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Pivagabine

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Pivagabine
Names
Seletal formula of pivagabine with some implicit hydrogens shown
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 theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Pivagabine (INN; brand nameTonerg), also known asN-pivaloyl-γ-aminobutyric acid orN-pivaloyl-GABA, is anantidepressant andanxiolytic drug which was introduced inItaly in 1997 for the treatment ofdepressive andmaladaptive syndromes. But it was discontinued in Italy (according toMartindale). Originally believed to function as aprodrug toGABA,^[1] pivagabine is now believed to act somehow via modulation ofcorticotropin-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)

Specificreuptake inhibitors orreceptor 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 andtetracyclic antidepressants

TCAsTooltip Tricyclic antidepressants	Amineptine^‡ Amitriptyline^# Amitriptylinoxide Amoxapine Butriptyline^‡ Clomipramine^# Demexiptiline^‡ Desipramine Dibenzepin Dimetacrine^‡ Dosulepin Doxepin Imipramine Imipraminoxide^‡ Iprindole^‡ Lofepramine Melitracen Metapramine^‡ Nitroxazepine Nortriptyline Noxiptiline Opipramol Pipofezine Propizepine^‡ Protriptyline Quinupramine^‡ Tianeptine Trimipramine
TeCAsTooltip Tetracyclic antidepressants	Maprotiline Mianserin Mirtazapine Setiptiline
Others	Tiazesim

Monoamine oxidase inhibitors

Non-selective	Irreversible:Benmoxin^‡ Iproclozide^‡ Iproniazid^‡ Isocarboxazid Isoniazid^# Linezolid^# Mebanazine^‡ Nialamide^‡ Octamoxin^‡ Phenelzine Pheniprazine^‡ Phenoxypropazine^‡ Pivhydrazine^‡ Safrazine^‡ Tedizolid Tranylcypromine Reversible:Caroxazone^‡ Mixed:Bifemelane
MAO_ATooltip Monoamine oxidase A-selective	Reversible:Eprobemide Metralindole Minaprine^‡ Moclobemide Pirlindole Tetrindole Toloxatone
MAO_BTooltip Monoamine oxidase 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
Ademetionine (SAMe) GABAkine neurosteroids (brexanolone,zuranolone) Hypericum perforatum (St. John's Wort) Oxitriptan (5-HTP) Rubidium chloride (RbCl) Tryptophan

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

v t e Anxiolytics (N05B)
5-HT_1ARTooltip 5-HT1A receptoragonists	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
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
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g.,prazosin) Alpha-2 agonists (e.g.,clonidine,dexmedetomidine,guanfacine) Beta blockers (e.g.,propranolol,atenolol,betaxolol,nadolol,oxprenolol,pindolol)
Others	Benzoctamine Cycloserine Fabomotizole Hydroxyzine Lorpiprazole Mebicar Mepiprazole Nicotine (tobacco) Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

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