Clotrimazole

Base Information

• Chemical Name: Clotrimazole
• CAS No.: 23593-75-1
• Deprecated CAS: 117829-71-7
• Molecular Formula: C22H17ClN2
• Molecular Weight: 344.843
• Hs Code.: 29332900
• European Community (EC) Number: 245-764-8
• NSC Number: 756700,257473
• UNII: G07GZ97H65
• DSSTox Substance ID: DTXSID7029871
• Nikkaji Number: J3.156I
• Wikipedia: Clotrimazole
• Wikidata: Q413546
• NCI Thesaurus Code: C381
• RXCUI: 2623
• Pharos Ligand ID: MRC3NXQ97R3Y
• Metabolomics Workbench ID: 37930
• ChEMBL ID: CHEMBL104
• Mol file: 23593-75-1.mol

Synonyms:Bay b 5097;Canesten;Clotrimazole;FB b 5097;Kanesten;Klotrimazole;Lotrimin;Mycelex

Chemical Property of Clotrimazole

Chemical Property:

• Appearance/Colour: Crystalline
• Vapor Pressure: 5.42E-09mmHg at 25°C
• Melting Point: 147-149 °C
• Refractive Index: 1.616
• Boiling Point: 482.3 °C at 760 mmHg
• PKA: pKa 4.7(EtOH 50%aq ) (Uncertain)
• Flash Point: 245.5 °C
• PSA: 17.82000
• Density: 1.13 g/cm³
• LogP: 5.37670
• Storage Temp.: Store at RT.
• Solubility.: Soluble in chloroform, DMSO, DMF and alcohols
• Water Solubility.: <10mg/L(25 oC)
• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 344.1080262
• Heavy Atom Count: 25
• Complexity: 396

Purity/Quality:

99% ^*data from raw suppliers

Hemagglutinin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn
• Statements: 22-36/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antifungal Agents
• Canonical SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3Cl)N4C=CN=C4
• Recent ClinicalTrials: SVT-15652 Otic Solution for the Treatment of Otomycosis
• Recent EU Clinical Trials: Double-blind, randomised clinical study comparing efficacy and safety of Mecloderm? Ointment (Test) vs. Lotricomb? Ointment (Reference) vs. Vehicle in patients with moderate to severely inflamed candidiasis of the skin
• Sources and Categories: Clotrimazole is an imidazole antimycotic agent discovered in the 1960s. It falls under the category of azole-type antifungal drugs.
• Chemical Composition and Structure: Clotrimazole has a specific chemical structure consisting of four aromatic rings, including an imidazole ring.
• Uses: Clotrimazole is widely used in medical applications and is available under various trade names. Its formulations for the treatment of vulvovaginal candidosis have been marketed for over 45 years.; Clotrimazole inhibits fungal cell growth by binding to the heme portion of cytochrome P-450 lanosterol 14α-demethylase enzyme, leading to inhibition of ergosterol formation and accumulation of toxic methylated sterols, ultimately stopping fungal cell growth.; Widely used for the treatment of tinea pedis, cutaneous mycoses, oropharyngeal candidosis, vulvovaginal candidosis, and Candida balanitis.
• History and Development: First registered as Canesten? in Germany in 1973, initially for the local treatment of vulvovaginal candidosis. Various formulations, including vaginal tablets, creams, and soft capsules, have been developed over the years.
• FDA Approval: Clotrimazole is FDA approved, with an approval date of 07/29/2004. It is available in various formulations, including topical lotions, powders, oral lozenges, and vaginal inserts/tablets, under different tradenames approved by the FDA. Clotrimazole is classified by the FDA as a class C drug in pregnancy risk classification. It is not known to cross the placenta.

Technology Process of Clotrimazole

There total 5 articles about Clotrimazole 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: 100.0%

1H-imidazole (288-32-4) + diphenyl phosphite (102-10-3) + o-chlorotriphenylmethanol (66774-02-5) + 4-methyl-2-pentanone (108-10-1) → clotrimazole (23593-75-1)

Guidance literature:

With sodium hydroxide;

Reference yield: 92.0%

1H-imidazole (288-32-4) + 2-chlorotrityl chloride (42074-68-0) → clotrimazole (23593-75-1)

Guidance literature:

With sodium carbonate; at 25 ℃; for 48h; Reagent/catalyst; Solvent; Concentration; Green chemistry;

Reference yield: 87.0%

→ clotrimazole (23593-75-1)

Guidance literature:

upstream raw materials:

1H-imidazole

2-chlorotrityl chloride

o-chlorotriphenylmethanol

diphenyl phosphite

Downstream raw materials:

o-chlorotriphenylmethanol

1-(2-chlorophenyl)-1,1-diphenyl methane

AuCl₃(1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole)

RhCl(1,5-cyclooctadiene)(1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole)

Refernces

Synthesis and antimicrobial activity of a new series of 1,4-dihydropyridine derivatives

10.2298/JSC091127003K

The research focuses on the synthesis and antimicrobial activity of a new series of 1,4-dihydropyridine derivatives. The purpose of the study was to prepare a series of 1,4-dihydropyridine derivatives (1a–g) using Hantzsch syntheses and then react these compounds with thiosemicarbazide to yield a new series of compounds (2a–g). The synthesized compounds were confirmed through IR, 1H-NMR, 13C-NMR, mass spectral, and elemental analysis. The research aimed to evaluate the antimicrobial activity of these compounds, with a particular interest in their potential as vasodilators, antihypertensive, anti-inflammatory, and calcium channel modulators. The conclusions drawn from the study indicated that compound 2c exhibited higher activity than ciprofloxacin against Staphylococcus aureus, and compound 2d showed greater activity than clotrimazole against Candida albicans, suggesting potential for further investigation in the field of antimicrobial agents.

Design, synthesis, and antimicrobial activity of novel spiroisoxazolo[2,3- b[[1,2,4]thiadiazole-2,2-thiazolidine-4-ones and spiroisoxazolo[2,3-b[[1,2,4] oxadiazole-2, 2-thiazolidine-4-ones

10.1080/17415993.2012.703671

The research explores the development of new antimicrobial compounds. The study aims to address the increasing resistance of bacteria and fungi to existing antimicrobial agents by synthesizing and evaluating the antimicrobial activity of novel spiroisoxazolo[2,3-b][1,2,4]thiadiazole-2,2′-thiazolidine-4′-ones (9a–9e) and spiroisoxazolo[2,3-b][1,2,4]oxadiazole-2,2′-thiazolidine-4′-ones (12a–12e). The synthesis involved key chemicals such as 3-amino-5-methylisoxazole, aryl isothiocyanates, aryl isocyanates, and mercaptoacetic acid. The compounds were tested for their antibacterial and antifungal activities against various bacterial and fungal strains, showing significant antimicrobial activity compared to standard drugs like Cipro?oxacin and Clotrimazole. The study concludes that these novel compounds, featuring isoxazole–thiadiazole–thiazolidone and isoxazole–oxadiazole–thiazolidone ring systems, have promising potential as new antimicrobial agents, particularly those with specific substituents on the benzene ring, such as chloro, methoxy, and bromo groups.