Ciclopirox olamine

Base Information

• Chemical Name: Ciclopirox olamine
• CAS No.: 41621-49-2
• Molecular Formula: C12H17NO2^.C2H7NO
• Molecular Weight: 268.356
• Hs Code.: 2933790002
• European Community (EC) Number: 255-464-9
• NSC Number: 756694,336278
• UNII: 50MD4SB4AP
• DSSTox Substance ID: DTXSID6045583
• NCI Thesaurus Code: C65327
• RXCUI: 52172
• ChEMBL ID: CHEMBL242580
• Mol file: 41621-49-2.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 olamine

Chemical Property:

• Appearance/Colour: White or pale yellow crystalline powder
• Vapor Pressure: 2.71E-06mmHg at 25°C
• Melting Point: 144 °C
• Boiling Point: 350 °C at 760 mmHg
• Flash Point: 165.5 °C
• PSA: 88.48000
• Density: 0.41g/cm3 at 25℃
• LogP: 2.07940
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Sparingly soluble in water, very soluble in ethanol (96 per cent) and in methylene chloride, slightly soluble in ethyl acetate, practically insoluble in cyclohexane.
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 268.17869263
• Heavy Atom Count: 19
• Complexity: 335

Purity/Quality:

98% ^*data from raw suppliers

Ciclopirox Ethanolamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-42/43-20/22
• Safety Statements: 26-36-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC(=O)N(C(=C1)C2CCCCC2)O.C(CO)N
• Recent ClinicalTrials: Study to Assess the Safety and Pharmacokinetics of ATL-001 (Ciclopirox Olamine) in Healthy Volunteers
• Recent EU Clinical Trials: Double-blind, randomised clinical study comparing efficacy and safety of Ciclopirox Olamine Cream 10 mg/g (Test) vs. Batrafen? Cream (Reference) vs. Vehicle in patients with skin mycoses
• Uses: Ciclopirox (C432800) derivative. Broad spectrum antimycotic agent with some antibacterial activity. Ciclopirox olamine (Loprox, Penlac) is a synthetic, broad-spectrum hydroxypyridone antifungal agent. It is chemically unrelated to the imidazoles or any other antifungal agent currently available in the United States. It appears to act through intracellular depletion of substrates and/or ions principally by inhibition of transmembrane transport of these substances. It is active against dermatophytes, yeast, and Pityrosporum orbiculare. It also demonstrates activity against Trichomonas vaginalis, some mycoplasma, and some gram-positive and gram-negative bacteria. Ciclopirox ethanolamine is a broad spectrum antimycotic agent with some antibacterial activity.
• Indications: Ciclopirox olamine (Loprox, Penlac) is a synthetic, broad-spectrum hydroxypyridone antifungal agent. It is chemically unrelated to the imidazoles or any other antifungal agent currently available in the United States. It appears to act through intracellular depletion of substrates and/or ions principally by inhibition of transmembrane transport of these substances. It is active against dermatophytes, yeast, and Pityrosporum orbiculare. It also demonstrates activity against Trichomonas vaginalis, some mycoplasma, and some gram-positive and gram-negative bacteria.
• Therapeutic Function: Antifungal
• Clinical Use: 6-Cyclohexyl-1-hydroxyl-4-methyl-2(1H)-pyridinoneethanolamine salt (Loprox) is a broad-spectrum antifungalagent intended only for topical use. It is active against dermatophytesas well as pathogenic yeasts (C. albicans) thatare causative agents for superficial fungal infections.Ciclopirox is considered an agent of choice in the treatmentof cutaneous candidiasis, tinea corporis, tinea cruris,tinea pedis, and tinea versicolor. It is a second-line agent forthe treatment of onychomycosis (ringworm of the nails).Loprox is formulated as a cream and a lotion, each containing1% of the water-soluble ethanolamine salt. Ciclopirox isbelieved to act on cell membranes of susceptible fungi atlow concentrations to block the transport of amino acids intothe cells. At higher concentrations, membrane integrity islost, and cellular constituents leak out. Ciclopirox olamine (Loprox) is a pyridone derivative available for the treatment of cutaneous dermatophyte infections, cutaneous C. albicans infections, and tinea versicolor caused by Malassezia furfur. It interferes with fungal growth by inhibiting macromolecule synthesis.

Technology Process of Ciclopirox olamine

There total 3 articles about Ciclopirox olamine 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:

CICLOPIROX (29342-05-0) + ethanolamine (141-43-5) → cyclopirox olamine (41621-49-2)

Guidance literature:

In ethyl acetate; at 50 ℃; for 0.5h;

Reference yield:

3-Methylbutenoic acid (541-47-9) → cyclopirox olamine (41621-49-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sulfuric acid / 5 h / Reflux

2.1: aluminum (III) chloride / dichloromethane / 3 h / Reflux

2.2: 20 h / 20 - 30 °C

2.3: 1 h / 20 °C

3.1: ethyl acetate / 0.5 h / 50 °C

With aluminum (III) chloride; sulfuric acid; In dichloromethane; ethyl acetate;

Reference yield:

Cyclohexanecarboxylic acid (98-89-5) → cyclopirox olamine (41621-49-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: pyridine; thionyl chloride / 3 h / Reflux

2.1: aluminum (III) chloride / dichloromethane / 3 h / Reflux

2.2: 20 h / 20 - 30 °C

2.3: 1 h / 20 °C

3.1: ethyl acetate / 0.5 h / 50 °C

With pyridine; aluminum (III) chloride; thionyl chloride; In dichloromethane; ethyl acetate;

upstream raw materials:

CICLOPIROX

ethanolamine

3-Methylbutenoic acid

Cyclohexanecarboxylic acid

Downstream raw materials:

CICLOPIROX

Refernces