Title: Bropirimine
CAS Registry Number: 56741-95-8
CAS Name: 2-Amino-5-bromo-6-phenyl-4(1H)-pyrimidinone
Additional Names: 5-bromo-6-phenylisocytosine; 5-bromo-2,3-dihydro-2-imino-6-phenyl-4[1H]-pyrimidinone; ABPP
Manufacturers' Codes: U-54461
Trademarks: Remisar (Pharmacia & Upjohn)
Molecular Formula: C10H8BrN3O
Molecular Weight: 266.09
Percent Composition: C 45.14%, H 3.03%, Br 30.03%, N 15.79%, O 6.01%
Literature References: Biological response modifier; induces production of a-interferon. Prepn: T. B. Brown, M. F. G. Stevens, J. Chem. Soc. Perkin Trans. 1 1975, 1023; M. F. G. Stevens et al., Anti-Cancer Drug Des. 10, 215 (1995). Antiviral and interferon-inducing effects: D. A. Stringfellow et al., J. Interferon Res. 1, 1 (1980). Structure-activity study: H. I. Skulnick et al., J. Med. Chem. 28, 1864 (1985). Crystal structure and 1H-NMR: M. F. G. Stevens et al., Anti-Cancer Drug Des. 10, 203 (1995). Review of clinical studies in bladder cancer: M. F. Sarosdy, Ann. N.Y. Acad. Sci. 685, 301-308 (1993).
Properties: Crystals from 2-ethoxyethanol, mp 285-287° (Stevens). Also reported as crystals from aq ethanol, mp 246-248° (Brown, Stevens). Tautomeric. pKa 3.18; 8.53. Soly in water: >200 mg/ml at pH 13; <40 mg/ml at pH 3-7.
Melting point: mp 285-287° (Stevens); mp 246-248° (Brown, Stevens)
pKa: pKa 3.18; 8.53
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Immunomodulators; Immunomodulator.
Status: This monograph has been retired and is no longer subject to revision or update.

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