Valpromide

Valpromide (marketed as Depamide by Sanofi-Aventis) is a carboxamide derivative of valproic acid used in the treatment of epilepsy and some affective disorders. It is rapidly metabolised (80%) to valproic acid (another anticonvulsant) but has anticonvulsant properties itself. It may produce more stable plasma levels than valproic acid or sodium valproate and may be more effective at preventing febrile seizures. However, it is over one hundred times more potent as an inhibitor of liver microsomal epoxide hydrolase. This makes it incompatible with carbamazepine and can affect the ability of the body to remove other toxins. Valpromide is no safer during pregnancy than valproic acid.

Valpromide
Names
Preferred IUPAC name
2-Propylpentanamide[1]
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.017.632
EC Number
  • 219-394-2
KEGG
MeSH dipropylacetamide
PubChem CID
UNII
InChI
  • InChI=1S/C8H17NO/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H2,9,10) Y
    Key: OMOMUFTZPTXCHP-UHFFFAOYSA-N Y
SMILES
  • CCCC(CCC)C(N)=O
Properties
Chemical formula
 C8H17NO
Molar mass 143.230 g·mol−1
Appearance White crystals
Melting point 125 °C (257 °F; 398 K)
log P 2.041
Pharmacology
N03AG02 (WHO)
Hazards
GHS labelling:
Pictograms
Signal word
 Warning
Hazard statements
 H302
Lethal dose or concentration (LD, LC):
  • 438 mg kg−1 (intraperitoneal, mouse)
  • 890.0 mg kg−1 (oral, rat)
Related compounds
Related amides
 Valnoctamide
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

Valpromide is formed through the reaction of valproic acid and ammonia via an intermediate acid chloride.

In pure form, valpromide is a white crystalline powder and has melting point 125–126 °C. It is soluble only in hot water. It is available on the market in some European countries.

See also

References
  • The Medical Treatment of Epilepsy by Stanley R Resor. Published by Marcel Dekker (1991). ISBN 0-8247-8549-5.
  • Hydrolysis in Drug and Prodrug Metabolism: Chemistry, Biochemistry, and Enzymology by Bernard Testa, Joachim M. Mayer (2003). ISBN 3-906390-25-X.
  • In Vitro Methods in Developmental Toxicology by Gary L Kimmel, Devendra M Kochhar, Baumann (1989). ISBN 0-8493-6919-3.
  1. "dipropylacetamide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 24 June 2005. Identification and Related Records. Retrieved 21 February 2012.



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