Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H18O10 |
| Molecular Weight | 418.3509 |
| Optical Activity | UNSPECIFIED |
| Additional Stereochemistry | Yes |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
| Stereo Comments | AXIAL, S |
SHOW SMILES / InChI
SMILES
COC(=O)C1=CC(OC)=C2OCOC2=C1C3=C(C=C(OC)C4=C3OCO4)C(=O)OC
InChI
InChIKey=JMZOMFYRADAWOG-UHFFFAOYSA-N
InChI=1S/C20H18O10/c1-23-11-5-9(19(21)25-3)13(17-15(11)27-7-29-17)14-10(20(22)26-4)6-12(24-2)16-18(14)30-8-28-16/h5-6H,7-8H2,1-4H3
| Molecular Formula | C20H18O10 |
| Molecular Weight | 418.3509 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/29335204 | https://www.ncbi.nlm.nih.gov/pubmed/16242290 | https://www.ncbi.nlm.nih.gov/pubmed/17046746 | https://www.ncbi.nlm.nih.gov/pubmed/22429509
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/29335204 | https://www.ncbi.nlm.nih.gov/pubmed/16242290 | https://www.ncbi.nlm.nih.gov/pubmed/17046746 | https://www.ncbi.nlm.nih.gov/pubmed/22429509
Bifendate is a synthetic intermediate of Schisandrin C and also an anti-HBV drug used in Chinese medicine for the treatment of chronic hepatitis B. Following the intake of Bifendate in rats, the drug was observed to improve liver function by increasing the detoxification process, reducing pathological lesions, and accelerating hepatocyte regeneration. Bifendate can also function as a membrane-stabilizing agent to protect the cell from damage. After treatment with Bifendate, the protein metabolic processes of hepatitis patients were improved, with increased serum albumin levels and decreased globulin levels. Bifendate is a potent inducer of cytochrome proteins (CYPs) and can result in clinically significant interactions. It has been proposed that the increased detoxification capability of Bifendate originates from an increase in the level of P450. Bifendate may function as a protecting agent to prevent drug-induced liver dysfunction by increasing the activity of CYP450.
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
209.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19845435/ |
15 mg 3 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
BIFENDATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3191.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19845435/ |
15 mg 3 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
BIFENDATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
10.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19845435/ |
15 mg 3 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
BIFENDATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Hepatoprotective effects of Mimic of Manganese superoxide dismutase against carbon tetrachloride-induced hepatic injury. | 2014-09 |
|
| Antiapoptotic effect of DDB against hepatic ischemia-reperfusion injury. | 2011-04 |
|
| Hepatoprotection in a rat model of acute liver damage through inhibition of CY2E1 activity by total alkaloids extracted from Rubus alceifolius Poir. | 2011-03 |
|
| Integral pharmacokinetics of multiple lignan components in normal, CCl4-induced hepatic injury and hepatoprotective agents pretreated rats and correlations with hepatic injury biomarkers. | 2010-09-15 |
|
| Electrochemical treatment of aqueous wastes containing pyrogallol by BDD-anodic oxidation. | 2009-01 |
|
| Self-nanoemulsifying drug delivery system for enhanced bioavailability and improved hepatoprotective activity of biphenyl dimethyl dicarboxylate. | 2008-07 |
|
| Effects of biphenyldimethyl-dicarboxylate administration alone or combined with silymarin in the CCL4 model of liver fibrosis in rats. | 2007-08-24 |
|
| Protective role of dimethyl diphenyl bicarboxylate (DDB) against erythromycin induced hepatotoxicity in male rats. | 2007-06 |
|
| Interferon signal transduction of biphenyl dimethyl dicarboxylate/amantadine and anti-HBV activity in HepG2 2.2.15. | 2006-05 |
|
| Separation of atropisomers of anti-hepatitis drug dimethyl diphenyl bicarboxylate analogues by capillary electrophoresis with vancomycin as the chiral selector. | 2006-03-03 |
|
| The potential anti-hBV effect of amantadine in combination with ursodeoxycholic acid and biphenyl dimethyl dicarboxylate in hepG2 2.2.15 cells. | 2005-04 |
|
| DDB treatment of patients with chronic hepatitis. | 2004-06 |
|
| Characterization of novel nucleoside analogs by electrospray ionization mass spectra. | 2004 |
|
| Hepatoprotective mechanism of schisandrin B: role of mitochondrial glutathione antioxidant status and heat shock proteins. | 2003-08-15 |
|
| Beta-glucuronidase inhibitor tectorigenin isolated from the flower of Pueraria thunbergiana protects carbon tetrachloride-induced liver injury. | 2003-08 |
|
| A polymeric micellar carrier for the solubilization of biphenyl dimethyl dicarboxylate. | 2003-02 |
|
| Effect of dimethyl diphenyl bicarboxylate on normal and chemically-injured liver. | 2002-01 |
|
| Characterization of the selectivity and mechanism of cytochrome P450 inhibition by dimethyl-4,4'-dimethoxy-5,6,5',6'-dimethylenedioxybiphenyl-2,2'-dicarboxylate. | 2001-12 |
|
| [Effect of dimethyl diphenyl bicarboxylate (DDB) on 9-amino-1,2,3,4-tetrahydroacridine-induced hepatotoxicity in mice]. | 2001-07 |
|
| Preparation and evaluation of biphenyl dimethyl dicarboxylate microemulsions for oral delivery. | 2001-01-29 |
|
| Anti-AIDS agents--XXVI. Structure-activity correlations of gomisin-G-related anti-HIV lignans from Kadsura interior and of related synthetic analogues. | 1997-08 |
|
| Anti-AIDS (acquired immune deficiency syndrome) agents. 17. New brominated hexahydroxybiphenyl derivatives as potent anti-HIV agents. | 1995-08-04 |
Patents
Sample Use Guides
1 x 10^4 K562 and K562/A02 cells were grown in 96-well microtiter plates and incubated for 24 h. Various concentrations of compounds (Bifendate, 100mkM) diluted with medium were added into the wells. And the exponentially growing cancer cells were incubated for 72 h at 37 C (5% CO2, 95% humidity). Then, MTS was added directly to the cells. After additional incubation for 3 h at 37 C, the absorbance at 490 nm was read on a microplate reader (Thermo, USA).
| Substance Class |
Chemical
Created
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CE2LBA6CBR
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Validated (UNII)
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