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 |
---|---|---|---|---|
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 Date1.24891195E12 |
||
Primary | COLCRYS Approved UseColchicine is indicated for Familial Mediterranean fever (FMF) in adults and children 4 years or older Launch Date1.24891195E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
8717.33 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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
61% |
COLCHICINE serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
50 mg single, oral Overdose |
unknown, 42 years n = 1 Health Status: unknown Age Group: 42 years Sex: M Population Size: 1 Sources: |
Other AEs: Myelosuppression... |
3 mg 1 times / day multiple, oral MTD Dose: 3 mg, 1 times / day Route: oral Route: multiple Dose: 3 mg, 1 times / day Sources: |
unhealthy, 44 years (range: 39.5–48.5 years) n = 15 Health Status: unhealthy Condition: familial Mediterranean fever Age Group: 44 years (range: 39.5–48.5 years) Sex: M+F Population Size: 15 Sources: |
|
1 mg 1 times / week multiple, intravenous Dose: 1 mg, 1 times / week Route: intravenous Route: multiple Dose: 1 mg, 1 times / week Sources: |
unhealthy, 44 years (range: 39.5–48.5 years) n = 15 Health Status: unhealthy Condition: familial Mediterranean fever Age Group: 44 years (range: 39.5–48.5 years) Sex: M+F Population Size: 15 Sources: |
Other AEs: Nausea, Vomiting... Other AEs: Nausea (27%) Sources: Vomiting (13%) Diarrhea (20%) Injection site reactions (20%) Myalgia (27%) Arthralgia (7%) Allergic reaction (7%) |
12 mg single, oral Overdose |
unknown, 56 years n = 1 Health Status: unknown Age Group: 56 years Sex: M Population Size: 1 Sources: |
Other AEs: Rhabdomyolysis... |
1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 79 years n = 1 Health Status: unhealthy Age Group: 79 years Sex: M Population Size: 1 Sources: |
Disc. AE: Acute pancreatitis, Epigastric pain... AEs leading to discontinuation/dose reduction: Acute pancreatitis (1 patient) Sources: Epigastric pain (severe, 1 patient) Nausea (1 patient) Vomiting (1 patient) |
0.6 mg 2 times / day multiple, oral Dose: 0.6 mg, 2 times / day Route: oral Route: multiple Dose: 0.6 mg, 2 times / day Sources: |
unhealthy n = 49 Health Status: unhealthy Condition: Thoracic Surgery Population Size: 49 Sources: |
Other AEs: Acute respiratory distress syndrome, Fall... Other AEs: Acute respiratory distress syndrome (serious, 3 patients) Sources: Fall (serious, 2 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Myelosuppression | grade 4, 1 patient | 50 mg single, oral Overdose |
unknown, 42 years n = 1 Health Status: unknown Age Group: 42 years Sex: M Population Size: 1 Sources: |
Vomiting | 13% | 1 mg 1 times / week multiple, intravenous Dose: 1 mg, 1 times / week Route: intravenous Route: multiple Dose: 1 mg, 1 times / week Sources: |
unhealthy, 44 years (range: 39.5–48.5 years) n = 15 Health Status: unhealthy Condition: familial Mediterranean fever Age Group: 44 years (range: 39.5–48.5 years) Sex: M+F Population Size: 15 Sources: |
Diarrhea | 20% | 1 mg 1 times / week multiple, intravenous Dose: 1 mg, 1 times / week Route: intravenous Route: multiple Dose: 1 mg, 1 times / week Sources: |
unhealthy, 44 years (range: 39.5–48.5 years) n = 15 Health Status: unhealthy Condition: familial Mediterranean fever Age Group: 44 years (range: 39.5–48.5 years) Sex: M+F Population Size: 15 Sources: |
Injection site reactions | 20% | 1 mg 1 times / week multiple, intravenous Dose: 1 mg, 1 times / week Route: intravenous Route: multiple Dose: 1 mg, 1 times / week Sources: |
unhealthy, 44 years (range: 39.5–48.5 years) n = 15 Health Status: unhealthy Condition: familial Mediterranean fever Age Group: 44 years (range: 39.5–48.5 years) Sex: M+F Population Size: 15 Sources: |
Myalgia | 27% | 1 mg 1 times / week multiple, intravenous Dose: 1 mg, 1 times / week Route: intravenous Route: multiple Dose: 1 mg, 1 times / week Sources: |
unhealthy, 44 years (range: 39.5–48.5 years) n = 15 Health Status: unhealthy Condition: familial Mediterranean fever Age Group: 44 years (range: 39.5–48.5 years) Sex: M+F Population Size: 15 Sources: |
Nausea | 27% | 1 mg 1 times / week multiple, intravenous Dose: 1 mg, 1 times / week Route: intravenous Route: multiple Dose: 1 mg, 1 times / week Sources: |
unhealthy, 44 years (range: 39.5–48.5 years) n = 15 Health Status: unhealthy Condition: familial Mediterranean fever Age Group: 44 years (range: 39.5–48.5 years) Sex: M+F Population Size: 15 Sources: |
Allergic reaction | 7% | 1 mg 1 times / week multiple, intravenous Dose: 1 mg, 1 times / week Route: intravenous Route: multiple Dose: 1 mg, 1 times / week Sources: |
unhealthy, 44 years (range: 39.5–48.5 years) n = 15 Health Status: unhealthy Condition: familial Mediterranean fever Age Group: 44 years (range: 39.5–48.5 years) Sex: M+F Population Size: 15 Sources: |
Arthralgia | 7% | 1 mg 1 times / week multiple, intravenous Dose: 1 mg, 1 times / week Route: intravenous Route: multiple Dose: 1 mg, 1 times / week Sources: |
unhealthy, 44 years (range: 39.5–48.5 years) n = 15 Health Status: unhealthy Condition: familial Mediterranean fever Age Group: 44 years (range: 39.5–48.5 years) Sex: M+F Population Size: 15 Sources: |
Rhabdomyolysis | grade 5, 1 patient | 12 mg single, oral Overdose |
unknown, 56 years n = 1 Health Status: unknown Age Group: 56 years Sex: M Population Size: 1 Sources: |
Acute pancreatitis | 1 patient Disc. AE |
1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 79 years n = 1 Health Status: unhealthy Age Group: 79 years Sex: M Population Size: 1 Sources: |
Nausea | 1 patient Disc. AE |
1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 79 years n = 1 Health Status: unhealthy Age Group: 79 years Sex: M Population Size: 1 Sources: |
Vomiting | 1 patient Disc. AE |
1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 79 years n = 1 Health Status: unhealthy Age Group: 79 years Sex: M Population Size: 1 Sources: |
Epigastric pain | severe, 1 patient Disc. AE |
1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 79 years n = 1 Health Status: unhealthy Age Group: 79 years Sex: M Population Size: 1 Sources: |
Fall | serious, 2 patients | 0.6 mg 2 times / day multiple, oral Dose: 0.6 mg, 2 times / day Route: oral Route: multiple Dose: 0.6 mg, 2 times / day Sources: |
unhealthy n = 49 Health Status: unhealthy Condition: Thoracic Surgery Population Size: 49 Sources: |
Acute respiratory distress syndrome | serious, 3 patients | 0.6 mg 2 times / day multiple, oral Dose: 0.6 mg, 2 times / day Route: oral Route: multiple Dose: 0.6 mg, 2 times / day Sources: |
unhealthy n = 49 Health Status: unhealthy Condition: Thoracic Surgery Population Size: 49 Sources: |
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 |
|
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 |
|
Serum interleukin-2 and tumor necrosis factor-alpha in primary biliary cirrhosis: decrease by colchicine and relationship to HLA-DR4. | 1992 Apr |
|
Colchicine-induced myoneuropathy in a renal transplant patient. | 1992 Jun |
|
Acute neuromyopathy after colchicine treatment. | 1992 Nov |
|
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 |
|
Developing a model of colchicine neuropathy. | 2002 |
|
Anti-inflammatory fibrosis suppression in threatened trabeculectomy bleb failure produces good long term control of intraocular pressure without risk of sight threatening complications. | 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 |
|
[Summary of the Dutch College of General Practitioners' "Gout" Standard]. | 2002 Feb 16 |
|
Colchicine myoneuropathy in a renal transplant patient. | 2002 Jul |
|
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 |
|
Mechanisms by which cAMP increases bile acid secretion in rat liver and canalicular membrane vesicles. | 2003 Aug |
|
[A case of Behçet's disease associated with neuromyopathy induced by combination therapy with colchicine and cyclosporin]. | 2003 Feb |
|
The role of the cytoskeleton in mechanotransduction in human osteoblast-like cells. | 2003 May |
|
Exocytotic "constipation" is a mechanism of tubulin/lysosomal interaction in colchicine myopathy. | 2003 May 1 |
|
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 |
|
[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 |
|
Cytoskeletal myotoxicity from simvastatin and colchicine. | 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 |
|
[Abdominal pain and recurrent cholestatic jaundice]. | 2004 Jun 9 |
|
Acute poisoning with autumn crocus (Colchicum autumnale L.). | 2004 Mar 31 |
|
Myelodysplasia and acute myeloid leukaemia in a case of rheumatoid arthritis with secondary amyloidosis treated with chlorambucil. | 2004 May |
|
Establishment of a P-glycoprotein substrate screening model and its preliminary application. | 2004 May 1 |
|
[Experimental study on Sorbaria sorbifolia extract against chronic liver damage in rats]. | 2004 Oct |
|
Celastraceae sesquiterpenes as a new class of modulators that bind specifically to human P-glycoprotein and reverse cellular multidrug resistance. | 2004 Oct 1 |
|
Effects of colchicine on the maximum biliary excretion of cholephilic compounds in rats. | 2004 Sep |
|
RhoA/ROCK and Cdc42 regulate cell-cell contact and N-cadherin protein level during neurodetermination of P19 embryonal stem cells. | 2004 Sep 5 |
|
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 |
|
Induction of resistance to Aplidin in a human ovarian cancer cell line related to MDR expression. | 2005 Dec |
|
Chromosomal aberrations in lymphocytes of healthy subjects and risk of cancer. | 2005 May |
|
[A case report of acute neuromyopathy induced by concomitant use of colchicine and bezafibrate]. | 2005 Sep |
|
An unusual cause of renal amyloidosis secondary to gout: the first description of familial occurrence. | 2006 |
|
Expression of corticosterone-binding globulin in the rat hypothalamus. | 2006 Apr |
|
Colchicine myoneuropathy in chronic renal failure patients with gout. | 2006 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 |
|
Cyclosporine not the only agent to cause Guillain-Barré-like syndrome after solid-organ transplant. | 2006 Nov |
|
Neuroprotective effects of resveratrol against intracerebroventricular colchicine-induced cognitive impairment and oxidative stress in rats. | 2007 |
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
by
admin
on
Edited
Thu Jul 06 00:39:59 UTC 2023
by
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on
Thu Jul 06 00:39:59 UTC 2023
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Record UNII |
SML2Y3J35T
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Record Status |
Validated (UNII)
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Record Version |
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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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D003078
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CHEMBL107
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6167
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N0000000239
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N0000182141
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C385
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COLCHICINE
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SUB01420MIG
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DB01394
Created by
admin on Thu Jul 06 00:39:59 UTC 2023 , Edited by admin on Thu Jul 06 00:39:59 UTC 2023
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PRIMARY |
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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METABOLIC ENZYME -> SUBSTRATE |
APICAL
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> SUBSTRATE |
Related Record | Type | Details | ||
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METABOLITE LESS ACTIVE -> PARENT |
URINE
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METABOLITE LESS ACTIVE -> PARENT |
URINE
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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Related Record | Type | Details | ||
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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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