Colchicine

Identification

Summary

Colchicine is an alkaloid used to treat gout and Familial Mediterranean Fever as well as prevent major cardiovascular events.

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

Colchicine is an alkaloid drug derived from a plant belonging to the Lily family, known as Colchicum autumnale, or "autumn crocus."4 Its use was first approved by the FDA in 1961.11 Colchicine is used in the treatment of gout flares and Familial Mediterranean fever,9 and prevention of major cardiovascular events.12 It has also been investigated in other inflammatory and fibrotic conditions.1

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 four years of age and older.9 It is also indicated to reduce the risk of myocardial infarction (MI), stroke, coronary revascularization, and cardiovascular death in adult patients with established atherosclerotic disease or with multiple risk factors for cardiovascular disease.12

Some off-label uses of colchicine include the treatment of the manifestations of Behcet's syndrome, pericarditis, and postpericardiotomy syndrome.5,6

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofBehcet syndrome••• •••••
Prevention ofCardiovascular mortality•••••••••••••••••••••••••••• ••••••••••••••• •••••••• •••••••••••••
Prevention ofCardiovascular mortality••••••••••••••••••••• •••• ••• •••••••••••••• •••• ••••••••••••
Prevention ofCoronary revascularization••••••••••••••••••••• •••• ••• •••••••••••••• •••• ••••••••••••
Prevention ofCoronary revascularization•••••••••••••••••••••••••••• ••••••••••••••• •••••••• •••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Colchicine ameliorates the symptoms of gout and Familial Mediterranean fever.1,9 It possesses anti-inflammatory, anti-fibrotic, and cardiovascular protective effects. Colchicine was shown to exhibit anticancer properties, such as the inhibition of cancer cell migration and angiogenesis. Colchicine has a narrow therapeutic window.1

Mechanism of action

The exact mechanism of action of colchicine has not been fully established; however, colchicine likely interferes with the intracellular assembly of the inflammasome complex present in neutrophils and monocytes that mediates activation of interleukin-1β, an inflammatory mediator.1,2,9 Colchicine also attenuates neutrophil adhesion and recruitment, as well as superoxide production.4 Clinical data demonstrate that colchicine reduces high-sensitivity C- reactive protein (hs-CRP).12

Colchicine is an anti-mitotic drug that disrupts cytoskeletal functions by inhibiting β-tubulin polymerization into microtubules. Consequently, it prevents the activation, degranulation, and migration of neutrophils. This pharmacological action is thought to be related to colchicine ameliorating gout symptoms and preventing major cardiovascular events.9,12 Colchicine blocks microtubule growth at low concentrations and causes the depolymerization of microtubules at high concentrations.1

TargetActionsOrganism
ATubulin beta chain
inhibitor
binder
Humans
Absorption

Colchicine is rapidly absorbed after oral administration from the gastrointestinal tract.9 The bioavailability of colchicine is about 45%:9,12 one study suggests that colchicine bioavailability is highly variable, ranging from 24 to 88%.3

In healthy adults, the mean Cmax of 2.5 ng/mL (range 1.1 to 4.4 ng/mL) was achieved in one to two hours (range 0.5 to 3 hours) after a single dose administered under fasting conditions.9 In a multiple-dose study of colchicine administration at a dose of 1 mg per day, steady-state concentrations were achieved by day 8 following administration.3

Administration of colchicine with food does not affect the colchicine absorption rate but decreases the extent of colchicine by approximately 15%.9

Volume of distribution

The mean apparent volume of distribution in young and healthy patients is about 5-8 L/kg. It is known to cross the placenta and distribute into the breast milk.9

Colchicine has been found to distribute to various tissues, mainly into the bile, liver, and kidney tissues. Smaller amounts have been detected in the heart, lungs, intestinal tissue, and stomach.11

Protein binding

The plasma protein binding for colchicine is low to moderate, at 39 ± 5%, and it is mainly bound to albumin regardless of concentration.11,12

Metabolism

Colchicine is metabolized in the liver. It undergoes CYP3A4-mediated demethylation into major metabolites, 2-O-demethylcolchicine and 3-O-demethylcolchicine. It also forms one minor metabolite, 10-O-demethylcolchicine (colchiceine).9,11 Plasma levels of these metabolites are less than 5% of parent drug.12

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Route of elimination

In a pharmacokinetic study of healthy research subjects who received 1 mg of oral colchicine, about 40% to 65% of the dose was recovered in the urine in the form of an unchanged drug. Colchicine undergoes enterohepatic recirculation and biliary excretion.7,9

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.9 Another study reported the elimination half-life ranging to be 20 to 40 hours.3

Clearance

In one pharmacokinetic study involving patients who received a single oral dose of 0.6 mg colchicine, the clearance was 0.0321 ± 0.0091 mL/min in young, healthy adults and 0.0292 ± 0.0071 mL/min in adults between the ages of 60 and 70 years. Patients with end-stage renal impairment showed a 75% lower clearance of colchicine.9

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.8

Adverse Effects
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Toxicity

The oral LD50 of colchicine in mice is 5.87 mg/kg.10

Acute overdose exceeding 0.5 mg/kg (35 mg for a 70 kg average adult) is usually fatal. Fatalities have been reported with as little as 7 mg.12 Colchicine poisoning presents in three sequential and usually overlapping phases. The first stage of acute colchicine toxicity typically occurs within 24 hours of ingestion and includes gastrointestinal symptoms such as abdominal pain, nausea, vomiting, diarrhea, and significant fluid loss, leading to volume depletion. Peripheral leukocytosis may also be seen. The second stage develops 24 to 72 hours after ingestion and is characterized by multi-organ failure. Death is usually a result of respiratory depression and cardiovascular collapse. Recovery may be accompanied by rebound leukocytosis about one week after ingestion.9,12

No specific antidote is known. Elimination of toxins by gastric lavage followed by activated charcoal should be attempted within 1-2 hours of ingestion. Colchicine is not effectively removed by hemodialysis.9,12

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.
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.
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
ColchicineTablet0.6 mg/1OralPhysicians Total Care, Inc.1995-05-122010-12-29US flag
ColchicineTablet1 mgOralEuro Pharm International Canada Inc1950-12-312012-06-14Canada flag
ColchicineTablet, film coated0.6 mg/1OralDirect Rx2021-07-23Not applicableUS flag
ColchicineCapsule0.6 mg/1Oralbryant ranch prepack2014-10-01Not applicableUS flag
ColchicineCapsule0.6 mg/1OralAmerican Health Packaging2018-03-14Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ColchicineTablet, film coated0.6 mg/1OralProficient Rx LP2018-07-01Not applicableUS flag
ColchicineTablet, film coated0.6 mg/1OralPar Pharmaceutical, Inc.2022-09-27Not applicableUS flag
ColchicineTablet, film coated0.6 mg/1OralPar Pharmaceutical, Inc.2018-07-01Not applicableUS flag
ColchicineTablet0.6 mg/1Oralbryant ranch prepack2019-02-10Not applicableUS flag
ColchicineTablet0.6 mg/1OralAurobindo Pharma Limited2022-03-22Not 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)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
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
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. 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]
  2. 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]
  3. Chappey O, Scherrmann JM: [Colchicine: recent data on pharmacokinetics and clinical pharmacology]. Rev Med Interne. 1995;16(10):782-9. [Article]
  4. 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]
  5. 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]
  6. 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]
  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]
  8. 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]
  9. FDA Approved Drug Products: Colcrys (colchicine) tablets for oral use (May 2020) [Link]
  10. Cayman Chemical: Colchicine MSDS [Link]
  11. FDA Pharmacology Review: Mitigare (colchicine) Oral Capsules [Link]
  12. FDA Approved Drug Products: LODOCO (colchicine) tablets, for oral use (June 2023) [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 11 more

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
4CompletedDiagnosticGout Flares1

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
TabletOral1000 MICROGRAMMI
TabletOral0372 mg
GranuleOral1 mg
CapsuleOral0.6 mg/1
TabletOral0.6 mg/1
TabletOral1 mg
TabletOral500 mcg
Tablet, coatedOral0.5 mg
TabletOral0.6 mg
TabletOral500.000 mcg
Tablet, film coatedOral0.5 MG
Tablet, film coatedOral0.6 mg/1
SolutionOral0.6 mg/5mL
TabletOral1.0 mg
TabletOral
TabletOral0.5 mg/1
Tablet, extended releaseOral0.5 mg
TabletOral
TabletOral1.000 mg
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
US9744144No2017-08-292035-01-22US flag
US10130585No2018-11-202034-12-31US flag
US10206891No2019-02-192035-01-22US flag
US10265281No2019-04-232035-01-22US flag
US10842762No2020-11-242035-01-22US flag
US11026899No2021-06-082035-01-22US flag
US11026900No2021-06-082035-01-22US flag
US11026901No2021-06-082035-01-22US 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
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0007900000-e4a4415b21177a3d13dc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zfs-1009000000-33d3087228d93bf1755f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-6a60f69f32f9951dec0a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-9003000000-678d8b8bac26b4769b41
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bt9-0019000000-519710ac4c945d5394ed
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f6x-2009000000-2416d43d594bae7365e0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-208.5603489
predicted
DarkChem Lite v0.1.0
[M-H]-207.2891489
predicted
DarkChem Lite v0.1.0
[M-H]-209.5759489
predicted
DarkChem Lite v0.1.0
[M-H]-190.23613
predicted
DeepCCS 1.0 (2019)
[M+H]+209.3615489
predicted
DarkChem Lite v0.1.0
[M+H]+206.5695489
predicted
DarkChem Lite v0.1.0
[M+H]+207.2020489
predicted
DarkChem Lite v0.1.0
[M+H]+192.59412
predicted
DeepCCS 1.0 (2019)
[M+Na]+208.8032489
predicted
DarkChem Lite v0.1.0
[M+Na]+206.6552489
predicted
DarkChem Lite v0.1.0
[M+Na]+208.5055489
predicted
DarkChem Lite v0.1.0
[M+Na]+198.68727
predicted
DeepCCS 1.0 (2019)

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]
  8. FDA Approved Drug Products: Colcrys (colchicine) tablets for oral use (May 2020) [Link]
  9. FDA Approved Drug Products: LODOCO (colchicine) tablets, for oral use (June 2023) [Link]

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. [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 (May 2020) [Link]
  5. FDA Pharmacology Review: Mitigare (colchicine) Oral Capsules [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. [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]

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 (May 2020) [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 (May 2020) [Link]

Drug created at July 08, 2007 17:02 / Updated at February 25, 2024 21:03