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Details

Stereochemistry RACEMIC
Molecular Formula C20H18O10
Molecular Weight 418.3509
Optical Activity ( + / - )
Additional Stereochemistry Yes
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0
Stereo Comments AXIAL, RACEMIC

SHOW SMILES / InChI
Structure of BIFENDATE

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

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 (DDB) on 9-amino-1,2,3,4-tetrahydroacridine-induced hepatotoxicity in mice].
2001 Jul
Interferon signal transduction of biphenyl dimethyl dicarboxylate/amantadine and anti-HBV activity in HepG2 2.2.15.
2006 May
Protective role of dimethyl diphenyl bicarboxylate (DDB) against erythromycin induced hepatotoxicity in male rats.
2007 Jun
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 Fri Dec 15 19:05:19 GMT 2023
Edited
by admin
on Fri Dec 15 19:05:19 GMT 2023
Record UNII
0G32E321W1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BIFENDATE
WHO-DD  
Common Name English
(4,4'-BI-1,3-BENZODIOXOLE)-5,5'-DICARBOXYLIC ACID, 7,7'-DIMETHOXY-, 5,5'-DIMETHYL ESTER
Common Name English
DDB
Common Name English
DIMETHYL DICARBOXYLATE BIPHENYL
Common Name English
.ALPHA.-DDB
Common Name English
DIPHENYL DIMETHYL BICARBOXYLATE
Common Name English
Bifendate [WHO-DD]
Common Name English
DIMETHYL-4,4'-DIMETHOXY-5,6,5',6'-DIMETHYLENEDIOXYBIPHENYL-2,2'-DICARBOXYLATE
Common Name English
Code System Code Type Description
MESH
C465548
Created by admin on Fri Dec 15 19:05:19 GMT 2023 , Edited by admin on Fri Dec 15 19:05:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID40223736
Created by admin on Fri Dec 15 19:05:19 GMT 2023 , Edited by admin on Fri Dec 15 19:05:19 GMT 2023
PRIMARY
EVMPD
SUB22931
Created by admin on Fri Dec 15 19:05:19 GMT 2023 , Edited by admin on Fri Dec 15 19:05:19 GMT 2023
PRIMARY
PUBCHEM
108213
Created by admin on Fri Dec 15 19:05:19 GMT 2023 , Edited by admin on Fri Dec 15 19:05:19 GMT 2023
PRIMARY
CAS
73536-69-3
Created by admin on Fri Dec 15 19:05:19 GMT 2023 , Edited by admin on Fri Dec 15 19:05:19 GMT 2023
PRIMARY
FDA UNII
0G32E321W1
Created by admin on Fri Dec 15 19:05:19 GMT 2023 , Edited by admin on Fri Dec 15 19:05:19 GMT 2023
PRIMARY
SMS_ID
100000087089
Created by admin on Fri Dec 15 19:05:19 GMT 2023 , Edited by admin on Fri Dec 15 19:05:19 GMT 2023
PRIMARY
Related Record Type Details
IMPURITY -> PARENT