BICYCLOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H18O9
Molecular Weight	390.3408
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)C1=C(C2=C(OCO2)C(OC)=C1)C3=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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19149648 | http://www.baisainuo.com/en/productinfo.asp?id=1476&big_id=987 | https://www.ncbi.nlm.nih.gov/pubmed/17253534

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Heat shock protein beta-1 1 Target ID: CHEMBL5976 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20139905	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Fatty liver disease 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19149648 http://www.baisainuo.com/en/productinfo.asp?id=1476&big_id=987	Primary	Approved 8429	Bicyclol Approved Use Bicyclol 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.
Hepatitis B 57 Sources: http://adisinsight.springer.com/drugs/800007756 https://www.ncbi.nlm.nih.gov/pubmed/17253534	Primary	Approved 8429	Bicyclol Approved Use Bicyclol 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.
Hepatitis C 42 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19149648 https://www.ncbi.nlm.nih.gov/pubmed/17253534	Primary	Approved 8429	Bicyclol Approved Use Hepatitis C treatment

PubMed

Title	Date	PubMed
Chemoprevention of bicyclol against hepatic preneoplastic lesions.	2006 Dec	17106253
[Protective effect of bicyclol against acute fatty liver induced by tetracycline in mice].	2008 Jan	18357727
Protect effect of bicyclol on cisplatin-induced nephrotoxicity in mice.	2009 Apr	18956176
Protective effect of bicyclol on tetracycline-induced fatty liver in mice.	2009 Jul 10	19427351

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

Common Name

English

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

Code System Code Type Description

CAS

118159-48-1