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
Zinc and the cytoskeleton in the neuronal modulation of transcription factor NFAT.	2007-01	17044076
Neuroprotective effects of resveratrol against intracerebroventricular colchicine-induced cognitive impairment and oxidative stress in rats.	2007	17135773
Comparison of the mutagenic potential of 17 physical and chemical agents analyzed by the flow cytometry mutation assay.	2006-12-01	17045307
Colchicine and HMG Co-A reductase inhibitors induced myopathy-a case report.	2006-12	17049607
Cyclosporine not the only agent to cause Guillain-Barré-like syndrome after solid-organ transplant.	2006-11	17097509
Microtubules are required for NF-kappaB nuclear translocation in neuroblastoma IMR-32 cells: modulation by zinc.	2006-10	17029595
Preplaced cell division: a critical mechanism of autoprotection against S-1,2-dichlorovinyl-L-cysteine-induced acute renal failure and death in mice.	2006-08	16495211
Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression.	2006-07-26	16930453
Colchicine therapy and the cognitive status of elderly patients with familial Mediterranean fever.	2006-07	16889161
[Effect of the ethyl acetate extract of zhi ju zi on serum makers and the expression of TGF-beta1 in rats with hepatic fibrosis].	2006-06	17039882
Sweet's syndrome from an Indian perspective: a report of four cases and review of the literature.	2006-06	16796632
Synthesis and biological evaluation of B-ring modified colchicine and isocolchicine analogs.	2006-05-15	16504507
Expression of corticosterone-binding globulin in the rat hypothalamus.	2006-04	16700006
Colchicine myoneuropathy in chronic renal failure patients with gout.	2006-04	16669978
Involvement of cytoskeleton in AhR-dependent CYP1A1 expression.	2006-04	16611024
A role for mixed lineage kinases in granule cell apoptosis induced by cytoskeletal disruption.	2006-03	16478524
An unusual cause of renal amyloidosis secondary to gout: the first description of familial occurrence.	2006	17065112
Induction of resistance to Aplidin in a human ovarian cancer cell line related to MDR expression.	2005-12	16258264
Acute renal failure associated with an accidental overdose of colchicine.	2005-10	16240705
Tetraparesis associated with colchicine is probably due to inhibition by verapamil of the P-glycoprotein efflux pump in the blood-brain barrier.	2005-09-17	16148013
[Nephrogenic diabetes insipidus induced by colchicine--a case report].	2005-09	16708563
[A case report of acute neuromyopathy induced by concomitant use of colchicine and bezafibrate].	2005-09	16248366
Fatal interaction between clarithromycin and colchicine in patients with renal insufficiency: a retrospective study.	2005-08-01	16007523
Acute myopathy in a patient with concomitant use of pravastatin and colchicine.	2005-05-26	15914514
Chromosomal aberrations in lymphocytes of healthy subjects and risk of cancer.	2005-05	15866756
Monozygotic twins concordant for intestinal Behçet's disease.	2005-04	15870978
[Acute coronary syndrome after diclofenac induced coronary spasm].	2005-04	15803264
Establishment and characterization of new cellular lymphoma model expressing transgenic human MDR1.	2005-04	15725475
Implication of cyclin-dependent kinase 5 in the neuroprotective properties of lithium.	2005	15979805
RLIP76 (RALBP1)-mediated transport of leukotriene C4 (LTC4) in cancer cells: implications in drug resistance.	2004-12-20	15386349
Microtubule disarray in primary cultures of human hepatocytes inhibits transcriptional activity of the glucocorticoid receptor via activation of c-jun N-terminal kinase.	2004-12	15744361
Colchicine myotoxicity: case reports and literature review.	2004-12	15585444
Cytoskeletal myotoxicity from simvastatin and colchicine.	2004-12	15389652
Analysis of ATP-binding cassette transporter expression in drug-selected cell lines by a microarray dedicated to multidrug resistance.	2004-12	15342794
Celastraceae sesquiterpenes as a new class of modulators that bind specifically to human P-glycoprotein and reverse cellular multidrug resistance.	2004-10-01	15466210
[Experimental study on Sorbaria sorbifolia extract against chronic liver damage in rats].	2004-10	15850357
RhoA/ROCK and Cdc42 regulate cell-cell contact and N-cadherin protein level during neurodetermination of P19 embryonal stem cells.	2004-09-05	15281068
Effects of colchicine on the maximum biliary excretion of cholephilic compounds in rats.	2004-09	15304119
[Abdominal pain and recurrent cholestatic jaundice].	2004-06-09	15318531
Establishment of a P-glycoprotein substrate screening model and its preliminary application.	2004-05-01	15112361
Myelodysplasia and acute myeloid leukaemia in a case of rheumatoid arthritis with secondary amyloidosis treated with chlorambucil.	2004-05	15656036
Acute poisoning with autumn crocus (Colchicum autumnale L.).	2004-03-31	15088997
[Neurotoxic effects of medications: an update].	2004	15244167
Abstracts of the Fourth International Symposium on Molecular Insect Science. May 28-June 2, 2002. Tucson, Arizona, USA.	2002	15455051
[Treatment of AL-amyloidosis and some other types of amyloidosis].	2001-01	15635868
Colchicine-induced myoneuropathy in a renal transplant patient.	1992-06	1604496
Serum interleukin-2 and tumor necrosis factor-alpha in primary biliary cirrhosis: decrease by colchicine and relationship to HLA-DR4.	1992-04	1553933
Colchicine myopathy in a case of familial Mediterranean fever: immunohistochemical and ultrastructural study of accumulated tubulin-immunoreactive material.	1992	1575022
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991-01-01	1710653
Colchicine-induced lesions in the rat duodenum.	1975	171611

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