Phenacemide

Phenacemide (INN, BAN) (brand name Phenurone), also known as phenylacetylurea, is an anticonvulsant of the ureide (acetylurea) class.[1] It is a congener and ring-opened analogue of phenytoin (a hydantoin),[2][3] and is structurally related to the barbiturates and to other hydantoins.[4] Phenacemide was introduced in 1949 for the treatment of epilepsy, but was eventually withdrawn due to toxicity.[2][3]

Phenacemide
Clinical data
Trade namesPhenurone
AHFS/Drugs.comMicromedex Detailed Consumer Information
ATC code
Pharmacokinetic data
Elimination half-life22–25 hours
Identifiers
IUPAC name
  • N-Carbamoyl-2-phenyl-acetamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.519
Chemical and physical data
FormulaC9H10N2O2
Molar mass178.191 g·mol−1
3D model (JSmol)
SMILES
  • O=C(NC(=O)N)Cc1ccccc1
InChI
  • InChI=1S/C9H10N2O2/c10-9(13)11-8(12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H3,10,11,12,13) Y
  • Key:XPFRXWCVYUEORT-UHFFFAOYSA-N Y
  (verify)

See also

References

  1. C.R. Ganellin; David J. Triggle (21 November 1996). Dictionary of Pharmacological Agents. CRC Press. pp. 1578–. ISBN 978-0-412-46630-4.
  2. Conceptual Pharmacology. Universities Press. 2010. pp. 236–. ISBN 978-81-7371-679-9.
  3. deStevens, G.; Zingel, V.; Leschke, C.; Hoeprich, P.D.; Schultz, R.M.; Mehrotra, P.K.; Batra, S.; Bhaduri, A.P.; Saxena, A.K.; Saxena, M., eds. (11 November 2013). Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des Recherches Pharmaceutiques. Basel: Birkhäuser. pp. 217–. ISBN 978-3-0348-7161-7. Retrieved 3 September 2016.
  4. S. S. Kadam (1 July 2007). PRINCIPLES OF MEDICINAL CHEMISTRY Vol. - II. Pragati Books Pvt. Ltd. pp. 147–. ISBN 978-81-85790-03-9.
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