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Pivagabine

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Pivagabine
Names

Preferred IUPAC name 4-(2,2-Dimethylpropanamido)butanoic acid
Identifiers
CAS Number	69542-93-4^Y
3D model (JSmol)	Interactive image
ChemSpider	62118^Y
ECHA InfoCard	100.067.287
EC Number	274-038-3
KEGG	D07342^Y
MeSH	N-trimethylacetyl-4-aminobutyric+acid
PubChem CID	68888
UNII	C53SV0WO4V^Y
CompTox Dashboard (EPA)	DTXSID3046162
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
ATC code	N06AX15 (WHO)
Routes of administration	Oral
Pharmacokinetics:
Biological half-life	6.4 hours
Legal status	In general: ℞ (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 acidorN-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 prodrugtoGABA,^[1] pivagabine is now believed to act somehow via modulation of corticotropin-releasing factor (CRF).^[2]^[3]^[4]^[5]^[6]

References[edit]

^ 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.

^ 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.

^ Esposito G, Luparini MR (November 1997). "Pivagabine: a novel psychoactive drug". Arzneimittelforschung. 47 (11A): 1306–9. PMID 9450153.

^ 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.

^ 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.

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

Antidepressants (N06A)

Specific reuptake inhibitors and/or receptor modulators

SSRIsTooltip Selective serotonin reuptake inhibitors	Citalopram Escitalopram Fluoxetine^# Fluvoxamine Indalpine^‡ Paroxetine Sertraline Zimelidine^‡
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors	Desvenlafaxine Duloxetine Levomilnacipran Milnacipran Tofenacin Venlafaxine
NRIsTooltip Norepinephrine reuptake inhibitors	Atomoxetine Reboxetine Viloxazine
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors	Amineptine^‡ Bupropion Nomifensine^‡
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants	Mianserin Mirtazapine Setiptiline
SARIsTooltip Serotonin antagonist and reuptake inhibitors	Etoperidone Nefazodone Trazodone
SMSTooltip Serotonin modulator and stimulators	Vilazodone Vortioxetine
Others	Agomelatine Amisulpride Dextromethorphan/bupropion Esketamine Etryptamine^‡ Gepirone Indeloxazine Flupentixol Ketamine^§ Medifoxamine^‡ Metryptamine^‡ Oxaflozane^‡ Pivagabine^‡ Tandospirone Teniloxazine Tianeptine

Tricyclic and tetracyclic antidepressants

TCAs

TeCAs

Others

Tiazesim

Monoamine oxidase inhibitors

Non-selective

Reversible: Caroxazone^‡

Mixed: Bifemelane

MAO_A-selective

MAO_B-selective

Irreversible: Selegiline

Adjunctive therapies

Atypical antipsychotics (aripiprazole, brexpiprazole, lurasidone, olanzapine, quetiapine, risperidone)
Buspirone
Lithium (lithium carbonate, lithium citrate)
Thyroid hormones (triiodothyronine (T₃), levothyroxine (T₄))

Miscellaneous

^#WHO-EM

^‡Withdrawn from market

Clinical trials:

^†Phase III
^§Never to phase III

v t e Anxiolytics (N05B)
5-HT_1ARTooltip 5-HT1A receptor agonists	Buspirone Gepirone Tandospirone
GABA_ARTooltip GABAA receptor PAMsTooltip positive allosteric modulators	Benzodiazepines: Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam^# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam^# Medazepam Nordazepam Oxazepam Pinazepam Prazepam; Others: Alpidem^‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Carisoprodol Chlormezanone^‡ Ethanol (alcohol) Etifoxine
Hypnotics	Zopiclone
Gabapentinoids (α₂δ VDCC blockers)	Gabapentin Gabapentin enacarbil Phenibut Pregabalin
Antidepressants	SSRIsTooltip Selective serotonin reuptake inhibitors (e.g., escitalopram) SNRIsTooltip Serotonin-norepinephrine reuptake inhibitors (e.g., duloxetine) SARIsTooltip Serotonin antagonist and reuptake inhibitors (e.g., trazodone) TCAsTooltip Tricyclic antidepressants (e.g., clomipramine^#) TeCAsTooltip Tetracyclic antidepressants (e.g., mirtazapine) MAOIsTooltip Monoamine oxidase inhibitors (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine
Antipsychotics	Quetiapine Flupentixol
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol)
Others	Benzoctamine Cycloserine Fabomotizole Hydroxyzine Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Retrieved from "https://en.wikipedia.org/w/index.php?title=Pivagabine&oldid=1175940543" Categories: ●Antidepressants ●Carboxamides ●Drugs with unknown mechanisms of action ●GABA analogues ●Gamma-Amino acids Hidden categories: ●Articles without InChI source ●Articles without EBI source ●ECHA InfoCard ID from Wikidata ●Drugs with non-standard legal status ●Articles containing unverified chemical infoboxes ●Articles with short description ●Short description matches Wikidata ●This page was last edited on 18 September 2023, at 12:12 (UTC). ●Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization. ●Privacy policy ●About Wikipedia ●Disclaimers ●Contact Wikipedia ●Code of Conduct ●Developers ●Statistics ●Cookie statement ●Mobile view