Colchiceine
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This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
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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
- Weight
- Average: 385.416
Monoisotopic: 385.152537465 - Chemical Formula
- C21H23NO6
- Synonyms
- 10-O-demethylcolchicine
- O-Demethylcolchicine
- O10-Demethylcolchicine
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UTubulin beta chain binderHumans UTubulin alpha-1A chain binderHumans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
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
- 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]
- 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]
- 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]
- External Links
- Human Metabolome Database
- HMDB0250402
- ChemSpider
- 9750
- BindingDB
- 66784
- 2174385
- ChEMBL
- CHEMBL323668
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 0.3 mg/1 Tablet Oral 0.6 mg/1 - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0671 mg/mL ALOGPS logP 0.98 ALOGPS logP 1.35 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 10.53 Chemaxon pKa (Strongest Basic) -1.2 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 94.09 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 106.62 m3·mol-1 Chemaxon Polarizability 40.16 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0009000000-d35fad6beb802b71ea05 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-1009000000-fc53e0130d8a2103f1a5 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-002f-0009000000-4127f72aeb79087dec8d Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-052f-9003000000-c0ab0d2869b3b00ac4cc Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-056s-0069000000-d97bb0bd664aa86ff80d Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-002g-3039000000-16f307fbc123f39f8c9d Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 188.99898 predictedDeepCCS 1.0 (2019) [M+H]+ 191.35698 predictedDeepCCS 1.0 (2019) [M+Na]+ 198.05988 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsTubulin 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
- Tubulin is the major constituent of microtubules, a cylinder consisting of laterally associated linear protofilaments composed of alpha- and beta-tubulin heterodimers. Microtubules grow by the addition of GTP-tubulin dimers to the microtubule end, where a stabilizing cap forms. Below the cap, tubulin dimers are in GDP-bound state, owing to GTPase activity of alpha-tubulin
- Specific Function
- GTP binding
- Gene Name
- TUBB
- Uniprot ID
- P07437
- Uniprot Name
- Tubulin beta chain
- Molecular Weight
- 49670.515 Da
References
- 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]
2. DetailsTubulin 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, a cylinder consisting of laterally associated linear protofilaments composed of alpha- and beta-tubulin heterodimers. Microtubules grow by the addition of GTP-tubulin dimers to the microtubule end, where a stabilizing cap forms. Below the cap, tubulin dimers are in GDP-bound state, owing to GTPase activity of alpha-tubulin
- Specific Function
- GTP binding
- Gene Name
- TUBA1A
- Uniprot ID
- Q71U36
- Uniprot Name
- Tubulin alpha-1A chain
- Molecular Weight
- 50135.25 Da
References
- 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
1. DetailsAlbumin
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- 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