Details of the Drug

General Information of Drug (ID: DM03CP7)

• Drug Name: Calcipotriol
• Synonyms: Calcipotriene; Divonex; Dovonex; BMS-181161; Daivonex (TN); Dovonex (TN); MC-903; (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol; (1S,5Z,7Z,17ALPHA,22E)-24-CYCLOPROPYL-9,10-SECOCHOLA-5,7,10,22-TETRAENE-1,3,24-TRIOL; 1-ALPHA,24S-(OH)2-22-ENE-26,27-DEHYDROVITAMIN D3

Indication

Disease Entry	ICD 11	Status	REF
Psoriasis vulgaris	EA90	Approved	[1], [2]

• Therapeutic Class: Antipsoriatic Agents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 412.6
  Topological Polar Surface Area (xlogp); 4.3
  Rotatable Bond Count (rotbonds); 5
  Hydrogen Bond Donor Count (hbonddonor); 3
  Hydrogen Bond Acceptor Count (hbondacc); 3
• ADMET Property:
  BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
  Elimination: 0.5% of drug is excreted from urine in the unchanged form [3]
  Metabolism: The drug is metabolized via the hepatic [4]
• Chemical Identifiers:
  Formula: C27H40O3
  IUPAC Name: (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
  Canonical SMILES: C[C@H](/C=C/[C@H](C1CC1)O)[C@H]2CC[C@@H]\\3[C@@]2(CCC/C3=C\\C=C/4\\C[C@H](C[C@@H](C4=C)O)O)C
  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
  InChIKey: LWQQLNNNIPYSNX-UROSTWAQSA-N
• Cross-matching ID:
  PubChem CID: 5288783
  ChEBI ID: CHEBI:50749
  CAS Number: 112965-21-6
  DrugBank ID: DB02300
  TTD ID: D01QUS
  ACDINA ID: D00905

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Vitamin D3 receptor (VDR)	TTK59TV	VDR_HUMAN	Antagonist	[5]

Molecular Expression Atlas of This Drug

• The Studied Disease: Psoriasis vulgaris
• ICD Disease Classification: EA90

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Vitamin D3 receptor (VDR)	DTT	VDR	1.69E-02	-0.23	-0.66

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Alpha-tocopherol	E00243	14985	Antimicrobial preservative; Antioxidant
Benzyl alcohol	E00010	244	Antimicrobial preservative; Solvent
Isopropyl alcohol	E00070	3776	Antimicrobial preservative; Solvent
Menthol	E00050	1254	Flavoring agent
Sodium citrate anhydrous	E00102	6224	Alkalizing agent; Buffering agent; Complexing agent; Emulsifying agent
Cetostearyl alcohol	E00353	62238	Emollient; Emulsifying agent; Viscosity-controlling agent
Edetate disodium	E00186	8759	Complexing agent
Glycerin	E00026	753	Antimicrobial preservative; Emollient; Flavoring agent; Humectant; Lubricant; Plasticizing agent; Solvent; Suppository base; Tonicity agent; Viscosity-controlling agent
Hydroxypropyl cellulose	E00632	Not Available	Binding agent; Coating agent; Emulsifying agent; Film/Membrane-forming agent; Modified-release agent; Suspending agent; Viscosity-controlling agent
Medium-chain triglyceride	E00640	Not Available	Emollient; Lubricant; Surfactant
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Water	E00035	962	Solvent
Diazolidinyl urea	E00354	62277	Antimicrobial preservative
Dichlorobenzyl alcohol	E00320	15684	Antimicrobial preservative
Polyoxyl 20 cetyl ether	E00452	2724259	Emulsifying agent; Ointment base; Solubilizing agent; Surfactant
Trisodium Phosphate	E00284	24243	Other agent

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Calcipotriene 0.005% solution	0.01%	Solution	Topical
Calcipotriene 0.005% ointment	0.01%	Ointment	Topical

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

• [1] URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2778).
• [2] Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
• [3] BDDCS applied to over 900 drugs
• [4] FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
• [5] Cellular and molecular mechanisms involved in the action of vitamin D analogs targeting vitiligo depigmentation. Curr Drug Targets. 2008 Apr;9(4):345-59.
• [6] Vitamin D in health and disease. Clin J Am Soc Nephrol. 2008 Sep;3(5):1535-41.
• [7] Kaposi sarcoma is a therapeutic target for vitamin D(3) receptor agonist. Blood. 2000 Nov 1;96(9):3188-94.
• [8] Emerging drugs for psoriasis. Expert Opin Emerg Drugs. 2009 Mar;14(1):145-63.
• [9] Synthesis and biological evaluations of A-ring isomers of 26,26,26,27,27,27-hexafluoro-1,25-dihydroxyvitamin D3. Bioorg Med Chem. 2000 Aug;8(8):2157-66.
• [10] In vivo metabolism of the vitamin D analog, dihydrotachysterol. Evidence for formation of 1 alpha,25- and 1 beta,25-dihydroxy-dihydrotachysterol metabolites and studies of their biological activity. J Biol Chem. 1993 Jan 5;268(1):282-92.
• [11] [Vitamin D2 or vitamin D3]. Rev Med Interne. 2008 Oct;29(10):815-20.
• [12] New acquisitions in therapy of secondary hyperparathyroidism in chronic kidney disease and peritoneal dialysis patients: role of vitamin D receptor... Contrib Nephrol. 2009;163:219-226.
• [13] How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
• [14] Evidence for tissue- and cell-type selective activation of the vitamin D receptor by Ro-26-9228, a noncalcemic analog of vitamin D3. J Cell Biochem. 2003 Feb 1;88(2):267-73.