Valpromide

Valpromide
Names
	Preferred IUPAC name 2-Propylpentanamide
Identifiers
CAS Number	2430-27-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:74562;
ChEMBL	ChEMBL93836 ;
ChemSpider	64264 ;
DrugBank	DB04165 ;
ECHA InfoCard	100.017.632
EC Number	219-394-2;
KEGG	D02766 ;
MeSH	dipropylacetamide
PubChem CID	71113;
UNII	RUA6CWU76G ;
CompTox Dashboard (EPA)	DTXSID1023734 ;
	InChI InChI=1S/C8H17NO/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H2,9,10) Key: OMOMUFTZPTXCHP-UHFFFAOYSA-N ;
	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
ATC code	N03AG02 (WHO)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	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). verify (what is ?) Infobox references

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 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 a melting point 125–126 °C. It is soluble only in hot water. It is available on the market in some European countries.

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.

^ "dipropylacetamide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 24 June 2005. Identification and Related Records. Retrieved 21 February 2012.