valofane

{{short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 470628187

| IUPAC_name = 3-allyl-N-(aminocarbonyl)-5-methyl-2-oxotetrahydrofuran-3-carboxamide

| image = Valofane.svg

| width = 180

| tradename =

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| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 3258-51-3

| ATC_prefix = none

| ATC_suffix =

| PubChem = 71122

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2104479

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 64272

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = X71N6E5IPO

| C=10 | H=14 | N=2 | O=4

| smiles = O=C(N)NC(=O)C1(C(=O)OC(C)C1)C\C=C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C10H14N2O4/c1-3-4-10(7(13)12-9(11)15)5-6(2)16-8(10)14/h3,6H,1,4-5H2,2H3,(H3,11,12,13,15)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = LVJAHKSVOQLCEV-UHFFFAOYSA-N

| synonyms = N-carbamoyl-5-methyl-2-oxo-3-prop-2-enyloxolane-3-carboxamide

}}

Valofane is a sedative drug structurally related to the barbiturates{{cite journal | vauthors = Traversa U, Puppini P, Jacquot C, Vertua R | title = Effect of an atypical barbiturate, the 2-allophanyl-2-allyl-4-valerolactone (valofan), on exploratory behaviour and brain serotonin concentrations in mice | journal = Journal de Pharmacologie | volume = 16 | issue = 3 | pages = 279–90 | date = 1985 | pmid = 2415778 }} and similar drugs such as primidone. It is metabolized once inside the body to form the barbiturate proxibarbital (proxibarbal) and is thus a prodrug.{{cite journal | vauthors = Lambrey B, Compagnon PL, Jacquot C | title = Pharmacokinetics of 14C-2-allophanyl-2-allyl -gamma-valero-lactone: a prodrug of proxibarbal in rats | journal = European Journal of Drug Metabolism and Pharmacokinetics | volume = 6 | issue = 3 | pages = 161–9 | date = 1981 | pmid = 6118275 | doi = 10.1007/BF03189485 | s2cid = 10197120 }}