Ciclopirox

Base Information

• Chemical Name: Ciclopirox
• CAS No.: 29342-05-0
• Molecular Formula: C12H17NO2
• Molecular Weight: 207.272
• Hs Code.: 2933790002
• European Community (EC) Number: 249-577-2
• UNII: 19W019ZDRJ
• DSSTox Substance ID: DTXSID9048564
• Nikkaji Number: J3.173I
• Wikipedia: Ciclopirox
• Wikidata: Q419468
• NCI Thesaurus Code: C61677
• RXCUI: 21090
• Metabolomics Workbench ID: 43404
• ChEMBL ID: CHEMBL1413
• Mol file: 29342-05-0.mol

Synonyms:6-cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone ethanolamine salt;Batrafen;ciclopirox;ciclopirox olamine;ciclopiroxolamine;cyclopirox;cyclopyroxolamine;Dafnegin CSC;Dafnegin-CSC;HOE 296;HOE-296;HOE296;Loprox;Penlac

Chemical Property of Ciclopirox

Chemical Property:

• Appearance/Colour: white or light-yellow powder
• Vapor Pressure: 2.71E-06mmHg at 25°C
• Melting Point: 144 °C
• Refractive Index: 1.582
• Boiling Point: 350 °C at 760 mmHg
• PKA: 6.25±0.58(Predicted)
• Flash Point: 165.5 °C
• PSA: 42.23000
• Density: 1.193 g/cm³
• LogP: 2.44170
• Storage Temp.: -20°C Freezer
• Solubility.: Slightly soluble in water, freely soluble in anhydrous ethanol and in methylene chloride
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 207.125928785
• Heavy Atom Count: 15
• Complexity: 325

Purity/Quality:

99% ,99.9%, ^*data from raw suppliers

Ciclopirox ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,O
• Hazard Codes: C,O

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)N(C(=C1)C2CCCCC2)O
• Recent ClinicalTrials: Mycosis Culture Collection From Dermatological Isolated
• Recent EU Clinical Trials: Diode laser and photodynamic therapy Versus Ciclopirox Hydroxypropyl Chitosan. Randomised controlled clinical trial.
• Uses: Pyridine ketones broad-spectrum antifungal agents, have inhibiting effects on a variety of skin fungi . They can prevent the substances necessary for Candida albicans cells survival such as amino acids, potassium ions, phosphate,going through the cell membrane ,which can cause by certain important matrix or intracellular ions failure,and then inhibit or kill fungal cells. There are a wide range of anti-fungal effects, they can have a killing effect on the skin filamentous bacteria, yeast fungi , they have inhibition effects on a variety of Gram positive and negative bacteria, chlamydia, trichomoniasis, Proteus, E. coli, Pseudomonas and Staphylococcus bacteria. They are used to treat fungal skin disease, tinea versicolor, vulvovaginal Candida disease, skin and fingers (toe) candidiasis ,they have significant effects , and lower side effects. Broad spectrum antimycotic agent with some antibacterial activity. Broad spectrum antimycotic agent with some antibacterial 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 ciclopir
• production method: 4-methyl-3-penten-2-one by oxidation of sodium hypochlorite (56% yield), is esterified to produce methyl-2-butenoate (the I), 67% yield, b.p. 135~139 ℃. Cyclohexane carboxylic acid and thionyl chloride react to obtain cyclohexane carboxylic acid chloride. In the role of aluminum chloride,it reacts with methyl-2-butenoate (I) in a methylene chloride solvent, and the reaction is stirred for 4h, after post-treatment, vacuum collect 140-145 ℃ (0.4kPa) the distillate, 3-methyl-5-oxo-5-cyclohexyl-3-pentenoate (ciclopirox, II) is generated in 75% yield. And then it is stirred at room temperature for 20h together with hydroxylamine hydrochloride, sodium acetate, methanol and water , then it is added 50% sodium hydroxide , then it is stirred for 1h. After cooling with benzene extraction, the aqueous phase is acidified to Ph = 6. The precipitated crystals are recrystallized from ethanol, to give ciclopirox, m.p. 140~142 ℃, yield 48.3%. Finally,it is salified with the hydroxyl amine in methylene chloride to give almost quantitative ciclopirox, melting point 97~99 ℃.
• Therapeutic Function: Antifungal
• Clinical Use: Ciclopirox is a hydroxylated pyridinone that is employed for superficial dermatophytic infections, principally onychomycosis.

Technology Process of Ciclopirox

There total 12 articles about Ciclopirox which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

2-cyclohexyl-6-methoxy-4-methylpyridine N-oxide → CICLOPIROX (29342-05-0)

Guidance literature:

2-cyclohexyl-6-methoxy-4-methylpyridine N-oxide; With acetyl chloride; for 1h; Reflux;

With methanol; at 20 ℃;

DOI:10.1021/acs.joc.6b02891

Reference yield: 84.0%

cyclopirox olamine (41621-49-2) → CICLOPIROX (29342-05-0)

Guidance literature:

With hydrogenchloride; In water;

Reference yield: 34.0%

Methyl 3,3-dimethylacrylate (924-50-5) + cyclohexanylcarbonyl chloride (2719-27-9) → CICLOPIROX (29342-05-0)

Guidance literature:

Methyl 3,3-dimethylacrylate; cyclohexanylcarbonyl chloride; With aluminum (III) chloride; In dichloromethane; for 3h; Reflux;

With hydroxylamine hydrochloride; sodium acetate; In methanol; water; at 20 - 30 ℃; for 20h;

With sodium hydroxide; In methanol; water; at 20 ℃; for 1h;

upstream raw materials:

4-methyl-6-cyclohexyl02-pyrone

Methyl 3,3-dimethylacrylate

cyclohexanylcarbonyl chloride

1H-imidazole

Downstream raw materials:

cyclopirox olamine

Refernces

• 1、 Zhang, Wen-Man,Dai, Jian-Jun,Xu, Jun,Xu, Hua-Jian. "Visible-Light-Induced C2 Alkylation of Pyridine N-Oxides". . p. 2059 - 2066. Retrieved 2017/02/26.
• 2、 -. "METHOD OF TREATMENT WITH PRODRUGS OF 6-CYCLOHEXYL-1-HYDROXY-4-METHYLPYRIDIN IN-2-1H-ONE AND DERIVATIVES THEREOF". Paragraph 0062. . Retrieved 2015/04/28.