Calcipotriol (CHEM002405)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:57 UTC
Update Date2026-05-14 17:33:52 UTC
Accession NumberCHEM002405
Identification
Common NameCalcipotriol
ClassSmall Molecule
DescriptionCalcipotriol is only found in individuals that have used or taken this drug. It is a synthetic derivative of calcitriol or Vitamin D.The precise mechanism of calcipotriol in remitting psoriasis is not well-understood. However, it has been shown to have comparable affinity with calcitriol for the Vitamin D receptor, while being less than 1% as active as the calcitriol in regulating calcium metabolism. The Vitamin D receptor (VDR) belongs to the steroid/thyroid receptor superfamily, and is found on the cells of many different tissues including the thyroid, bone, kindney, and T cells of the immune system. T cells are known to play a role in psoriasis, and it is thought that the binding of calcipotriol to the VDR modulates the T cells gene transcription of cell differentiation and proliferation related genes.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Antipsoriatic Agent
  • Dermatologic Agent
  • Drug
  • Metabolite
  • Organic Compound
  • Synthetic Compound
  • Vitamin D3 Receptor inhibitor
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
CalcipotrieneChEBI
DaivonexChEBI
DovonexChEBI
Bristol-myers squibb brand OF calcipotrieneHMDB
PsorcutanHMDB
1,24(OH)2-22-Ene-24-cyclopropyl D3HMDB
Leo brand OF calcipotrieneHMDB
Schering brand OF calcipotrieneHMDB
CSL Brand OF calcipotrieneHMDB
Senosiain brand OF calcipotrieneHMDB
SoriluxHMDB
Farmacusi brand OF calcipotrieneHMDB
Heximar win careHMDB
(22E)-(24S)-1a,24-Dihydroxy-26,27-cyclo-22,23-didehydrovitamin D3 / (22E)-(24S)-1a,24-dihydroxy-26,27-cyclo-22,23-didehydrocholecalciferol / calcipotriolHMDB
(22E)-(24S)-1Α,24-dihydroxy-26,27-cyclo-22,23-didehydrovitamin D3 / (22E)-(24S)-1α,24-dihydroxy-26,27-cyclo-22,23-didehydrocholecalciferol / calcipotriolHMDB
EnstilarHMDB
CalcipotriolKEGG
Chemical FormulaC27H40O3
Average Molecular Mass412.605 g/mol
Monoisotopic Mass412.298 g/mol
CAS Registry Number112965-21-6
IUPAC Name(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
Traditional Namecalcipotriol
SMILESO[C@H](\C=C\[C@@H](C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C)C1CC1
InChI IdentifierInChI=1S/C27H40O3/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3/b13-6+,19-7+,21-10-/t17-,22-,23-,24+,25-,26+,27-/m1/s1
InChI KeyLWQQLNNNIPYSNX-UROSTWAQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassVitamin D and derivatives
Direct ParentVitamin D and derivatives
Alternative Parents
Substituents
  • Triterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility1.35e-02 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP4.63ALOGPS
logP3.84ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)14.39ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity125.45 m³·mol⁻¹ChemAxon
Polarizability49.59 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-00kg-2019000000-25fe74385dfaaadc4f64Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03di-2200159000-60ddca8d21526e4244deSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0019100000-dd8b67e911e2c011a451Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fr-3349000000-721114fcaf3ed169df5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fki-9568000000-c7e61ad61191fce88abeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0006900000-01ce5bd91cb0ca4dcbecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-2009300000-7f4afaeab87ae0e61d8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9005000000-075615c00f3c0728d5edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06tb-0139300000-4a9257a0b1cf140f5b7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0cki-1269200000-926c7873d1b6b3d9d144Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000b-2494000000-3044d26933d8919ecbfbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-6b048e3e028e205ac598Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1505900000-d9fa5fd00776cc0e0e28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0101900000-12080aba78c8a692b2abSpectrum
Toxicity Profile
Route of ExposureClinical studies with radiolabeled ointment indicate that approximately 6% (+3%, SD) of the applied dose of calcipotriene is absorbed systemically when the ointment is applied topically to psoriasis plaques or 5% (+2.6%, SO) when applied to normal skin.
Mechanism of ToxicityThe precise mechanism of calcipotriol in remitting psoriasis is not well-understood. However, it has been shown to have comparable affinity with calcitriol for the Vitamin D receptor, while being less than 1% as active as the calcitriol in regulating calcium metabolism. The Vitamin D receptor (VDR) belongs to the steroid/thyroid receptor superfamily, and is found on the cells of many different tissues including the thyroid, bone, kindney, and T cells of the immune system. T cells are known to play a role in psoriasis, and it is thought that the binding of calcipotriol to the VDR modulates the T cells gene transcription of cell differentiation and proliferation related genes.
MetabolismHepatic. Calcipotriene metabolism following systemic uptake is rapid, and occurs via a similar pathway to the natural hormone. The primary metabolites are much less potent than the parent compound. Route of Elimination: The active form of the vitamin, 1,25-dihydroxy vitamin D3 (calcitriol), is known to be recycled via the liver and excreted in the bile. There is evidence that maternal 1,25-dihydroxy vitamin D3 (calcitriol) may enter the fetal circulation, but it is not known whether it is excreted in human milk.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of moderate plaque psoriasis in adults.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsTopically applied calcipotriene can be absorbed in sufficient amounts to produce systemic effects. Elevated serum calcium has been observed with excessive use of calcipotriene.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB02300
HMDB IDHMDB0015567
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDMC9
Wikipedia LinkCalcipotriol
Chemspider ID4450880
ChEBI ID50749
PubChem Compound ID5288783
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Andrzej Kutner, Michal Chodynski, Teresa Ryznar, Hanna Fitak, Jerzy Winiarski, Bartlomiej Gorecki, Agnieszka Burzynska, Wieslaw Szelejewski, “Process for Preparation of Pharmaceutically Pure Anhydrous Calcipotriol.” U.S. Patent US20080214876, issued September 04, 2008.

MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. The lipid handbook with CD-ROM
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23441902
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23621170
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24090798
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24286371
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24419155
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24533503
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24592364
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=24593129
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=24670691
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24788893
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=24907534
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=25027750
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=25355140
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=25484388
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=25561873
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=25574190
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=25592908
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=25904071
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=26081515
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=26224733
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=7994616