<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3104</id>
  <title>T3D3062</title>
  <common-name>Calcipotriol</common-name>
  <description>Calcipotriol 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.</description>
  <cas>112965-21-6</cas>
  <pubchem-id>5288783</pubchem-id>
  <chemical-formula>C27H40O3</chemical-formula>
  <weight>412.297750</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>1.35e-02 g/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Clinical 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.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>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.</mechanism-of-toxicity>
  <metabolism>Hepatic. 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.</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the treatment of moderate plaque psoriasis in adults.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Topically applied calcipotriene can be absorbed in sufficient amounts to produce systemic effects. Elevated serum calcium has been observed with excessive use of calcipotriene.</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-21T20:28:57Z</created-at>
  <updated-at type="dateTime">2026-05-14T17:33:52Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Calcipotriol</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>50749</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Calcipotriol</stitch-id>
  <drugbank-id>DB02300</drugbank-id>
  <pdb-id>MC9</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>O[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</moldb-smiles>
  <moldb-formula>C27H40O3</moldb-formula>
  <moldb-inchi>InChI=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</moldb-inchi>
  <moldb-inchikey>LWQQLNNNIPYSNX-UROSTWAQSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">412.6047</moldb-average-mass>
  <moldb-mono-mass type="decimal">412.297745146</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>3.84</logp>
  <hmdb-id>HMDB15567</hmdb-id>
  <chembl-id>CHEMBL1234231</chembl-id>
  <chemspider-id>4450880</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Andrzej Kutner, Michal Chodynski, Teresa Ryznar, Hanna Fitak, Jerzy Winiarski, Bartlomiej Gorecki, Agnieszka Burzynska, Wieslaw Szelejewski, &amp;#8220;Process for Preparation of Pharmaceutically Pure Anhydrous Calcipotriol.&amp;#8221; U.S. Patent US20080214876, issued September 04, 2008.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002405</chemdb-id>
  <dsstox-id>DTXSID0046648</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00001835</susdat-id>
  <iupac>(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</iupac>
  <moldb-polar-surface-area>60.69</moldb-polar-surface-area>
  <moldb-refractivity>125.44929999999998</moldb-refractivity>
  <moldb-polarizability>49.59111678976198</moldb-polarizability>
  <moldb-rotatable-bond-count>5</moldb-rotatable-bond-count>
  <moldb-acceptor-count>3</moldb-acceptor-count>
  <moldb-donor-count>3</moldb-donor-count>
  <moldb-pka-strongest-acidic>14.392873609816359</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-1.5903047523657756</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>4</moldb-number-of-rings>
  <moldb-alogps-logp>4.63</moldb-alogps-logp>
  <moldb-alogps-logs>-4.49</moldb-alogps-logs>
  <moldb-alogps-solubility>1.35e-02 g/l</moldb-alogps-solubility>
</compound>
