Valofane

Valofane
Clinical data
Other names	N-carbamoyl-5-methyl-2-oxo-3-prop-2-enyloxolane-3-carboxamide
ATC code	none;
Identifiers
	IUPAC name 3-allyl-N-(aminocarbonyl)-5-methyl-2-oxotetrahydrofuran-3-carboxamide;
CAS Number	3258-51-3 ;
PubChem CID	71122;
ChemSpider	64272 ;
UNII	X71N6E5IPO;
ChEMBL	ChEMBL2104479 ;
CompTox Dashboard (EPA)	DTXSID20863139 ;
ECHA InfoCard	100.019.871
Chemical and physical data
Formula	C10H14N2O4
Molar mass	226.232 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(N)NC(=O)C1(C(=O)OC(C)C1)C\C=C;
	InChI InChI=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) ; Key:LVJAHKSVOQLCEV-UHFFFAOYSA-N ;
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Valofane is a sedative drug structurally related to the barbiturates^[1] and similar drugs such as primidone. It is metabolized once inside the body to form the barbiturate proxibarbital (proxibarbal) and is thus a prodrug.^[2]

^ Traversa U, Puppini P, Jacquot C, Vertua R (1985). "Effect of an atypical barbiturate, the 2-allophanyl-2-allyl-4-valerolactone (valofan), on exploratory behaviour and brain serotonin concentrations in mice". Journal de Pharmacologie. 16 (3): 279–90. PMID 2415778.
^ 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.

[pmid2415778-1] Traversa U, Puppini P, Jacquot C, Vertua R (1985). "Effect of an atypical barbiturate, the 2-allophanyl-2-allyl-4-valerolactone (valofan), on exploratory behaviour and brain serotonin concentrations in mice". Journal de Pharmacologie. 16 (3): 279–90. PMID 2415778.

[pmid6118275-2] 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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