CAS No 104-06-3 , N-[4-[(E)-(carbamothioylhydrazinylidene)methyl]phenyl]acetamide

Title: Thiacetazone
CAS Registry Number: 104-06-3
CAS Name: N-[4-[[(Aminothioxomethyl)hydrazono]methyl]phenyl]acetamide
Synonyms: 2-[[4-(acetylamino)phenyl]methylene]hydrazinecarbothioamide; 4￠-formylacetanilide thiosemicarbazone; p-acetamidobenzaldehyde thiosemicarbazone; p-acetylaminobenzaldehyde thiosemicarbazone; p-acetaminobenzylidenethiosemicarbazone; amithiozone; thibone; thioacetazone
Manufacturers' Codes: Tb I-698
Trademarks: Conteben (Bayer); Livazone (Specia); Myrizone (Squibb); Neustab (Boots); Panrone (Panray); Seroden (Allen & Hanburys); Tebethion; Thiocarbazil; Thioparamizone (Smith & Nephew); Tibione (Schenley); Tiobicina
Molecular Formula: C10H12N4OS
Molecular Weight: 236.29
Percent Composition: C 50.83%, H 5.12%, N 23.71%, O 6.77%, S 13.57%
Literature References: Prepn: G. Domagk et al., Naturwissenschaften 33, 315 (1946); Behnisch et al., Angew. Chem. 60A, 113 (1948); Chabrier, Cattelain, Bull. Soc. Chim. Fr. 1950M, 52; Das, Mukherjee, J. Am. Chem. Soc. 75, 1241 (1953). Toxicity data: Bavin et al., J. Pharm. Pharmacol. 2, 764 (1950). HPLC determn in body fluids: P. J. Jenner, J. Chromatogr. 276, 463 (1983). Review of clinical experience: H. C. Hinshaw, W. McDermott, Am. Rev. Tuberc. 61, 145-157 (1950); of clinical safety and efficacy: P. Nunn et al., Trans. R. Soc. Trop. Med. Hyg. 87, 578 (1993).
Properties: Minute, pale yellow crystals from abs alc. Bitter taste. Darkens on exposure to light. Dec 225-230°. uv max (ethanol): 328 nm, extinction 0.580. Sol in hot alc; very sparingly sol in cold alc. Insol in water, acetone, benzene, carbon tetrachloride, chloroform, carbon disulfide, petr ether. Practically insol in the other common organic solvents except glycols. Soly in propylene glycol ~1%. LD50 s.c. in mice: 1-2 g/kg (Bavin).
Absorption maximum: uv max (ethanol): 328 nm
Toxicity data: LD50 s.c. in mice: 1-2 g/kg (Bavin)
Therap-Cat: Antibacterial (tuberculostatic).
Keywords: Antibacterial (Tuberculostatic).