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
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
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 |
DescriptionSources: https://www.drugs.com/pro/colchicine.html
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
Sources: https://link.springer.com/article/10.1007/BF02432374
Curator's Comment: Known to be CNS non-penetrant in rats. Human data not available.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095182 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26132075 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Sources: https://www.drugs.com/pro/colchicine.html |
Preventing | COLCRYS Approved UseColchicine 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 Date2009 |
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Primary | COLCRYS Approved UseColchicine is indicated for Familial Mediterranean fever (FMF) in adults and children 4 years or older Launch Date2009 |
Cmax
Value | Dose | Co-administered | 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 |
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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
Value | Dose | Co-administered | 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 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
61% |
unknown, oral |
COLCHICINE serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as victim
Target | Modality | Activity | Metabolite | Clinical 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 |
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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
Title | Date | PubMed |
---|---|---|
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
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Accumulation of microtubule-based motor protein in a patient with colchicine myopathy. | 2000 Nov 14 |
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Discovery of a novel compound: insight into mechanisms for acrylamide-induced axonopathy and colchicine-induced apoptotic neuronal cell death. | 2001 Aug 3 |
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Decreased expression of Bcl-x protein during hepatocarcinogenesis induced exogenously and endogenously in rats. | 2001 Dec |
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The stability of cytokeratin 18 in human liver cells during colchicine-induced microtubule disruption. | 2001 Jan |
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[Myopathy caused by colchicine with myotonia]. | 2002 Jul 16-31 |
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Colchicine-induced myopathy in a teenager with familial Mediterranean fever. | 2003 Dec |
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[A case of Behçet's disease associated with neuromyopathy induced by combination therapy with colchicine and cyclosporin]. | 2003 Feb |
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Colchicine induces apoptosis in organotypic hippocampal slice cultures. | 2003 Feb 28 |
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Neuroprotective action of flavopiridol, a cyclin-dependent kinase inhibitor, in colchicine-induced apoptosis. | 2003 Oct |
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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 |
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Colchicine-induced myopathy with myotonia in a patient with chronic renal failure. | 2003 Sep |
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[Neurotoxic effects of medications: an update]. | 2004 |
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Colchicine myotoxicity: case reports and literature review. | 2004 Dec |
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[Experimental study on Sorbaria sorbifolia extract against chronic liver damage in rats]. | 2004 Oct |
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RhoA/ROCK and Cdc42 regulate cell-cell contact and N-cadherin protein level during neurodetermination of P19 embryonal stem cells. | 2004 Sep 5 |
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[Acute coronary syndrome after diclofenac induced coronary spasm]. | 2005 Apr |
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Involvement of cytoskeleton in AhR-dependent CYP1A1 expression. | 2006 Apr |
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Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression. | 2006 Jul 26 |
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Sweet's syndrome from an Indian perspective: a report of four cases and review of the literature. | 2006 Jun |
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Synthesis and biological evaluation of B-ring modified colchicine and isocolchicine analogs. | 2006 May 15 |
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Microtubules are required for NF-kappaB nuclear translocation in neuroblastoma IMR-32 cells: modulation by zinc. | 2006 Oct |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/colchicine.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2299625
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
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Record UNII |
SML2Y3J35T
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Record Status |
Validated (UNII)
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WHO-VATC |
QM04AC01
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FDA ORPHAN DRUG |
11085
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FDA ORPHAN DRUG |
245707
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FDA ORPHAN DRUG |
245807
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NCI_THESAURUS |
C67421
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WHO-ATC |
M04AC01
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LIVERTOX |
NBK548068
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200-598-5
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3044
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COLCHICINE
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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. | ||
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Colchicine
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m3725
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CHEMBL107
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6167
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N0000000239
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N0000182141
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PRIMARY | Cytochrome P450 3A4 Inhibitors [MoA] | ||
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C385
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COLCHICINE
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SUB01420MIG
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DB01394
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Related Record | Type | Details | ||
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BINDER->LIGAND |
BINDING
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TARGET->INHIBITOR OF AGGREGATION |
DESTABILIZES TUBULIN POLYMERS
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DERIVATIVE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
APICAL
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> SUBSTRATE |
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METABOLITE LESS ACTIVE -> PARENT |
URINE
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METABOLITE LESS ACTIVE -> PARENT |
URINE
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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