COLCHICEINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H23NO6
Molecular Weight	385.4104
Optical Activity	UNSPECIFIED
Additional Stereochemistry	Yes
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0
Stereo Comments	M-helix

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(C(OC)=C1OC)C3=CC=C(O)C(=O)C=C3[C@H](CC2)NC(C)=O

InChI

InChIKey=PRGILOMAMBLWNG-HNNXBMFYSA-N

InChI=1S/C21H23NO6/c1-11(23)22-15-7-5-12-9-18(26-2)20(27-3)21(28-4)19(12)13-6-8-16(24)17(25)10-14(13)15/h6,8-10,15H,5,7H2,1-4H3,(H,22,23)(H,24,25)/t15-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9041381

Colchiceine, a metabolite of colchicine, commonly used to treat gout, was studied as an effective compound in the model of liver damage.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cirrhosis 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9041381	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effects of colchicine and colchiceine in a biochemical model of liver injury and fibrosis.	1998 Summer	9650324

Sample Use Guides

In Vivo Use Guide

in rats: CCl4 for 8 weeks followed by colchiceine (60 microg kg(-1)) + CCl4 for 5 weeks

Route of Administration: Oral

In Vitro Use Guide

It was determined the cytotoxicity of colchiceine (EIN) in comparison with that of colchicine (COL); to evaluate the effect of EIN on cytochrome P450 (CYP) expression and activity. Primary human hepatocytes were the model of choice for cytotoxicity and CYP expression experiments. EIN was less toxic than COL based on both parameters within the concentration range 1-100 microM. 10 microM concentration of EIN did not induce the expression of CYP1A2, CYP2A6, CYP2C9, CYP2C19, CYP2E1 and CYP3A4 isoforms, which were evaluated at the levels of mRNAs, proteins and specific activities in culture. EIN in concentrations up to 200 microM had no effect on marker activities of CYP1A2, 2C9, 2E1 and 3A4 in human liver microsomes. It was concluded that EIN in concentrations up to 10 microM is not cytotoxic in primary human hepatocytes as revealed by albumin secretion and LDH leakage.

Name

Type

Language

COLCHICEINE

Common Name

English

O10-DEMETHYLCOLCHICINE

Common Name

English

COLCHICEINE [MI]

Common Name

English

NSC-33411

Code

English

N-((7S)-5,6,7,9-TETRAHYDRO-10-HYDROXY-1,2,3-TRIMETHOXY-9-OXOBENZO(A)HEPTALEN-7-YL)ACETAMIDE

Systematic Name

English

COLCHICINE IMPURITY F [EP IMPURITY]

Common Name

English

ACETAMIDE, N-((7S)-5,6,7,9-TETRAHYDRO-10-HYDROXY-1,2,3-TRIMETHOXY-9-OXOBENZO(A)HEPTALEN-7-YL)-

Systematic Name

English

NSC-123396

Code

English

Code System Code Type Description

FDA UNII

HJ30158L57