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Details

Stereochemistry ACHIRAL
Molecular Formula C19H18O9
Molecular Weight 390.3408
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BICYCLOL

SMILES

COC(=O)C1=CC(OC)=C2OCOC2=C1C3=C(CO)C=C(OC)C4=C3OCO4

InChI

InChIKey=KXMTXZACPVCDMH-UHFFFAOYSA-N
InChI=1S/C19H18O9/c1-22-11-4-9(6-20)13(17-15(11)25-7-27-17)14-10(19(21)24-3)5-12(23-2)16-18(14)28-8-26-16/h4-5,20H,6-8H2,1-3H3

HIDE SMILES / InChI

Description

Bicyclol, also known as SY 801, is a hepatoprotective agent. Bicyclol upregulates transcription factor Nrf2, HO-1 expression and protects rat brains against focal ischemia. Bicyclol induces cell cycle arrest and autophagy in HepG2 human hepatocellular carcinoma cells through the PI3K/AKT and Ras/Raf/MEK/ERK pathways. Bicyclol attenuates tetracycline-induced fatty liver associated with inhibition of hepatic ER stress and apoptosis in mice. Bicyclol promotes toll-like 2 receptor recruiting inosine 5'-monophosphate dehydrogenase II to exert its anti-inflammatory effect. Phase Ⅰ~Ⅳ clinical trials and extensive application after market launch prove that, Bicyclol is suitable for the treatment of chronic viral and non-viral liver disease with elevated serum aminotransferase abnormalities, and is excellent in safety. This drug is recommended for liver protection and anti-inflammatory medication by Chinese Medical Association in Guidelines for Management of Alcoholic Fatty Liver Disease, Guidelines for Management of Non-alcoholic Fatty Liver Disease, The Guideline of Prevention and Treatment for Chronic Hepatitis B, Expert Consensus On Hepatic Inflammation and Its Prevention and other professional guidelines and consensus.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Bicyclol
Primary
Bicyclol
Primary
Bicyclol
PubMed

PubMed

TitleDatePubMed
[Protective effects of bicyclol on liver fibrosis induced by carbon tetrachloride].
2004 Dec 17
Mechanism of protective action of bicyclol against CCl-induced liver injury in mice.
2005 Aug
[Protective effects of bicyclol on alcohol-induced liver damage in mice].
2005 Dec 21
Chemoprevention of bicyclol against hepatic preneoplastic lesions.
2006 Dec
Effects of bicyclol on dimethylnitrosamine-induced liver fibrosis in mice and its mechanism of action.
2006 Jul 4
[Protective effect of bicyclol against acute fatty liver induced by tetracycline in mice].
2008 Jan
Protect effect of bicyclol on cisplatin-induced nephrotoxicity in mice.
2009 Apr
Protective effect of bicyclol on tetracycline-induced fatty liver in mice.
2009 Jul 10
Patents

Sample Use Guides

In Vivo Use Guide
Patients received bicyclol 25mg thrice daily for six months, then stopped treatment and followed up for 3 months. Oral administration of bicyclol normalized the elevated serum transaminases (ALT, AST) by approximately 50% in chronic viral hepatitis B and C, and also showed certain level of inhibiting HBV and HCV replication.
Route of Administration: Oral
In Vitro Use Guide
Bicyclol 50 umol/L induced HSP27 expression in HepG2 cells in a time-dependent manner.
Name Type Language
BICYCLOL
WHO-DD  
Common Name English
4,4'-BI-1,3-BENZODIOXOLE)-5-CARBOXYLIC ACID, 5'-(HYDROXYMETHYL)-7,7'-DIMETHOXY-, METHYL ESTER
Common Name English
BICYCLOL [WHO-DD]
Common Name English
Code System Code Type Description
CAS
118159-48-1
Created by admin on Tue Mar 06 11:33:08 UTC 2018 , Edited by admin on Tue Mar 06 11:33:08 UTC 2018
PRIMARY
PUBCHEM
9821754
Created by admin on Tue Mar 06 11:33:08 UTC 2018 , Edited by admin on Tue Mar 06 11:33:08 UTC 2018
PRIMARY SWITZERF
EPA CompTox
118159-48-1
Created by admin on Tue Mar 06 11:33:08 UTC 2018 , Edited by admin on Tue Mar 06 11:33:08 UTC 2018
PRIMARY
EVMPD
SUB32557
Created by admin on Tue Mar 06 11:33:08 UTC 2018 , Edited by admin on Tue Mar 06 11:33:08 UTC 2018
PRIMARY