Thiamphenicol
Title: Thiamphenicol
CAS Registry Number: 15318-45-3
CAS Name: 2,2-Dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]acetamide
Additional Names: D-d-threo-2-dichloroacetamido-1-(4-methylsulfonyl)phenyl-1,3-propanediol; dextrosulphenidol
Manufacturers' Codes: Win-5063-2; 8053CB
Trademarks: Hyrazin (Kowa); Igralin (Zeria); Neomyson (Eisai); Rigelon (Dojin); Thiamcol (Morishita); Thionicol (Mohan); Thiophenicol (Clin Comar); Urfamycine (Inpharzam); Urophenil (Nippon Seiyaku)
Molecular Formula: C12H15Cl2NO5S
Molecular Weight: 356.22
Percent Composition: C 40.46%, H 4.24%, Cl 19.91%, N 3.93%, O 22.46%, S 9.00%
Literature 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).
Properties: Crystals, mp 164.3-166.3°. [a]D25 +12.9° (ethanol). uv max (95% ethanol): 224, 266, 274 nm (e 13,700, 800, 700). Appreciably sol in water. Soluble in alcohol.
Melting point: mp 164.3-166.3°
Optical Rotation: [a]D25 +12.9° (ethanol)
Absorption maximum: uv max (95% ethanol): 224, 266, 274 nm (e 13,700, 800, 700)
 
Derivative Type: DL-Form
CAS Registry Number: 847-25-6
Additional Names: Raceophenidol; racephenicol
Trademarks: Dexawin (Winthrop); Thiocymetin (Winthrop)
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: D-Form as antimicrobial; DL-form in control of fowl cholera.
Keywords: Antibacterial (Antibiotics); Amphenicols.

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