Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H25NO6 |
| Molecular Weight | 399.437 |
| Optical Activity | UNSPECIFIED |
| Additional Stereochemistry | Yes |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
| Stereo Comments | P-helix |
SHOW SMILES / InChI
SMILES
COC1=C(OC)C(OC)=C2C(CC[C@H](NC(C)=O)C3=CC(=O)C(OC)=CC=C23)=C1
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 |
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2095182 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| 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 |
|||
| 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 |
|
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 |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
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 |
|||
| 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 |
|---|---|---|
| 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 myoneuropathy and renal dysfunction. | 1992 Dec |
|
| Colchicine-induced myoneuropathy in a renal transplant patient. | 1992 Jun |
|
| Acute neuromyopathy after colchicine treatment. | 1992 Nov |
|
| Acute myopathy induced by colchicine in a cyclosporine treated heart transplant recipient: possible role of the multidrug resistance transporter. | 1999 Aug |
|
| Induced differentiation in HT29, a human colon adenocarcinoma cell line. | 1999 Aug |
|
| [Neuromuscular complications of long-term treatment of inflammatory diseases. 3 cases]. | 1999 Dec |
|
| Treatment of linear IgA bullous dermatosis of childhood with colchicine. | 1999 Jan-Feb |
|
| Hypernatraemia and polyuria due to high-dose colchicine in a suicidal patient. | 1999 Jun |
|
| Colchicine protects mice from the lethal effect of an agonistic anti-Fas antibody. | 2000 Feb |
|
| [Fibroblastic rheumatism: a case report]. | 2001 Apr |
|
| Developing a model of colchicine neuropathy. | 2002 |
|
| Colchicine myopathy: a vacuolar myopathy with selective type I muscle fiber involvement. An immunohistochemical and electron microscopic study of two cases. | 2002 Feb |
|
| Mechanisms by which cAMP increases bile acid secretion in rat liver and canalicular membrane vesicles. | 2003 Aug |
|
| Colchicine-induced rhabdomyolysis in a patient with chronic heart failure. | 2003 Dec |
|
| 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 |
|
| Permanent activation of the human P-glycoprotein by covalent modification of a residue in the drug-binding site. | 2003 Jun 6 |
|
| [Neurotoxic effects of medications: an update]. | 2004 |
|
| Microtubule disarray in primary cultures of human hepatocytes inhibits transcriptional activity of the glucocorticoid receptor via activation of c-jun N-terminal kinase. | 2004 Dec |
|
| Colchicine myotoxicity: case reports and literature review. | 2004 Dec |
|
| Establishment of a P-glycoprotein substrate screening model and its preliminary application. | 2004 May 1 |
|
| Effects of colchicine on the maximum biliary excretion of cholephilic compounds in rats. | 2004 Sep |
|
| Implication of cyclin-dependent kinase 5 in the neuroprotective properties of lithium. | 2005 |
|
| Establishment and characterization of new cellular lymphoma model expressing transgenic human MDR1. | 2005 Apr |
|
| Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression. | 2006 Jul 26 |
|
| [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 Jun |
|
| Cyclosporine not the only agent to cause Guillain-Barré-like syndrome after solid-organ transplant. | 2006 Nov |
Sample Use Guides
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
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 |
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| Record Version |
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Preferred Name | English | ||
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Common Name | English | ||
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Created by
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