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 EA90 Approved [1]
Psoriasis vulgaris EA90 Approved [2]
Therapeutic Class
Antipsoriatic Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 412.6
Logarithm of the Partition Coefficient (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 []
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
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

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 [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial (CYP24A1) OTG2T749 CP24A_HUMAN Gene/Protein Processing [5]
ATP-binding cassette sub-family C member 3 (ABCC3) OTC3IJV4 MRP3_HUMAN Gene/Protein Processing [6]
Beclin-1 (BECN1) OT4X293M BECN1_HUMAN Gene/Protein Processing [7]
Cytochrome P450 7A1 (CYP7A1) OT8Z5KLD CP7A1_HUMAN Gene/Protein Processing [6]
Filaggrin (FLG) OTE9QDV6 FILA_HUMAN Gene/Protein Processing [8]
Involucrin (IVL) OT4VPNGY INVO_HUMAN Gene/Protein Processing [8]
Keratin, type I cytoskeletal 10 (KRT10) OTSVRD3Q K1C10_HUMAN Gene/Protein Processing [8]
Keratin, type I cytoskeletal 16 (KRT16) OTGA0EQN K1C16_HUMAN Gene/Protein Processing [8]
Keratin, type I cytoskeletal 17 (KRT17) OT6Y1DPK K1C17_HUMAN Gene/Protein Processing [8]
Nuclear receptor subfamily 0 group B member 2 (NR0B2) OT7UVICX NR0B2_HUMAN Gene/Protein Processing [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Psoriasis
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
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

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
⏷ Show the Full List of 16 Pharmaceutical Excipients of This Drug
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 Calcipotriol and psoriasis. Int J Dermatol. 1992 Aug;31(8):549-50.
2 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).
3 BDDCS applied to over 900 drugs
4 Cellular and molecular mechanisms involved in the action of vitamin D analogs targeting vitiligo depigmentation. Curr Drug Targets. 2008 Apr;9(4):345-59.
5 Actions of Vitamin D3, analogs on human prostate cancer cell lines: comparison with 1,25-dihydroxyvitamin D3. Endocrinology. 1995 Jan;136(1):20-6.
6 Adaptive homeostasis of the vitamin D-vitamin D nuclear receptor axis in 8-methoxypsoralen-induced hepatotoxicity. Toxicol Appl Pharmacol. 2019 Jan 1;362:150-158. doi: 10.1016/j.taap.2018.11.002. Epub 2018 Nov 10.
7 Calcipotriol induces autophagy in HeLa cells and keratinocytes. J Invest Dermatol. 2011 Apr;131(4):990-3. doi: 10.1038/jid.2010.423. Epub 2011 Jan 13.
8 Effects of 1 alpha,25-dihydroxy-vitamin D3 and calcipotriol on organotypic cultures of outer root sheath cells: a potential model to evaluate antipsoriatic drugs. Arch Dermatol Res. 1993;285(7):402-9. doi: 10.1007/BF00372133.