7230. Pheneturide

Nomenclature

CAS number: 90-49-3
N-(Aminocarbonyl)-α-ethylbenzeneacetamide; (2-phenylbutyryl)urea; α-phenyl-α-ethylacetylurea; N-(α-phenylbutyryl)urea; α-ethyl-α-phenylacetylurea; ethylphenacemide; EPA; PBU; Benuride (Bengue).
C11H14N2O2; mol wt 206.24.
C 64.06%, H 6.84%, N 13.58%, O 15.52%.

Description and references

Prepd by heating α-phenylbutyric acid chloride with urea: DE 249241 (1912 to Bayer); Chem. Zentralbl. 1912, II, 396; Frdl. 10, 1165. From α-phenylbutyric acid chloride, urea, and antipyrine: Gold-Aubert, Helv. Chim. Acta 41, 1512 (1958); CH 374644 (1964 to Labs. Sapos). Pharmacokinetics: R. L. Galeazzi et al., J. Pharmacokinet. Biopharm. 7, 453 (1979). Toxicity: M. J. Orloff et al., Neurology 1, 377 (1951). Clinical studies: J. C. Bowe, Br. J. Clin. Pract. 27, 174 (1973); F. B. Gibberd et al., J. Neurol. Neurosurg. Psychiatry 45, 1113 (1982).

Chemical structure

Derivative

dl-Form.

Properties

Needles from ethanol, mp 149-150°.

Derivative

d-Form.

Properties

Needles from ethanol, mp 168-169°. [α]D17 +54.0° (c = 1 in ethanol); [α]D22 +53.8° (c = 1 in acetone); +48.2° (c = 1 in dioxane).

Derivative

l-Form.

Properties

Crystals from 50% ethanol, mp 162-163°. [α]D30 -51.6° (c = 1 in ethanol).

Therapeutic Category

Anticonvulsant.

Keywords

Anticonvulsant