药品详细

Ciclopirox(环吡酮)

基本信息
剂型规格
适应症
药理
临床
理化性质
相互作用
文档
专利
Pathway
文献
序列

化学结构式图

中文名

环吡酮

英文名

Ciclopirox

分子式

C₁₂H₁₇NO₂

化学名

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

分子量

Average: 207.2689
Monoisotopic: 207.125928793

CAS号

29342-05-0

ATC分类

D01A 未知;G01A 未知

药物类型

small molecule

阶段

approved

商品名

同义名

基本介绍

Ciclopirox (also called Loprox®, Penlac® and Stieprox®) is a synthetic antifungal agent for topical dermatologic use. [Wikipedia]

生产厂家

Actavis mid atlantic llc
Altana inc
Apotex corp
G and w laboratories inc
Glenmark pharmaceuticals inc usa
Hi tech pharmacal co inc
Medicis pharmaceutical corp
Nycomed us inc
Paddock laboratories inc
Perrigo co
Perrigo new york inc
Sanofi aventis us llc
Synerx pharma llc
Taro pharmaceutical industries ltd
Taro pharmaceuticals usa inc
Teva pharmaceuticals usa
Tolmar inc
Versapharm inc
Watson laboratories inc

封装厂家

参考

Synthesis Reference

Not Available

General Reference

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

剂型

规格

化合物类型

Type	small molecule

Classes

Pyridines and Derivatives
Pyridines

Substructures

Hydroxy Compounds
Hydroxamic Acids
Pyridines and Derivatives
Pyridines
Heterocyclic compounds
Aromatic compounds
Imines

适应症

药理

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.
Pharmacodynamics	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.
Mechanism of action	Unlike antifungals such as itraconazole and terbinafine, which affect sterol synthesis, ciclopirox is thought to act through the chelation of polyvalent metal cations, such as Fe³⁺ and Al³⁺. These cations inhibit many enzymes, including cytochromes, thus disrupting cellular activities such as mitochondrial electron transport processes and energy production. Ciclopirox also appears to modify the plasma membrane of fungi, resulting in the disorganization of internal structures. The anti-inflammatory action of ciclopirox is most likely due to inhibition of 5-lipoxygenase and cyclooxygenase. ciclopirox may exert its effect by disrupting DNA repair, cell division signals and structures (mitotic spindles) as well as some elements of intracellular transport.
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.
Volume of distribution	Not Available
Protein binding	Protein binding is 94-97% following topical administration.
Metabolism	Glucuronidation is the main metabolic pathway of ciclopirox.
Route of 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.
Half life	1.7 hours for 1% topical solution.
Clearance	Not Available
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
Pathways	Not Available

理化性质

Properties

State

solid

Experimental Properties

Property	Value	Source
melting point	144 °C	PhysProp
logP	2.3	Not Available

Predicted Properties

Property	Value	Source
water solubility	1.41e+00 g/l	ALOGPS
logP	2.15	ALOGPS
logP	2.22	ChemAxon
logS	-2.2	ALOGPS
pKa (strongest acidic)	6.84	ChemAxon
pKa (strongest basic)	-6.2	ChemAxon
physiological charge	-1	ChemAxon
hydrogen acceptor count	2	ChemAxon
hydrogen donor count	1	ChemAxon
polar surface area	40.54	ChemAxon
rotatable bond count	1	ChemAxon
refractivity	60.91	ChemAxon
polarizability	23.12	ChemAxon

药物相互作用

食物相互作用

Not Available

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