Pivagabine

Pivagabine (INN; brand name Tonerg), also known as N-pivaloyl-γ-aminobutyric acid or N-pivaloyl-GABA, is an antidepressant and anxiolytic drug which was introduced in Italy in 1997 for the treatment of depressive and maladaptive syndromes. But it was discontinued in Italy (according to Martindale). Originally believed to function as a prodrug to GABA,[1] pivagabine is now believed to act somehow via modulation of corticotropin-releasing factor (CRF).[2][3][4][5][6]

Pivagabine
Names
Preferred IUPAC name
4-(2,2-Dimethylpropanamido)butanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.067.287
EC Number
  • 274-038-3
KEGG
MeSH N-trimethylacetyl-4-aminobutyric+acid
PubChem CID
UNII
InChI
  • InChI=1S/C9H17NO3/c1-9(2,3)8(13)10-6-4-5-7(11)12/h4-6H2,1-3H3,(H,10,13)(H,11,12) Y
    Key: SRPNQDXRVRCTNK-UHFFFAOYSA-N Y
SMILES
  • CC(C)(C)C(=O)NCCCC(O)=O
Properties
Chemical formula
 C9H17NO3
Molar mass 187.239 g·mol−1
Pharmacology
N06AX15 (WHO)
Oral
Pharmacokinetics:
6.4 hours
Legal status
  • In general: ℞ (Prescription only)
Related compounds
Related alkanoic acids
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. Bianchi M, Quadro G, Mourier G, Galzigna L (1983). "Pharmacokinetics and in vitro effects of a 4-aminobutyric acid derivative with anticonvulsant action". Pharmacology. 27 (4): 237–40. doi:10.1159/000137876. PMID 6634934.
  2. Scapagnini U, Matera M (November 1997). "Effects of pivagabine on psychophysical performance and behavioural response in experimental models of stress". Arzneimittel-Forschung. 47 (11A): 1310–4. PMID 9450154.
  3. Esposito G, Luparini MR (November 1997). "Pivagabine: a novel psychoactive drug". Arzneimittelforschung. 47 (11A): 1306–9. PMID 9450153.
  4. Gerra G, Zaimovic A, Giusti F, et al. (July 2001). "Pivagabine effects on neuroendocrine responses to experimentally-induced psychological stress in humans". Behavioural Brain Research. 122 (1): 93–101. doi:10.1016/S0166-4328(01)00177-2. PMID 11287080. S2CID 23067609.
  5. Serra M, Concas A, Mostallino MC, et al. (April 1999). "Antagonism by pivagabine of stress-induced changes in GABAA receptor function and corticotropin-releasing factor concentrations in rat brain". Psychoneuroendocrinology. 24 (3): 269–84. doi:10.1016/S0306-4530(98)00049-3. PMID 10101733. S2CID 11382166.
  6. George I. Papakostas; Maurizio Fava (2010). Pharmacotherapy for Depression and Treatment-resistant Depression. World Scientific. pp. 370–. ISBN 978-981-4287-59-3.
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