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Valnoctamide

Valnoctamide
Skeletal formula of valnoctamide
Valnoctamide3D.gif
Names
IUPAC name
2-Ethyl-3-methylpentanamide
Identifiers
4171-13-5 N
3D model (Jmol) Interactive image
ChEMBL ChEMBL1075733 YesY
ChemSpider 18974 YesY
8488661 2R,3S YesY
ECHA InfoCard 100.021.849
EC Number 224-033-7
KEGG D02717 N
MeSH valnoctamide
PubChem 20140
36689722 2R,3R
10313196 2R,3S
25271745 2S,3R
12015994 2S,3S
RTECS number YV5950000
UNII 3O25NRX9YG YesY
Properties
C8H17NO
Molar mass 143.23 g·mol−1
Appearance White crystals
log P 1.885
Pharmacology
N05CM13 (WHO)
  • Intravenous
  • Oral
Pharmacokinetics:
94%
Hepatic
10 hours
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
H302
Harmful Xn
R-phrases R22
Lethal dose or concentration (LD, LC):
LD50 (median dose)
760 mg kg−1(oral, rat)
Related compounds
Related alkanamides
Valpromide
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
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.

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.

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

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.

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.


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