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Valpromide

Skeletal formula of valpromide
colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other This page is a soft redirect. Names #REDIRECTmw:Help:Magic words#Other This page is a soft redirect.-	IUPAC name 2-Propylpentanamide
colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other This page is a soft redirect. Identifiers #REDIRECTmw:Help:Magic words#Other This page is a soft redirect.-	ATC code	N03AG02
CAS Registry Number	2430-27-5 7pxN
ChEMBL	ChEMBL93836 7pxY
ChemSpider	64264 7pxY
DrugBank	DB04165 7pxY
EC number	219-394-2
InChI InChI=1S/C8H17NO/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H2,9,10) 7pxY Key: OMOMUFTZPTXCHP-UHFFFAOYSA-N 7pxY
Jmol-3D images	Image Image
KEGG	D02766 7pxN
MeSH	dipropylacetamide
PubChem	Template:Chembox PubChem/format
SMILES Template:Chembox SMILES/format Template:Chembox SMILES/format
colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other This page is a soft redirect. Properties #REDIRECTmw:Help:Magic words#Other This page is a soft redirect.-	Molecular formula	C8H17NO
Molar mass	g·mol−1
Appearance	White crystals
Melting point
log P	2.041
colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other This page is a soft redirect. Hazards #REDIRECTmw:Help:Magic words#Other This page is a soft redirect.-	GHS pictograms	The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word	WARNING
GHS hazard statements	H302
EU classification	Harmful Xn
R-phrases	R22
LD50 (Median lethal dose)	438 mg kg−1 (intraperitoneal, mouse) 890.0 mg kg−1 (oral, rat)
colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other This page is a soft redirect. Related compounds #REDIRECTmw:Help:Magic words#Other This page is a soft redirect.-	Related amides	Valnoctamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

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.