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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
Structure of Bifendate, (S)-

SMILES

COC(=O)C1=CC(OC)=C2OCOC2=C1C3=C4OCOC4=C(OC)C=C3C(=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

HIDE SMILES / InChI

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

Description
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.

Originator

Sources: Yaoxue Xuebao (1979), 14, (10), 598-604.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Anti-AIDS agents--XXVI. Structure-activity correlations of gomisin-G-related anti-HIV lignans from Kadsura interior and of related synthetic analogues.
1997 Aug
Effect of dimethyl diphenyl bicarboxylate on normal and chemically-injured liver.
2002 Jan
Beta-glucuronidase inhibitor tectorigenin isolated from the flower of Pueraria thunbergiana protects carbon tetrachloride-induced liver injury.
2003 Aug
Hepatoprotective mechanism of schisandrin B: role of mitochondrial glutathione antioxidant status and heat shock proteins.
2003 Aug 15
A polymeric micellar carrier for the solubilization of biphenyl dimethyl dicarboxylate.
2003 Feb
Characterization of novel nucleoside analogs by electrospray ionization mass spectra.
2004
DDB treatment of patients with chronic hepatitis.
2004 Jun
The potential anti-hBV effect of amantadine in combination with ursodeoxycholic acid and biphenyl dimethyl dicarboxylate in hepG2 2.2.15 cells.
2005 Apr
Self-nanoemulsifying drug delivery system for enhanced bioavailability and improved hepatoprotective activity of biphenyl dimethyl dicarboxylate.
2008 Jul
Electrochemical treatment of aqueous wastes containing pyrogallol by BDD-anodic oxidation.
2009 Jan
Patents

Patents

Sample Use Guides

30- 67.5 mg/d for up to 12 months
Route of Administration: Oral
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
by admin
on Sat Dec 16 19:50:49 GMT 2023
Edited
by admin
on Sat Dec 16 19:50:49 GMT 2023
Record UNII
CE2LBA6CBR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Bifendate, (S)-
Systematic Name English
[4,4′-Bi-1,3-benzodioxole]-5,5′-dicarboxylic acid, 7,7′-dimethoxy-, dimethyl ester, (S)-
Systematic Name English
[4,4′-Bi-1,3-benzodioxole]-5,5′-dicarboxylic acid, 7,7′-dimethoxy-, dimethyl ester, (4S)-
Systematic Name English
Code System Code Type Description
FDA UNII
CE2LBA6CBR
Created by admin on Sat Dec 16 19:50:49 GMT 2023 , Edited by admin on Sat Dec 16 19:50:49 GMT 2023
PRIMARY
PUBCHEM
108213
Created by admin on Sat Dec 16 19:50:49 GMT 2023 , Edited by admin on Sat Dec 16 19:50:49 GMT 2023
PRIMARY
CAS
111897-25-7
Created by admin on Sat Dec 16 19:50:49 GMT 2023 , Edited by admin on Sat Dec 16 19:50:49 GMT 2023
PRIMARY