Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01226)
Name
Luliconazole
Synonyms    Click to Show/Hide the Synonyms of This API
Luliconazole; 187164-19-8; Lulicon; NND-502; Luzu; PR-2699; UNII-RE91AN4S8G; NND 502; RE91AN4S8G; NCGC00182704-01; NCGC00182704-02; (R,E)-2-(4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene)-2-(1H-imidazol-1-yl)acetonitrile; CHEBI:34825; (2E)-2-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-yl-acetonitrile; NCGC00182704-03; DSSTox_CID_28533; DSSTox_RID_82805; DSSTox_GSID_48607; (2E)-2-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-ylacetonitrile; NND502; CAS-187164-19-8; Luliconazole [USAN:INN]; 4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene-1-imidazolylacetonitrile; Lulicon (TN); Imidazole antimycotic; Luzu (TN); Lulicon; ; ; NND 502; SCHEMBL342362; GTPL7366; Luliconazole (JAN/USAN/INN); CHEMBL2105689; DTXSID3048607; Luliconazole, >=98% (HPLC); ZINC3929486; Tox21_112942; Tox21_112974; MFCD00953915; s4258; AKOS015897320; Tox21_112974_1; AM84645; BCP9000863; CCG-268075; CS-0587; DB08933; DS-3278; SB18987; NCGC00182704-08; HY-14283; SW219226-1; A11481; C13478; D01980; W-5249; 164L198; SR-01000945039; SR-01000945039-1; Q15624030; UNII-5JA16R08FJ component YTAOBBFIOAEMLL-REQDGWNSSA-N; (-)-(E)-((4R)-4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene)(1H-imidazol-1-yl)acetonitrile; 1H-Imidazole-1-acetonitrile, alpha-((4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene)-, (alphaE)-; 2-[(2E,4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-(1H-imidazol-1-yl)acetonitrile
Clinical Status
Approved
PubChem CID
3003141
Formula
C14H9Cl2N3S2
Canonical SMILES
C1[C@H](S/C(=C(\\C#N)/N2C=CN=C2)/S1)C3=C(C=C(C=C3)Cl)Cl
InChI
1S/C14H9Cl2N3S2/c15-9-1-2-10(11(16)5-9)13-7-20-14(21-13)12(6-17)19-4-3-18-8-19/h1-5,8,13H,7H2/b14-12+/t13-/m0/s1
InChIKey
YTAOBBFIOAEMLL-REQDGWNSSA-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=3003141"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 354.3 Topological Polar Surface Area 92.2
XlogP 4 Complexity 476
Heavy Atom Count 21 Rotatable Bond Count 2
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Full List of Drug Formulations (DFMs) Containing This API
          Luliconazole 1% cream 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
Benzyl Alcohol; Butylated Hydroxytoluene; Cetostearyl Alcohol; Isopropyl Myristate; Medium-Chain Triglycerides; Methylparaben; Polysorbate 60; Propylene Glycol; Purified Water; Sorbitan Monostearate
                   Dosage Form Cream
                   Company Medicis
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Butylated hydroxytoluene DIG Info Carbonic anhydrase II (Ki = 630 nM) [1]
methylparaben DIG Info Carbonic anhydrase VII (Ki = 780 nM) [2]
Benzyl alcohol DIG Info Indoleamine 2,3-dioxygenase 1 (IC50 = 1400 nM) [3]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [4]
Medium-chain triglyceride DIG Info Colon cancer Caco-2 cells (Inhibition ratio > 36 %) [5]
References
1 Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols. Bioorg Med Chem. 2009 Apr 15; 17(8):3207-11.
2 Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15; 21(6):1564-9.
3 O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1. Eur J Med Chem. 2016 Jan 27; 108:564-576.
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 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.

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