12-10052. Vamicamide [Archived]

Nomenclature

CAS number: 132373-81-0
(αR)-rel-α-[(2R)-2-(Dimethylamino)propyl]-α-phenyl-2-pyridineacetamide; 4-dimethylamino-2-phenyl-2-(2-pyridyl)valeramide; FK-176.
C18H23N3O; mol wt 297.39.
C 72.70%, H 7.80%, N 14.13%, O 5.38%.

Description and 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).

Chemical structure

Properties

Crystals from 40% aq ethanol, mp 156-157°.

Derivative

()-(2R,4R)-Form.

Properties

Prisms from ethyl acetate/isopropyl ether, mp 104°. [α]D 103.1° (c = 0.5 in methanol).

Derivative

(+)-(2S,4S)-Form.

Properties

Prisms from ethyl acetate/isopropyl ether (1:4), mp 103-104°. [α]D +103.3° (c = 0.5 in methanol).

Therapeutic Category

In treatment of urinary incontinence.

Keywords

Antimuscarinic

Status

This monograph has been retired and is no longer subject to revision or update.