Colchicine

Identification

Summary

Colchicine is an alkaloid used in the symptomatic relief of pain in attacks of gout and to treat the inflammatory symptoms of Familial Mediterranean Fever (FMF).

Brand Names
Colcrys, Gloperba, Mitigare
Generic Name
Colchicine
DrugBank Accession Number
DB01394
Background

First approved by the FDA in 1961, colchicine is an alkaloid drug commonly used in the management of gout, a condition associated with the painful deposition of urate crystals in the joints.6,13 It is derived from a plant belonging to the Lily family, known as Colchicum autumnale, or "autumn crocus".5 Other than its use in gout, colchicine has been approved for managing exacerbations of Familial Mediterranean Fever (FMF), a hereditary autoinflammatory condition.7,14

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 399.443
Monoisotopic: 399.168187529
Chemical Formula
C22H25NO6
Synonyms
  • Colchicin
  • Colchicina
  • Colchicine
  • Colchicinum

Pharmacology

Indication

Colchicine is indicated for the prophylaxis and treatment of gout flares. It is also indicated in Familial Mediterranean fever (FMF) in children and adults of 4 years of age and older. It is important to note that this medication is not a pain reliever to be used for other painful conditions. Consider analgesics for this purpose.13 Some off-label uses of colchicine include the treatment of the manifestations of Behcet's syndrome, pericarditis, and postpericardiotomy syndrome.8,9

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Colchicine reduces the pain resulting from gout and reduces flares of Familial Mediterranean fever by interfering with inflammatory pathways.2,13 This drug has a narrow therapeutic index.12

Mechanism of action

The exact mechanism of action of colchicine has not been fully established, however likely occurs via the downstream inhibition of inflammation caused by tubulin disruption.2 Studies have implied that that colchicine causes disruption of the inflammasome complex that is present in both monocytes and neutrophils, which normally leads to the activation of interleukin-1, an important mediator of inflammation.3 In addition to the above actions, colchicine acts to interfere with pathways including neutrophil adhesion and recruitment, superoxide production, the RhoA/Rho effector kinase (ROCK) pathway, as well as a type of nuclear factor κΒ (NF-κΒ) pathway, reducing inflammation.5

On a molecular level, colchicine can be described as an anti-mitotic drug, blocking the mitotic activity cells in the metaphase part of the cell cycle. Specifically, colchicine binds to tubulin, forming complexes that bind to microtubules. This stops their elongation. At low concentrations, colchicine stops microtubule growth and, at elevated concentrations, colchicine causes the depolymerization of microtubules.2

TargetActionsOrganism
ATubulin beta chain
inhibitor
binder
Humans
Absorption

Colchicine is rapidly absorbed after oral administration from the gastrointestinal tract. During a pharmacokinetic study, a mean Cmax of 2.5 ng/mL was achieved within 1-2 h (range 0.5 to three hours) after an orally administered dose of colchicine. The bioavailability of colchicine is about 45%, according to the FDA label, however, another reference indicates that the bioavailability is highly variable, ranging from 24 to 88%.4 In a multiple-dose study of colchicine administration at a dose of 1 mg per day, steady-state concentrations were achieved by 8 days following administration.4

Volume of distribution

According to the FDA label, the mean apparent volume of distribution in young and healthy patients is calculated to be about 5-8 L/kg. It is known to cross the placenta and to distribute into the breast milk.13 Colchicine has been found to distribute to various tissues but mainly into the bile, liver, and kidney tissues. Smaller amounts have been detected in the heart, lungs, intestinal tissue, and stomach.16

Protein binding

The plasma protein binding for colchicine is low to moderate, at 39 ± 5%, and it is mainly bound to albumin.4,13

Metabolism

Colchicine is found to be metabolized in the liver and demethylated to major metabolites, which include 2-O-demethylcolchicine and 3-O-demethylcolchicine, and one minor metabolite, 10-O-demethylcolchicine (colchiceine). According to in vitro studies, CYP3A4 metabolizes colchicine to 2- and 3-demethylcolchicine.13,16

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Route of elimination

In a pharmacokinetic study of healthy research subjects(n=12), 40% to 65% of a 1 mg oral colchicine dose was measured as unchanged drug in the urine. Both enterohepatic recirculation and biliary excretion are routes which are involved with the excretion of colchicine.10,13

Half-life

After several doses of 0.6 mg twice daily, the average elimination half-life of colchicine ranges from 26.6 to 31.2 hours.13 Another reference measures that the elimination half-life ranges from 20 to 40 hours.4

Clearance

The FDA label reports a clearance of and 0.0292 ± 0.0071 to 0.0321 ± 0.0091 mL/min after a single oral dose of one 0.6 mg of colchicine. Patients with end-stage renal impairment showed a 75% lower clearance of colchicine.13 In a pharmacokinetic study of patients with Familial Mediterranean Fever (FMF), the apparent mean clearance was calculated at 0.726 ± 0.110 L/h/kg.11

Adverse Effects
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Toxicity

The oral LD50 of colchicine in mice is 5.87 mg/kg.15

Overdose information

Fatal overdoses have been reported in adults and children following the ingestion of colchicine. There are several stages involved in colchicine toxicity. The signs and symptoms generally occur within 24 hours of colchicine ingestion. Gastrointestinal disturbance, including abdominal pain, nausea, vomiting, diarrhea, and volume depletion. Elevated leucocyctes may also be detected during laboratory testing. Dangerous complications may occur during the second stage of a colchicine overdose, is generally during the time frame of 24 to 72 hours after ingestion. Multiorgan failure may occur and death is usually caused by respiratory depression in addition to cardiovascular collapse.10,13

In the case of a colchicine overdose, gastric lavage and supportive measures to prevent shock should be undertaken. Treat symptoms related to the overdose. There is currently no antidote to a colchicine overdose. This drug should be kept out of the reach of children. Colchicine is not well removed by dialysis.13

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Colchicine which could result in a higher serum level.
AbametapirThe serum concentration of Colchicine can be increased when it is combined with Abametapir.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Colchicine.
AbirateroneThe metabolism of Colchicine can be decreased when combined with Abiraterone.
AbrocitinibThe serum concentration of Colchicine can be increased when it is combined with Abrocitinib.
AcalabrutinibThe metabolism of Colchicine can be decreased when combined with Acalabrutinib.
AceclofenacAceclofenac may decrease the excretion rate of Colchicine which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Colchicine which could result in a higher serum level.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Colchicine.
AcetaminophenThe metabolism of Colchicine can be decreased when combined with Acetaminophen.
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Food Interactions
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Images
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ColchicineCapsule0.6 mg/1OralHikma Pharmaceuticals USA Inc.2014-10-01Not applicableUS flag
ColchicineTablet0.6 mg/1OralWest Ward Pharmaceutical1990-10-082010-12-28US flag
ColchicineCapsule0.6 mg/1OralAmerican Health Packaging2018-03-14Not applicableUS flag
ColchicineTablet0.6 mg/1OralRemedy Repack2010-11-102011-11-10US flag
ColchicineTablet0.6 mg/1OralRebel Distributors1990-10-082011-04-13US flag
ColchicineCapsule0.6 mg/1OralA-S Medication Solutions2014-10-01Not applicableUS flag
ColchicineCapsule0.6 mg/1OralMajor Pharmaceuticals2014-10-01Not applicableUS flag
ColchicineTablet1 mgOralEuro Pharm International Canada Inc1950-12-312012-06-14Canada flag
ColchicineTablet, film coated0.6 mg/1OralDirect Rx2021-07-23Not applicableUS flag
ColchicineTablet0.6 mg/1OralPhysicians Total Care, Inc.1995-05-122010-12-29US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ColchicineTablet0.6 mg/1OralNucare Pharmaceuticals,inc.2019-02-10Not applicableUS flag
ColchicineTablet, film coated0.6 mg/1OralAmerican Health Packaging2023-04-15Not applicableUS flag
ColchicineTablet0.6 mg/1OralZydus Lifesciences Limited2019-06-12Not applicableUS flag
ColchicineTablet0.6 mg/1OralAmneal Pharmaceuticals LLC2016-09-30Not applicableUS flag
ColchicineTablet, film coated0.6 mg/1OralCamber Pharmaceuticals, Inc.2021-08-13Not applicableUS flag
ColchicineTablet0.6 mg/1OralProficient Rx LP2020-06-11Not applicableUS flag
ColchicineTablet, film coated0.6 mg/1OralAmerican Health Packaging2018-08-01Not applicableUS flag
ColchicineTablet0.6 mg/1OralAscend Laboratories, LLC2019-02-10Not applicableUS flag
ColchicineTablet0.6 mg/1OralDirect Rx2022-03-01Not applicableUS flag
ColchicineTablet, film coated0.6 mg/1Oralbryant ranch prepack2018-07-01Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
โคชิกTablet0.6 mgOralบริษัท พอนด์ เคมีคอล จำกัด1997-12-19Not applicableThailand flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Probenecid and ColchicineColchicine (0.5 mg/1) + Probenecid (500 mg/1)TabletOralActavis Pharma, Inc.1982-10-01Not applicableUS flag
Probenecid and ColchicineColchicine (0.5 mg/1) + Probenecid (500 mg/1)TabletOralPhysicians Total Care, Inc.1995-04-242013-05-30US flag
Probenecid and ColchicineColchicine (0.5 mg/1) + Probenecid (500 mg/1)TabletOralIngenus Pharmaceuticals, LLC2019-05-16Not applicableUS flag
Probenecid and ColchicineColchicine (0.5 mg/1) + Probenecid (500 mg/1)TabletOralIngenus Pharmaceuticals Nj, Llc2008-05-132008-05-13US flag
Probenecid and ColchicineColchicine (0.5 mg/1) + Probenecid (500 mg/1)TabletOralRising Pharmaceuticals, Inc.2008-05-132021-09-30US flag
Probenecid and ColchicineColchicine (0.5 mg/1) + Probenecid (500 mg/1)TabletOralAv Kare, Inc.2012-05-082016-02-01US flag
Verban OntColchicine (100 mg / 100 g) + Podophyllin (2 g / 100 g)OintmentTopicalWelcker Lyster Ltd., Division Of Technilab Inc.1963-12-311999-09-17Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ColchicineColchicine (0.6 mg/1)TabletOralPhysicians Total Care, Inc.1995-05-122010-12-29US flag
ColchicineColchicine (0.6 mg/1)TabletOralRemedy Repack2010-11-102011-11-10US flag
ColchicineColchicine (0.6 mg/1)TabletOralWest Ward Pharmaceutical1990-10-082010-12-28US flag
ColchicineColchicine (0.6 mg/1)TabletOralRebel Distributors1990-10-082011-04-13US flag

Categories

ATC Codes
M04AC01 — Colchicine
Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
SML2Y3J35T
CAS number
64-86-8
InChI Key
IAKHMKGGTNLKSZ-INIZCTEOSA-N
InChI
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
IUPAC Name
N-[(10S)-3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.0^{2,7}]hexadeca-1(16),2(7),3,5,11,14-hexaen-10-yl]acetamide
SMILES
COC1=CC2=C(C(OC)=C1OC)C1=CC=C(OC)C(=O)C=C1[C@H](CC2)NC(C)=O

References

Synthesis Reference

Christian Wehrey, "Colchicine derivatives, process for preparing them, products obtained therefrom and use thereof." U.S. Patent US20040138182, issued July 15, 2004.

US20040138182
General References
  1. Shekelle PG, Newberry SJ, FitzGerald JD, Motala A, O'Hanlon CE, Tariq A, Okunogbe A, Han D, Shanman R: Management of Gout: A Systematic Review in Support of an American College of Physicians Clinical Practice Guideline. Ann Intern Med. 2017 Jan 3;166(1):37-51. doi: 10.7326/M16-0461. Epub 2016 Nov 1. [Article]
  2. Leung YY, Yao Hui LL, Kraus VB: Colchicine--Update on mechanisms of action and therapeutic uses. Semin Arthritis Rheum. 2015 Dec;45(3):341-50. doi: 10.1016/j.semarthrit.2015.06.013. Epub 2015 Jun 26. [Article]
  3. Dalbeth N, Lauterio TJ, Wolfe HR: Mechanism of action of colchicine in the treatment of gout. Clin Ther. 2014 Oct 1;36(10):1465-79. doi: 10.1016/j.clinthera.2014.07.017. Epub 2014 Aug 21. [Article]
  4. Chappey O, Scherrmann JM: [Colchicine: recent data on pharmacokinetics and clinical pharmacology]. Rev Med Interne. 1995;16(10):782-9. [Article]
  5. Angelidis C, Kotsialou Z, Kossyvakis C, Vrettou AR, Zacharoulis A, Kolokathis F, Kekeris V, Giannopoulos G: Colchicine Pharmacokinetics and Mechanism of Action. Curr Pharm Des. 2018;24(6):659-663. doi: 10.2174/1381612824666180123110042. [Article]
  6. Schumacher HR Jr: The pathogenesis of gout. Cleve Clin J Med. 2008 Jul;75 Suppl 5:S2-4. [Article]
  7. Sonmez HE, Batu ED, Ozen S: Familial Mediterranean fever: current perspectives. J Inflamm Res. 2016 Mar 17;9:13-20. doi: 10.2147/JIR.S91352. eCollection 2016. [Article]
  8. Campbell KB, Cicci TA, Vora AK, Burgess LD: Beyond Gout: Colchicine Use in the Cardiovascular Patient. Hosp Pharm. 2015 Nov;50(10):859-867. doi: 10.1310/hpj5010-859. Epub 2015 Nov 19. [Article]
  9. Saleh Z, Arayssi T: Update on the therapy of Behcet disease. Ther Adv Chronic Dis. 2014 May;5(3):112-34. doi: 10.1177/2040622314523062. [Article]
  10. Finkelstein Y, Aks SE, Hutson JR, Juurlink DN, Nguyen P, Dubnov-Raz G, Pollak U, Koren G, Bentur Y: Colchicine poisoning: the dark side of an ancient drug. Clin Toxicol (Phila). 2010 Jun;48(5):407-14. doi: 10.3109/15563650.2010.495348. [Article]
  11. Ben-Chetrit E, Scherrmann JM, Zylber-Katz E, Levy M: Colchicine disposition in patients with familial Mediterranean fever with renal impairment. J Rheumatol. 1994 Apr;21(4):710-3. [Article]
  12. Loue C, Tod M: Reliability and extension of quantitative prediction of CYP3A4-mediated drug interactions based on clinical data. AAPS J. 2014 Nov;16(6):1309-20. doi: 10.1208/s12248-014-9663-y. Epub 2014 Oct 2. [Article]
  13. FDA Approved Drug Products: Colcrys (colchicine) tablets for oral use [Link]
  14. Colchicine: Up to Date [Link]
  15. Cayman chem MSDS [Link]
  16. Pharmacology review, FDA [Link]
  17. Medline NIH: Colchicine [Link]
Human Metabolome Database
HMDB0015466
KEGG Drug
D00570
KEGG Compound
C07592
PubChem Compound
2833
PubChem Substance
46505639
ChemSpider
5933
BindingDB
50014846
RxNav
2683
ChEBI
27882
ChEMBL
CHEMBL107
ZINC
ZINC000000621853
Therapeutic Targets Database
DAP001254
PharmGKB
PA449092
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
LOC
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Colchicine
PDB Entries
3e22 / 3ut5 / 4lzr / 4o2b / 4x1i / 4x1k / 4x1y / 4x20 / 5eyp / 5itz
show 8 more
MSDS
Download (74.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentCoronavirus Disease 2019 (COVID‑19) / Pulmonary Fibrosis Interstitial1
4CompletedBasic ScienceChronic Kidney Disease (CKD)1
4CompletedBasic ScienceHealthy Subjects (HS)1
4CompletedBasic SciencePharmacokinetics1
4CompletedDiagnosticGouty Arthritis1
4CompletedPreventionAdvanced Fibrosis / Cirrhosis of the Liver / Hepatitis C Virus (HCV) Infection1
4CompletedTreatmentAcute Coronary Syndrome (ACS) / Drug Eluting Stents (DES)1
4CompletedTreatmentAnterior MI / Colchicine1
4CompletedTreatmentColchicine Adverse Reaction / New-onset Atrial Fibrillation (NOAF)1
4CompletedTreatmentCoronary Artery Disease (CAD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amneal Pharmaceuticals
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Bedford Labs
  • Bryant Ranch Prepack
  • Comprehensive Consultant Services Inc.
  • Concord Labs
  • Consolidated Midland Corp.
  • DispenseXpress Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Excellium Pharmaceutical Inc.
  • Heartland Repack Services LLC
  • Major Pharmaceuticals
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Schein Pharmaceutical Inc.
  • Southwood Pharmaceuticals
  • Spectrum Pharmaceuticals
  • Sunrise Pharmaceutical Inc.
  • United Research Laboratories Inc.
  • Vangard Labs Inc.
  • Vintage Pharmaceuticals Inc.
  • Vision Pharma LLC
  • West-Ward Pharmaceuticals
Dosage Forms
FormRouteStrength
TabletOral0372 mg
GranuleOral1 mg
CapsuleOral0.6 mg/1
TabletOral0.6 mg/1
TabletOral1 mg
TabletOral500 mcg
Tablet, coatedOral0.5 mg
TabletOral0.6 mg
Tablet, film coatedOral0.5 MG
Tablet, film coatedOral0.6 mg/1
SolutionOral0.6 mg/5mL
TabletOral1.0 mg
TabletOral
Tablet, extended releaseOral0.5 mg
TabletOral
OintmentTopical
TabletOral0.5 mg
Prices
Unit descriptionCostUnit
Colchicine powder306.6USD g
Colcrys 0.6 mg tablet5.82USD tablet
Colchicine 0.6 mg tablet0.58USD tablet
Colchicine 1 mg Tablet0.55USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7601758No2009-10-132029-02-10US flag
US7619004No2009-11-172028-12-03US flag
US7820681No2010-10-262029-02-17US flag
US7906519No2011-03-152029-02-17US flag
US7915269No2011-03-292029-02-17US flag
US7935731No2011-05-032028-12-03US flag
US7964647No2011-06-212028-10-06US flag
US7964648No2011-06-212028-10-06US flag
US7981938No2011-07-192028-10-06US flag
US8093296No2012-01-102028-10-06US flag
US8093297No2012-01-102028-10-06US flag
US8093298No2012-01-102028-10-06US flag
US8097655No2012-01-172028-10-06US flag
US8415395No2013-04-092028-10-06US flag
US8415396No2013-04-092028-10-06US flag
US8440721No2013-05-142029-02-17US flag
US8440722No2013-05-142029-02-17US flag
US8927607No2015-01-062033-08-22US flag
US9399036No2016-07-262033-08-22US flag
US9675613No2017-06-132033-08-22US flag
US9555029No2017-01-312033-08-22US flag
US9789108No2017-10-172033-08-22US flag
US9907751No2018-03-062036-11-22US flag
US10226423No2019-03-122037-12-20US flag
US10383820No2019-08-202036-11-22US flag
US10383821No2019-08-202036-11-22US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)150-160https://www.chemicalbook.com/ChemicalProductProperty_US_CB6391144.aspx
boiling point (°C)522.37https://www.chemicalbook.com/ChemicalProductProperty_US_CB6391144.aspx
water solubility10 mg/mLhttps://www.chemicalbook.com/ChemicalProductProperty_US_CB6391144.aspx
logP1.07https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL107/
pKa12.36https://www.chemicalbook.com/ChemicalProductProperty_US_CB6391144.aspx
Predicted Properties
PropertyValueSource
Water Solubility0.0276 mg/mLALOGPS
logP1.59ALOGPS
logP1.46Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)15.06Chemaxon
pKa (Strongest Basic)-1.2Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area83.09 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity111.38 m3·mol-1Chemaxon
Polarizability41.89 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9856
Blood Brain Barrier+0.7865
Caco-2 permeable+0.5119
P-glycoprotein substrateNon-substrate0.594
P-glycoprotein inhibitor INon-inhibitor0.8007
P-glycoprotein inhibitor IINon-inhibitor0.6956
Renal organic cation transporterNon-inhibitor0.8997
CYP450 2C9 substrateNon-substrate0.8042
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7359
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7959
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9208
BiodegradationReady biodegradable0.6489
Rat acute toxicity2.3748 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9877
hERG inhibition (predictor II)Non-inhibitor0.7394
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (2.96 KB)
Spectra
Not Available

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
Binder
General Function
Ubiquitin protein ligase binding
Specific Function
Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
Gene Name
TUBB
Uniprot ID
P07437
Uniprot Name
Tubulin beta chain
Molecular Weight
49670.515 Da
References
  1. Yee KW, Hagey A, Verstovsek S, Cortes J, Garcia-Manero G, O'Brien SM, Faderl S, Thomas D, Wierda W, Kornblau S, Ferrajoli A, Albitar M, McKeegan E, Grimm DR, Mueller T, Holley-Shanks RR, Sahelijo L, Gordon GB, Kantarjian HM, Giles FJ: Phase 1 study of ABT-751, a novel microtubule inhibitor, in patients with refractory hematologic malignancies. Clin Cancer Res. 2005 Sep 15;11(18):6615-24. [Article]
  2. Acharya BR, Choudhury D, Das A, Chakrabarti G: Vitamin K3 disrupts the microtubule networks by binding to tubulin: a novel mechanism of its antiproliferative activity. Biochemistry. 2009 Jul 28;48(29):6963-74. doi: 10.1021/bi900152k. [Article]
  3. Li CM, Lu Y, Ahn S, Narayanan R, Miller DD, Dalton JT: Competitive mass spectrometry binding assay for characterization of three binding sites of tubulin. J Mass Spectrom. 2010 Oct;45(10):1160-6. doi: 10.1002/jms.1804. [Article]
  4. Cerquaglia C, Diaco M, Nucera G, La Regina M, Montalto M, Manna R: Pharmacological and clinical basis of treatment of Familial Mediterranean Fever (FMF) with colchicine or analogues: an update. Curr Drug Targets Inflamm Allergy. 2005 Feb;4(1):117-24. [Article]
  5. Dalbeth N, Lauterio TJ, Wolfe HR: Mechanism of action of colchicine in the treatment of gout. Clin Ther. 2014 Oct 1;36(10):1465-79. doi: 10.1016/j.clinthera.2014.07.017. Epub 2014 Aug 21. [Article]
  6. Lu Y, Chen J, Xiao M, Li W, Miller DD: An overview of tubulin inhibitors that interact with the colchicine binding site. Pharm Res. 2012 Nov;29(11):2943-71. doi: 10.1007/s11095-012-0828-z. Epub 2012 Jul 20. [Article]
  7. Finkelstein Y, Aks SE, Hutson JR, Juurlink DN, Nguyen P, Dubnov-Raz G, Pollak U, Koren G, Bentur Y: Colchicine poisoning: the dark side of an ancient drug. Clin Toxicol (Phila). 2010 Jun;48(5):407-14. doi: 10.3109/15563650.2010.495348. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
This enzyme action is obtained from the results of one in vitro study. The clinical significance of this enzyme action in relation to colchicine use is unknown.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Dvorak Z, Modriansky M, Pichard-Garcia L, Balaguer P, Vilarem MJ, Ulrichova J, Maurel P, Pascussi JM: Colchicine down-regulates cytochrome P450 2B6, 2C8, 2C9, and 3A4 in human hepatocytes by affecting their glucocorticoid receptor-mediated regulation. Mol Pharmacol. 2003 Jul;64(1):160-9. doi: 10.1124/mol.64.1.160. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
This enzyme action is obtained from the results of one in vitro study. The clinical significance of this enzyme action in relation to colchicine use is unknown.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Dvorak Z, Modriansky M, Pichard-Garcia L, Balaguer P, Vilarem MJ, Ulrichova J, Maurel P, Pascussi JM: Colchicine down-regulates cytochrome P450 2B6, 2C8, 2C9, and 3A4 in human hepatocytes by affecting their glucocorticoid receptor-mediated regulation. Mol Pharmacol. 2003 Jul;64(1):160-9. doi: 10.1124/mol.64.1.160. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
Curator comments
This enzyme action is obtained from the results of one in vitro study. The clinical significance of this enzyme action in relation to colchicine use is unknown.
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Dvorak Z, Ulrichova J, Modriansky M, Maurel P: Effect of colchicine and its derivatives on the expression of selected isoforms of cytochrome P450 in primary cultures of human hepatocytes. Acta Univ Palacki Olomuc Fac Med. 2000;143:47-50. [Article]
Details
4. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Dvorak Z, Ulrichova J, Modriansky M, Maurel P: Effect of colchicine and its derivatives on the expression of selected isoforms of cytochrome P450 in primary cultures of human hepatocytes. Acta Univ Palacki Olomuc Fac Med. 2000;143:47-50. [Article]
  2. Tateishi T, Soucek P, Caraco Y, Guengerich FP, Wood AJ: Colchicine biotransformation by human liver microsomes. Identification of CYP3A4 as the major isoform responsible for colchicine demethylation. Biochem Pharmacol. 1997 Jan 10;53(1):111-6. doi: 10.1016/s0006-2952(96)00693-4. [Article]
  3. Dvorak Z, Modriansky M, Pichard-Garcia L, Balaguer P, Vilarem MJ, Ulrichova J, Maurel P, Pascussi JM: Colchicine down-regulates cytochrome P450 2B6, 2C8, 2C9, and 3A4 in human hepatocytes by affecting their glucocorticoid receptor-mediated regulation. Mol Pharmacol. 2003 Jul;64(1):160-9. doi: 10.1124/mol.64.1.160. [Article]
  4. FDA Approved Drug Products: Colcrys (colchicine) tablets for oral use [Link]
  5. Pharmacology review, FDA [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Hu YJ, Liu Y, Zhao RM, Qu SS: Interaction of colchicine with human serum albumin investigated by spectroscopic methods. Int J Biol Macromol. 2005 Nov 15;37(3):122-6. doi: 10.1016/j.ijbiomac.2005.09.007. Epub 2005 Oct 18. [Article]
  2. Trnavska Z, Kuchar M, Rejholec V, Trnavsky K: The binding of colchicine and its derivatives to bovine and human serum albumin and human plasma. Pharmacology. 1979;18(3):123-7. doi: 10.1159/000137240. [Article]
  3. Maciazek-Jurczyk M, Sulkowska A, Bojko B, Rownicka-Zubik J, Sulkowski WW: Interaction of phenylbutazone and colchicine in binding to serum albumin in rheumatoid therapy: 1H NMR study. Spectrochim Acta A Mol Biomol Spectrosc. 2009 Sep 15;74(1):1-9. doi: 10.1016/j.saa.2009.06.043. Epub 2009 Jun 25. [Article]
  4. FDA Approved Drug Products: Colcrys (colchicine) tablets for oral use [Link]

Transporters

Details
1. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Silva R, Carmo H, Vilas-Boas V, Barbosa DJ, Palmeira A, Sousa E, Carvalho F, Bastos Mde L, Remiao F: Colchicine effect on P-glycoprotein expression and activity: in silico and in vitro studies. Chem Biol Interact. 2014 Jul 25;218:50-62. doi: 10.1016/j.cbi.2014.04.009. Epub 2014 Apr 20. [Article]
  2. Drion N, Lemaire M, Lefauconnier JM, Scherrmann JM: Role of P-glycoprotein in the blood-brain transport of colchicine and vinblastine. J Neurochem. 1996 Oct;67(4):1688-93. doi: 10.1046/j.1471-4159.1996.67041688.x. [Article]
  3. Decleves X, Niel E, Debray M, Scherrmann JM: Is P-glycoprotein (ABCB1) a phase 0 or a phase 3 colchicine transporter depending on colchicine exposure conditions? Toxicol Appl Pharmacol. 2006 Dec 1;217(2):153-60. doi: 10.1016/j.taap.2006.08.004. Epub 2006 Aug 10. [Article]
  4. FDA Approved Drug Products: Colcrys (colchicine) tablets for oral use [Link]

Drug created at July 08, 2007 17:02 / Updated at June 05, 2023 06:28