6-cyclohexyl-1-hydroxy-4-methyl-1,2-dihydropyridin-2-one

• ChemBase ID: 1059
• Molecular Formular: C12H17NO2
• Molecular Mass: 207.26888
• Monoisotopic Mass: 207.12592879
• SMILES: On1c(C2CCCCC2)cc(cc1=O)C
• Canonical SMILES: Cc1cc(C2CCCCC2)n(c(=O)c1)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

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-cyclohexyl-1-hydroxy-4-methyl-1,2-dihydropyridin-2-one
• IUPAC Traditional name: ciclopirox; penlac
• Brand Name: Loprox; Penlac; Penlac Nail Lacquer; Stieprox; Loprox Shampoo
• Synonyms: ciclopiroxolamine; Ciclopiroxum [INN-Latin]; CPO; HOE 296b; HOE-296b; Ciclopirox Olamin; Ciclopirox-Olamin; ciclopirox; Ciclopirox; Batrafen; Loprox; Mycoster; Stieprox; 6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone

Database IDs

• CAS Number: 29342-05-0
• PubChem SID: 46506333; 160964522
• PubChem CID: 2749

CALCULATED PROPERTIES

JChem

• Molar Refractivity: 60.9074 cm^3
• Polarizability: 22.719618 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• Acid pKa: 6.8421407
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.197355
• LogD (pH = 7.4): 1.5591586
• Log P: 2.2165895

ALOGPS 2.1

• Solubility (Water): 1.41e+00 g/l
• Log P: 2.15
• LOG S: -2.17

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White or Light-Yellow Solid
• Melting Point: 128-130°C
• Hydrophobicity(logP): 2.3

Safety Information

• Storage Condition: -20°C; -20°C Freezer

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB01188

• Drug Groups: approved; investigational
• Description: Ciclopirox (also called Loprox?, Penlac? and Stieprox?) is a synthetic antifungal agent for topical dermatologic use. [Wikipedia]
• Indication: Used as a topical treatment in immunocompetent patients with mild to moderate onychomycosis of fingernails and toenails without lunula involvement, due to Trichophyton rubrum.
• Pharmacology: Ciclopirox is a broad-spectrum antifungal medication that also has antibacterial and anti-inflammatory properties. Its main mode of action is thought to be its high affinity for trivalent cations, which inhibit essential co-factors in enzymes. Ciclopirox exhibits either fungistatic or fungicidal activity in vitro against a broad spectrum of fungal organisms, such as dermatophytes, yeasts, dimorphic fungi, eumycetes, and actinomycetes. In addition to its broad spectrum of action, ciclopirox also exerts antibacterial activity against many Gram-positive and Gram-negative bacteria. Furthermore, the anti-inflammatory effects of ciclopirox have been demonstrated in human polymorphonuclear cells, where ciclopirox has inhibited the synthesis of prostaglandin and leukotriene. Ciclopirox can also exhibit its anti-inflammatory effects by inhibiting the formation of 5-lipoxygenase and cyclooxygenase.
• Toxicity: Oral LD₅₀ in rat is >10 ml/kg. Symptoms of overexposure include drowsiness and headache.
• Affected Organisms: Humans and other mammals; Yeast and other fungi
• Biotransformation: Glucuronidation is the main metabolic pathway of ciclopirox.
• Absorption: Rapidly absorbed after oral administration. Mean absorption of ciclopirox after application to nails of all twenty digits and adjacent 5 millimeters of skin once daily for 6 months in patients with dermatophytic onychomycoses was less than 5% of the applied dose. Ciclopirox olamine also penetrates into hair and through the epidermis and hair follicles into sebaceous glands and dermis.
• Half Life: 1.7 hours for 1% topical solution.
• Protein Binding: Protein binding is 94-97% following topical administration.
• Elimination: Most of the compound is excreted either unchanged or as glucuronide. After oral administration of 10 mg of radiolabeled drug (14C-ciclopirox) to healthy volunteers, approximately 96% of the radioactivity was excreted renally within 12 hours of administration. Ninety-four percent of the renally excreted radioactivity was in the form of glucuronides.
• References: Niewerth M, Kunze D, Seibold M, Schaller M, Korting HC, Hube B: Ciclopirox olamine treatment affects the expression pattern of Candida albicans genes encoding virulence factors, iron metabolism proteins, and drug resistance factors. Antimicrob Agents Chemother. 2003 Jun;47(6):1805-17. [Pubmed] ; Sigle HC, Thewes S, Niewerth M, Korting HC, Schafer-Korting M, Hube B: Oxygen accessibility and iron levels are critical factors for the antifungal action of ciclopirox against Candida albicans. J Antimicrob Chemother. 2005 May;55(5):663-73. Epub 2005 Mar 24. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S2528

Research Area: Infection
Biological Activity:
Ciclopirox (Penlac) is a synthetic antifungal agent. Ciclopirox (Penlac) is used for topical dermatologic treatment of superficial mycoses. Ciclopirox (Penlac) is most useful against Tinea versicolor. [1] In a study conducted to further elucidate ciclopirox’s mechanism, several Saccharomyces cerevisiae mutants were screened and tested. Results from interpretation of the effects of both the drug treatment and mutation suggested that ciclopirox (Penlac) may exert its effect by disrupting DNA repair, cell division signals and structures (mitotic spindles) as well as some elements of intracellular transport. [2] Ciclopirox (Penlac)) acts by inhibiting the membrane transfer system by interrupting the Na+ K+ ATPase. Ciclopirox (Penlac) is currently being investigated as an alternative treatment to ketoconazole for seborrhoeic dermatitis as it suppresses growth of the yeast Malassezia furfur. [3]

Toronto Research Chemicals - C432800

Broad spectrum antimycotic agent with some antibacterial activity.

REFERENCES

• Niewerth M, Kunze D, Seibold M, Schaller M, Korting HC, Hube B: Ciclopirox olamine treatment affects the expression pattern of Candida albicans genes encoding virulence factors, iron metabolism proteins, and drug resistance factors. Antimicrob Agents Chemother. 2003 Jun;47(6):1805-17. Pubmed
• Sigle HC, Thewes S, Niewerth M, Korting HC, Schafer-Korting M, Hube B: Oxygen accessibility and iron levels are critical factors for the antifungal action of ciclopirox against Candida albicans. J Antimicrob Chemother. 2005 May;55(5):663-73. Epub 2005 Mar 24. Pubmed
• Leem SH et al. Mol Cells. 2003 Feb 28; 15(1):55-61
• Jue, S.G., et al.: Drugs, 29, 330 (1985)
• Starova, A., et al.: Expert Opin. Drug Saf., 4, 235 (1985)