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 names	Proxibarbital, Centralgol, Ipronal, 5-Allyl-5-(β-hydroxypropyl)barbituric acid
ATC code	N05CA22 (WHO)
Identifiers
IUPAC name (RS)-5-allyl-5-(2-hydroxypropyl)pyrimidine-2,4,6(1H,3H,5H)-trione
CAS Number	2537-29-3 N
PubChem CID	17336
ChemSpider	16406 Y
UNII	F97OMS297F
ChEMBL	ChEMBL2105233
CompTox Dashboard (EPA)	DTXSID20862980
ECHA InfoCard	100.018.004
Chemical and physical data
Formula	C10H14N2O4
Molar mass	226.232 g·mol−1
3D model (JSmol)	Interactive image
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.{{cite book}}: CS1 maint: location missing publisher (link)
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.