Valpromide

Valpromide
IUPAC name 2-Propylpentanamide
Other names Depamide[citation needed]
Identifiers
CAS number	2430-27-5 Y
PubChem	71113
ChemSpider	64264 Y
UNII	RUA6CWU76G Y
EC number	219-394-2
DrugBank	DB04165
KEGG	D02766 Y
MeSH	dipropylacetamide
ChEMBL	CHEMBL93836 Y
ATC code	N03AG02
Jmol-3D images	Image 1
SMILES CCCC(CCC)C(N)=O
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
Properties
Molecular formula	C8H17NO
Molar mass	143.23 g mol−1
Exact mass	143.131014171 g mol−1
Appearance	White crystals
Melting point	125 °C, 398 K, 257 °F
log P	2.041
Hazards
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H302
EU classification	Xn
R-phrases	R22
LD50	890.0 mg kg−1 (oral, rat) 438 mg kg−1 (intraperitoneal, mouse)
Related compounds
Related compounds	Valnoctamide 2-Ethylhexanoic acid
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 effectively at preventing febrile seizures. However it is over one hundred times more potent 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 melting point 125–126 °C. It is practically insoluble in water but soluble in hot water. It is available on the market in some European countries.

See also

• Valproate pivoxil
• Valnoctamide

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.