Colchicine

First marketed in 1921

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 Search

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

Molecular Formula	C22H25NO6
Molecular Weight	399.437
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugs.com/pro/colchicine.html

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 Target	Pharmacology	Condition	Potency
Tubulin 69 Target ID: CHEMBL2095182 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26132075	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Gout 28 Sources: https://www.drugs.com/pro/colchicine.html	Preventing		Approved 8583	COLCRYS Approved Use Colchicine capsules are indicated for prophylaxis of gout flares in adults. Colchicine disrupts the polymerization of β-tubulin into microtubules, thereby preventing the activation, degranulation, and migration of neutrophils to sites of inflammation. Launch Date 2009
Familial mediterranean fever 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/022351lbl.pdf	Primary		Approved 8583	COLCRYS Approved Use Colchicine is indicated for Familial Mediterranean fever (FMF) in adults and children 4 years or older Launch Date 2009

C_max

Value	Dose	Analyte	Population
2023.29 pg/mL CLINICAL TRIAL https://clinicaltrials.gov/ct2/show/NCT00960323	0.6 mg single, oral dose: 0.6 mg route of administration: oral experiment type: SINGLE co-administered:	COLCHICINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
2.16 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210942s000lbl.pdf	0.6 mg single, oral dose: 0.6 mg route of administration: Oral experiment type: SINGLE co-administered:	COLCHICINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
1.68 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210942s000lbl.pdf	0.6 mg single, oral dose: 0.6 mg route of administration: Oral experiment type: SINGLE co-administered:	COLCHICINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED

AUC

Value	Dose	Analyte	Population
87 pg × h/mL CLINICAL TRIAL https://clinicaltrials.gov/ct2/show/NCT00960323	0.6 mg single, oral dose: 0.6 mg route of administration: oral experiment type: SINGLE co-administered:	COLCHICINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
19.9 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210942s000lbl.pdf	0.6 mg single, oral dose: 0.6 mg route of administration: Oral experiment type: SINGLE co-administered:	COLCHICINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
18.47 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210942s000lbl.pdf	0.6 mg single, oral dose: 0.6 mg route of administration: Oral experiment type: SINGLE co-administered:	COLCHICINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
31.04 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210942s000lbl.pdf	0.6 mg single, oral dose: 0.6 mg route of administration: Oral experiment type: SINGLE co-administered:		COLCHICINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
30.54 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210942s000lbl.pdf	0.6 mg single, oral dose: 0.6 mg route of administration: Oral experiment type: SINGLE co-administered:		COLCHICINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
61% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210942s000lbl.pdf	unknown, oral		COLCHICINE serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2A6 626 CYP2C19 1119 CYP2E1 729 P-gp 2052

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8960070/	no
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8960070/	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8960070/	no
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8960070/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/8960070/	no
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210942s000lbl.pdf#page=2; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/204820Orig1s000ClinPharmR.pdf#page=11 Page: 2.0	yes	likely (co-administration study) Comment: Although there are no published case reports for colchicine toxicity when co-administered with the 4 inhibitors that the sponsor employed, i.e., voriconazole, fluconazole, cimetidine and propafenone, several published case reports indicate that colchicine toxicity is observed when it is co-administered with drugs that are potent inhibitors of both P-gp and CYP3A4 (e.g., clarithromycin, ketoconazole) as well as potent P-gp inhibitors (e.g., cyclosporine). Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210942s000lbl.pdf#page=2; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/204820Orig1s000ClinPharmR.pdf#page=11 Page: 2.0
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210942s000lbl.pdf#page=2; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/204820Orig1s000ClinPharmR.pdf#page=11 Page: 2.0	yes	yes (co-administration study) Comment: Co-administration with posaconazole (considered a strong CYP3A4 inhibitor) increased AUC of colchcine by approximately 3-fold; Although there are no published case reports for colchicine toxicity when co-administered with the 4 inhibitors that the sponsor employed, i.e., voriconazole, fluconazole, cimetidine and propafenone, several published case reports indicate that colchicine toxicity is observed when it is co-administered with drugs that are potent inhibitors of both P-gp and CYP3A4 (e.g., clarithromycin, ketoconazole) and strong to moderate inhibitors of CYP3A4 (e.g., grapefruit juice, erythromycin). Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/210942s000lbl.pdf#page=2; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/204820Orig1s000ClinPharmR.pdf#page=11 Page: 2.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:23359	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:23359
eMolecules	1970918	https://www.emolecules.com/cgi-bin/more?vid=1970918
eMolecules	729203	https://www.emolecules.com/cgi-bin/more?vid=729203
MolPort	MolPort-001-785-612	https://www.molport.com/shop/molecule-link/MolPort-001-785-612

PubMed

Title	Date	PubMed
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991 Jan-Feb	1710653
Accumulation of microtubule-based motor protein in a patient with colchicine myopathy.	2000 Nov 14	11087798
Discovery of a novel compound: insight into mechanisms for acrylamide-induced axonopathy and colchicine-induced apoptotic neuronal cell death.	2001 Aug 3	11478917
Decreased expression of Bcl-x protein during hepatocarcinogenesis induced exogenously and endogenously in rats.	2001 Dec	11749691
The stability of cytokeratin 18 in human liver cells during colchicine-induced microtubule disruption.	2001 Jan	11259854
[Myopathy caused by colchicine with myotonia].	2002 Jul 16-31	12221632
Colchicine-induced myopathy in a teenager with familial Mediterranean fever.	2003 Dec	14632592
[A case of Behçet's disease associated with neuromyopathy induced by combination therapy with colchicine and cyclosporin].	2003 Feb	12692989
Colchicine induces apoptosis in organotypic hippocampal slice cultures.	2003 Feb 28	12576187
Neuroprotective action of flavopiridol, a cyclin-dependent kinase inhibitor, in colchicine-induced apoptosis.	2003 Oct	12941380
Case records of the Massachusetts General Hospital. Weekly clinicopathological exercises. Case 33-2003. A 37-year-old man with a history of alcohol and drug abuse and sudden onset of leg weakness.	2003 Oct 23	14573738
Colchicine-induced myopathy with myotonia in a patient with chronic renal failure.	2003 Sep	12954545
[Neurotoxic effects of medications: an update].	2004	15244167
Colchicine myotoxicity: case reports and literature review.	2004 Dec	15585444
[Experimental study on Sorbaria sorbifolia extract against chronic liver damage in rats].	2004 Oct	15850357
RhoA/ROCK and Cdc42 regulate cell-cell contact and N-cadherin protein level during neurodetermination of P19 embryonal stem cells.	2004 Sep 5	15281068
[Acute coronary syndrome after diclofenac induced coronary spasm].	2005 Apr	15803264
Involvement of cytoskeleton in AhR-dependent CYP1A1 expression.	2006 Apr	16611024
Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression.	2006 Jul 26	16930453
Sweet's syndrome from an Indian perspective: a report of four cases and review of the literature.	2006 Jun	16796632
Synthesis and biological evaluation of B-ring modified colchicine and isocolchicine analogs.	2006 May 15	16504507
Microtubules are required for NF-kappaB nuclear translocation in neuroblastoma IMR-32 cells: modulation by zinc.	2006 Oct	17029595

Patents

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:44:26 GMT 2025` Edited by `admin` on `Mon Mar 31 18:44:26 GMT 2025`
Record UNII	SML2Y3J35T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

COLCHICINUM

Preferred Name

English

Colchicine

Official Name

English

NSC-757

Code

English

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

Common Name

English

COLCHICINE [WHO-IP]

Common Name

English

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

Systematic Name

English

COLCHICINE [USP MONOGRAPH]

Common Name

English

MYINFLA

Brand Name

English

COLBENEMID COMPONENT COLCHICINE

Common Name

English

Colchicine [WHO-DD]

Common Name

English

COLCHICINE [USP-RS]

Common Name

English

COLCHICINE [EP IMPURITY]

Common Name

English

COLCHCINE [VANDF]

Common Name

English

LODOCO

Brand Name

English

GLOPERBA

Brand Name

English

(-)-COLCHICINE

Common Name

English

MITIGARE COMPONENT COLCHICINE

Brand Name

English

PROBEN-C COMPONENT COLCHICINE

Common Name

English

COLCHICINUM [WHO-IP LATIN]

Common Name

English

COLCRYS

Brand Name

English

COLCHINEOS

Common Name

English

COLCHICINE [ORANGE BOOK]

Common Name

English

COLCHICINE [MI]

Common Name

English

COLCHICINUM [HPUS]

Common Name

English

COLCHICINE [EP MONOGRAPH]

Common Name

English

COLCHICINE [JAN]

Common Name

English

COLCHICINE [MART.]

Common Name

English

COL-PROBENECID COMPONENT COLCHICINE

Common Name

English

COLCHISOL

Common Name

English

COLCHICINE [HSDB]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QM04AC01