This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Colchiceine
Accession Number
DB15534
Description

Colchiceine is one of several metabolites of the anti-gout medication colchicine.1

Type
Small Molecule
Groups
Approved, Experimental
Structure
Thumb
Weight
Average: 385.416
Monoisotopic: 385.152537465
Chemical Formula
C21H23NO6
Synonyms
  • O-Demethylcolchicine
  • O10-Demethylcolchicine

Pharmacology

Indication
Not Available
Contraindications & Blackbox Warnings
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Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UTubulin beta chain
binder
Humans
UTubulin alpha-1A chain
binder
Humans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half-life
Not Available
Clearance
Not Available
Adverse Effects
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Toxicity
Not Available
Affected organisms
Not Available
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.
Not Available
Food Interactions
No interactions found.

Products

Categories

Drug Categories
Classification
Not classified

Chemical Identifiers

UNII
HJ30158L57
CAS number
477-27-0
InChI Key
PRGILOMAMBLWNG-UHFFFAOYSA-N
InChI
InChI=1S/C21H23NO6/c1-11(23)22-15-7-5-12-9-18(26-2)20(27-3)21(28-4)19(12)13-6-8-16(24)17(25)10-14(13)15/h6,8-10,15H,5,7H2,1-4H3,(H,22,23)(H,24,25)
IUPAC Name
N-{14-hydroxy-3,4,5-trimethoxy-13-oxotricyclo[9.5.0.0^{2,7}]hexadeca-1(16),2,4,6,11,14-hexaen-10-yl}acetamide
SMILES
COC1=C(OC)C(OC)=C2C(CCC(NC(C)=O)C3=CC(=O)C(O)=CC=C23)=C1

References

General References
  1. Dvorak Z, Ulrichova J, Pichard-Garcia L, Modriansky M, Maurel P: Comparative effect of colchicine and colchiceine on cytotoxicity and CYP gene expression in primary human hepatocytes. Toxicol In Vitro. 2002 Jun;16(3):219-27. doi: 10.1016/s0887-2333(02)00004-8. [PubMed:12020594]
  2. Hastie SB, Macdonald TL: Binding of colchiceine to tubulin. Mechanisms of ligand association with tubulin. Biochem Pharmacol. 1990 Apr 15;39(8):1271-6. doi: 10.1016/0006-2952(90)90002-3. [PubMed:2322310]
  3. Bosca F, Tormos R: Behavior of drug excited states within macromolecules: binding of colchicine and derivatives to albumin. J Phys Chem B. 2013 Jun 27;117(25):7528-34. doi: 10.1021/jp402489j. Epub 2013 Jun 14. [PubMed:23730875]
ChemSpider
9750
BindingDB
66784
RxNav
2174385
ChEMBL
CHEMBL323668

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0671 mg/mLALOGPS
logP0.98ALOGPS
logP1.35ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)10.53ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area94.09 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity106.62 m3·mol-1ChemAxon
Polarizability40.16 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
Curator comments
Little research has been conducted looking at the specific binding site of colchiceine, but it appears to interact with tubulin in a similar manner to colchicine (i.e. at the interface of the alpha- and beta-subunits). The specific proteins within these subunits to which colchiceine binds have not been elucidated.
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. Hastie SB, Macdonald TL: Binding of colchiceine to tubulin. Mechanisms of ligand association with tubulin. Biochem Pharmacol. 1990 Apr 15;39(8):1271-6. doi: 10.1016/0006-2952(90)90002-3. [PubMed:2322310]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
Curator comments
Little research has been conducted looking at the specific binding site of colchiceine, but it appears to interact with tubulin in a similar manner to colchicine (i.e. at the interface of the alpha- and beta-subunits). The specific proteins within these subunits to which colchiceine binds have not been elucidated.
General 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.
Specific Function
Gtp binding
Gene Name
TUBA1A
Uniprot ID
Q71U36
Uniprot Name
Tubulin alpha-1A chain
Molecular Weight
50135.25 Da
References
  1. Hastie SB, Macdonald TL: Binding of colchiceine to tubulin. Mechanisms of ligand association with tubulin. Biochem Pharmacol. 1990 Apr 15;39(8):1271-6. doi: 10.1016/0006-2952(90)90002-3. [PubMed:2322310]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. Bosca F, Tormos R: Behavior of drug excited states within macromolecules: binding of colchicine and derivatives to albumin. J Phys Chem B. 2013 Jun 27;117(25):7528-34. doi: 10.1021/jp402489j. Epub 2013 Jun 14. [PubMed:23730875]

Drug created on October 09, 2019 16:05 / Updated on June 12, 2020 10:53

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