13-01434. Bropirimine [Archived]
Nomenclature
CAS number: 56741-95-8
2-Amino-5-bromo-6-phenyl-4(1H)-pyrimidinone; 5-bromo-6-phenylisocytosine; 5-bromo-2,3-dihydro-2-imino-6-phenyl-4[1H]-pyrimidinone; ABPP; U-54461; Remisar (Pharmacia & Upjohn). C10H8BrN3O; mol wt 266.09.
C 45.14%, H 3.03%, Br 30.03%, N 15.79%, O 6.01%.
Description and references
Biological response modifier; induces production of α-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 μg/ml at pH 3-7.Therapeutic Category
Antineoplastic.
Keywords
Antineoplastic; Immunomodulators; Immunomodulator
Status
This monograph has been retired and is no longer subject to revision or update.