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
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
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 |
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 |
---|---|---|---|---|
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 |
||
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 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 |
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 |
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Record Status |
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Record Version |
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