Identification

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Name
Colchicine
Accession Number
DB01394
Type
Small Molecule
Groups
Approved
Description

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.14

Structure
Thumb
Synonyms
  • Colchicin
  • Colchicina
  • Colchicine
  • Colchicinum
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ColchicineTablet0.6 mg/1OralPhysicians Total Care, Inc.1995-05-122010-12-29Us
ColchicineTablet0.6 mg/1OralWest Ward Pharmaceutical1990-10-082010-12-28Us0143 120120180906 25352 1nfrw6k
ColchicineCapsule0.6 mg/1OralA-S Medication Solutions2014-10-01Not applicableUs
ColchicineCapsule0.6 mg/1OralAmerican Health Packaging2018-03-14Not applicableUs
ColchicineCapsule0.6 mg/1Oralbryant ranch prepack2014-10-01Not applicableUs
ColchicineTablet0.6 mg/1OralRemedy Repack2010-11-102011-11-10Us
ColchicineCapsule0.6 mg/1OralHikma Pharmaceuticals USA Inc.2014-10-01Not applicableUs0143 301820180913 8702 ndobl1
ColchicineCapsule0.6 mg/1OralMajor Pharmaceuticals2014-10-01Not applicableUs
ColchicineTablet0.6 mg/1OralRebel Distributors1990-10-082011-04-13Us
ColchicineTabletOralEuro Pharm International Canada Inc1950-12-312012-06-14Canada
Additional Data Available
  • Application Number
    Application Number

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ColchicineTablet, film coated0.6 mg/1OralPar Pharmaceutical2018-07-01Not applicableUs
ColchicineTablet, film coated0.6 mg/1OralAmerican Health Packaging2018-08-01Not applicableUs
ColchicineTablet, film coated0.6 mg/1OralAmerincan Health Packaging2017-07-132018-12-31Us
ColchicineTablet0.6 mg/1OralAscend Laboratories, LLC2019-02-10Not applicableUs
ColchicineTablet, film coated0.6 mg/1OralProficient Rx LP2018-07-01Not applicableUs
ColchicineTablet0.6 mg/1OralAmneal Pharmaceuticals LLC2016-09-30Not applicableUs
ColchicineTablet, film coated0.6 mg/1OralPrasco Laboratories2015-01-122021-10-31Us66993 0165 02 nlmimage10 8e404752
Euro-colchicineTabletOralEuro Pharm International Canada IncNot applicableNot applicableCanada
Jamp-colchicineTabletOralJamp Pharma Corporation2011-10-07Not applicableCanada
Jamp-colchicineTabletOralJamp Pharma Corporation2011-10-072013-04-03Canada
Additional Data Available
  • Application Number
    Application Number

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Probenecid and ColchicineColchicine (0.5 mg/1) + Probenecid (500 mg/1)TabletOralAv Kare, Inc.2012-05-082016-02-01Us
Probenecid and ColchicineColchicine (0.5 mg/1) + Probenecid (500 mg/1)TabletOralIngenus Pharmaceuticals, LLC2019-05-16Not applicableUs
Probenecid and ColchicineColchicine (0.5 mg/1) + Probenecid (500 mg/1)TabletOralPhysicians Total Care, Inc.1995-04-242013-05-30Us
Probenecid and ColchicineColchicine (0.5 mg/1) + Probenecid (500 mg/1)TabletOralRising Pharmaceuticals, Inc.2008-05-132021-09-30Us
Probenecid and ColchicineColchicine (0.5 mg/1) + Probenecid (500 mg/1)TabletOralActavis Pharma, Inc.1982-10-01Not applicableUs00591 5325 01 nlmimage10 240e1210
Probenecid and ColchicineColchicine (0.5 mg/1) + Probenecid (500 mg/1)TabletOralIngenus Pharmaceuticals Nj, Llc2008-05-132008-05-13Us
Verban OntColchicine (100 mg) + Podophyllin (2 g)OintmentTopicalWelcker Lyster Ltd., Division Of Technilab Inc.1963-12-311999-09-17Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ColchicineColchicine (0.6 mg/1)TabletOralPhysicians Total Care, Inc.1995-05-122010-12-29Us
ColchicineColchicine (0.6 mg/1)TabletOralWest Ward Pharmaceutical1990-10-082010-12-28Us0143 120120180906 25352 1nfrw6k
ColchicineColchicine (0.6 mg/1)TabletOralRemedy Repack2010-11-102011-11-10Us
ColchicineColchicine (0.6 mg/1)TabletOralRebel Distributors1990-10-082011-04-13Us
Categories
UNII
SML2Y3J35T
CAS number
64-86-8
Weight
Average: 399.437
Monoisotopic: 399.168187537
Chemical Formula
C22H25NO6
InChI Key
IAKHMKGGTNLKSZ-UHFFFAOYSA-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)
IUPAC Name
N-{3,4,5,14-tetramethoxy-13-oxotricyclo[9.5.0.0²,⁷]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=C1C(CC2)NC(C)=O

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

Associated Conditions
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
Additional Data Available
Adverse Effects

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Contraindications

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Blackbox Warnings

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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

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

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

Affected organisms
  • Humans and other mammals
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
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Colchicine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Colchicine.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when Colchicine is combined with 2-Methoxyethanol.
3,5-diiodothyropropionic acidThe metabolism of Colchicine can be decreased when combined with 3,5-diiodothyropropionic acid.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Colchicine.
5-androstenedioneThe metabolism of Colchicine can be decreased when combined with 5-androstenedione.
6-Deoxyerythronolide BThe metabolism of Colchicine can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of Colchicine can be decreased when combined with 6-O-benzylguanine.
7-ethyl-10-hydroxycamptothecinThe metabolism of Colchicine can be decreased when combined with 7-ethyl-10-hydroxycamptothecin.
9-(N-methyl-L-isoleucine)-cyclosporin AThe risk or severity of adverse effects can be increased when Colchicine is combined with 9-(N-methyl-L-isoleucine)-cyclosporin A.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

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  • Evidence Level
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  • Action
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Food Interactions
  • Avoid alcohol since it increases uric acid levels.
  • Drink liberally.
  • Take without regard to meals.

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. [PubMed:27802478]
  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. [PubMed:26228647]
  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. [PubMed:25151572]
  4. Chappey O, Scherrmann JM: [Colchicine: recent data on pharmacokinetics and clinical pharmacology]. Rev Med Interne. 1995;16(10):782-9. [PubMed:8525161]
  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. [PubMed:29359661]
  6. Schumacher HR Jr: The pathogenesis of gout. Cleve Clin J Med. 2008 Jul;75 Suppl 5:S2-4. [PubMed:18822468]
  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. [PubMed:27051312]
  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. [PubMed:27729672]
  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. [PubMed:24790727]
  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. [PubMed:20586571]
  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. [PubMed:8035398]
  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. [PubMed:25274605]
  13. Colchicine FDA label [Link]
  14. Colchicine: Up to Date [Link]
  15. Cayman chem MSDS [Link]
  16. Pharmacology review, FDA [Link]
External Links
Human Metabolome Database
HMDB0015466
KEGG Drug
D00570
KEGG Compound
C07592
PubChem Compound
2833
PubChem Substance
46505639
ChemSpider
2731
ChEBI
23359
ChEMBL
CHEMBL87
Therapeutic Targets Database
DAP001254
PharmGKB
PA449092
Guide to Pharmacology
GtP Drug Page
HET
LOC
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Colchicine
ATC Codes
M04AC01 — Colchicine
AHFS Codes
  • 92:16.00 — Antigout Agents
MSDS
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceAcute Gouty Arthritis / Hypertriglyceridemias / Pericarditis1
1CompletedBasic ScienceFamilial Mediterranean Fever (FMF )1
1CompletedBasic ScienceHealthy Volunteers6
1CompletedBasic ScienceHealthy Volunteers / Pharmacokinetics1
1CompletedBasic ScienceHealthy; Adult; Volunteer; Colchicine; Pharmacokinetics; Diltiazem; Cytochrome p450 3A4; P-glycoprotein1
1CompletedBasic SciencePharmacokinetics11
1CompletedTreatmentRenal Replacement Therapies1
1RecruitingTreatmentAcute Gouty Arthritis1
1Unknown StatusTreatmentLiver Cirrhosis1
1, 2CompletedTreatmentBMI >30 kg/m2 / Metabolic Diseases1
1, 2RecruitingTreatmentDiabetic Nephropathies1
2Active Not RecruitingOtherCoronary Artery Disease1
2Active Not RecruitingOtherCoronary Artery Disease / Human Immunodeficiency Virus (HIV)1
2CompletedPreventionAcute Gouty Arthritis1
2CompletedPreventionCardiovascular Disease (CVD) / Rheumatoid Arthritis1
2CompletedSupportive CareAtherosclerotic Vascular Diseases1
2CompletedTreatmentAcute Gouty Arthritis3
2CompletedTreatmentAcute Gouty Arthritis / Hyperuricemia3
2CompletedTreatmentAcute Gouty Arthritis / Moderate Renal Impairment1
2CompletedTreatmentBehcet's Syndrome1
2CompletedTreatmentNonvalvular Atrial Fibrillation1
2Not Yet RecruitingTreatmentAmyotrophic Lateral Sclerosis (ALS)1
2RecruitingTreatmentBehçet Disease Affecting Oral Mucosa1
2RecruitingTreatmentChagas Disease / Colchicine Resistance1
2RecruitingTreatmentColchicine / Coronary Artery Disease / Inflammatory Reaction / Severe or persistent diarrhea / Type 2 Diabetes Mellitus / White Blood Cell1
2RecruitingTreatmentCutaneous Polyarteritis Nodosa / Henoch-Schönlein Purpura / IgA Vasculitis / Primary Cutaneous Vasculitis1
2RecruitingTreatmentHepatocellular,Carcinoma / Invasion / Metastasis1
2RecruitingTreatmentMyocardial Infarction1
2TerminatedTreatmentChronic Hepatitis C Virus (HCV) Infection1
2Unknown StatusTreatmentDiabetic Nephropathies1
2Unknown StatusTreatmentStomatitis, Aphthous1
2WithdrawnTreatmentProstate Cancer1
2, 3CompletedTreatmentAcute Coronary Syndromes (ACS)1
2, 3CompletedTreatmentKnee Osteoarthritis (Knee OA)1
2, 3RecruitingPreventionPostoperative Atrial Fibrillation1
2, 3RecruitingTreatmentHeart Diseases / Single-ventricle1
3Active Not RecruitingPreventionCoronary Artery Disease / Myocardial Infarction1
3CompletedPreventionArrythmias1
3CompletedPreventionNonvalvular Atrial Fibrillation / Thoracic Surgery1
3CompletedPreventionPostpericardiotomy Syndrome1
3CompletedTreatmentAcute Gouty Arthritis2
3CompletedTreatmentLiver Cirrhosis, Biliary1
3CompletedTreatmentPericarditis1
3CompletedTreatmentPericarditis / Recurrences1
3Not Yet RecruitingPreventionStrokes / Transient Ischaemic Attack (TIA)1
3Not Yet RecruitingTreatmentIgA Vasculitis1
3RecruitingPreventionAtrial Flutter / Nonvalvular Atrial Fibrillation / Thoracic Surgery1
3RecruitingPreventionColchicine Adverse Reaction / Nonvalvular Atrial Fibrillation / Surgery, Cardiac1
3RecruitingPreventionNonvalvular Atrial Fibrillation / Strokes1
3RecruitingTreatmentChondrocalcinosis pyrophosphate1
3RecruitingTreatmentST Elevation Myocardial Infarction1
3Unknown StatusPreventionNonvalvular Atrial Fibrillation / Pericardial Effusion / Pleural Effusions / Post-pericardiotomy Syndrome / Surgery, Cardiac1
3Unknown StatusTreatmentConstriction / Nonvalvular Atrial Fibrillation / Post-pericardiotomy Syndrome1
3Unknown StatusTreatmentRhegmatogenous Retinal Detachments1
3Unknown StatusTreatmentVitreoretinopathy, Proliferative1
3WithdrawnTreatmentAsthma Bronchial / Chronic Lung Diseases1
3WithdrawnTreatmentNonvalvular Atrial Fibrillation1
4Active Not RecruitingTreatmentCoronary Artery Disease1
4CompletedBasic ScienceChronic Kidney Disease (CKD)1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedBasic SciencePharmacokinetics1
4CompletedDiagnosticAcute Gouty Arthritis1
4CompletedTreatmentAcute Gouty Arthritis2
4CompletedTreatmentElective Coronary Artery Bypass Grafting (CABG) Surgery1
4CompletedTreatmentFamilial Mediterranean Fever (FMF )1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentIntercritical Gout1
4CompletedTreatmentPericarditis / Recurrences1
4CompletedTreatmentPrimary Gout1
4Not Yet RecruitingTreatmentGout Flares1
4Not Yet RecruitingTreatmentKnee Osteoarthritis (Knee OA) / Osteoarthritis (OA)1
4RecruitingTreatmentAcute Myocardial Infarction (AMI)1
4RecruitingTreatmentManipulation Under Anesthesia1
4RecruitingTreatmentPericardial Effusion1
4Unknown StatusPreventionAdvanced Fibrosis / Hepatitis C Virus (HCV) Infection / Liver Cirrhosis1
4Unknown StatusTreatmentAcute Coronary Syndromes (ACS)1
4Unknown StatusTreatmentAcute Myocardial Infarction (AMI)1
4WithdrawnTreatmentMyocardial Infarction1
Not AvailableActive Not RecruitingTreatmentDiabetic Nephropathies1
Not AvailableCompletedTreatmentFibrosis, Liver1
Not AvailableNot Yet RecruitingPreventionInflammatory Reaction / Myocardial Infarction1
Not AvailableRecruitingNot AvailableNeutrophils.Hypersegmented | Bld-Ser-Plas / ST Elevation Myocardial Infarction (STEMI)1
Not AvailableUnknown StatusTreatmentCalcific Tendonitis1
Not AvailableWithdrawnTreatmentNon ST Segment Elevation Myocardial Infarction (NSTEMI)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
CapsuleOral0.6 mg/1
TabletOral0.6 mg/1
Tablet, film coatedOral0.6 mg/1
SolutionOral0.6 mg/5mL
TabletOral
TabletOral
OintmentTopical
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)
US7601758No2009-10-132029-02-10Us
US7619004No2009-11-172028-12-03Us
US7820681No2010-10-262029-02-17Us
US7906519No2011-03-152029-02-17Us
US7915269No2011-03-292029-02-17Us
US7935731No2011-05-032028-12-03Us
US7964647No2011-06-212028-10-06Us
US7964648No2011-06-212028-10-06Us
US7981938No2011-07-192028-10-06Us
US8093296No2012-01-102028-10-06Us
US8093297No2012-01-102028-10-06Us
US8093298No2012-01-102028-10-06Us
US8097655No2012-01-172028-10-06Us
US8415395No2013-04-092028-10-06Us
US8415396No2013-04-092028-10-06Us
US8440721No2013-05-142029-02-17Us
US8440722No2013-05-142029-02-17Us
US8927607No2015-01-062033-08-22Us
US9399036No2016-07-262033-08-22Us
US9675613No2017-06-132033-08-22Us
US9555029No2017-01-312033-08-22Us
US9789108No2017-10-172033-08-22Us
US9907751No2018-03-062036-11-22Us
US10226423No2019-03-122037-12-20Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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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)-0.038ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.09 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity111.38 m3·mol-1ChemAxon
Polarizability42.41 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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0000900000-c73c5a28a750cece607a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0049400000-2a76bd81d41e1bc5925c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0gba-0091000000-fb24bc910ffe7bd74811

Taxonomy

Description
This compound belongs to the class of organic compounds known as tropones. These are compounds containing a tropone ring, which is a cycloheptatrienone ring bearing a ketone group.
Kingdom
Organic compounds
Super Class
Hydrocarbon derivatives
Class
Tropones
Sub Class
Not Available
Direct Parent
Tropones
Alternative Parents
Anisoles / Alkyl aryl ethers / Cyclic ketones / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
Substituents
Anisole / Tropone / Alkyl aryl ether / Benzenoid / Cyclic ketone / Carboximidic acid / Carboximidic acid derivative / Ether / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
aromatic ether, alkaloid, acetamides, carbotricyclic compound (CHEBI:23359) / an alkaloid (CPD-9785)

Targets

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. [PubMed:16166440]
  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. [PubMed:19527023]
  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. [PubMed:20814887]
  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. [PubMed:15720245]
  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. [PubMed:25151572]
  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. [PubMed:22814904]
  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. [PubMed:20586571]

Enzymes

Details
1. 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. [PubMed:11144118]
  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. [PubMed:8960070]
  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. [PubMed:12815172]
  4. Colchicine FDA label [Link]
  5. Pharmacology review, FDA [Link]
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. [PubMed:12815172]
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. [PubMed:12815172]
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. [PubMed:11144118]

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. [PubMed:16239027]
  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. [PubMed:572067]
  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. [PubMed:19615934]
  4. Colchicine FDA label [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. [PubMed:24759273]
  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. [PubMed:8858954]
  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. [PubMed:16978677]
  4. Colchicine FDA label [Link]

Drug created on July 08, 2007 11:02 / Updated on October 16, 2019 13:15