COLCHICINE SALICYLATE

First marketed in 1921

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H25NO6.C7H6O3
Molecular Weight	537.5577
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=CC=CC=C1O.COC2=CC3=C(C(OC)=C2OC)C4=CC=C(OC)C(=O)C=C4[C@H](CC3)NC(C)=O

InChI

InChIKey=FJDBYGKCGURUGE-NTISSMGPSA-N

InChI=1S/C22H25NO6.C7H6O3/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;8-6-4-2-1-3-5(6)7(9)10/h7,9-11,16H,6,8H2,1-5H3,(H,23,24);1-4,8H,(H,9,10)/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

Molecular Formula	C7H6O3
Molecular Weight	138.1207
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Colchicine-induced lesions in the rat duodenum.	1975	171611
Acute myelomonocytic leukaemia and multiple myeloma after sulphinpyrazone and colchicine treatment of gout.	1976 Jul 10	1064465
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991 Jan-Feb	1710653
Colchicine myopathy in a case of familial Mediterranean fever: immunohistochemical and ultrastructural study of accumulated tubulin-immunoreactive material.	1992	1575022
Colchicine-induced myopathy in renal failure.	1997 Oct	10904571
[Neuromuscular complications of long-term treatment of inflammatory diseases. 3 cases].	1999 Dec	10686640
Colchicine protects mice from the lethal effect of an agonistic anti-Fas antibody.	2000 Feb	10675359
Slow polymerization of Mycobacterium tuberculosis FtsZ.	2000 Jul	10869082
Accumulation of microtubule-based motor protein in a patient with colchicine myopathy.	2000 Nov 14	11087798
[Fibroblastic rheumatism: a case report].	2001 Apr	11339131
Discovery of a novel compound: insight into mechanisms for acrylamide-induced axonopathy and colchicine-induced apoptotic neuronal cell death.	2001 Aug 3	11478917
Danggui shaoyao san improve colchichine-induced learning acquisition impairment in rats.	2001 Dec	11749816
Decreased expression of Bcl-x protein during hepatocarcinogenesis induced exogenously and endogenously in rats.	2001 Dec	11749691
Colchicine-induced myopathy with normal creatine phosphokinase level in a renal transplant patient.	2002 Dec	12399640
Colchicine myopathy: a vacuolar myopathy with selective type I muscle fiber involvement. An immunohistochemical and electron microscopic study of two cases.	2002 Feb	11810174
2-Alkoxycarbonylaminopyridines: inhibitors of Mycobacterium tuberculosis FtsZ.	2002 Jul	12096015
[Myopathy caused by colchicine with myotonia].	2002 Jul 16-31	12221632
Functional analysis of MRP1 cloned from bovine.	2002 Jun 19	12067707
Improvement of combination chemotherapy tolerance by introduction of polycistronic retroviral vector drug resistance genes MGMT and MDR1 into human umbilical cord blood CD34+ cells.	2002 Mar	11792417
Nocodazole-induced p53-dependent c-Jun N-terminal kinase activation reduces apoptosis in human colon carcinoma HCT116 cells.	2002 Nov 15	12221076
Colchicine-induced acute myopathy in a patient with concomitant use of simvastatin.	2002 Sep-Oct	12410059
Mechanisms by which cAMP increases bile acid secretion in rat liver and canalicular membrane vesicles.	2003 Aug	12702492
Exocytotic "constipation" is a mechanism of tubulin/lysosomal interaction in colchicine myopathy.	2003 May 1	12706115
Cytoskeletal myotoxicity from simvastatin and colchicine.	2004 Dec	15389652
Analysis of ATP-binding cassette transporter expression in drug-selected cell lines by a microarray dedicated to multidrug resistance.	2004 Dec	15342794
RLIP76 (RALBP1)-mediated transport of leukotriene C4 (LTC4) in cancer cells: implications in drug resistance.	2004 Dec 20	15386349
Severe respiratory muscle weakness related to long-term colchicine therapy.	2004 Feb	14744269
Implication of cyclin-dependent kinase 5 in the neuroprotective properties of lithium.	2005	15979805
[Acute coronary syndrome after diclofenac induced coronary spasm].	2005 Apr	15803264
Acute myopathy in a patient with concomitant use of pravastatin and colchicine.	2005 Jul-Aug	15914514
Acute renal failure associated with an accidental overdose of colchicine.	2005 Oct	16240705
[A case report of acute neuromyopathy induced by concomitant use of colchicine and bezafibrate].	2005 Sep	16248366
Colchicine therapy and the cognitive status of elderly patients with familial Mediterranean fever.	2006 Jul	16889161
Sweet's syndrome from an Indian perspective: a report of four cases and review of the literature.	2006 Jun	16796632
A role for mixed lineage kinases in granule cell apoptosis induced by cytoskeletal disruption.	2006 Mar	16478524

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 17:48:33 GMT 2025` Edited by `admin` on `Mon Mar 31 17:48:33 GMT 2025`
Record UNII	I59XKK41WY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SALICYLATED COLCHICINE

Preferred Name

English

COLCHICINE SALICYLATE

Common Name

English

Code System Code Type Description

PUBCHEM

25113322