Title: Formoterol
CAS Registry Number: 73573-87-2
CAS Name: rel-N-[2-Hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]formamide
Additional Names: 3-formylamino-4-hydroxy-a-[N-[1-methyl-2-(p-methoxyphenyl)ethyl]aminomethyl]benzyl alcohol; (±)-2¢-hydroxy-5¢-[(RS)-1-hydroxy-2-[[(RS)-p-methoxy-a-methylphenethyl]amino]ethyl]formanilide
Molecular Formula: C19H24N2O4
Molecular Weight: 344.40
Percent Composition: C 66.26%, H 7.02%, N 8.13%, O 18.58%
Literature References: Selective b2-adrenergic receptor agonist. Mixture of R,R (-) and S,S (+) enantiomers. Prepn: M. Murakami et al., DE 2305092; eidem, US 3994974 (1973, 1976 both to Yamanouchi); K. Murase et al., Chem. Pharm. Bull. 25, 1368 (1977). Absolute configuration and activity of isomers: eidem, ibid. 26, 1123 (1978). Toxicity studies: T. Yoshida et al., Pharmacometrics 26, 811 (1983). HPLC determn in plasma: J. Campestrini et al., J. Chromatogr. B 704, 221 (1997). Review of pharmacology: G. P. Anderson, Life Sci. 52, 2145-2160 (1993); and clinical efficacy: R. A. Bartow, R. N. Brogden, Drugs 55, 303-322 (1998).
Derivative Type: Fumarate dihydrate
CAS Registry Number: 43229-80-7
Manufacturers' Codes: BD-40A
Trademarks: Atock (Yamanouchi); Foradil (Novartis); Oxeze (AstraZeneca)
Molecular Formula: (C19H24N2O4)2.C4H4O4.2H2O
Molecular Weight: 840.91
Percent Composition: C 59.99%, H 6.71%, N 6.66%, O 26.64%
Properties: Crystals from 95% isopropyl alcohol, mp 138-140°. pKa1 7.9; pKa2 9.2. Log P (octanol/water): 0.4 (pH 7.4). Freely sol in glacial acetic acid; sol in methanol; sparingly sol in ethanol, isopropanol; slightly sol in water. Practically insol in acetone, ethyl acetate, diethyl ether. LD50 in male, female, rats, mice (mg/kg): 3130, 5580, 6700, 8310 orally; 98, 100, 72, 71 i.v.; 1000, 1100, 640, 670 s.c.; 170, 210, 240, 210 i.p. (Yoshida).
Melting point: mp 138-140°
pKa: pKa1 7.9; pKa2 9.2
Log P: Log P (octanol/water): 0.4 (pH 7.4)
Toxicity data: LD50 in male, female, rats, mice (mg/kg): 3130, 5580, 6700, 8310 orally; 98, 100, 72, 71 i.v.; 1000, 1100, 640, 670 s.c.; 170, 210, 240, 210 i.p. (Yoshida)
Derivative Type: R,R-Form
CAS Registry Number: 67346-49-0
Additional Names: Arformoterol
Derivative Type: R,R-Form L-tartrate
CAS Registry Number: 200815-49-2
Additional Names: Arformoterol tartrate
Molecular Formula: C19H24N2O4.C4H6O6
Molecular Weight: 494.49
Percent Composition: C 55.86%, H 6.12%, N 5.67%, O 32.36%
Literature References: Prepn: Y. Gao et al., WO 9821175; eidem, US 6040344 (1998, 2000 both to Sepracor). Pharmacology: D. A. Handley et al., Pulm. Pharmacol. Ther. 15, 135 (2002).
Properties: Off-white powder, mp 184°.
Melting point: mp 184°
Therap-Cat: Antiasthmatic.
Keywords: ?Adrenergic Agonist; Bronchodilator; Ephedrine Derivatives. |