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Valpromide

From Wikipedia, the free encyclopedia
Valpromide
Skeletal formula of valpromide
Skeletal formula of valpromide
Names
Preferred IUPAC name
2-Propylpentanamide[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.017.632Edit this at Wikidata
EC Number
  • 219-394-2
KEGG
MeSHdipropylacetamide
UNII
  • 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
  • CCCC(CCC)C(N)=O
Properties
C8H17NO
Molar mass143.230 g·mol−1
AppearanceWhite crystals
Melting point125 °C (257 °F; 398 K)
logP2.041
Pharmacology
N03AG02 (WHO)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302
Lethal dose or concentration (LD, LC):
  • 438 mg kg−1(intraperitoneal, mouse)
  • 890.0 mg kg−1(oral, rat)
Related compounds
Relatedamides
Valnoctamide
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Valpromide (marketed asDepamide bySanofi-Aventis) is acarboxamide derivative ofvalproic acid used in the treatment ofepilepsy and someaffective disorders. It is rapidly metabolised (80%) tovalproic acid (anotheranticonvulsant) but has anticonvulsant properties itself. It may produce more stable plasma levels than valproic acid orsodium valproate and may be more effective at preventing febrile seizures. However, it is over one hundred times more potent as an inhibitor of liver microsomalepoxide hydrolase. This makes it incompatible withcarbamazepine 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 andammonia via an intermediateacid 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

[edit]

References

[edit]
  • 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.
  1. ^"dipropylacetamide - Compound Summary".PubChem Compound. USA: National Center for Biotechnology Information. 24 June 2005. Identification and Related Records. Retrieved21 February 2012.


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