9301. Thiamphenicol

Nomenclature

CAS number: 15318-45-3
2,2-Dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]acetamide; d-d-threo-2-dichloroacetamido-1-(4-methylsulfonyl)phenyl-1,3-propanediol; dextrosulphenidol; Win-5063-2; 8053CB; Hyrazin (Kowa); Igralin (Zeria); Neomyson (Eisai); Rigelon (Dojin); Thiamcol (Morishita); Thionicol (Mohan); Thiophenicol (Clin Comar); Urfamycine (Inpharzam); Urophenil (Nippon Seiyaku).
C12H15Cl2NO5S; mol wt 356.22.
C 40.46%, H 4.24%, Cl 19.91%, N 3.93%, O 22.46%, S 9.00%.

Description and references

Synthesis: Cutler et al., J. Am. Chem. Soc. 74, 5475 (1952); Suter et al., ibid. 75, 4330 (1953); Suter, US 2759927; US 2759970; US 2759971; US 2759972; US 2759976 (all 1956 to Sterling Drugs); GB 770277 (1957 to Parke, Davis).

Chemical structure

Properties

Crystals, mp 164.3-166.3°. [α]D25 +12.9° (ethanol). uv max (95% ethanol): 224, 266, 274 nm (ε 13,700, 800, 700). Appreciably sol in water. Soluble in alcohol.

Derivative

dl-Form.

Nomenclature

CAS number: 847-25-6
Raceophenidol; racephenicol; Dexawin (Winthrop); Thiocymetin (Winthrop).

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

d-Form as antimicrobial; dl-form in control of fowl cholera.

Keywords

Antibacterial (Antibiotics); Amphenicols