7758. Procarbazine
Nomenclature
CAS number: 671-16-9
N-(1-Methylethyl)-4-[(2-methylhydrazinyl)methyl]benzamide; N-isopropyl-α-(2-methylhydrazino)-p-toluamide; N-4-isopropylcarbamoylbenzyl-N′-methylhydrazine; p-(N1-methylhydrazinomethyl)-N-isopropylbenzamide; ibenzmethyzin; MIH; Ro-4-6467. C12H19N3O; mol wt 221.30.
C 65.13%, H 8.65%, N 18.99%, O 7.23%.
Description and references
Alkylating agent. Prepn: BE 618638; W. Bollag et al., US 3520926 (1962, 1970 to Hoffmann-La Roche). Comprehensive description: R. J. Rucki, Anal. Profiles Drug Subs. 5, 403-427 (1976). HPLC determn in plasma: X. He et al., J. Chromatogr. B 799, 281 (2004). Veterinary use in treatment of granulomatous meningoencephalomyelitis: J. R. Coates et al., J. Vet. Intern. Med. 21, 100 (2007). Review of clinical experience in hematological malignancies: M. Massoud et al., Eur. J. Cancer 40, 1924-1927 (2004).
Derivative
Hydrochloride.Nomenclature
CAS number: 366-70-1
Matulane (Sigma-Tau); Natulan (Sigma-Tau). C12H19N3O.HCl; mol wt 257.76.
C 55.92%, H 7.82%, N 16.30%, O 6.21%, Cl 13.75%.
Properties
Crystals from methanol, mp 223-226°. Soluble but unstable in water or aq. solutions. LD50 orally in rats: 785 ±34 mg/kg See E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971).Derivative
Hydrobromide.Nomenclature
CAS number: 18969-59-0
C12H19N3O.HBr; mol wt 302.21.
C 47.69%, H 6.67%, N 13.90%, O 5.29%, Br 26.44%.
Properties
Crystals from methanol + ether, dec 216-217°.Caution
Procarbazine hydrochloride is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-222.Therapeutic Category
Antineoplastic.
Therapeutic Category (Veterinary)
Antineoplastic. In treatment of granulomatous meningoencephalitis in dogs.Keywords
Antineoplastic; Alkylating Agents