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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Colchicine (DB01394)

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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

• Behcet's Syndrome
• Familial Mediterranean Fever (FMF )
• Gout Flares
• Pericarditis
• Postpericardiotomy Syndrome

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

Target	Actions	Organism
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

Hover over products below to view reaction partners

• Colchicine
  • 2-Demethylcolchicine + 3-Desmethylchochicine

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abacavir	Abacavir may decrease the excretion rate of Colchicine which could result in a higher serum level.
Abametapir	The serum concentration of Colchicine can be increased when it is combined with Abametapir.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Colchicine.
Abiraterone	The metabolism of Colchicine can be decreased when combined with Abiraterone.
Abrocitinib	The serum concentration of Colchicine can be increased when it is combined with Abrocitinib.
Acalabrutinib	The metabolism of Colchicine can be decreased when combined with Acalabrutinib.
Aceclofenac	Aceclofenac may decrease the excretion rate of Colchicine which could result in a higher serum level.
Acemetacin	Acemetacin may decrease the excretion rate of Colchicine which could result in a higher serum level.
Acenocoumarol	The serum concentration of Acenocoumarol can be increased when it is combined with Colchicine.
Acetaminophen	The 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

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Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Colchicine	Capsule	0.6 mg/1	Oral	Hikma Pharmaceuticals USA Inc.	2014-10-01	Not applicable
Colchicine	Tablet	0.6 mg/1	Oral	West Ward Pharmaceutical	1990-10-08	2010-12-28
Colchicine	Capsule	0.6 mg/1	Oral	American Health Packaging	2018-03-14	Not applicable
Colchicine	Tablet	0.6 mg/1	Oral	Remedy Repack	2010-11-10	2011-11-10
Colchicine	Tablet	0.6 mg/1	Oral	Rebel Distributors	1990-10-08	2011-04-13
Colchicine	Capsule	0.6 mg/1	Oral	A-S Medication Solutions	2014-10-01	Not applicable
Colchicine	Capsule	0.6 mg/1	Oral	Major Pharmaceuticals	2014-10-01	Not applicable
Colchicine	Tablet	1 mg	Oral	Euro Pharm International Canada Inc	1950-12-31	2012-06-14
Colchicine	Tablet, film coated	0.6 mg/1	Oral	Direct Rx	2021-07-23	Not applicable
Colchicine	Tablet	0.6 mg/1	Oral	Physicians Total Care, Inc.	1995-05-12	2010-12-29

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Colchicine	Tablet	0.6 mg/1	Oral	Nucare Pharmaceuticals,inc.	2019-02-10	Not applicable
Colchicine	Tablet, film coated	0.6 mg/1	Oral	American Health Packaging	2023-04-15	Not applicable
Colchicine	Tablet	0.6 mg/1	Oral	Zydus Lifesciences Limited	2019-06-12	Not applicable
Colchicine	Tablet	0.6 mg/1	Oral	Amneal Pharmaceuticals LLC	2016-09-30	Not applicable
Colchicine	Tablet, film coated	0.6 mg/1	Oral	Camber Pharmaceuticals, Inc.	2021-08-13	Not applicable
Colchicine	Tablet	0.6 mg/1	Oral	Proficient Rx LP	2020-06-11	Not applicable
Colchicine	Tablet, film coated	0.6 mg/1	Oral	American Health Packaging	2018-08-01	Not applicable
Colchicine	Tablet	0.6 mg/1	Oral	Ascend Laboratories, LLC	2019-02-10	Not applicable
Colchicine	Tablet	0.6 mg/1	Oral	Direct Rx	2022-03-01	Not applicable
Colchicine	Tablet, film coated	0.6 mg/1	Oral	bryant ranch prepack	2018-07-01	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
โคชิก	Tablet	0.6 mg	Oral	บริษัท พอนด์ เคมีคอล จำกัด	1997-12-19	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Probenecid and Colchicine	Colchicine (0.5 mg/1) + Probenecid (500 mg/1)	Tablet	Oral	Actavis Pharma, Inc.	1982-10-01	Not applicable
Probenecid and Colchicine	Colchicine (0.5 mg/1) + Probenecid (500 mg/1)	Tablet	Oral	Physicians Total Care, Inc.	1995-04-24	2013-05-30
Probenecid and Colchicine	Colchicine (0.5 mg/1) + Probenecid (500 mg/1)	Tablet	Oral	Ingenus Pharmaceuticals, LLC	2019-05-16	Not applicable
Probenecid and Colchicine	Colchicine (0.5 mg/1) + Probenecid (500 mg/1)	Tablet	Oral	Ingenus Pharmaceuticals Nj, Llc	2008-05-13	2008-05-13
Probenecid and Colchicine	Colchicine (0.5 mg/1) + Probenecid (500 mg/1)	Tablet	Oral	Rising Pharmaceuticals, Inc.	2008-05-13	2021-09-30
Probenecid and Colchicine	Colchicine (0.5 mg/1) + Probenecid (500 mg/1)	Tablet	Oral	Av Kare, Inc.	2012-05-08	2016-02-01
Verban Ont	Colchicine (100 mg / 100 g) + Podophyllin (2 g / 100 g)	Ointment	Topical	Welcker Lyster Ltd., Division Of Technilab Inc.	1963-12-31	1999-09-17

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Colchicine	Colchicine (0.6 mg/1)	Tablet	Oral	Physicians Total Care, Inc.	1995-05-12	2010-12-29
Colchicine	Colchicine (0.6 mg/1)	Tablet	Oral	Remedy Repack	2010-11-10	2011-11-10
Colchicine	Colchicine (0.6 mg/1)	Tablet	Oral	West Ward Pharmaceutical	1990-10-08	2010-12-28
Colchicine	Colchicine (0.6 mg/1)	Tablet	Oral	Rebel Distributors	1990-10-08	2011-04-13

Categories

ATC Codes

M04AC01 — Colchicine

• M04AC — Preparations with no effect on uric acid metabolism
• M04A — ANTIGOUT PREPARATIONS
• M04 — ANTIGOUT PREPARATIONS
• M — MUSCULO-SKELETAL SYSTEM

Drug Categories

• Agents Causing Muscle Toxicity
• Alkaloids
• Antigout Preparations
• Antimitotic Agents
• Cytochrome P-450 CYP2B6 Inhibitors
• Cytochrome P-450 CYP2B6 Inhibitors (strength unknown)
• Cytochrome P-450 CYP2C8 Inhibitors
• Cytochrome P-450 CYP2C8 Inhibitors (strength unknown)
• Cytochrome P-450 CYP2E1 Inducers
• Cytochrome P-450 CYP2E1 Inducers (strength unknown)
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 Enzyme Inducers
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Drugs that are Mainly Renally Excreted
• Experimental Unapproved Treatments for COVID-19
• Mitosis Modulators
• Musculo-Skeletal System
• P-glycoprotein inducers
• P-glycoprotein substrates
• Preparations With No Effect on Uric Acid Metabolism
• Tubulin Modulators

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]

External Links

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

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Coronavirus Disease 2019 (COVID‑19) / Pulmonary Fibrosis Interstitial	1
4	Completed	Basic Science	Chronic Kidney Disease (CKD)	1
4	Completed	Basic Science	Healthy Subjects (HS)	1
4	Completed	Basic Science	Pharmacokinetics	1
4	Completed	Diagnostic	Gouty Arthritis	1
4	Completed	Prevention	Advanced Fibrosis / Cirrhosis of the Liver / Hepatitis C Virus (HCV) Infection	1
4	Completed	Treatment	Acute Coronary Syndrome (ACS) / Drug Eluting Stents (DES)	1
4	Completed	Treatment	Anterior MI / Colchicine	1
4	Completed	Treatment	Colchicine Adverse Reaction / New-onset Atrial Fibrillation (NOAF)	1
4	Completed	Treatment	Coronary 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

Form	Route	Strength
Tablet	Oral	0372 mg
Granule	Oral	1 mg
Capsule	Oral	0.6 mg/1
Tablet	Oral	0.6 mg/1
Tablet	Oral	1 mg
Tablet	Oral	500 mcg
Tablet, coated	Oral	0.5 mg
Tablet	Oral	0.6 mg
Tablet, film coated	Oral	0.5 MG
Tablet, film coated	Oral	0.6 mg/1
Solution	Oral	0.6 mg/5mL
Tablet	Oral	1.0 mg
Tablet	Oral
Tablet, extended release	Oral	0.5 mg
Tablet	Oral
Ointment	Topical
Tablet	Oral	0.5 mg

Prices

Unit description	Cost	Unit
Colchicine powder	306.6USD	g
Colcrys 0.6 mg tablet	5.82USD	tablet
Colchicine 0.6 mg tablet	0.58USD	tablet
Colchicine 1 mg Tablet	0.55USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US7601758	No	2009-10-13	2029-02-10
US7619004	No	2009-11-17	2028-12-03
US7820681	No	2010-10-26	2029-02-17
US7906519	No	2011-03-15	2029-02-17
US7915269	No	2011-03-29	2029-02-17
US7935731	No	2011-05-03	2028-12-03
US7964647	No	2011-06-21	2028-10-06
US7964648	No	2011-06-21	2028-10-06
US7981938	No	2011-07-19	2028-10-06
US8093296	No	2012-01-10	2028-10-06
US8093297	No	2012-01-10	2028-10-06
US8093298	No	2012-01-10	2028-10-06
US8097655	No	2012-01-17	2028-10-06
US8415395	No	2013-04-09	2028-10-06
US8415396	No	2013-04-09	2028-10-06
US8440721	No	2013-05-14	2029-02-17
US8440722	No	2013-05-14	2029-02-17
US8927607	No	2015-01-06	2033-08-22
US9399036	No	2016-07-26	2033-08-22
US9675613	No	2017-06-13	2033-08-22
US9555029	No	2017-01-31	2033-08-22
US9789108	No	2017-10-17	2033-08-22
US9907751	No	2018-03-06	2036-11-22
US10226423	No	2019-03-12	2037-12-20
US10383820	No	2019-08-20	2036-11-22
US10383821	No	2019-08-20	2036-11-22

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	150-160	https://www.chemicalbook.com/ChemicalProductProperty_US_CB6391144.aspx
boiling point (°C)	522.37	https://www.chemicalbook.com/ChemicalProductProperty_US_CB6391144.aspx
water solubility	10 mg/mL	https://www.chemicalbook.com/ChemicalProductProperty_US_CB6391144.aspx
logP	1.07	https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL107/
pKa	12.36	https://www.chemicalbook.com/ChemicalProductProperty_US_CB6391144.aspx

Predicted Properties

Property	Value	Source
Water Solubility	0.0276 mg/mL	ALOGPS
logP	1.59	ALOGPS
logP	1.46	Chemaxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	15.06	Chemaxon
pKa (Strongest Basic)	-1.2	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	6	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	83.09 Å2	Chemaxon
Rotatable Bond Count	5	Chemaxon
Refractivity	111.38 m3·mol-1	Chemaxon
Polarizability	41.89 Å3	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9856
Blood Brain Barrier	+	0.7865
Caco-2 permeable	+	0.5119
P-glycoprotein substrate	Non-substrate	0.594
P-glycoprotein inhibitor I	Non-inhibitor	0.8007
P-glycoprotein inhibitor II	Non-inhibitor	0.6956
Renal organic cation transporter	Non-inhibitor	0.8997
CYP450 2C9 substrate	Non-substrate	0.8042
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Substrate	0.7359
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9025
CYP450 3A4 inhibitor	Non-inhibitor	0.831
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.7959
Ames test	Non AMES toxic	0.9132
Carcinogenicity	Non-carcinogens	0.9208
Biodegradation	Ready biodegradable	0.6489
Rat acute toxicity	2.3748 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9877
hERG inhibition (predictor II)	Non-inhibitor	0.7394

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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Details1. Tubulin beta chain

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]

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