Pivagabine

Pivagabine

Names
IUPAC name 4-(2,2-Dimethylpropanoylamino)butanoic acid
Identifiers
CAS Number	69542-93-4
3D model (Jmol)	Interactive image
ChemSpider	62118
ECHA InfoCard	100.067.287
EC Number	274-038-3
KEGG	D07342
MeSH	N-trimethylacetyl-4-aminobutyric+acid
PubChem	68888
UNII	C53SV0WO4V
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) Key: SRPNQDXRVRCTNK-UHFFFAOYSA-N
SMILES CC(C)(C)C(=O)NCCCC(O)=O
Properties
Chemical formula	C9H17NO3
Molar mass	187.24 g·mol^−1
Pharmacology
ATC code	N06AX15 (WHO)
Routes of administration	Oral
Pharmacokinetics:
Biological half-life	6.4 hours
Legal status	℞ (Prescription only)
Related compounds
Related alkanoic acids	Aceglutamide N-Acetylglutamic acid Citrulline
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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]}

See also

• Fengabine

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.
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.
6. George I. Papakostas; Maurizio Fava (2010). Pharmacotherapy for Depression and Treatment-resistant Depression. World Scientific. pp. 370–. ISBN 978-981-4287-59-3.