Details of the Drug

General Information of Drug (ID: DMN5T2A)

• Drug Name: Ciclopirox
• Synonyms: Ciclopiroxum; Cyclopirox; Cyclopyroxolamine; Loprox; Penlac; Stieprox; Terit; Ciclopirox Olamin; Ciclopirox gel; Loprox Gel; Loprox Shampoo; Loprox cream; Penlac nail lacquer; HOE 296b; Batrafen (TN); Ciclopirox-Olamin; Ciclopiroxum [INN-Latin]; Dafnegin-CSC; HOE-296; HOE-296b; Loprox (TN); Penlac (TN); Stieprox (TN); Ciclopirox (USP/INN); Ciclopirox [USAN:BAN:INN]; (6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone); 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone; 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone; 6-Cyclohexyl-1-hydroxy-4-methyl-2-(1H)-pyridone; 6-cyclohexyl-1-hydroxy-4-methyl-2(1 H)-pyridinone; 6-cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one; 6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one

Indication

Disease Entry	ICD 11	Status	REF
Cutaneous candidiasis	1F23.14	Approved	[1]
Fungal infection	1F29-1F2F	Approved	[2]
Mycoses	1F2Z	Approved	[1]
Onychomycosis	EE12.1	Approved	[1]
Pityriasis simplex	N.A.	Approved	[1]
Tinea corporis	1F28.Y	Approved	[1]
Tinea cruris	1F28.3	Approved	[1]
Tinea versicolor	1F2D.0	Approved	[1]
Tinea pedis	1F28.2	Investigative	[1]

• Therapeutic Class: Antifungal Agents
• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 207.27
  Logarithm of the Partition Coefficient (xlogp); 2
  Rotatable Bond Count (rotbonds); 1
  Hydrogen Bond Donor Count (hbonddonor); 1
  Hydrogen Bond Acceptor Count (hbondacc); 2
• ADMET Property:
  Half-life: The concentration or amount of drug in body reduced by one-half in 1.7 hours [3]
  Metabolism: The drug is metabolized via the glucuronidation []
• Chemical Identifiers:
  Formula: C12H17NO2
  IUPAC Name: 6-cyclohexyl-1-hydroxy-4-methylpyridin-2-one
  Canonical SMILES: CC1=CC(=O)N(C(=C1)C2CCCCC2)O
  InChI: 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
• Cross-matching ID:
  PubChem CID: 2749
  ChEBI ID: CHEBI:453011
  CAS Number: 29342-05-0
  DrugBank ID: DB01188
  TTD ID: D07GRH
  VARIDT ID: DR00986
  ACDINA ID: D00945
• Repurposed Drugs (RPD): Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
HIF-prolyl hydroxylase (HPH)	TTJQFBG	NOUNIPROTAC	Modulator	[4]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Baculoviral IAP repeat-containing protein 5 (BIRC5)	OTILXZYL	BIRC5_HUMAN	Gene/Protein Processing	[5]
Cellular tumor antigen p53 (TP53)	OTIE1VH3	P53_HUMAN	Gene/Protein Processing	[6]
Glucocorticoid receptor (NR3C1)	OTCI2YDI	GCR_HUMAN	Gene/Protein Processing	[7]
Heme oxygenase 1 (HMOX1)	OTC1W6UX	HMOX1_HUMAN	Protein Interaction/Cellular Processes	[8]
Hypoxia-inducible factor 1-alpha (HIF1A)	OTADSC03	HIF1A_HUMAN	Protein Interaction/Cellular Processes	[9]
Microtubule-associated protein tau (MAPT)	OTMTP2Z7	TAU_HUMAN	Gene/Protein Processing	[10]

Molecular Expression Atlas of This Drug

• The Studied Disease: Cutaneous candidiasis
• ICD Disease Classification: 1F23.14

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
HIF-prolyl hydroxylase (HPH)	DTT	NO-GeName	7.70E-01	4.40E-03	0.02

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

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Benzyl alcohol	E00010	244	Antimicrobial preservative; Solvent
Cetyl alcohol	E00061	2682	Coating agent; Emollient; Emulsifying agent; Stiffening agent
Docusate sodium	E00563	23673837	Surfactant
Ethyl acetate	E00192	8857	Flavoring agent; Solvent
Isopropyl alcohol	E00070	3776	Antimicrobial preservative; Solvent
Lactic acid	E00020	612	Acidulant
Sodium chloride	E00077	5234	Diluent; Tonicity agent
Sodium hydroxide	E00234	14798	Alkalizing agent
Sodium laureth-3 sulfate	E00564	23674622	Surfactant
Stearyl alcohol	E00172	8221	Emollient; Emulsifying agent; Stiffening agent; Viscosity-controlling agent
Water	E00035	962	Solvent
Laureth-2	E00376	76457	Dispersing agent; Emulsifying agent; Gelling agent; Penetration agent; Solubilizing agent; Surfactant; Viscosity-controlling agent
Myristyl alcohol	E00171	8209	Emollient; Emulsion stabilizing agent; Oleaginous vehicle; Surfactant; Viscosity-controlling agent
Octyldodecanol	E00269	21414	Emollient; Emulsifying agent; Lubricant; Solvent; Viscosity-controlling agent
Sorbitan monostearate	E00524	16218600	Dispersing agent; Emulsifying agent; Solubilizing agent; Surfactant; Suspending agent; Vaccine adjuvant
Disodium laureth sulfosuccinate	E00713	10173122	Surfactant

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Ciclopirox 0.77% cream	0.77%	Cream	Topical
Ciclopirox 0.77% suspension	0.77%	Suspension	Topical
Ciclopirox 0.77% gel	0.77%	Gel	Topical
Ciclopirox 8% solution	8%	Solution	Topical
Ciclopirox 1% shampoo	1%	Shampoo	Topical

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

• [1] Ciclopirox FDA Label
• [2] FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 076435.
• [3] Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
• [4] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
• [5] Chelation of intracellular iron with the antifungal agent ciclopirox olamine induces cell death in leukemia and myeloma cells. Blood. 2009 Oct 1;114(14):3064-73. doi: 10.1182/blood-2009-03-209965. Epub 2009 Jul 9.
• [6] Identification of environmental chemicals that activate p53 signaling after in vitro metabolic activation. Arch Toxicol. 2022 Jul;96(7):1975-1987. doi: 10.1007/s00204-022-03291-5. Epub 2022 Apr 18.
• [7] Discovery of selective glucocorticoid receptor modulators by multiplexed reporter screening. Proc Natl Acad Sci U S A. 2009 Mar 24;106(12):4929-34. doi: 10.1073/pnas.0812308106. Epub 2009 Mar 2.
• [8] Non-hypoxic stabilization of hypoxia-inducible factor alpha (HIF-alpha): relevance in neural progenitor/stem cells. Neurotox Res. 2009 May;15(4):367-80. doi: 10.1007/s12640-009-9043-z. Epub 2009 Mar 20.
• [9] Copper-dependent activation of hypoxia-inducible factor (HIF)-1: implications for ceruloplasmin regulation. Blood. 2005 Jun 15;105(12):4613-9. doi: 10.1182/blood-2004-10-3980. Epub 2005 Mar 1.
• [10] Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression. Mol Neurodegener. 2006 Jul 26;1:6. doi: 10.1186/1750-1326-1-6.