CAS No 38304-91-5 , 3-hydroxy-2-imino-6-piperidin-1-ylpyrimidin-4-amine

Title: Minoxidil
CAS Registry Number: 38304-91-5
CAS Name: 6-(1-Piperidinyl)-2,4-pyrimidinediamine 3-oxide
Synonyms: 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine; 2,3-dihydro-3-hydroxy-2-imino-6-(1-piperidinyl)-4-pyrimidinamine; 2,4-diamino-6-piperidinopyrimidine 3-oxide; 6-piperidino-2,4-diaminopyrimidine 3-oxide; PDP
Manufacturers' Codes: U-10858
Trademarks: Alopexil (Fabre); Alostil (Pfizer); Loniten (Pfizer); Lonolox (Pfizer); Minoximen (Menarini); Normoxidil (Medosan); Prexidil (Bioindustria); Regaine (Pfizer); Rogaine (Pfizer); Tricoxidil (Pfizer)
Molecular Formula: C9H15N5O
Molecular Weight: 209.25
Percent Composition: C 51.66%, H 7.23%, N 33.47%, O 7.65%
Literature References: Prepn: NL 6615385; W. C. Anthony et al., US 3382247 (1967, 1968 both to Upjohn); J. M. McCall et al., J. Org. Chem. 40, 3304 (1975). See also W. C. Anthony, US 3644364 (1972 to Upjohn). Metabolism: R. C. Thomas et al., J. Pharm. Sci. 64, 1360 (1975). Pharmacology and pharmacokinetics: D. T. Lowenthal et al., J. Clin. Pharmacol. 18, 500 (1978). Percutaneous absorption and excretion: T. J. Franz, Arch. Dermatol. 121, 203 (1985). Clinical studies: O. Andersson, R. Sivertsson, Acta Med. Scand. 205, 213 (1979); M. Moser, Adv. Cardiol. 26, 38 (1979). Clinical trial in early male pattern baldness: E. A. Olsen et al., J. Am. Acad. Dermatol. 13, 185 (1985). Toxicology: R. G. Carlson, E. S. Feenstra, Toxicol. Appl. Pharmacol. 39, 1 (1977). Review of pharmacology and therapeutic use: V. M. Campese, Drugs 22, 257-278 (1981). Review of topical application in baldness: E. Novak et al., Int. J. Dermatol. 24, 82 (1985). Comprehensive description: D. K. J. Gorecki, Anal. Profiles Drug Subs. 17, 185-219 (1988).
Properties: Crystals from methanol-acetonitrile, mp 248°, dec 259-261° (Anthony, 1972). pKa 4.61. uv max (ethanol): 230, 261, 285 nm (e 35210, 11210, 11790); (0.01N H2SO4): 232, 280 nm (e 26350, 23850); (0.01N KOH): 231, 261.5, 285 nm (e 36100, 11400, 12040). Soly (mg/ml): propylene glycol 75, methanol 44, ethanol 29, 2-propanol 6.7, dimethylsulfoxide 6.5, water 2.2, chloroform 0.5, acetone <0.5, ethylacetate <0.5, diethyl ether <0.5, benzene <0.5, acetonitrile <0.5. LD50 in rats, mice (mg/kg): 49, 51 i.v. (Carlson, Feenstra).
Melting point: mp 248°
pKa: pKa 4.61
Absorption maximum: uv max (ethanol): 230, 261, 285 nm (e 35210, 11210, 11790); (0.01N H2SO4): 232, 280 nm (e 26350, 23850); (0.01N KOH): 231, 261.5, 285 nm (e 36100, 11400, 12040)
Toxicity data: LD50 in rats, mice (mg/kg): 49, 51 i.v. (Carlson, Feenstra)
Therap-Cat: Antihypertensive. Antialopecia agent.
Keywords: Antialopecia Agent; Antihypertensive.