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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

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

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
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
Accumulation of microtubule-based motor protein in a patient with colchicine myopathy.
2000 Nov 14
Discovery of a novel compound: insight into mechanisms for acrylamide-induced axonopathy and colchicine-induced apoptotic neuronal cell death.
2001 Aug 3
Decreased expression of Bcl-x protein during hepatocarcinogenesis induced exogenously and endogenously in rats.
2001 Dec
The stability of cytokeratin 18 in human liver cells during colchicine-induced microtubule disruption.
2001 Jan
[Myopathy caused by colchicine with myotonia].
2002 Jul 16-31
Colchicine-induced myopathy in a teenager with familial Mediterranean fever.
2003 Dec
[A case of Behçet's disease associated with neuromyopathy induced by combination therapy with colchicine and cyclosporin].
2003 Feb
Colchicine induces apoptosis in organotypic hippocampal slice cultures.
2003 Feb 28
Neuroprotective action of flavopiridol, a cyclin-dependent kinase inhibitor, in colchicine-induced apoptosis.
2003 Oct
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
Colchicine-induced myopathy with myotonia in a patient with chronic renal failure.
2003 Sep
[Neurotoxic effects of medications: an update].
2004
Colchicine myotoxicity: case reports and literature review.
2004 Dec
[Experimental study on Sorbaria sorbifolia extract against chronic liver damage in rats].
2004 Oct
RhoA/ROCK and Cdc42 regulate cell-cell contact and N-cadherin protein level during neurodetermination of P19 embryonal stem cells.
2004 Sep 5
[Acute coronary syndrome after diclofenac induced coronary spasm].
2005 Apr
Involvement of cytoskeleton in AhR-dependent CYP1A1 expression.
2006 Apr
Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression.
2006 Jul 26
Sweet's syndrome from an Indian perspective: a report of four cases and review of the literature.
2006 Jun
Synthesis and biological evaluation of B-ring modified colchicine and isocolchicine analogs.
2006 May 15
Microtubules are required for NF-kappaB nuclear translocation in neuroblastoma IMR-32 cells: modulation by zinc.
2006 Oct
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
  • Download
Name Type Language
COLCHICINUM
HPUS   WHO-IP LATIN  
Preferred Name English
Colchicine
EP   HSDB   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USP  
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
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
FDA ORPHAN DRUG 11085
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
FDA ORPHAN DRUG 245707
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
FDA ORPHAN DRUG 245807
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
NCI_THESAURUS C67421
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
WHO-ATC M04AC01
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
LIVERTOX NBK548068
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
Code System Code Type Description
ECHA (EC/EINECS)
200-598-5
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY
HSDB
3044
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
COLCHICINE
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY Description: Pale yellow to pale greenish yellow crystals, amorphous scales or a powder; odourless or almost odourless.Solubility: Soluble in water; freely soluble in ethanol (~750 g/l) TS; slightly soluble in ether R.Category: Antigout drug.Storage: Colchicine should be kept in a tightly closed container, protected from light.Additional information: Colchicine is an alkaloid obtained from Colchicum autumnale L. (Fam. Liliaceae). It darkens on exposureto light. CAUTION: Colchicine is extremely poisonous and must be handled with care.
LACTMED
Colchicine
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY
MERCK INDEX
m3725
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY Merck Index
FDA UNII
SML2Y3J35T
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY
MESH
D003078
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PRIMARY
ChEMBL
CHEMBL107
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PRIMARY
PUBCHEM
6167
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY
NDF-RT
N0000000239
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY P-Glycoprotein Interactions [MoA]
NDF-RT
N0000182141
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY Cytochrome P450 3A4 Inhibitors [MoA]
DAILYMED
SML2Y3J35T
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY
CAS
64-86-8
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PRIMARY
NCI_THESAURUS
C385
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY
CHEBI
27882
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PRIMARY
EPA CompTox
DTXSID5024845
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY
DRUG CENTRAL
726
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY
IUPHAR
2367
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY
NSC
757
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY
RS_ITEM_NUM
1146006
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY
RXCUI
2683
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY RxNorm
WIKIPEDIA
COLCHICINE
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY
EVMPD
SUB01420MIG
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY
SMS_ID
100000090556
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY
DRUG BANK
DB01394
Created by admin on Mon Mar 31 18:44:26 GMT 2025 , Edited by admin on Mon Mar 31 18:44:26 GMT 2025
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
TARGET->INHIBITOR OF AGGREGATION
DESTABILIZES TUBULIN POLYMERS
DERIVATIVE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
APICAL
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Related Record Type Details
METABOLITE LESS ACTIVE -> PARENT
URINE
METABOLITE LESS ACTIVE -> PARENT
URINE
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC