(2R,3R)-3-(2,5-Difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyramide
[CAS# 368421-58-3]

Identification

• Name: (2R,3R)-3-(2,5-Difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyramide
• Molecular Formula: C₁₃H₁₄F₂N₄OS
• Molecular Weight: 312.34
• CAS Registry Number: 368421-58-3
• EC Number: 609-299-8
• SMILES: C[C@@H](C(=S)N)[C@](CN1C=NC=N1)(C2=C(C=CC(=C2)F)F)O

Properties

• Solubility: 454.9 mg/L (25 °C water)
• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.630, Calc.^*
• Melting point: 170.86 °C
• Boiling Point: 536.4±60.0 °C (760 mmHg), Calc.^*, 410.64 °C
• Flash Point: 278.2±32.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2015 ACD/Labs)

Safety Data

• Hazard Symbols: GHS08 Warning
• Risk Statements: H371
• Safety Statements: P260-P264-P270-P308+P316-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	2	H371

Discovery and Applications

The discovery of (2R,3R)-3-(2,5-Difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyramide, often referred to as ""fluconazole,"" traces back to research efforts focused on developing antifungal agents. It was synthesized in the late 20th century by researchers at Pfizer as part of a program to identify novel azole antifungal compounds.

(2R,3R)-3-(2,5-Difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyramide, commonly known as ""fluconazole,"" is a broad-spectrum antifungal medication used in the treatment of various fungal infections. It inhibits the synthesis of ergosterol, a key component of fungal cell membranes, thereby disrupting fungal growth and replication. Fluconazole is indicated for the treatment of superficial and systemic fungal infections, including candidiasis, cryptococcosis, and dermatophyte infections. It is available in oral and intravenous formulations and is considered a first-line therapy for many fungal infections due to its broad spectrum of activity, favorable pharmacokinetics, and low toxicity. Additionally, fluconazole has been used prophylactically in immunocompromised patients to prevent fungal infections associated with invasive procedures or prolonged neutropenia.

References

2016. Isavuconazole. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-09-0093