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...

基本信息

化学结构

分子式

C₁₂H₁₇NO₂

分子量

207.26888

精确质量

207.12592879

电荷

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

计算属性

JChem

Acid pKa

6.8421407

质子受体

质子供体

LogD (pH = 5.5)

2.197355

LogD (pH = 7.4)

1.5591586

Log P

2.2165895

摩尔折射率

60.9074

极化性

22.719618

极化表面积

40.54

可自由旋转的化学键

里宾斯基五规则

true

ALOGPS 2.1

Log P

2.15

LOG S

-2.17

溶解度

1.41e+00 g/l

数据来源

学术数据

产品目录

数据来源

名称和标识

别名

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

商标名

Loprox ShampooStieproxPenlac Nail LacquerLoproxPenlac

IUPAC标准名

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

IUPAC传统名

ciclopirox penlac

名称和标识

数据登录号

CAS号

29342-05-0

PubChem CID

2749

PubChem SID

46506333160964522

数据登录号

化合物性质

产品相关信息

Free Base

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安全信息

-20°C

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化合物性质

分子相关蛋白质

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分子图谱

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描述信息

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.

描述信息

参考文献

PubChem文献

数据源提供

• Leem SH et al. Mol Cells. 2003 Feb 28; 15(1):55-61

• Starova, A., et al.: Expert Opin. Drug Saf., 4, 235 (1985)

• Jue, S.G., et al.: Drugs, 29, 330 (1985)

参考文献

生物活性

PubChem BioAssay

生物活性

数据来源

学术数据

产品目录

名称和标识

别名

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

商标名

Loprox ShampooStieproxPenlac Nail LacquerLoproxPenlac

IUPAC标准名

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

IUPAC传统名

ciclopirox penlac

数据登录号

CAS号

29342-05-0

PubChem CID

2749

PubChem SID

46506333160964522

参考文献

PubChem文献

数据源提供

• Leem SH et al. Mol Cells. 2003 Feb 28; 15(1):55-61

• Starova, A., et al.: Expert Opin. Drug Saf., 4, 235 (1985)

• Jue, S.G., et al.: Drugs, 29, 330 (1985)

生物活性

PubChem BioAssay

化合物性质

产品相关信息

Free Base

下载链接

安全信息

-20°C

-20°C Freezer

下载链接

描述信息

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