Colchicine (CHEM002980)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (10)XML
Record Information
Version1.0
Creation Date2014-08-29 04:49:18 UTC
Update Date2016-11-09 01:09:01 UTC
Accession NumberCHEM002980
Identification
Common NameColchicine
ClassSmall Molecule
DescriptionColchicine is only found in individuals that have used or taken this drug. It is a major alkaloid from Colchicum autumnale L. and found also in other Colchicum species. Its primary therapeutic use is in the treatment of gout, but it has been used also in the therapy of familial Mediterranean fever (periodic disease). The precise mechanism of action has not been completely established. In patients with gout, colchicine apparently interrupts the cycle of monosodium urate crystal deposition in joint tissues and the resultant inflammatory response that initiates and sustains an acute attack. Colchicine decreases leukocyte chemotaxis and phagocytosis and inhibits the formation and release of a chemotactic glycoprotein that is produced during phagocytosis of urate crystals. Colchicine also inhibits urate crystal deposition, which is enhanced by a low pH in the tissues, probably by inhibiting oxidation of glucose and subsequent lactic acid production in leukocytes. Colchicine has no analgesic or antihyperuricemic activity. Colchicine inhibits microtubule assembly in various cells, including leukocytes, probably by binding to and interfering with polymerization of the microtubule subunit tubulin. Although some studies have found that this action probably does not contribute significantly to colchicine's antigout action, a recent in vitro study has shown that it may be at least partially involved.
Contaminant Sources
  • Clean Air Act Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • Suspected Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Drug
  • Ester
  • Ether
  • Gout Suppressant
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
  • Tubulin Modulator
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
ColchicinHMDB
ColchicinaHMDB
ColchicinumHMDB
Chemical FormulaC22H25NO6
Average Molecular Mass399.437 g/mol
Monoisotopic Mass399.168 g/mol
CAS Registry Number64-86-8
IUPAC NameN-{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
Traditional Namecolchicine
SMILESCOC1=CC2=C(C(OC)=C1OC)C1=CC=C(OC)C(=O)C=C1C(CC2)NC(C)=O
InChI IdentifierInChI=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)
InChI KeyIAKHMKGGTNLKSZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tropones. Tropones are compounds containing a tropone ring, which is a cycloheptatrienone ring bearing a ketone group.
KingdomOrganic compounds
Super ClassHydrocarbon derivatives
ClassTropones
Sub ClassNot Available
Direct ParentTropones
Alternative Parents
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
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point156°C
Boiling PointNot Available
Solubility4.5E+004 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility0.028 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity111.38 m³·mol⁻¹ChemAxon
Polarizability42.41 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053u-1009000000-7a8d292bb6a5673c9d7cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0000900000-c73c5a28a750cece607aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0049400000-2a76bd81d41e1bc5925cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0gba-0091000000-fb24bc910ffe7bd74811Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03gi-0096000000-1604b0f123208b25b949Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0zfr-0029400000-dc08a845d6fb327eec56Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-d360bbc1ca27b2e657d4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000900000-44e9ac8566ca5c684603Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-9d973f7afeacb8db799dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-0gc1-0192000000-dcb2736f710df3f17b01Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0049500000-27383218cdc648739307Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0gba-0091000000-fb24bc910ffe7bd74811Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-0009700000-00c1abf086f6716cac6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0009100000-4f6b3c625a6887981670Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05dl-0049000000-75fafbc5e28d11766c0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-cc76299babee13af8502Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0537-1009000000-247faa52698339d3e544Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pi3-9077000000-eb1350fc19fa611668aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0001900000-958a463c4e2f7c3dd588Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-0009500000-8181c90153beb9e9a4f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052g-5079000000-81182c306cc4f86cf2c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-b40b49dac61f8e9864faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-7009000000-666c5fffe6918e3020f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9007000000-7e1ec907f14345d7e992Spectrum
Toxicity Profile
Route of ExposureColchicine is rapidly absorbed after oral administration, probably from the jejunum and ileum. However, the rate and extent of absorption are variable, depending on the tablet dissolution rate; variability in gastric emptying, intestinal motility, and pH at the absorption site; and the extent to which colchicine is bound to microtubules in gastrointestinal mucosal cells.
Mechanism of ToxicityColchicine inhibits microtubule assembly in various cells, including leukocytes, probably by binding to and interfering with polymerization of the microtubule subunit tubulin. Although some studies have found that this action probably does not contribute significantly to colchicine's antigout action, a recent in vitro study has shown that it may be at least partially involved.
MetabolismProbably hepatic. Although colchicine metabolites have not been identified in humans, metabolism by mammalian hepatic microsomes has been demonstrated in vitro. Route of Elimination: In healthy volunteers (n=12) 40 - 65% of 1 mg orally administered colchicine was recovered unchanged in urine. Enterohepatic recirculation and biliary excretion are also postulated to play a role in colchicine elimination. Half Life: Elimination half-life is approximately 1 hour in healthy subjects, although a study with an extended sampling time reported mean terminal elimination half-life values of approximately 9 to 10.5 hours. Other studies have reported half-life values of approximately 2 hours in patients with alcoholic cirrhosis and approximately 2.5 hours in patients with familial Mediterranean fever.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor treatment and relief of pain in attacks of acute gouty arthritis.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01394
HMDB IDHMDB0015466
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkColchicine
Chemspider ID2731
ChEBI ID23359
PubChem Compound ID2833
Kegg Compound IDC07592
YMDB IDNot Available
ECMDB IDNot Available
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.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10680067
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24074178
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=7200520
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=9819133