Valnoctamide

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Valnoctamide
Skeletal formula of valnoctamide
Valnoctamide3D.gif
Names
IUPAC name
2-Ethyl-3-methylpentanamide[1]
Identifiers
4171-13-5 N
ChEMBL ChEMBL1075733 YesY
ChemSpider 18974 YesY
8488661 2R,3S YesY
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 YesY
Properties
C8H17NO
Molar mass 143.23 g·mol−1
Appearance White crystals
log P 1.885
Pharmacology
ATC code N05CM13
  • Intravenous
  • Oral
Pharmacokinetics:
94%
Hepatic
10 hours
Vapor pressure {{{value}}}
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 verify (what is YesYN ?)
Infobox references

Valnoctamide (INN, USAN) has been used in France as a sedative-hypnotic since 1964.[2] 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.[3]

Indications

In addition to being a sedative, valnoctamide has been investigated for use in epilepsy.[4][5][6]

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.[7]

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.[8]

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.[9]

Chemistry

Valnoctamide is a racemic compound with four stereoisomers,[10] 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.[11]

References

  1. "valnoctamide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification and Related Records. Retrieved 20 February 2012.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  2. Harl, F. M. (March 1964). "[Clinical Study Of Valnoctamide On 70 Neuropsychiatric Clinic Patients Undergoing Ambulatory Treatment]". La Presse Médicale (in French). 72: 753–754. PMID 14119722. <templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
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  4. Mattos Nda, S. (May 1969). "[Use of Valnoctamide (nirvanil) in oligophrenic erethics and epileptics]". Hospital (Rio J) (in Portuguese). 75 (5): 1701–1704. PMID 5306499. <templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
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  8. RH Belmaker; Yuly Bersudsky; Alex Mishory; Beersheva Mental Health Center (2005). "Valnoctamide in Mania". ClinicalTrials.gov. United States National Institutes of Health. Retrieved 25 February 2006.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
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  10. Shimon Barel, Boris Yagen, Volker Schurig, Stephan Sobak, Francesco Pisani, Emilio Perucca and Meir Bialer. Stereoselective pharmacokinetic analysis of valnoctamide in healthy subjects and in patients with epilepsy. Clinical Pharmacology & Therapeutics 61, 442–449 (April 1997) doi:10.1016/S0009-9236(97)90194-6
  11. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).