Valnoctamide

Valnoctamide

Names
IUPAC name 2-Ethyl-3-methylpentanamide
Identifiers
CAS Number	4171-13-5 N
ChEMBL	ChEMBL1075733 Y
ChemSpider	18974 Y 8488661 2R,3S Y
EC Number	224-033-7
Jmol 3D model	Interactive image Interactive image
KEGG	D02717 N
MeSH	valnoctamide
PubChem	20140 36689722 2R,3R 10313196 2R,3S 25271745 2S,3R 12015994 2S,3S
RTECS number	YV5950000
UNII	3O25NRX9YG Y
InChI InChI=1S/C8H17NO/c1-4-6(3)7(5-2)8(9)10/h6-7H,4-5H2,1-3H3,(H2,9,10) Y Key: QRCJOCOSPZMDJY-UHFFFAOYSA-N Y
SMILES CCC(C)C(CC)c(:[nH2]):[o] CCC(C)C(CC)C(N)=O
Properties
Chemical formula	C8H17NO
Molar mass	143.23 g·mol−1
Appearance	White crystals
log P	1.885
Pharmacology
ATC code	N05CM13
Routes of administration	Intravenous Oral
Pharmacokinetics:
Bioavailability	94%
Metabolism	Hepatic
Biological half-life	10 hours
Vapor pressure	{{{value}}}
Related compounds
Related alkanamides	Valpromide
Related compounds	2-Methylpentane 3-Methylpentane 3-Ethylpentane 2-Ethyl-1-butanol 2-Methylhexane 3-Methylhexane 2-Methylheptane 3-Methylheptane 2-Ethylhexanol 2-Ethylhexanoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Valnoctamide (INN, USAN) has been used in France as a sedative-hypnotic since 1964. It is a structural isomer of valpromide, a valproic acid prodrug; unlike valpromide, however, valnoctamide is not transformed into its homologous acid, valnoctic acid, in vivo.

Indications

In addition to being a sedative, valnoctamide has been investigated for use in epilepsy.

It was studied for neuropathic pain in 2005 by Winkler et al., with good results: it had minimal effects on motor coordination and alertness at effective doses, and appeared to be equally effective as gabapentin.

RH Belmaker, Yuly Bersudsky and Alex Mishory started a clinical trial of valnoctamide for prophylaxis of mania in lieu of the much more teratogenic valproic acid or its salts.

Side effects

The side effects of valnoctamide are mostly minor and include somnolence and the slight motor impairments mentioned above.

Interactions

Valnoctamide is known to increase through inhibition of epoxide hydrolase the serum levels of carbamazepine-10,11-epoxide, the active metabolite of carbamazepine, sometimes to toxic levels.

Chemistry

Valnoctamide is a racemic compound with four stereoisomers, all of which were shown to be more effective than valproic acid in animal models of epilepsy and one of which [(2S,3S]-valnoctamide) was considered to be a good candidate by Isoherranen, et al. for an anticonvulsant in August 2003.