Proxibarbital

Proxibarbital (Ipronal) is a barbiturate derivative synthesized in 1956. It has anti-anxiety properties and is, in contrast to most barbiturates, almost without hypnotic action.[1]

Proxibarbital
Clinical data
Other namesProxibarbital, Centralgol, Ipronal, 5-Allyl-5-(β-hydroxypropyl)barbituric acid
ATC code
Identifiers
IUPAC name
  • (RS)-5-allyl-5-(2-hydroxypropyl)pyrimidine-2,4,6(1H,3H,5H)-trione
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
ECHA InfoCard100.018.004
Chemical and physical data
FormulaC10H14N2O4
Molar mass226.232 g·mol−1
3D model (JSmol)
SMILES
  • O=C1NC(=O)NC(=O)C1(CC(O)C)C\C=C
InChI
  • InChI=1S/C10H14N2O4/c1-3-4-10(5-6(2)13)7(14)11-9(16)12-8(10)15/h3,6,13H,1,4-5H2,2H3,(H2,11,12,14,15,16) Y
  • Key:VNLMRPAWAMPLNZ-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

It was also used in the treatment of migraine headaches in a similar manner to butalbital.[2]

Valofane isomerises to Proxibarbal in vivo.

References
  1. Zajdel P, Kulig K, Zejc A (2008). Zejc A, Gorczyca M (eds.). Chemia leków, podręcznik dla studentów farmacji i farmaceutów [Drug chemistry, textbook for pharmacy students and pharmacists] (in Polish). Warszawa, Poland. ISBN 978-83-200-3652-7.
  2. Sulman FG, Pfeifer Y, Tal E (December 1976). "[Migraine therapy by enzyme induction with proxibarbital]". Therapie der Gegenwart (in German). 115 (12): 2088–103. PMID 14412.
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