Aprobarbital: Difference between revisions

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{{drugbox |
{{Drugbox
| IUPAC_name       = 5-propan-2-yl-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
| Watchedfields = changed
| synonyms = Aprobarbital, Oramon, Allylpropymal, Alurate, 5-Isopropyl-5-allylbarbituric acid
| verifiedrevid = 443395571
| image             = Aprobarbital.svg
| IUPAC_name = 5-propan-2-yl-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
| width            = 120
| image = Aprobarbital Structural Formulae.svg
| CAS_number        = 77-02-1
| image2 = Aprobarbital ball-and-stick animation.gif
| ATC_prefix        = N05
 
| ATC_suffix        = CA05
<!--Clinical data-->
| PubChem          = 6464
| tradename =
| DrugBank          =  
| Drugs.com = {{drugs.com|CONS|aprobarbital}}
| C = 10 | H = 14 | N = 2 | O = 3
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| molecular_weight  = 210.23 g/mol
| pregnancy_US = <!-- A / B            / C / D / X -->
| bioavailability  =
| pregnancy_category =   
| protein_bound    =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| metabolism        =
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| elimination_half-life =
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| excretion        =
| legal_US = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| pregnancy_AU     = <!-- A / B1 / B2 / B3 / C / D / X -->
| legal_status =
| pregnancy_US     = <!-- A / B            / C / D / X -->
| routes_of_administration =
| pregnancy_category=   
 
| legal_AU         = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
<!--Pharmacokinetic data-->
| legal_CA         = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| bioavailability = 
| legal_UK         = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| protein_bound = 
| legal_US         = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| metabolism = 
| legal_status     =  
| elimination_half-life = 
| routes_of_administration =  
| excretion = 
 
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 77-02-1
| ATC_prefix = N05
| ATC_suffix = CA05
| PubChem = 6464
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01352
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6221
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Q0YKG9L6RF
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00698
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 2791
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 7863
 
<!--Chemical data-->
| C=10 | H=14 | N=2 | O=3
| molecular_weight = 210.23 g/mol
| smiles = O=C1NC(=O)NC(=O)C1(C(C)C)C\C=C
| InChI = 1/C10H14N2O3/c1-4-5-10(6(2)3)7(13)11-9(15)12-8(10)14/h4,6H,1,5H2,2-3H3,(H2,11,12,13,14,15)
| InChIKey = UORJNBVJVRLXMQ-UHFFFAOYAV
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H14N2O3/c1-4-5-10(6(2)3)7(13)11-9(15)12-8(10)14/h4,6H,1,5H2,2-3H3,(H2,11,12,13,14,15)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UORJNBVJVRLXMQ-UHFFFAOYSA-N
| synonyms = aprobarbital, Oramon, allylpropymal, Alurate, 5-isopropyl- 5-allylbarbituric acid
}}
}}


'''Aprobarbital''' (Oramon) is a [[barbiturate]] derivative invented in the 1920s by Ernst Preiswerk. It has [[sedative]], [[hypnotic]] and [[anticonvulsant]] properties, and was used primarily for the treatment of [[insomnia]]. <ref> Reddemann H, Turk E. Oramon poisoning in infancy and childhood. Observations on 12 aprobarbital poisonings (German). Das Deutsche Gesundheitswesen. 1966 May 12;21(19):878-81. </ref>  Aprobarbital was never as widely used as more common barbiturate derivatives such as [[phenobarbital]] and is now rarely prescribed as it has been replaced by newer drugs with a better safety margin.
'''Aprobarbital''' (as known in the [[United States]], or '''aprobarbitone''' (as known elsewhere), sold as '''Oramon''', '''Somnifaine''', and '''Allonal''', is a [[barbiturate]] derivative invented in the 1920s by Ernst Preiswerk. It has [[sedative]], [[hypnotic]] and [[anticonvulsant]] properties, and was used primarily for the treatment of [[insomnia]].<ref> Reddemann H, Turk E. Oramon poisoning in infancy and childhood. Observations on 12 aprobarbital poisonings (German). Das Deutsche Gesundheitswesen. 1966 May 12;21(19):878-81. </ref>  Aprobarbital was never as widely used as more common barbiturate derivatives such as [[phenobarbital]] and is now rarely prescribed as it has been replaced by newer drugs with a better safety margin.
 


== References ==
== References ==
{{reflist|2}}
{{reflist}}


{{pharma-stub}}
{{Barbiturates}}
{{Hypnotics and sedatives}}
{{GABAAR PAMs}}


{{barbiturates}}
{{Hypnotics and sedatives}}
[[Category:Barbiturates]]
[[Category:Barbiturates]]
[[Category:Sedatives]]
[[Category:Alkenes]]
[[Category:Anesthetics]]
[[Category:GABAA receptor positive allosteric modulators]]
[[de:Aprobarbital]]
 
[[sv:Aprobarbital]]
 
{{sedative-stub}}

Revision as of 14:33, 13 April 2015

Aprobarbital
File:Aprobarbital Structural Formulae.svg
Clinical data
Synonymsaprobarbital, Oramon, allylpropymal, Alurate, 5-isopropyl- 5-allylbarbituric acid
AHFS/Drugs.comMicromedex Detailed Consumer Information
ATC code
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC10H14N2O3
Molar mass210.23 g/mol
3D model (JSmol)
  (verify)

Aprobarbital (as known in the United States, or aprobarbitone (as known elsewhere), sold as Oramon, Somnifaine, and Allonal, is a barbiturate derivative invented in the 1920s by Ernst Preiswerk. It has sedative, hypnotic and anticonvulsant properties, and was used primarily for the treatment of insomnia.[1] Aprobarbital was never as widely used as more common barbiturate derivatives such as phenobarbital and is now rarely prescribed as it has been replaced by newer drugs with a better safety margin.

References

  1. ↑ Reddemann H, Turk E. Oramon poisoning in infancy and childhood. Observations on 12 aprobarbital poisonings (German). Das Deutsche Gesundheitswesen. 1966 May 12;21(19):878-81.

Template:Barbiturates

Template:GABAAR PAMs


Template:Sedative-stub

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