NAV

Colchiceine

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

Identification

Generic Name
Colchiceine
DrugBank Accession Number
DB15534
Background

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

Type
Small Molecule
Groups
Approved, Experimental
Structure
3D
Similar Structures
Weight
Average: 385.416
Monoisotopic: 385.152537465
Chemical Formula
C21H23NO6
Synonyms
  • 10-O-demethylcolchicine
  • O-Demethylcolchicine
  • O10-Demethylcolchicine
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Pharmacology

Indication

Not Available

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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

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

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Product Images
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ColchicineTablet0.3 mg/1OralZydus Pharmaceuticals USA Inc.2021-05-10Not applicableUS flag
ColchicineTablet0.3 mg/1OralZydus Lifesciences Limited2021-05-10Not applicableUS flag
ColchicineTablet0.6 mg/1OralNorthstar Rx Llc.2020-11-10Not applicableUS flag

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

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. [Article]
  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. [Article]
  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. [Article]
Human Metabolome Database
HMDB0250402
ChemSpider
9750
BindingDB
66784
RxNav
2174385
ChEMBL
CHEMBL323668

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral0.3 mg/1
TabletOral0.6 mg/1
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
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-d35fad6beb802b71ea05
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-1009000000-fc53e0130d8a2103f1a5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-002f-0009000000-4127f72aeb79087dec8d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-9003000000-c0ab0d2869b3b00ac4cc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-056s-0069000000-d97bb0bd664aa86ff80d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-002g-3039000000-16f307fbc123f39f8c9d
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]-188.99898
predicted
DeepCCS 1.0 (2019)
[M+H]+191.35698
predicted
DeepCCS 1.0 (2019)
[M+Na]+198.05988
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Tubulin beta chain
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. [Article]
Details2. Tubulin alpha-1A chain
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. [Article]

Carriers

Details1. Serum albumin
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. [Article]

Drug created at October 09, 2019 22:05 / Updated at August 03, 2023 15:04