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Nov. 2020/10/14 14:42:49 By LEAP Chem


LEAPChem - Pharmaceutical Chemicals is a premier supplier of pharmaceutical chemicals and other chemical raw materials for global customers including drug manufacturers, universities, research labs, R&D centers, and other industries that use chemical raw materials such as polymers, textiles, agriculture, coatings, etc. As an ISO 9001:2015 certified company, our team of experts in customer service, product sourcing, logistics, regulatory and compliance operate at the highest standard. LEAPChem's experienced sales team will work tirelessly to find the chemicals you need for a price you can afford. All of which allow us to ensure you will receive the same high quality service and chemicals each and every time. LEAPChem is proud to shed awareness on Ketoconazole, a very promising chemical in the global market.

 

Basic Information of Ketoconazole

Chemical Name: Ketoconazole

Cas No.: 65277-42-1

Molecular Formula: C26H28Cl2N4O4

Chemical Structure:

 65277-42-1.gif

 

Ketoconazole is an antifungal medication which is used primarily to treat fungal infections. Ketoconazole is sold commercially as a tablet for oral administration (although this use has been discontinued in a number of countries), and in a variety of formulations for topical administration, such as creams (used to treat tinea; cutaneous candidiasis, including candidal paronychia; and pityriasis versicolor) and shampoos (used primarily to treat dandruff – seborrhoeic dermatitis of the scalp).

Topically administered ketoconazole is usually prescribed for fungal infections of the skin and mucous membranes, such as athlete's foot, ringworm, candidiasis (yeast infection or thrush), jock itch, and tinea versicolor. Topical ketoconazole is also used as a treatment for dandruff (seborrheic dermatitis of the scalp) and for seborrheic dermatitis on other areas of the body, perhaps acting in these conditions by suppressing levels of the fungus Malassezia furfur on the skin.

As an antifungal, ketoconazole is structurally similar to imidazole, and interferes with the fungal synthesis of ergosterol, a constituent of fungal cell membranes, as well as certain enzymes. As with all azole antifungal agents, ketoconazole works principally by inhibiting the enzyme cytochrome P450 14α-demethylase (CYP51A1). This enzyme participates in the sterol biosynthesis pathway that leads from lanosterol to ergosterol. Lower doses of fluconazole and itraconazole are required to kill fungi compared to ketoconazole, as they have been found to have a greater affinity for fungal cell membranes.

Resistance to ketoconazole has been observed in a number of clinical fungal isolates, including Candida albicans. Experimentally, resistance usually arises as a result of mutations in the sterol biosynthesis pathway. Defects in the sterol 5-6 desaturase enzyme reduce the toxic effects of azole inhibition of the 14-alpha demethylation step. Multidrug-resistance (MDR) genes can also play a role in reducing cellular levels of the drug. As azole antifungals all act at the same point in the sterol pathway, resistant isolates are normally cross-resistant to all members of the azole family.

Ketoconazole is a synthetic imidazole. It is a nonsteroidal compound. It is a racemic mixture of two enantiomers, levoketoconazole ((2S,4R)-(?)-ketoconazole) and dextroketoconazole ((2R,4S)-(+)-ketoconazole). Levoketoconazole is under development for potential clinical use as a steroidogenesis inhibitor with better tolerability and less toxicity than ketoconazole. Other steroidogenesis inhibitors besides ketoconazole and levoketoconazole include the nonsteroidal compound aminoglutethimide and the steroidal compound abiraterone acetate.

 

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References:

https://en.wikipedia.org/wiki/Ketoconazole

https://www.ncbi.nlm.nih.gov/pubmed/9669136

https://www.ncbi.nlm.nih.gov/pubmed/15863844

 

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