Ciclo Pirox
Ciclopirox
CAS: 29342-05-0
Molecular Formula: C12H17NO2
Ciclo Pirox - 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 |
Ciclo Pirox - Physico-chemical Properties
| Molecular Formula | C12H17NO2 |
| Molar Mass | 207.27 |
| Density | 1.193±0.06 g/cm3(Predicted) |
| Melting Point | 1440C |
| Boling Point | 350.0±25.0 °C(Predicted) |
| Flash Point | 165.5°C |
| Solubility | DMSO 42 mg/mL Water <1 mg/mL Ethanol 42 mg/mL |
| Vapor Presure | 2.71E-06mmHg at 25°C |
| Appearance | Solid |
| Color | Off-White |
| pKa | 6.25±0.58(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Sensitive | Sensitive to heat and light |
| Refractive Index | 1.582 |
| Physical and Chemical Properties | Solid, 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. |
Ciclo Pirox - Risk and Safety
| UN IDs | UN 3077 9 / PGIII |
| HS Code | 2933790002 |
Ciclo Pirox - 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
Ciclo Pirox - 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
Ciclo Pirox - 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
Ciclo Pirox - Safety
Open Data Verified Data
mouse, rat oral LD50 (mg/kg): 2898,3290.
Last Update：2022-01-01 09:08:43
Ciclo Pirox - 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
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View History
Ciclo Pirox
1-BROMO-4-(TRIMETHYLSILYL)BENZENE 1-溴-4-(三甲基硅基)苯
spiro[3.5]nonan-2-one
2,4-二氨基吡啶-6-羧酸
Methyllinderone
Carbonylchlorohydrido[6-(di-t-butylphosphinomethyl)-2-(N,N-diethylaminomethyl)pyridine]ruthenium(II), min. 98% (Milstein Catalyst Precursor)
铁(III)磷酸四水合物
1-BROMO-4-(TRIMETHYLSILYL)BENZENE 1-溴-4-(三甲基硅基)苯
spiro[3.5]nonan-2-one
2,4-二氨基吡啶-6-羧酸
Methyllinderone
Carbonylchlorohydrido[6-(di-t-butylphosphinomethyl)-2-(N,N-diethylaminomethyl)pyridine]ruthenium(II), min. 98% (Milstein Catalyst Precursor)
铁(III)磷酸四水合物