
AID1351130Cytotoxicity against human HL7702 cells assessed as reduction in cell viability at 10 uM by MTT assay2018European journal of medicinal chemistry, Jan-20, Volume: 144Development of tacrine-bifendate conjugates with improved cholinesterase inhibitory and pro-cognitive efficacy and reduced hepatotoxicity.
AID1211912Hepatoprotective activity in thioacetamide-induced Sprague-Dawley rat liver cirrhosis model assessed as reversal of thioacetamide-induced change in serum TBIL level at 200 mg/kg administered intragastrically qd for 2 weeks by hematoxylin and eosin stainin2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1351123Cytotoxicity against human HepG2 cells assessed as inhibition of cell viability at 1 uM by MTT assay relative to control2018European journal of medicinal chemistry, Jan-20, Volume: 144Development of tacrine-bifendate conjugates with improved cholinesterase inhibitory and pro-cognitive efficacy and reduced hepatotoxicity.
AID1211898Reversal of thioacetamide-induced CYP2E1 inactivation in rat liver microsomes at 0.2 to 5 mM in presence of NADPH2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1211915Hepatoprotective activity in thioacetamide-induced Sprague-Dawley rat liver cirrhosis model assessed as reversal of thioacetamide-induced change in serum ALT level at 200 mg/kg administered intragastrically qd for 2 weeks by hematoxylin and eosin staining2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1211909Downregulation of CYP1A2 in Sprague-Dawley rat liver at 200 mg/kg administered intragastrically qd for 2 weeks by Western blotting analysis2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1351118Inhibition of equine serum BuChE at 50 uM using butyrylthiocholine chloride as substrate preincubated for 15 mins followed by substrate addition measured every minute by Ellman's method2018European journal of medicinal chemistry, Jan-20, Volume: 144Development of tacrine-bifendate conjugates with improved cholinesterase inhibitory and pro-cognitive efficacy and reduced hepatotoxicity.
AID629521Hepatoprotective activity in BALB/c mouse hepatitis model assessed as reduction in concanavalin A-induced increase in serum ALT level at 50 mg/kg, po administered 20 hrs before concanavalin A challenge relative to control2011European journal of medicinal chemistry, Dec, Volume: 46, Issue:12
Synthesis and biological evaluation of novel dimethyl[1,1'-biphenyl]-2,2'-dicarboxylate derivatives containing thiazolidine-2,4-dione for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID1211911Hepatoprotective activity in thioacetamide-induced Sprague-Dawley rat liver cirrhosis model assessed as reversal of thioacetamide-induced change in serum AST level at 200 mg/kg administered intragastrically qd for 2 weeks by hematoxylin and eosin staining2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID656819Inhibition of Pgp-mediated rhodamine 123 efflux in human K562/A02 cells assessed as intracellular rhodamine 123 accumulation at 10 uM preincubated for 1 hr prior rhodamine 123 addition measured after 30 mins by flow cytometry relative to control2012Bioorganic & medicinal chemistry, Apr-15, Volume: 20, Issue:8
Synthesis and biological evaluation of bifendate-chalcone hybrids as a new class of potential P-glycoprotein inhibitors.
AID1570981Antimigratory activity against human MDA-MB-231 cells assessed as reduction in cell migration towards wound area at 45 uM measured up to 24 hrs by inverted microscopic analysis2018MedChemComm, Nov-01, Volume: 9, Issue:11
Assessment of a bifendate derivative bearing a 6,7-dihydro-dibenzo[
AID1211904Activity of CYP2E1 in thioacetamide-induced Sprague-Dawley rat liver cirrhosis model assessed as intrinsic clearance for enzyme-mediated chlorzoxazone 6-hydroxylation in liver microsomes per mg protein at 200 mg/kg administered intragastrically qd for 2 w2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1211903Activity of CYP3A2 in thioacetamide-induced Sprague-Dawley rat liver cirrhosis model assessed as intrinsic clearance for enzyme-mediated midazolam 4-hydroxylation in liver microsomes per mg protein at 200 mg/kg administered intragastrically qd for 2 weeks2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1129459Hepatoprotective activity against carbon tetrachloride-induced toxicity in human HL-7702 cells assessed as increase of cell survival rate at 0.2 ug/ul pretreated for 12 hrs before carbon tetrachloride addition by MTS assay relative to control2014Bioorganic & medicinal chemistry letters, Apr-01, Volume: 24, Issue:7
Synthesis and the hepatoprotective activity of dibenzocyclooctadiene lignan derivatives.
AID656817Cytotoxicity against human K562/A02 cells overexpress P-gp after 72 hrs by MTS assay2012Bioorganic & medicinal chemistry, Apr-15, Volume: 20, Issue:8
Synthesis and biological evaluation of bifendate-chalcone hybrids as a new class of potential P-glycoprotein inhibitors.
AID1351137Hepatotoxicity in Kunming mouse assessed as histomorphological changes in liver at 106 mg/kg, ig after 48 hrs by H and E staining based assay2018European journal of medicinal chemistry, Jan-20, Volume: 144Development of tacrine-bifendate conjugates with improved cholinesterase inhibitory and pro-cognitive efficacy and reduced hepatotoxicity.
AID1211905Activity of CYP1A2 in Sprague-Dawley rat assessed as intrinsic clearance for enzyme-mediated phenacetin O-deethylation in liver microsomes per mg protein at 200 mg/kg administered intragastrically qd for 2 weeks2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1351138Hepatotoxicity in Kunming mouse assessed as inflammatory cell infiltration in liver at 35 mg/kg, ig cotreated with THA after 48 hrs by H and E staining based assay2018European journal of medicinal chemistry, Jan-20, Volume: 144Development of tacrine-bifendate conjugates with improved cholinesterase inhibitory and pro-cognitive efficacy and reduced hepatotoxicity.
AID1573632Cytoprotection against H2O2-induced cell death in rat HBZY-1 cells assessed as cell viability at 6 uM preincubated for 2 hrs followed by H2O2 addition and measured after 24 hrs by MTT assay (Rvb = 62.1%)2019European journal of medicinal chemistry, Jan-15, Volume: 162Synthesis and biological evaluation of bifendate derivatives bearing acrylamide moiety as novel antioxidant agents.
AID1211910Upregulation of CYP2C6 in Sprague-Dawley rat liver at 200 mg/kg administered intragastrically qd for 2 weeks by Western blotting analysis2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1351113Inhibition of electric eel AChE using acetylthiocholine chloride as substrate preincubated for 15 mins followed by substrate addition measured every minute by Ellman's method2018European journal of medicinal chemistry, Jan-20, Volume: 144Development of tacrine-bifendate conjugates with improved cholinesterase inhibitory and pro-cognitive efficacy and reduced hepatotoxicity.
AID1351144Hepatotoxicity in Kunming mouse assessed as serum ASAT level at 106 mg/kg, ig after 48 hrs by colorimetric method (Rvb = 101.5 +/- 22.3 U/L)2018European journal of medicinal chemistry, Jan-20, Volume: 144Development of tacrine-bifendate conjugates with improved cholinesterase inhibitory and pro-cognitive efficacy and reduced hepatotoxicity.
AID1351143Hepatotoxicity in Kunming mouse assessed as serum ALT level at 106 mg/kg, ig after 48 hrs by colorimetric method (Rvb = 42.7 +/- 6.3 U/L)2018European journal of medicinal chemistry, Jan-20, Volume: 144Development of tacrine-bifendate conjugates with improved cholinesterase inhibitory and pro-cognitive efficacy and reduced hepatotoxicity.
AID1351127Cytotoxicity against rat PC12 cells assessed as inhibition of cell viability at 10 uM by MTT assay relative to control2018European journal of medicinal chemistry, Jan-20, Volume: 144Development of tacrine-bifendate conjugates with improved cholinesterase inhibitory and pro-cognitive efficacy and reduced hepatotoxicity.
AID1211913Hepatoprotective activity in thioacetamide-induced Sprague-Dawley rat liver cirrhosis model assessed as downregulation of CYP1A2 protein level at 200 mg/kg administered intragastrically qd for 2 weeks by Western blotting analysis relative to control2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1211889Upregulation of CYP3A2 in Sprague-Dawley rat liver at 200 mg/kg administered intragastrically qd for 2 weeks by Western blotting analysis2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1211894Reversal of thioacetamide-induced CYP1A2 inactivation in rat liver microsomes at 0.2 to 5 mM in presence of NADPH2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1211906Activity of CYP2C6 in Sprague-Dawley rat assessed as intrinsic clearance for enzyme-mediated diclofenac 4-hydroxylation in liver microsomes per mg protein at 200 mg/kg administered intragastrically qd for 2 weeks2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1211914Hepatoprotective activity in thioacetamide-induced Sprague-Dawley rat liver cirrhosis model assessed as downregulation of CYP2C6 protein level at 200 mg/kg administered intragastrically qd for 2 weeks by Western blotting analysis relative to control2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID653306Inhibition of p-glycoprotein in human K562/A02 cells assessed as accumulation of rhodamine 123 at 10 uM by flow cytometry relative to control2012European journal of medicinal chemistry, May, Volume: 51Synthesis and biological evaluation of novel bifendate derivatives bearing 6,7-dihydro-dibenzo[c,e]azepine scaffold as potent P-glycoprotein inhibitors.
AID1351128Cytotoxicity against rat PC12 cells assessed as inhibition of cell viability at 50 uM by MTT assay relative to control2018European journal of medicinal chemistry, Jan-20, Volume: 144Development of tacrine-bifendate conjugates with improved cholinesterase inhibitory and pro-cognitive efficacy and reduced hepatotoxicity.
AID1211908Activity of CYP2E1 in Sprague-Dawley rat assessed as intrinsic clearance for enzyme-mediated chlorzoxazone 6-hydroxylation in liver microsomes per mg protein at 200 mg/kg administered intragastrically qd for 2 weeks2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1211897Reversal of thioacetamide-induced CYP2E1 inactivation in rat liver microsomes at 2 to 50 uM in presence of NADPH2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1426654Anti-proliferative activity against human K562 cells measured after 72 hrs by MTS assay2017Journal of medicinal chemistry, 02-09, Volume: 60, Issue:3
Potent Inhibition of Nitric Oxide-Releasing Bifendate Derivatives against Drug-Resistant K562/A02 Cells in Vitro and in Vivo.
AID1573635Cytoprotection against H2O2-induced cell death in rat HBZY-1 cells assessed as cell viability at 100 uM preincubated for 2 hrs followed by H2O2 addition and measured after 24 hrs by MTT assay (Rvb = 62.1%)2019European journal of medicinal chemistry, Jan-15, Volume: 162Synthesis and biological evaluation of bifendate derivatives bearing acrylamide moiety as novel antioxidant agents.
AID1211901Activity of CYP1A2 in thioacetamide-induced Sprague-Dawley rat liver cirrhosis model assessed as intrinsic clearance for enzyme-mediated phenacetin O-deethylation in liver microsomes per mg protein at 200 mg/kg administered intragastrically qd for 2 weeks2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1351117Inhibition of electric eel AChE at 50 uM using acetylthiocholine chloride as substrate preincubated for 15 mins followed by substrate addition measured every minute by Ellman's method2018European journal of medicinal chemistry, Jan-20, Volume: 144Development of tacrine-bifendate conjugates with improved cholinesterase inhibitory and pro-cognitive efficacy and reduced hepatotoxicity.
AID1211896Reversal of thioacetamide-induced CYP3A2 inactivation in rat liver microsomes at 0.2 to 5 mM in presence of NADPH2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID235005Anti-HIV activity evaluated by measuring the growth inhibition of acutely infected H9 lymphocytes as therapeutic index.1995Journal of medicinal chemistry, Aug-04, Volume: 38, Issue:16
Anti-AIDS (acquired immune deficiency syndrome) agents. 17. New brominated hexahydroxybiphenyl derivatives as potent anti-HIV agents.
AID1351146Hepatotoxicity in Kunming mouse assessed as serum ASAT level at 106 mg/kg, ig cotreated with THA after 48 hrs by colorimetric method (Rvb = 101.5 +/- 22.3 U/L)2018European journal of medicinal chemistry, Jan-20, Volume: 144Development of tacrine-bifendate conjugates with improved cholinesterase inhibitory and pro-cognitive efficacy and reduced hepatotoxicity.
AID1211907Activity of CYP3A2 in Sprague-Dawley rat assessed as intrinsic clearance for enzyme-mediated midazolam 4-hydroxylation in liver microsomes per mg protein at 200 mg/kg administered intragastrically qd for 2 weeks2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID1351126Cytotoxicity against rat PC12 cells assessed as inhibition of cell viability at 1 uM by MTT assay relative to control2018European journal of medicinal chemistry, Jan-20, Volume: 144Development of tacrine-bifendate conjugates with improved cholinesterase inhibitory and pro-cognitive efficacy and reduced hepatotoxicity.
AID1211895Reversal of thioacetamide-induced CYP3A2 inactivation in rat liver microsomes at 2 to 50 uM in presence of NADPH2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
AID78927Anti-HIV activity was evaluated by measuring the growth inhibition of acutely infected H9 lymphocytes as IC50.1995Journal of medicinal chemistry, Aug-04, Volume: 38, Issue:16
Anti-AIDS (acquired immune deficiency syndrome) agents. 17. New brominated hexahydroxybiphenyl derivatives as potent anti-HIV agents.
AID1211890Upregulation of CYP2E1 in Sprague-Dawley rat liver at 200 mg/kg administered intragastrically qd for 2 weeks by Western blotting analysis2012Drug metabolism and disposition: the biological fate of chemicals, Apr, Volume: 40, Issue:4
Cytochrome P450 dysregulations in thioacetamide-induced liver cirrhosis in rats and the counteracting effects of hepatoprotective agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (123)

TimeframeStudies, This Drug (%)All Drugs %
pre-199017 (13.82)18.7374
1990's25 (20.33)18.2507
2000's34 (27.64)29.6817
2010's45 (36.59)24.3611
2020's2 (1.63)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 44.20

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index44.20 (24.57)
Research Supply Index4.89 (2.92)
Research Growth Index4.70 (4.65)
Search Engine Demand Index49.00 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (44.20)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials8 (6.45%)5.53%
Reviews2 (1.61%)6.00%
Case Studies1 (0.81%)4.05%
Observational0 (0.00%)0.25%
Other113 (91.13%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]