Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00945)
Name
Ciclopirox
Synonyms    Click to Show/Hide the Synonyms of This API
CICLOPIROX; 29342-05-0; Loprox; HOE 296b; Ciclopiroxum; 2(1H)-Pyridinone, 6-cyclohexyl-1-hydroxy-4-methyl-; Ciclopiroxum [INN-Latin]; HOE-296b; 6-cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one; 6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one; 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone; Penlac; 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone; HOE296b; UNII-19W019ZDRJ; Ciclopirox (Penlac); Loprox (TN); 19W019ZDRJ; Terit; CHEBI:453011; 29342-05-0 (free); Stieprox; Ciclopirox gel; Loprox cream; Loprox Gel; Ciclopirox Olamin; Ciclopirox-Olamin; 6-cyclohexyl-4-methyl-1-oxidanyl-pyridin-2-one; 6-CYCLOHEXYL-1-HYDROXY-4-METHYL-1H-PYRIDIN-2-ONE; MLS002153867; Penlac (TN); Ciclopirox (USP/INN); CNL8; SMR001233223; EINECS 249-577-2; Ciclodan; Ciclopirox [USAN:USP:INN:BAN]; 2-aminoethanol;6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one; 2(1H)-Pyridone, 6-cyclohexyl-1-hydroxy-4-methyl-; Prestwick0_000541; Prestwick1_000541; Prestwick2_000541; Prestwick3_000541; Spectrum2_000146; Spectrum3_000351; Spectrum4_000288; Spectrum5_000747; 6-cyclohexyl-1-hydroxy-4-methyl-pyridin-2-one; CHEMBL1413; SCHEMBL34424; BSPBio_000581; BSPBio_002041; KBioGR_000816; 6-Cyclohexyl-1-hydroxy-4-methyl-2-(1H)-pyridone; cid_38911; BIDD:GT0080; (6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone); SPBio_000252; SPBio_002502; BPBio1_000641; ZINC1145; Ciclopirox, >=98% (HPLC); DTXSID9048564; BDBM66087; GTPL11349; KBio3_001261; HMS3656I12; BCP28530; HY-B0450; MFCD00599441; s2528; AKOS015895717; AB06517; CCG-266632; DB01188; KS-5085; NCGC00017112-04; NCGC00017112-05; NCGC00017112-06; NCGC00017112-08; NCGC00017112-11; NCGC00178850-01; NCGC00178850-02; AC-24195; AK544043; SBI-0206690.P002; AB0011605; DB-047566; HOE 296; HOE-296;Ciclopiroxum; Penlac; 1-hydroxy-4-methyl-6-cyclohexyl-2-pyridone; FT-0602961; SW196923-5; 6-cyclohexyl-1-hydroxy-4-methyl-2-pyridinone; D03488; AB00053438_09; AB00053438_10; AB00053438_11; 342C050; A819878; Q419468; SR-05000001589-5; W-106995; 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone #; BRD-K13044802-213-04-1; BRD-K13044802-213-09-0; 2-aminoethanol;6-cyclohexyl-1-hydroxy-4-methyl-2-pyridone; 6-cyclohexyl-1-hydroxy-4-methyl-1,2-dihydropyridin-2-one; Ciclopirox, European Pharmacopoeia (EP) Reference Standard; 2-aminoethanol;6-cyclohexyl-1-hydroxy-4-methyl-2-pyridinone; 2-azanylethanol;6-cyclohexyl-4-methyl-1-oxidanyl-pyridin-2-one; Ciclopirox, United States Pharmacopeia (USP) Reference Standard
Clinical Status
Approved
PubChem CID
2749
Formula
C12H17NO2
Canonical SMILES
CC1=CC(=O)N(C(=C1)C2CCCCC2)O
InChI
1S/C12H17NO2/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10/h7-8,10,15H,2-6H2,1H3
InChIKey
SCKYRAXSEDYPSA-UHFFFAOYSA-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=2749"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 207.27 Topological Polar Surface Area 40.5
XlogP 2 Complexity 325
Heavy Atom Count 15 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Full List of Drug Formulations (DFMs) Containing This API
          Ciclopirox 0.77% 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
Purified Water Usp; Cetyl Alcohol Nf; Light Mineral Oil Nf; Octyldodecanol Nf; Stearyl Alcohol Nf; Polysorbate 60 Nf; Myristyl Alcohol; Sorbitan Monostearate Nf; Lactic Acid Usp; Benzyl Alcohol Nf
                   Dosage Form Cream
                   Company Medimetriks Pharms
                   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) [1]
Cetyl alcohol DIG Info Breast cancer FM3A cells (EC50 = 1600 nM) [2]
Lactic acid DIG Info Fetal lung MRC5 cells (IC50 = 23930 nM) [3]
          Ciclopirox 0.77% suspension 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
Purified Water Usp; Cocamide Dea; Octyldodecanol Nf; Mineral Oil Usp; Stearyl Alcohol Nf; Cetyl Alcohol Nf; Polysorbate 60 Nf; Myristyl Alcohol Nf; Lactic Acid Usp; Sorbitan Monostearate Nf; Benzyl Alcohol Nf
                   Dosage Form Suspension
                   Company Medimetriks Pharms
                   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) [1]
Cetyl alcohol DIG Info Breast cancer FM3A cells (EC50 = 1600 nM) [2]
Lactic acid DIG Info Fetal lung MRC5 cells (IC50 = 23930 nM) [3]
          Ciclopirox 0.77% gel 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
Purified Water Usp; Isopropyl Alcohol Usp; Octyldodecanol Nf; Dimethicone Copolyol 190; Carbomer 980; Sodium Hydroxide Nf; Docusate Sodium Usp
                   Dosage Form Gel
                   Company County Line Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Docusate sodium DIG Info Solute carrier SLCO2B1 (Ki = 2.3 uM) [4]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [5]
          Ciclopirox 8% 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
Ethyl Acetate Nf; Isopropyl Alcohol Usp; Butyl Monoester Of Poly[Methylvinyl Ether/Maleic Acid] In Isopropyl Alcohol
                   Dosage Form Solution
                   Company Valeant International Bermuda
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Ethyl acetate DIG Info Cathepsin L (IC50 > 10000 nM) [6]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [5]
          Ciclopirox 1% shampoo 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
Disodium Laureth Sulfosuccinate; Laureth-2; Purified Water; Sodium Chloride; Sodium Laureth Sulfate
                   Dosage Form Shampoo
                   Company Bausch Health Us
References
1 O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1. Eur J Med Chem. 2016 Jan 27; 108:564-576.
2 Synthesis and notable antimalarial activity of acyclic peroxides, L-(alkyldioxy)-L-(methyldioxy)cyclododecanes. J Med Chem. 2002 Mar 14; 45(6):1374-8.
3 Design, synthesis and biological studies of a library of NK1-Receptor Ligands Based on a 5-arylthiosubstituted 2-amino-4,6-diaryl-3-cyano-4H-pyran core: Switch from antagonist to agonist effect by chemical modification. Eur J Med Chem. 2017 Sep 29; 138:644-660.
4 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
5 Synthesis and evaluation of dihydropyrroloquinolines that selectively antagonize P-glycoprotein. J Med Chem. 2004 Mar 11; 47(6):1413-22.
6 Synthesis and biochemical evaluation of benzoylbenzophenone thiosemicarbazone analogues as potent and selective inhibitors of cathepsin L. Bioorg Med Chem. 2015 Nov 1; 23(21):6974-92.

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