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Ciclopirox

Ciclopirox

CAS: 29342-05-0

Molecular Formula: C12H17NO2

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Ciclopirox - Names and Identifiers

Name Ciclopirox
Synonyms geprox
Brumixol
Dafnegin
Cidochem
Ciclopirox
Ciciopirox
CICLOPIROX
CIELOPIROX
Ciclo Pirox
6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone
6-CYCLOHEXYL-1-HYDROXY-4-METHYL-1H-PYRIDIN-2-ONE
6-Cyclohexyl-1-hydroxy-4-methyl-2[1H]-pyridinone
6-cyclohexyl-1-hydroxy-4-methylpyridin-2(1H)-one
CAS 29342-05-0
EINECS 249-577-2
InChI InChI=1/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

Ciclopirox - Physico-chemical Properties

Molecular FormulaC12H17NO2
Molar Mass207.27
Density1.193±0.06 g/cm3(Predicted)
Melting Point1440C
Boling Point350.0±25.0 °C(Predicted)
Flash Point165.5°C
Solubility DMSO 42 mg/mL Water <1 mg/mL Ethanol 42 mg/mL
Vapor Presure2.71E-06mmHg at 25°C
AppearanceSolid
ColorOff-White
pKa6.25±0.58(Predicted)
Storage ConditionKeep in dark place,Sealed in dry,Room Temperature
SensitiveSensitive to heat and light
Refractive Index1.582
Physical and Chemical PropertiesSolid, melting point 144 °c. Ciclopirox olamin: C12H17NO2? C2H7NO. [41621-49-2]. White crystalline powder, odorless, bitter taste. Soluble in methanol, ethanol or chloroform, slightly soluble in dimethylformamide or water, slightly soluble in ether. Melting point 124-128 °c. Acute toxicity LD50 mice, rats (mg/kg):2898,3290 oral.

Ciclopirox - Risk and Safety

UN IDsUN 3077 9 / PGIII
HS Code2933790002

Ciclopirox - Nature

Open Data Verified Data

Solid, melting point 144 °c. Ci2h17 No2.C2 H7 NO,CAS accession number [416-49-2]. White crystalline powder, odorless, bitter taste. Soluble in methanol, ethanol or chloroform, slightly soluble in dimethylformamide or water, slightly soluble in ether. Melting point 12 4~128 °c.

Last Update：2024-01-02 23:10:35

Ciclopirox - Preparation Method

Open Data Verified Data

4-methyl-3-penten-2-one is oxidized by sodium hypochlorite and then methyl-esterified to give methyl 3-methyl-2-butene-3. The reaction of cyclohexane carboxylic acid with thionyl chloride gives cyclohexanecarbonyl chloride. Cyclohexanoyl chloride and 3 methyl -2-methyl-under the action of aluminum trichloride, in dichloromethane solvent, stirring reaction, after post-treatment, vacuum collection of fractions, and the resulting material and hydroxylamine hydrochloride, sodium acetate, methanol and water were stirred at room temperature for a certain period of time, and sodium hydroxide solution was added to stir. After cold extraction with benzene, the aqueous phase was acidified to pH = 6. The precipitated crystals are recrystallized with ethanol, and then Ciclopirox is obtained, and finally a salt is formed with hydroxyethanolamine in dichloromethane to obtain cyclopyrrolidone amine.

Last Update：2022-01-01 09:08:43

Ciclopirox - Use

Open Data Verified Data

developed by Hoechst Roussol pharmaceutical company, Germany. Pyridone broad-spectrum antifungal agents have inhibitory effect on a variety of skin fungi. The fungal cells can be inhibited or killed by preventing substances necessary for the survival of Candida albicans cells, such as amino acids, potassium ions, and phosphate, from passing through the cell membrane to cause certain important matrix or ion depletion in the cell. Has a wide range of antifungal effect, the skin filamentous bacteria, yeast fungi have a killing effect on a variety of gram-positive and negative bacteria, chlamydia, trichomonas, Proteus, Escherichia coli, pseudomonas and Staphylococcus aureus have inhibitory effect. Commonly used in the treatment of dermatomycosis, tinea versicolor, vulvovaginal candidiasis, skin and finger (toe) Candida disease.

Last Update：2022-01-01 09:08:43

Ciclopirox - Safety

Open Data Verified Data

mouse, rat oral LD50 (mg/kg): 2898,3290.

Last Update：2022-01-01 09:08:43

Ciclopirox - Reference Information

External antifungal drug Ciclopiroxamine is a new type of broad-spectrum external antifungal drug, which was successfully developed by the Federal German Pharmaceutical Factory. The mechanism of action is by changing the integrity of the fungal cell membrane, causing the outflow of intracellular substances, and blocking the uptake of protein precursor substances, leading to the death of fungal cells, it has strong antibacterial and bactericidal effects on dermatophytes, yeasts, molds, etc., and has strong permeability. At higher concentrations, it can also inhibit various actinomycetes, Gram-positive and Gram-negative bacteria, mycoplasma, chlamydia, trichomonas vaginalis and Pseudomonas aeruginosa.
Compared with imidazole antifungal drugs, ciclopyrone amine has a strong penetration force on the stratum corneum, which is the survival of skin fungi, so it has a significant effect on the deep stratum corneum fungi, such as onychomycosis. Bacteriostasis.
Clinically, it is mainly used for superficial skin fungal infections, such as tinea corporis, tinea pedis, tinea cruris, tinea pedis (especially keratosis thickening type), tinea versicolor, skin candidiasis, Candida albicans and onychomycosis treatment.
pharmacological action this product is a salt formed by the combination of synthetic antifungal drugs cicyclone and ethanolamine. it is used for local fungal infection, mainly by changing the integrity of fungal cell membrane, causing the outflow of intracellular substances, and blocking the uptake of protein precursor substances, leading to fungal cell death. It has strong antibacterial and bactericidal effects on dermatophytes, yeasts, molds, etc., and has strong permeability. It also has a certain inhibitory effect on various actinomycetes, gram-positive and gram-negative bacteria, mycoplasma, chlamydia, trichomonas, etc.
Application Ciclopiroxamine mainly changes the integrity of the fungal cell membrane, causes the outflow of intracellular substances, and blocks the uptake of protein precursor substances, leading to its death. It has strong penetration, can reach the deep part of the infected skin, and can resist most pathogenic molds, including skin fungi and Candida albicans, as well as a variety of non-pathogenic molds, gram-positive bacteria, gram-negative bacteria, etc.
use pyridone broad-spectrum antifungal drugs have inhibitory effects on various skin fungi. It can prevent the substances necessary for the survival of Candida albicans cells such as amino acids, potassium ions, and phosphates through the cell membrane to cause some important matrix or ion failure in the cell, and inhibit or kill fungal cells. It has a wide range of antifungal effects, killing skin filamentous bacteria and yeast fungi, and has an inhibitory effect on a variety of Gram-positive and negative bacteria, chlamydia, trichomonas, Proteus, Escherichia coli, Pseudomonas and Staphylococcus aureus. It is often used to treat skin mycosis, tinea versicolor, vulvovaginal candidiasis, skin and finger (toe) candidiasis, etc., with significant curative effects and low toxic and side effects.
Ciclopirox is a synthetic antifungal drug.
Production method 4-methyl-3-penten-2-one is oxidized by sodium hypochlorite (yield 56%), and then methylated to obtain 3-Methyl-2-butenoic acid methyl ester (I) with a yield of 67% and a boiling point of 135~139 ℃. Cyclohexane carboxylic acid reacts with thionyl chloride to obtain cyclohexane formyl chloride. Under the action of aluminum trichloride, methyl 3-methyl -2-butenoic acid (I) is stirred and reacted in dichloromethane solvent for 4 hours. After post-treatment, the fraction at 140-145 ℃(0.4kPa) is collected in vacuum to obtain methyl 5-oxo -3-methyl -5-cyclohexyl -3-pentenoic acid (cicropyr, II) with 75% yield. Stir with hydroxylamine hydrochloride, sodium acetate, methanol and water at room temperature for 20h, add 50% sodium hydroxide and stir for 1h. After cooling, benzene is used for extraction, and the water phase is acidified to Ph = 6. The precipitated crystals are recrystallized with ethanol to obtain cyclione with a melting point of 140~142 ℃ and a 48.3% yield. Finally, it is salted with hydroxyethanolamine in dichloromethane to obtain almost a certain amount of cyclopyrone amine with a melting point of 97~99 ℃.
Last Update：2024-04-09 15:16:49
Ciclopirox
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Hefei TNJ Chemical Industry Co.,Ltd.
Product Name: Ciclopirox Request for quotation
CAS: 29342-05-0
Tel: 0086-551-65418684
Email: sales@tnjchem.com
　　　　 info@tnjchem.com
Mobile: 0086 189 4982 3763
QQ: 2881500840 Click to send a QQ message
Wechat: 0086 189 4982 3763
WhatsApp: 0086 189 4982 3763
Product List: View Catalog
Shanghai Yuanye Bio-Technology Co., Ltd.
Product Name: Ciclopirox Visit Supplier Webpage Request for quotation
CAS: 29342-05-0
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409 Click to send a QQ message
Wechat: 18301782025
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Ciclopirox
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