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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 of COLCHICINE SALICYLATE

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

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

Curator's Comment: Known to be CNS non-penetrant in rats. Human data not available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
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
Primary
COLCRYS

Approved Use

Colchicine is indicated for Familial Mediterranean fever (FMF) in adults and children 4 years or older

Launch Date

2009
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2023.29 pg/mL
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
87 pg × h/mL
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
31.04 h
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
61%
unknown, oral
COLCHICINE serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
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).
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).
Page: 2.0
PubMed

PubMed

TitleDatePubMed
Colchicine-induced lesions in the rat duodenum.
1975
Acute myelomonocytic leukaemia and multiple myeloma after sulphinpyrazone and colchicine treatment of gout.
1976 Jul 10
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
Colchicine myopathy in a case of familial Mediterranean fever: immunohistochemical and ultrastructural study of accumulated tubulin-immunoreactive material.
1992
Colchicine-induced myopathy in renal failure.
1997 Oct
[Neuromuscular complications of long-term treatment of inflammatory diseases. 3 cases].
1999 Dec
Colchicine protects mice from the lethal effect of an agonistic anti-Fas antibody.
2000 Feb
Slow polymerization of Mycobacterium tuberculosis FtsZ.
2000 Jul
Accumulation of microtubule-based motor protein in a patient with colchicine myopathy.
2000 Nov 14
[Fibroblastic rheumatism: a case report].
2001 Apr
Discovery of a novel compound: insight into mechanisms for acrylamide-induced axonopathy and colchicine-induced apoptotic neuronal cell death.
2001 Aug 3
Danggui shaoyao san improve colchichine-induced learning acquisition impairment in rats.
2001 Dec
Decreased expression of Bcl-x protein during hepatocarcinogenesis induced exogenously and endogenously in rats.
2001 Dec
Colchicine-induced myopathy with normal creatine phosphokinase level in a renal transplant patient.
2002 Dec
Colchicine myopathy: a vacuolar myopathy with selective type I muscle fiber involvement. An immunohistochemical and electron microscopic study of two cases.
2002 Feb
2-Alkoxycarbonylaminopyridines: inhibitors of Mycobacterium tuberculosis FtsZ.
2002 Jul
[Myopathy caused by colchicine with myotonia].
2002 Jul 16-31
Functional analysis of MRP1 cloned from bovine.
2002 Jun 19
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
Nocodazole-induced p53-dependent c-Jun N-terminal kinase activation reduces apoptosis in human colon carcinoma HCT116 cells.
2002 Nov 15
Colchicine-induced acute myopathy in a patient with concomitant use of simvastatin.
2002 Sep-Oct
Mechanisms by which cAMP increases bile acid secretion in rat liver and canalicular membrane vesicles.
2003 Aug
Exocytotic "constipation" is a mechanism of tubulin/lysosomal interaction in colchicine myopathy.
2003 May 1
Cytoskeletal myotoxicity from simvastatin and colchicine.
2004 Dec
Analysis of ATP-binding cassette transporter expression in drug-selected cell lines by a microarray dedicated to multidrug resistance.
2004 Dec
RLIP76 (RALBP1)-mediated transport of leukotriene C4 (LTC4) in cancer cells: implications in drug resistance.
2004 Dec 20
Severe respiratory muscle weakness related to long-term colchicine therapy.
2004 Feb
Implication of cyclin-dependent kinase 5 in the neuroprotective properties of lithium.
2005
[Acute coronary syndrome after diclofenac induced coronary spasm].
2005 Apr
Acute myopathy in a patient with concomitant use of pravastatin and colchicine.
2005 Jul-Aug
Acute renal failure associated with an accidental overdose of colchicine.
2005 Oct
[A case report of acute neuromyopathy induced by concomitant use of colchicine and bezafibrate].
2005 Sep
Colchicine therapy and the cognitive status of elderly patients with familial Mediterranean fever.
2006 Jul
Sweet's syndrome from an Indian perspective: a report of four cases and review of the literature.
2006 Jun
A role for mixed lineage kinases in granule cell apoptosis induced by cytoskeletal disruption.
2006 Mar
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
Created by admin on Mon Mar 31 17:48:33 GMT 2025 , Edited by admin on Mon Mar 31 17:48:33 GMT 2025
PRIMARY
CAS
7541-98-2
Created by admin on Mon Mar 31 17:48:33 GMT 2025 , Edited by admin on Mon Mar 31 17:48:33 GMT 2025
SUPERSEDED
FDA UNII
I59XKK41WY
Created by admin on Mon Mar 31 17:48:33 GMT 2025 , Edited by admin on Mon Mar 31 17:48:33 GMT 2025
PRIMARY
CAS
8013-62-5
Created by admin on Mon Mar 31 17:48:33 GMT 2025 , Edited by admin on Mon Mar 31 17:48:33 GMT 2025
PRIMARY
EPA CompTox
DTXSID60230088
Created by admin on Mon Mar 31 17:48:33 GMT 2025 , Edited by admin on Mon Mar 31 17:48:33 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY