Isoniazid
Title: Isoniazid
CAS Registry Number: 54-85-3
CAS Name: 4-Pyridinecarboxylic acid hydrazide
Additional Names: isonicotinic acid hydrazide; isonicotinoylhydrazine; isonicotinylhydrazine; INH; rimitsid; tubazid
Manufacturers' Codes: RP-5015; FSR-3
Trademarks: Isonex (Pfizer); Isotamine (Valeant); Isozid (Fatol); Neoteben (Bayer); Nicizina (Pharmacia); Nicozid (Piam); Nydrazid (BMS); Rimifon (Pharmion); tebesium (Pharma Wernigerode); Tibinide (Recip); Valifol (Valdecasas)
Molecular Formula: C6H7N3O
Molecular Weight: 137.14
Percent Composition: C 52.55%, H 5.14%, N 30.64%, O 11.67%
Literature References: Prepn: Meyer, Mally, Monatsh. Chem. 33, 400 (1912); Lock, Pharm. Ind. 14, 366 (1952); Urbanski et al., Rocz. Chem. 27, 161 (1953); Gasson, US 2830994 (1958 to Distillers). Compositions for combating tuberculosis: H. H. Fox, US 2596069 (1952 to Hoffmann-La Roche). Pharmacokinetics: W. W. Weber, D. W. Hein, Clin. Pharmacokinet. 4, 401 (1979). Mechanism of action study: K. Johnsson et al., J. Am. Chem. Soc. 117, 5009 (1995). Toxicity data: E. H. Jenney, C. C. Pfeiffer, J. Pharmacol. Exp. Ther. 122, 110 (1958). Evaluation of carcinogenic risk: IARC Monographs 4, 159 (1974). Comprehensive description: G. A. Brewer, Anal. Profiles Drug Subs. 6, 183-258 (1977). Clinical trial in HIV-positive patients: J. W. Pape et al., Lancet 342, 268 (1993). Review of use in prevention and treatment of TB: American Thoracic Society, Am. Rev. Respir. Dis. 134, 355-363 (1986); T. J. Jordan et al., ibid. 144, 1357-1360 (1991).
Properties: Crystals from alc, mp 171.4°. uv max (water): 266 nm (E1%1cm 378); (0.01N HCl): 265 nm (E1%1cm ~420). Soly in water at 25°: about 14%; at 40°: about 26%; in alc at 25°: about 2%, in boiling alc: about 10%; in chloroform: about 0.1%. Practically insol in ether, benzene. pH of a 1% aq soln 5.5 to 6.5. Aqueous solns may be sterilized at 120° for 30 min. LD50 in mice (mg/kg): 151 i.p., 149 i.v. (Jenney, Pfeiffer).
Melting point: mp 171.4°
Absorption maximum: uv max (water): 266 nm (E1%1cm 378); (0.01N HCl): 265 nm (E1%1cm ~420)
Toxicity data: LD50 in mice (mg/kg): 151 i.p., 149 i.v. (Jenney, Pfeiffer)
 
Derivative Type: 4-Aminosalicylate
CAS Registry Number: 2066-89-9
Additional Names: Pasiniazide
Manufacturers' Codes: GEWO-399
Molecular Formula: C13H14N4O4
Molecular Weight: 290.27
Percent Composition: C 53.79%, H 4.86%, N 19.30%, O 22.05%
Literature References: An equimolecular salt produced by dissolving the components in hot dil alc, followed by cooling and evapn: Charonnat, Boime, Compt. Rend. 236, 2140 (1953). Prepn: CH 303085 (1955 to Hoffmann-La Roche).
Properties: Yellow crystals from methanol or ethanol, mp 142-144°. Sparingly sol in water. uv max 272, 303 nm (E1%1cm 550, 445).
Melting point: mp 142-144°
Absorption maximum: uv max 272, 303 nm (E1%1cm 550, 445)
 
Derivative Type: Methanesulfonate
CAS Registry Number: 13447-95-5
CAS Name: 4-Pyridinecarboxylic acid 2-(sulfomethyl)hydrazide
Additional Names: methaniazide
Molecular Formula: C7H9N3O4S
Molecular Weight: 231.23
Percent Composition: C 36.36%, H 3.92%, N 18.17%, O 27.68%, S 13.87%
Literature References: Prepn: Logemann, US 2759944 (1956 to Carlo Erba).
Properties: Crystals, dec 187-189°.
 
Derivative Type: Methanesulfonate sodium
CAS Registry Number: 3804-89-5
Additional Names: Sodium isonicotinylhydrazide methanesulfonate
Molecular Formula: C7H8N3NaO4S
Molecular Weight: 253.21
Percent Composition: C 33.20%, H 3.18%, N 16.59%, Na 9.08%, O 25.27%, S 12.66%
Properties: Yellow crystals from water, dec 164-167°.
 
Therap-Cat: Antibacterial (tuberculostatic).
Therap-Cat-Vet: Antibacterial (tuberculostatic); anti-actinomycotic agent.
Keywords: Antibacterial (Tuberculostatic).

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