65899-73-2 Usage
Uses
Used in Pharmaceutical Industry:
Vagistat is used as an antithrombotic agent for preventing blood clot formation and reducing the risk of thrombotic events.
Used in Antifungal Applications:
Vagistat is used as an antifungal agent, particularly effective against Candida glabrata mutant strains. It is more potent than other antifungal agents like Fluconazole and Voriconazole, making it suitable for the topical treatment of superficial fungal infections.
Used in Drug Development:
Vagistat is used as a potent inhibitor of cytochrome-P450, an enzyme involved in the metabolism of drugs and other substances in the body. This property makes it valuable in the development of new drugs and understanding the metabolic pathways of existing medications.
Originator
Pfizer (United Kiugdom)
Manufacturing Process
A solution of 1-(2,4-dichlorophenyl)-2-(1-imidazolyl)ethanol (1.5 g, 5.8 mmol)
dissolved in dry tetrahydrofuran (10 ml) was added to a stirred suspension of
sodium hydride (0.39 g, as 80% dispersion in oil, 16 mmol) in dry
tetrahydrofuran (10 ml) and warmed to 70°C for 90 minutes.
The mixture was cooled in ice and a solution of 2-chloro-3-
chloromethylthiophene (8.8 mmol) in dry tetrahydrofuran was added. The
mixture was heated at 70°C for 3 hours and allowed to stir at room
temperature overnight. The solvent was removed under vacuum and the
residue stirred with dry ether (200 ml). The ether solution was filtered
through Celite and saturated with hydrogen chloride gas to precipitate an oil
which was solidified by trituration with ether and ethyl acetate. The solid
product was collected and recrystallized from a mixture of acetone and
diisopropyl ether to give the product, melting point 168°C to 170°C.
Therapeutic Function
Antifungal
Clinical Use
1-[2-[(2-chloro-3-thienyl)methoxy]2-(2,4-dichlorophenyl)-ethyl]-1H-imidazole (Vagistat) is used for the treatment ofvulvovaginal candidiasis. A vaginal ointment containing6.5% of the free base is available. Tioconazole is more effectiveagainst Torulopsis glabrata than are other azoles.
Check Digit Verification of cas no
The CAS Registry Mumber 65899-73-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,5,8,9 and 9 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 65899-73:
(7*6)+(6*5)+(5*8)+(4*9)+(3*9)+(2*7)+(1*3)=192
192 % 10 = 2
So 65899-73-2 is a valid CAS Registry Number.
InChI:InChI=1/C16H13Cl3N2OS/c17-12-1-2-13(14(18)7-12)15(8-21-5-4-20-10-21)22-9-11-3-6-23-16(11)19/h1-7,10,15H,8-9H2
65899-73-2Relevant academic research and scientific papers
1-Aryl-2-(1-imidazolyl) alkyl ethers and thioethers
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, (2008/06/13)
Novel 1-aryl-2-(1-imidazolyl)alkyl ethers and thioethers having anti-fungal properties are disclosed.
