Pheneturide
Title: Pheneturide
CAS Registry Number: 90-49-3
CAS Name: N-(Aminocarbonyl)-a-ethylbenzeneacetamide
Additional Names: (2-phenylbutyryl)urea; a-phenyl-a-ethylacetylurea; N-(a-phenylbutyryl)urea; a-ethyl-a-phenylacetylurea; ethylphenacemide; EPA; PBU
Trademarks: Benuride (Bengue)
Molecular Formula: C11H14N2O2
Molecular Weight: 206.24
Percent Composition: C 64.06%, H 6.84%, N 13.58%, O 15.52%
Literature References: Prepd by heating a-phenylbutyric acid chloride with urea: DE 249241 (1912 to Bayer); Chem. Zentralbl. 1912, II, 396; Frdl. 10, 1165. From a-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).
 
Derivative Type: dl-Form
Properties: Needles from ethanol, mp 149-150°.
Melting point: mp 149-150°
 
Derivative Type: d-Form
Properties: Needles from ethanol, mp 168-169°. [a]D17 +54.0° (c = 1 in ethanol); [a]D22 +53.8° (c = 1 in acetone); +48.2° (c = 1 in dioxane).
Melting point: mp 168-169°
Optical Rotation: [a]D17 +54.0° (c = 1 in ethanol); [a]D22 +53.8° (c = 1 in acetone); +48.2° (c = 1 in dioxane)
 
Derivative Type: l-Form
Properties: Crystals from 50% ethanol, mp 162-163°. [a]D30 -51.6° (c = 1 in ethanol).
Melting point: mp 162-163°
Optical Rotation: [a]D30 -51.6° (c = 1 in ethanol)
 
Therap-Cat: Anticonvulsant.
Keywords: Anticonvulsant.

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