Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00905)
Name
Calcipotriene
Synonyms    Click to Show/Hide the Synonyms of This API
Calcipotriol; calcipotriene; Dovonex; Daivonex; Psorcutan; Sorilux; 112965-21-6; Calcitrene; MC 903; MC-903; Calcipotriol hydrate; UNII-143NQ3779B; CHEBI:50749; Dovonex (TN); 143NQ3779B; (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; 112828-00-9; NCGC00167465-01; Calciptriol; DSSTox_CID_26648; DSSTox_RID_81793; DSSTox_GSID_46648; Divonex; (22E)-(24S)-1alpha,24-dihydroxy-26,27-cyclo-22,23-didehydrovitamin D3 / (22E)-(24S)-1alpha,24-dihydroxy-26,27-cyclo-22,23-didehydrocholecalciferol / Calcipotriol; (5Z,7E,22E)-(1S,3R,24S)-26,27-cyclo-9,10-seco-5,7,10(19),22-cholestatetraene-1,3,24-triol; SMR000466353; CAS-112965-21-6; Calcipotriene [USAN]; SR-01000762910; CCRIS 7700; MFCD10567086; (5Z,7E,22E,24S)-24-Cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1alpha,3beta,24-triol; PRI 2201; Calcipotriol (JAN); Calcipotriol [INN]; Calcipotriene (USP); BMS-181161; PubChem18810; PubChem19334; Epitope ID:114242; SCHEMBL2853; MLS000759467; MLS001424130; GTPL2778; CHEMBL1200666; DTXSID0046648; AMY2864; 1s19; HMS2051N11; HMS2089J08; HMS3269P03; HMS3413D04; HMS3677D04; HMS3713K08; MC903; EX-A4430; PRI-2201; ZINC3921872; Tox21_112469; BDBM50369964; LMST03020106; s3739; AKOS015855239; Tox21_112469_1; CCG-100949; CS-0387; DB02300; NC00199; STF-115469; NCGC00167465-02; AS-56390; CPD000466353; HY-10001; O763; D01125; U-0267; W-5148; 24207-EP2275420A1; 24207-EP2295055A2; 24207-EP2295416A2; 24207-EP2298748A2; 24207-EP2298764A1; 24207-EP2298765A1; 24207-EP2305640A2; 24207-EP2305642A2; 24207-EP2308861A1; 24207-EP2311453A1; 24207-EP2314590A1; AB00698343-05; 828C009; Q155683; SR-01000762910-3; SR-01000762910-4; (1?,3?,5Z,7E,22E,24S)-24-Cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1,3,24-triol; (1S,3R,5Z,7E,14beta,17alpha,22E,24S)-26,27-cyclo-9,10-secocholesta-5,7,10,22-tetraene-1,3,24-triol; (5Z,7E,22E,24S)-24-Cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1alpha,3beta,24-triol hydrate; (5Z,7E,24S)-26,27-Cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1alpha,3beta,24-triol; 9,10-Secochola-5,7,10(19),22-tetraene-1,3,24-triol, 24-cyclopropyl-, (1alpha,3beta,5Z,7E,22E,24S)-
Clinical Status
Approved
PubChem CID
5288783
Formula
C27H40O3
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
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=5288783"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 412.6 Topological Polar Surface Area 60.7
XlogP 4.3 Complexity 743
Heavy Atom Count 30 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Full List of Drug Formulations (DFMs) Containing This API
          Calcipotriene 0.005% solution Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Isopropyl Alcohol; Propylene Glycol; Hydroxypropyl Cellulose (1200000 Wamw); Sodium Citrate; Menthol; Water
                   Dosage Form Solution
                   Company Fougera Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sodium citrate anhydrous DIG Info Carbonic anhydrase IV (Ki = 99 nM) [1]
Menthol DIG Info Transient receptor potential p8 (EC50 = 3000 nM) [2]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
Hydroxypropyl cellulose DIG Info Mephenytoin 4-hydroxylase (EC50 = 89.5 uM) [5]
          Calcipotriene 0.005% ointment Click to Show/Hide the Full List of Formulation(s):          2 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Benzyl Alcohol; Cetostearyl Alcohol; Ceteth-20; Sodium Phosphate; Glycerin; Medium-Chain Triglycerides; Mineral Oil; Sodium Phosphate; Water; Petrolatum
                   Dosage Form Ointment
                   Company Northstar Rx
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Benzyl alcohol DIG Info Indoleamine 2,3-dioxygenase 1 (IC50 = 1400 nM) [6]
Polyoxyl 20 cetyl ether DIG Info Cholesterol 25-hydroxylase (EC50 = 211.5 uM) [5]
Medium-chain triglyceride DIG Info Colon cancer Caco-2 cells (Inhibition ratio > 36 %) [7]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Cetostearyl Alcohol; Ceteth-20; Dichlorobenzyl Alcohol; Sodium Phosphate; Edetate Disodium; Glycerin; Mineral Oil; Petrolatum; Water; Alpha-Tocopherol; Diazolidinyl Urea
                   Dosage Form Ointment
                   Company Prasco Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Alpha-tocopherol DIG Info Glutathione S-transferase P (IC50 = 500 nM) [8]
Polyoxyl 20 cetyl ether DIG Info Cholesterol 25-hydroxylase (EC50 = 211.5 uM) [5]
References
1 Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with carboxylates. Bioorg Med Chem Lett. 2005 Feb 1; 15(3):573-8.
2 Serendipity in drug-discovery: a new series of 2-(benzyloxy)benzamides as TRPM8 antagonists. Bioorg Med Chem Lett. 2013 Nov 15; 23(22):6118-22.
3 Synthesis and evaluation of dihydropyrroloquinolines that selectively antagonize P-glycoprotein. J Med Chem. 2004 Mar 11; 47(6):1413-22.
4 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
5 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
6 O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1. Eur J Med Chem. 2016 Jan 27; 108:564-576.
7 Interactions between human multidrug resistance related protein (MRP2; ABCC2) and excipients commonly used in self-emulsifying drug delivery systems (SEDDS). Int J Pharm. 2013 Apr 15;447(1-2):192-8.
8 Reviewing Hit Discovery Literature for Difficult Targets: Glutathione Transferase Omega-1 as an Example. J Med Chem. 2018 Sep 13; 61(17):7448-7470.

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