Valpromide

Valpromide

Names
IUPAC name 2-Propylpentanamide
Identifiers
CAS Number	2430-27-5 N
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL93836 Y
ChemSpider	64264 Y
DrugBank	DB04165 Y
ECHA InfoCard	100.017.632
EC Number	219-394-2
KEGG	D02766 N
MeSH	dipropylacetamide
PubChem	71113
UNII	RUA6CWU76G Y
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	143.23 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 pictograms
GHS signal word	WARNING
GHS hazard statements	H302
EU classification (DSD)	Xn
R-phrases	R22
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  (what is YN ?)
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 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.