Valpromide

Valpromide

Skeletal formula of valpromide Skeletal formula of valpromide
Names
Preferred IUPAC name 2-Propylpentanamide
Identifiers
CAS Number	2430-27-5 ☒N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:74562
ChEMBL	ChEMBL93836 checkY
ChemSpider	64264 checkY
DrugBank	DB04165 checkY
ECHA InfoCard
EC Number	219-394-2
E number
KEGG	D02766 ☒N
MeSH	dipropylacetamide
PubChem CID	71113
UNII	RUA6CWU76G checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C8H17NO/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H2,9,10) checkY Key: OMOMUFTZPTXCHP-UHFFFAOYSA-N checkY
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	GHS07: Exclamation mark
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). ☒N verify (what is checkY☒N ?) 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.

See also

• Valproate pivoxil
• Valnoctamide
• Carbromide
• Ibrotamide

References

• The Medical Treatment of Epilepsy by Stanley R Resor. Published by Marcel Dekker (1991). .
• Hydrolysis in Drug and Prodrug Metabolism: Chemistry, Biochemistry, and Enzymology by Bernard Testa, Joachim M. Mayer (2003). .
• In Vitro Methods in Developmental Toxicology by Gary L Kimmel, Devendra M Kochhar, Baumann (1989). .