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{{Drugbox|
{{Drugbox|
|IUPAC_name = 2-ethyl-3-methyl-pentanamide
|IUPAC_name = 2-ethyl-3-methyl-pentanamide
| image=Valnoctamide.svg
| image=Valnoctamide.png
| CAS_number=4171-13-5
| CAS_number=4171-13-5
| ATC_prefix=N05
| ATC_prefix=N05
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| routes_of_administration= Oral, [[Intravenous therapy|intravenous]]
| routes_of_administration= Oral, [[Intravenous therapy|intravenous]]
}}
}}
__Notoc__
{{SI}}
{{CMG}}
==Overview==
'''Valnoctamide''' ([[International Nonproprietary Name|INN]], [[United States Approved Name|USAN]]) has been used in France as an [[sedative]]-[[hypnotic]] since 1964.<ref name=Harl_1964> {{fr icon}} {{cite journal | first = F. M. | last = HARL | month = March | year = 1964 | title = [CLINICAL STUDY OF VALNOCTAMIDE ON 70 NEUROPSYCHIATRIC CLINIC PATIENTS UNDERGOING AMBULATORY TREATMENT.] | journal = La Presse Médicale | volume = 72 | pages = 753-4. | id = PMID 14119722}}</ref> It is a [[structural isomer]] of [[valpromide]], a [[valproic acid]] [[prodrug]]; unlike valpromide, however, valnoctamide is not transformed into its [[acid|homologous acid]], [[valnoctic acid]], ''[[in vivo]]''.<ref name=not-into-vpa>{{cite journal | first = Abdullah | last = Haj-Yehia | coauthors = Meir Bialer | month = August | year = 1989 | title = Structure-pharmacokinetic relationships in a series of valpromide derivatives with antiepileptic activity | journal = Pharmaceutical Research | volume = 6 | issue = 8 | pages = 683-9 | id = PMID 2510141}}</ref>
'''Valnoctamide''' ([[International Nonproprietary Name|INN]], [[United States Approved Name|USAN]]) has been used in France as an [[sedative]]-[[hypnotic]] since 1964.<ref name=Harl_1964> {{fr icon}} {{cite journal | first = F. M. | last = HARL | month = March | year = 1964 | title = [CLINICAL STUDY OF VALNOCTAMIDE ON 70 NEUROPSYCHIATRIC CLINIC PATIENTS UNDERGOING AMBULATORY TREATMENT.] | journal = La Presse Médicale | volume = 72 | pages = 753-4. | id = PMID 14119722}}</ref> It is a [[structural isomer]] of [[valpromide]], a [[valproic acid]] [[prodrug]]; unlike valpromide, however, valnoctamide is not transformed into its [[acid|homologous acid]], [[valnoctic acid]], ''[[in vivo]]''.<ref name=not-into-vpa>{{cite journal | first = Abdullah | last = Haj-Yehia | coauthors = Meir Bialer | month = August | year = 1989 | title = Structure-pharmacokinetic relationships in a series of valpromide derivatives with antiepileptic activity | journal = Pharmaceutical Research | volume = 6 | issue = 8 | pages = 683-9 | id = PMID 2510141}}</ref>


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==External links==
==External links==


{{Anticonvulsants}}
{{Anticonvulsants}}
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[[Category:Anticonvulsants]]
[[Category:Anticonvulsants]]
[[Category:Anxiolytics]]
[[Category:Anxiolytics]]
[[Category:Drug]]


[[de:valnoctamide]]
[[es:valnoctamida]]
[[es:valnoctamida]]
[[fr:valnoctamide]]
[[fr:valnoctamide]]
[[ja: バルノクタミド]]
[[no:valnoktamid]]
[[pt:valnoctamida]]
[[pt:valnoctamida]]
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Latest revision as of 15:38, 13 April 2015

Valnoctamide
Clinical data
Routes of
administration		Oral, intravenous
ATC code
Legal status
Legal status
  • Not a controlled substance
Pharmacokinetic data
Bioavailability94%[1]
MetabolismHepatic
Elimination half-life10 hours
Identifiers
CAS Number
PubChem CID
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC8H17NO
Molar mass143.227 g/mol

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Valnoctamide (INN, USAN) has been used in France as an 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 since 1969[4] and was still being investigated in 2000[5] and 2003.

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.[6]

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.[7]

Side effects

The side effects of valnoctamide are mostly minor and include somnolence[8] 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, 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 of 2003.[10]

Notes and references

  1. ↑ Haj-Yehia, Abdullah (1988). "Pharmacokinetics of a valpromide isomer, valnoctamide, in dogs". Journal of Pharmaceutical Science. 77 (10): 831–4. PMID 3148708. Unknown parameter |coauthors= ignored (help); Unknown parameter |month= ignored (help)
  2. ↑ Template:Fr icon HARL, F. M. (1964). "[CLINICAL STUDY OF VALNOCTAMIDE ON 70 NEUROPSYCHIATRIC CLINIC PATIENTS UNDERGOING AMBULATORY TREATMENT.]". La Presse Médicale. 72: 753-4. PMID 14119722. Unknown parameter |month= ignored (help)
  3. ↑ Haj-Yehia, Abdullah (1989). "Structure-pharmacokinetic relationships in a series of valpromide derivatives with antiepileptic activity". Pharmaceutical Research. 6 (8): 683–9. PMID 2510141. Unknown parameter |coauthors= ignored (help); Unknown parameter |month= ignored (help)
  4. ↑ Template:Pt icon Mattos Nda, S. (1969). "[Use of Valnoctamide (nirvanil) in oligophrenic erethics and epileptics.]". Hospital (Rio J). 75 (5): 1701–4. PMID 5306499. Unknown parameter |month= ignored (help)
  5. ↑ Lindekens (2000). "In vivo study of the effect of valpromide and valnoctamide in the pilocarpine rat model of focal epilepsy". Pharmaceutical Research. 17 (11): 1408–13. PMID 11205735. Text " Hilde " ignored (help); Unknown parameter |coauthors= ignored (help); Unknown parameter |month= ignored (help)
  6. ↑ Winkler, Ilan (2005). "Efficacy of antiepileptic isomers of valproic acid and valpromide in a rat model of neuropathic pain". British Journal of Pharmacology. PMID 15997234. Unknown parameter |coauthors= ignored (help); Unknown parameter |month= ignored (help)
  7. ↑ RH Belmaker, Yuly Bersudsky, Alex Mishory and Beersheva Mental Health Center (2005). "Valnoctamide in Mania". ClinicalTrials.gov. United States National Institutes of Health. Unknown parameter |accessyear= ignored (|access-date= suggested) (help); Unknown parameter |accessdaymonth= ignored (help)
  8. ↑ VALNOCTAMIDE Biam French.
  9. ↑ Pisani F, Fazio A, Artesi C, Oteri G, Spina E, Tomson T, Perucca E. "Impairment of carbamazepine-10, 11-epoxide elimination by valnoctamide, a valpromide isomer, in healthy subjects." British Journal of Clinical Pharmacology. 1992 Jul;34(1):85-7. PMID 1352988
  10. ↑ Isoherranen, Nina (2003). "Pharmacokinetic-pharmacodynamic relationships of (2S,3S)-valnoctamide and its stereoisomer (2R,3S)-valnoctamide in rodent models of epilepsy". Pharmaceutical Research. 8 (8): 1293–301. PMID 12948028. Unknown parameter |coauthors= ignored (help); Unknown parameter |month= ignored (help)

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