Valnoctamide

• 2-ethyl- 3- methylpentanamide
• 2-ethyl- 3- methylvaleramide

• 4171-13-5 ( mixture of stereoisomers )
• 189189-74-0 [( 2R, 3R )-isomer ]
• 189189-75-1 [( 2S, 3S)- isomer ]
• 189189-73-9 [( 2S, 3R )-isomer ]
• 189189-76-2 [( 2R, 3S )-isomer ]

N05CM13

Hypnotic, sedative

From 113.5 to 114 ° C ( mixture of stereoisomers )

Attention

• 760 mg · kg -1 ( LD50, rat, oral)
• 540 mg · kg -1 ( LD50, mouse, ip)

Template: Infobox chemical / molecular formula search available

Valnoctamide is a mixture of several chemical compounds from the group of carboxylic acid amides, which is in France since 1964 as a sleep aid and sedative in use. It is at the drug valnoctamide to a structural isomer of valpromide, a prodrug of valproic acid precursor. As opposed to valnoctamide valpromide is not converted into the corresponding carboxylic acid in the body.

Areas of application

In addition to its effect as a sedative valnoctamide was investigated as a means to treat epilepsy since 1969. Investigations in this direction were also 2000 and 2003 still continues.

As a means for neuropathic pain, it was founded in 2005 by Winkler et al. investigated with encouraging results: it showed only minimal effects on the co-ordination and attention at effective doses and seemed to be as effective as gabapentin.

RH Belmaker, Yuly Bersudsky and Alex Mishory started a clinical study on valnoctamide as a substitute medication for much more teratogenic active valproic acid and its salts for the prophylaxis of mania.

Side effects

The known side effects of valnoctamide are mostly negligible, and consist in somnolence and mild incoordination.

Contraindications

Valnoctamide increases serum concentration of carbamazepine -10 ,11- epoxide, the active metabolite of carbamazepine, sometimes because it inhibits the epoxide to a toxic level.

Chemistry

Valnoctamide is a chiral drug that because of its two stereocenters ( 2 - and 3- position ) has four stereoisomers: the (2R, 3R ) form and its enantiomeric (2S, 3S)- form and the (2S, 3R )-isomer and the (2R, 3S )-isomer. As a drug, the mixture of the four stereoisomers is employed. Each of the stereoisomers in an animal model for epilepsy effective than valproic acid, and one of them - ( 2S, 3S)- valnoctamide - was established in August 2003 by Isoherranen et al. described as a good candidate for an anticonvulsant.