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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H25NO6
Molecular Weight 399.437
Optical Activity ( - )
Additional Stereochemistry Yes
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0
Stereo Comments M-helix

SHOW SMILES / InChI
Structure of Colchicine

SMILES

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

InChI

InChIKey=IAKHMKGGTNLKSZ-INIZCTEOSA-N
InChI=1S/C22H25NO6/c1-12(24)23-16-8-6-13-10-19(27-3)21(28-4)22(29-5)20(13)14-7-9-18(26-2)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)/t16-/m0/s1

HIDE SMILES / InChI

Description

Colchicine is an alkaloid obtained from the plant colchicum autumnale (also known as "meadow saffron"). Colchicine is an alternative medication for those unable to tolerate NSAIDs in gout. Mechanism of action of colchicine is inhibition of microtubule polymerization by binding to tubulin. Availability of tubulin is essential to mitosis, so colchicine effectively unctions as a "mitotic poison" or spindle poison.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
COLCRYS
Primary
COLCRYS

Cmax

ValueDoseCo-administeredAnalytePopulation
1.68 ng/mL
0.6 mg single, oral
COLCHICINE plasma
Homo sapiens
2.16 ng/mL
0.6 mg single, oral
COLCHICINE plasma
Homo sapiens
2023.29 pg/mL
0.6 mg single, oral
COLCHICINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
18.47 ng × h/mL
0.6 mg single, oral
COLCHICINE plasma
Homo sapiens
19.9 ng × h/mL
0.6 mg single, oral
COLCHICINE plasma
Homo sapiens
8717.33 pg*h/mL
0.6 mg single, oral
COLCHICINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
30.54 h
0.6 mg single, oral
COLCHICINE plasma
Homo sapiens
31.04 h
0.6 mg single, oral
COLCHICINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
61%
COLCHICINE serum
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
For prophylaxis of gout flares, the recommended dosage of Colchicine capsules is 0.6 mg once or twice daily. The maximum dose is 1.2 mg per day. Colchicine capsules are administered orally, without regard to meals.
Route of Administration: Oral
In Vitro Use Guide
Inhibition of the polymerization of brain tubulin was evaluated. Solution of compound in DMSO in serial dilutions was prepared. Reaction mixture contained 0.25 mg of tubulin, 1.0 M monosodium glutamate and approptiate drug concentrations. The reaction mixtures were incubated at 37 °C for 15 min to allow slow binding drugs like colchicine to bind to the tubulin. The reaction mixtures were then chilled on ice, and the polymerization reaction was followed turbidimetrically for 20 min. Polymer formation was confirmed by evaluation of depolymerization at 0°C. Extent of inhibition of polymerization at 20 min in drug-treated samples was always calculated by comparing them to a pair of drug-free samples in each experimental set.