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Valpromide

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
Names
Preferred IUPAC name
2-Propylpentanamide[1]
Identifiers
  • 2430-27-5 N
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:74562
ChEMBL
  • ChEMBL93836 Y
ChemSpider
  • 64264 Y
DrugBank
  • DB04165 Y
ECHA InfoCard 100.017.632
EC Number
  • 219-394-2
KEGG
  • D02766 N
MeSH dipropylacetamide
  • 71113
UNII
  • RUA6CWU76G Y
  • DTXSID1023734
  • 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
  • CCCC(CCC)C(N)=O
Properties
C8H17NO
Molar mass 143.230 g·mol−1
Appearance White crystals
Melting point 125 °C (257 °F; 398 K)
log P 2.041
Pharmacology
N03AG02 (WHO)
Hazards
GHS labelling:
Warning
H302
Lethal dose or concentration (LD, LC):
  • 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 YN ?)

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 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. Retrieved 21 February 2012.



valpromide, marketed, depamide, sanofi, aventis, carboxamide, derivative, valproic, acid, used, treatment, epilepsy, some, affective, disorders, rapidly, metabolised, valproic, acid, another, anticonvulsant, anticonvulsant, properties, itself, produce, more, s. 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 NamesPreferred IUPAC name 2 Propylpentanamide 1 IdentifiersCAS Number 2430 27 5 N3D model JSmol Interactive imageChEBI CHEBI 74562ChEMBL ChEMBL93836 YChemSpider 64264 YDrugBank DB04165 YECHA InfoCard 100 017 632EC Number 219 394 2KEGG D02766 NMeSH dipropylacetamidePubChem CID 71113UNII RUA6CWU76G YCompTox Dashboard EPA DTXSID1023734InChI InChI 1S C8H17NO c1 3 5 7 6 4 2 8 9 10 h7H 3 6H2 1 2H3 H2 9 10 YKey OMOMUFTZPTXCHP UHFFFAOYSA N YSMILES CCCC CCC C N OPropertiesChemical formula C 8H 17N OMolar mass 143 230 g mol 1Appearance White crystalsMelting point 125 C 257 F 398 K log P 2 041PharmacologyATC code N03AG02 WHO HazardsGHS labelling PictogramsSignal word WarningHazard statements H302Lethal dose or concentration LD LC LD50 median dose 438 mg kg 1 intraperitoneal mouse 890 0 mg kg 1 oral rat Related compoundsRelated amides ValnoctamideExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references 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 EditValproate pivoxil Valnoctamide Carbromide Ibrotamide M 25 1186293 14 0 is also one of the compounds that has a reputation References EditThe 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 dipropylacetamide Compound Summary PubChem Compound USA National Center for Biotechnology Information 24 June 2005 Identification and Related Records Retrieved 21 February 2012 nbsp This anticonvulsant related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Valpromide amp oldid 1138631054, wikipedia, wiki, book, books, library,

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