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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 of COLCHICEINE

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

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

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

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.