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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
⚫
| verifiedrevid = 447735986
| Watchedfields = changed
⚫
| IUPAC_name = 5-allyl-5-(2-hydroxypropyl)pyrimidine-2,4,6(1''H'',3''H'',5''H'')-trione
⚫
| verifiedrevid = 464375627
⚫
| IUPAC_name = (''RS'')-5-allyl-5-(2-hydroxypropyl)pyrimidine-2,4,6(1''H'',3''H'',5''H'')-trione
| image = Proxibarbital.svg
| image = Proxibarbital.svg
| width = 120
| width = 120
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<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 2537-29-3
| CAS_number = 2537-29-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = F97OMS297F
| ATC_prefix = N05
| ATC_prefix = N05
| ATC_suffix = CA22
| ATC_suffix = CA22
| PubChem = 17336
| PubChem = 17336
| ChEMBL = 2105233
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| DrugBank =
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<!--Chemical data-->
<!--Chemical data-->
| C=10 | H=14 | N=2 | O=4
| C=10 | H=14 | N=2 | O=4
| molecular_weight = 226.229 g/mol
| smiles = O=C1NC(=O)NC(=O)C1(CC(O)C)C\C=C
| smiles = O=C1NC(=O)NC(=O)C1(CC(O)C)C\C=C
| InChI = 1/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)
| InChIKey = VNLMRPAWAMPLNZ-UHFFFAOYAU
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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)
| StdInChI = 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)
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}}
}}


'''Proxibarbital''' (Ipronal) is a [[barbiturate]] derivative synthesized in 1956. It has anti-anxiety properties and in opposite to all barbiturates almost without hypnotic result.<ref>
'''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.<ref>{{cite book | veditors = Zejc A, Gorczyca M | vauthors = Zajdel P, Kulig K, Zejc A | trans-title = Drug chemistry, textbook for pharmacy students and pharmacists | title = Chemia leków, podręcznik dla studentów farmacji i farmaceutów | language = polish | year = 2008| location = Warszawa, Poland | isbn = 978-83-200-3652-7 }}</ref>
{{ cite book
| editor1 = Zejc, A.
| editor2 = Gorczyca, M.
| last1 = Zajdel | first1 = P.
| last2 = Kulig | first2 = K.
| last3 = Zejc | first3 = A.
| title = Chemia leków, podręcznik dla studentów farmacji i farmaceutów
| language = polish
| year = 2008
| location = Warszawa, Poland
| isbn = 9788320036527
}}</ref>


It was also used in the treatment of [[migraine]] headaches in a similar manner to [[butalbital]].<ref>{{ cite pmid | 14412 }}</ref>
It was also used in the treatment of [[migraine]] headaches in a similar manner to [[butalbital]].<ref>{{cite journal | vauthors = Sulman FG, Pfeifer Y, Tal E | title = [Migraine therapy by enzyme induction with proxibarbital] | language = German | journal = Therapie der Gegenwart | volume = 115 | issue = 12 | pages = 2088–103 | date = December 1976 | pmid = 14412 }}</ref>


[[Valofane]] isomerises to Proxibarbal in vivo.
== References ==
== References ==
{{reflist}}
{{reflist}}


{{barbiturates}}
{{Hypnotics and sedatives}}
{{Hypnotics and sedatives}}
{{GABAAR PAMs}}

[[Category:Barbiturates]]
[[Category:Barbiturates]]
[[Category:Alkenes]]
[[Category:Antimigraine drugs]]
[[Category:Allyl compounds]]

{{sedative-stub}}
{{sedative-stub}}

[[de:Proxibarbal]]
[[pl:Proksybarbal]]

Latest revision as of 07:41, 7 December 2023

Proxibarbital
Clinical data
Other namesProxibarbital, Centralgol, 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 Edit this at Wikidata
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. It has anti-anxiety properties and is, in contrast to most barbiturates, almost without hypnotic action.[1]

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

Valofane isomerises to Proxibarbal in vivo.

References

[edit]
  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.
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