CAS 29342-05-0|Ciclopiroxum [INN-Latin]|Stieprox|ciclopiroxolamine|ciclopirox|Ciclopirox-Olamin|Loprox Shampoo|HOE 296b|HOE-296b|6-cyclohexyl-1-hydroxy-4-methyl-1,2-dihydropyridin-2-one|ciclopirox|P...

General Information

Structure

Molecular Formula

C₁₂H₁₇NO₂

Molecular Mass

207.26888

Exact Mass

207.12592879

Charge

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

Canonic Smiles

Cc1cc(C2CCCCC2)n(c(=O)c1)O

Isomeric Smiles

On1c(C2CCCCC2)cc(cc1=O)C

Calculated Properties

JChem

Acid pKa

6.8421407

H Acceptors

H Donor

LogD (pH = 5.5)

2.197355

LogD (pH = 7.4)

1.5591586

Log P

2.2165895

Molar Refractivity

60.9074

Polarizability

22.719618

Polar Surface Area

40.54

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

2.15

LOG S

-2.17

Solubility (Water)

1.41e+00 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

ciclopiroxolamineCiclopirox-OlaminCiclopiroxum [INN-Latin]ciclopiroxHOE 296bHOE-296bCiclopiroxCPOCiclopirox OlaminLoproxMycosterBatrafenStieprox6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone

Brand Name

Loprox ShampooStieproxPenlac Nail LacquerLoproxPenlac

IUPAC name

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

IUPAC Traditional name

ciclopirox penlac

Names and Identifiers

Registration numbers

CAS Number

29342-05-0

PubChem CID

2749

PubChem SID

46506333160964522

Registration numbers

Properties

Physical Property

Safety Information

Storage Condition

-20°C

-20°C Freezer

MSDS Link

Download link

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

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]

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]

TRC

C432800

Broad spectrum antimycotic agent with some antibacterial activity.

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Commercial Catalog

Names and Identifiers

Synonyms

ciclopiroxolamineCiclopirox-OlaminCiclopiroxum [INN-Latin]ciclopiroxHOE 296bHOE-296bCiclopiroxCPOCiclopirox OlaminLoproxMycosterBatrafenStieprox6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinone

Brand Name

Loprox ShampooStieproxPenlac Nail LacquerLoproxPenlac

IUPAC name

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

IUPAC Traditional name

ciclopirox penlac

Registration numbers

CAS Number

29342-05-0

PubChem CID

2749

PubChem SID

46506333160964522

Properties

Physical Property

Safety Information

Storage Condition

-20°C

-20°C Freezer

MSDS Link

Download link

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Molecule Details

Selleck Chemicals

S2528

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

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

Half Life

1.7 hours for 1% topical solution.

Protein Binding