Vamicamide
Title: Vamicamide
CAS Registry Number: 132373-81-0
CAS Name: (aR)-rel-a-[(2R)-2-(Dimethylamino)propyl]-a-phenyl-2-pyridineacetamide
Additional Names: 4-dimethylamino-2-phenyl-2-(2-pyridyl)valeramide
Manufacturers' Codes: FK-176
Molecular Formula: C18H23N3O
Molecular Weight: 297.39
Percent Composition: C 72.70%, H 7.80%, N 14.13%, O 5.38%
Literature References: Prepn: I. Ueda et al., EP 105458; eidem, US 4564621 (1984, 1986 both to Fujisawa); H. Oyasu et al., J. Med. Chem. 37, 1378 (1994). Comparative pharmacology: idem et al., Arzneim.-Forsch. 44, 1242 (1994); T. Yamamoto et al., Drug Dev. Res. 34, 9 (1995). HPLC determn of enantiomers in serum and urine: A. Suzuki et al., J. Chromatogr. 617, 279 (1993). Clinical pharmacokinetics: M. Terakawa, N. Iyota, Yakubutsu Dotai 9, 799 (1994), C.A. 122, 204469g (1995).
Properties: Crystals from 40% aq ethanol, mp 156-157°.
Melting point: mp 156-157°
 
Derivative Type: (-)-(2R,4R)-Form
Properties: Prisms from ethyl acetate/isopropyl ether, mp 104°. [a]D -103.1° (c = 0.5 in methanol).
Melting point: mp 104°
Optical Rotation: [a]D -103.1° (c = 0.5 in methanol)
 
Derivative Type: (+)-(2S,4S)-Form
Properties: Prisms from ethyl acetate/isopropyl ether (1:4), mp 103-104°. [a]D +103.3° (c = 0.5 in methanol).
Melting point: mp 103-104°
Optical Rotation: [a]D +103.3° (c = 0.5 in methanol)
 
Therap-Cat: In treatment of urinary incontinence.
Keywords: Antimuscarinic.
 
 
Status: This monograph has been retired and is no longer subject to revision or update.

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