Proxibarbital

Proxibarbital
Clinical data
Other namesProxibarbal, Proxibarbitone, Centralgal, Ipronal, 5-Allyl-5-(β-hydroxypropyl)barbituric acid
ATC code
Identifiers
  • (RS)-5-allyl-5-(2-hydroxypropyl)pyrimidine-2,4,6(1H,3H,5H)-trione
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.018.004
Chemical and physical data
FormulaC10H14N2O4
Molar mass226.232 g·mol−1
3D model (JSmol)
  • O=C1NC(=O)NC(=O)C1(CC(O)C)C\C=C
  • 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) checkY
  • Key:VNLMRPAWAMPLNZ-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Proxibarbital (Ipronal) is a barbiturate derivative synthesized in 1956 in Poland by Bogusław Bobrański. It has anti-anxiety and sedative properties and is, in contrast to most barbiturates, almost without hypnotic action.[1] It was used as a sedative and anti-anxiety drug. It was also used in the treatment of migraine headaches in a similar manner to butalbital.[2] It was a prescription drug available in Poland from the 1950s to the 1990s under trade name Ipronal.

Valofane isomerizes to proxibarbal in vivo.[3]

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.
  3. ^ Lambrey B, Compagnon PL, Jacquot C (1981). "Pharmacokinetics of 14C-2-allophanyl-2-allyl -gamma-valero-lactone: a prodrug of proxibarbal in rats". European Journal of Drug Metabolism and Pharmacokinetics. 6 (3): 161–9. doi:10.1007/BF03189485. PMID 6118275. S2CID 10197120.
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