194798-83-9

Usage

Uses

Used in Pharmaceutical Industry:
Fosfluconazole is used as an intravenous injection for the treatment of candidiasis and cryptococcosis infections. It offers a solution to the high-volume infusion issue associated with fluconazole by providing approximately 40-fold higher water solubility, allowing for a substantial reduction in infusion volume. This makes it particularly beneficial for critically ill patients where fluid overload must be avoided.
Used in Antifungal Treatments:
Fosfluconazole is used as an antifungal agent, rapidly hydrolyzed to fluconazole by phosphatase enzymes in vivo. It exhibits similar efficacy to fluconazole in experimental models of fungal disease, providing an effective treatment option for patients with deep-seated mycosis due to Candida or Cryptococcus.
Brand Name:
The brand name for fosfluconazole is Prodif.

Originator

Pfizer (Japan)

InChI:InChI=1/C13H13F2N6O4P/c14-10-1-2-11(12(15)3-10)13(25-26(22,23)24,4-20-8-16-6-18-20)5-21-9-17-7-19-21/h1-3,6-9H,4-5H2,(H2,22,23,24)

Upstream product

• 194602-25-0 2,4-difluoro-α,α-bis(1H-1,2,4-triazol-1-ylmethyl)benzyl alcohol dibenzyl phosphate 
• 86386-73-4 fluconazole 

Relevant academic research and scientific papers

Preparation method of fosfluconazole

The invention provides a preparation method of fosfluconazole. The method comprises the following steps: preparing fluconazole dichlorophosphate: under the protection of nitrogen, controlling the temperature to be-10 DEG C to 0 DEG C, slowly dropwise adding phosphorus oxychloride into a dichloromethane solution of triethylamine, maintaining the temperature to be-10 DEG C to 0 DEG C, performing stirring for 1 hour, slowly dropwise adding a dichloromethane solution of fluconazole, and monitoring the completion of the reaction by TLC; maintaining temperature between-10 DEG C and 0 DEG C, adding water and stirring for 30 minutes, adding inorganic base until the pH value of the water phase is at least 8; and performing standing stratification, separating out the fluconazole, wherein the organicphase contains the fluconazole dichlorophosphate, the fluconazole is prepared through the fluconazole-fluconazole dichlorophosphate-fluconazole dibenzyl phosphate-fosfluconazole ammonium salt-fosfluconazole process, the yield is increased, all intermediates are controllably prepared, the raw materials can be recycled, and raw material waste and organic waste pollution are reduced.

Compound and preparation method and application thereof

The invention discloses a compound of 2-(2,4-difluorophenyl)-1,3-di(1H-1,2,4,-triazole-1-yl)-2-propyl di-tert-butylphosphate, a preparation method thereof, and an application of 2-(2,4-difluorophenyl)-1,3-di(1H-1,2,4,-triazole-1-yl)-2-propyl di-tert-butylphosphate to prepare 2,4-difluoro-alpha, alpha-di(1H-1,2,4,-triazole-1-yl methyl) benzyl alcohol dihydrogen phosphate. The method is mild in reaction conditions and can well protect the environment.

Triazole derivatives useful in therapy

The invention provides compounds of formula 1, R1—OP(O)(OH)2??I wherein R1 represents the non-hydroxy portion of a triazole antifungal compound of the type comprising a tertiary hydroxy group; or a pharmaceutically accepta

The discovery and process development of a commercial route to the water soluble prodrug, fosfluconazole

A case history detailing the rationale behind the discovery of 2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazole-1-yl)-2-propyl dihydrogen phosphate, fosfluconazole (2), a water-soluble prodrug of Diflucan, and the subsequent development of a commercial route is presented. Particular items to note are (i) that this compound was discovered in the Chemical Research and Development Department, hence Chemical Research and Development can play a key role in prodrug discovery, (ii) the strategy behind the selection of phosphate ester promoiety, by phosphorylation of a sterically hindered tertiary alcohol, (iii) the development of the initial route to remove thermally hazardous reagents and to improve processing to allow scale-up, and (iv) the identification and development of the proposed commercial process.