Imagabalin

Imagabalin
Clinical data
Other names	PD-0332334; PD-332,334
ATC code	None;
Identifiers
	IUPAC name (3S,5R)-3-amino-5-methyloctanoic acid;
CAS Number	610300-07-7 ; 610300-00-0 (hydrochloride);
PubChem CID	10236037;
ChemSpider	8411525;
UNII	NDG6931B7H;
KEGG	D09627;
CompTox Dashboard (EPA)	DTXSID00976534 ;
Chemical and physical data
Formula	C9H19NO2
Molar mass	173.256 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)C[C@@H](N)C[C@@H](CCC)C;
	InChI InChI=1S/C9H19NO2/c1-3-4-7(2)5-8(10)6-9(11)12/h7-8H,3-6,10H2,1-2H3,(H,11,12)/t7-,8+/m1/s1; Key:JXEHXYFSIOYTAH-SFYZADRCSA-N;

Imagabalin (INN, USAN; PD-0332334) was an investigational drug that acts as a ligand for the α₂δ subunit of the voltage-dependent calcium channel,^[1] with some selectivity for the α₂δ₁ subunit over α₂δ₂.^[2] It was under development by Pfizer as a pharmaceutical medication due to its hypothesized anxiolytic, analgesic, hypnotic, and anticonvulsant-like activity. It reached phase-III clinical trials for treatment of generalized anxiety disorder; however, the trials were terminated by the manufacturer.^[3]^[4]^[5]^[6] The drug is no longer under development.

References

^ Quintero JE, Pomerleau F, Huettl P, Johnson KW, Offord J, Gerhardt GA (July 2011). "Methodology for rapid measures of glutamate release in rat brain slices using ceramic-based microelectrode arrays: basic characterization and drug pharmacology". Brain Research. 1401: 1–9. doi:10.1016/j.brainres.2011.05.025. PMC 3197737. PMID 21664606.
^ Larry Ereshefsky (2008). "Therapies in the Pipeline for Sleep Disorders: Focus on Novel Mechanisms and Disease Models" (PDF) (Press release). p. 11. Retrieved 2012-04-22.
^ Pfizer (2012-11-09). "A Phase 3, Randomized, Double-Blind, Parallel Group, 10-Week Placebo Controlled Fixed Dose Study Of PD 0332334 And Paroxetine Evaluating The Efficacy And Safety Of PD 0332334 For The Treatment Of Generalized Anxiety Disorder". Archived from the original on 2021-03-28. Retrieved 2020-09-08.
^ Pfizer (2012-11-09). "A Phase 3, Randomized, Double-Blind, Parallel Group, 10-Week Placebo Controlled Fixed Dose Study Of PD 0332334 And Paroxetine Evaluating The Efficacy And Safety Of PD 0332334 For The Treatment Of Generalized Anxiety Disorder". Archived from the original on 2021-03-30. Retrieved 2020-09-08.
^ Pfizer (2012-11-09). "A Phase 3, Randomized, Double-Blind, Parallel Group, 10-Week Placebo Controlled Fixed Dose Study of PD 0332334 and Paroxetine Evaluating the Efficacy and Safety of PD 0332334 for the Treatment of Generalized Anxiety Disorder". Archived from the original on 2021-03-31. Retrieved 2020-09-08.
^ Pfizer (2012-11-09). "A 52-Week Open-Label Safety Study of PD 0332334 in Subjects With Generalized Anxiety Disorder". Archived from the original on 2021-04-01. Retrieved 2020-09-08.

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[pmid21664606-1] Quintero JE, Pomerleau F, Huettl P, Johnson KW, Offord J, Gerhardt GA (July 2011). "Methodology for rapid measures of glutamate release in rat brain slices using ceramic-based microelectrode arrays: basic characterization and drug pharmacology". Brain Research. 1401: 1–9. doi:10.1016/j.brainres.2011.05.025. PMC 3197737. PMID 21664606.

[Ereshefsky2008-2] Larry Ereshefsky (2008). "Therapies in the Pipeline for Sleep Disorders: Focus on Novel Mechanisms and Disease Models" (PDF) (Press release). p. 11. Retrieved 2012-04-22.

[3] Pfizer (2012-11-09). "A Phase 3, Randomized, Double-Blind, Parallel Group, 10-Week Placebo Controlled Fixed Dose Study Of PD 0332334 And Paroxetine Evaluating The Efficacy And Safety Of PD 0332334 For The Treatment Of Generalized Anxiety Disorder". Archived from the original on 2021-03-28. Retrieved 2020-09-08.

[4] Pfizer (2012-11-09). "A Phase 3, Randomized, Double-Blind, Parallel Group, 10-Week Placebo Controlled Fixed Dose Study Of PD 0332334 And Paroxetine Evaluating The Efficacy And Safety Of PD 0332334 For The Treatment Of Generalized Anxiety Disorder". Archived from the original on 2021-03-30. Retrieved 2020-09-08.

[5] Pfizer (2012-11-09). "A Phase 3, Randomized, Double-Blind, Parallel Group, 10-Week Placebo Controlled Fixed Dose Study of PD 0332334 and Paroxetine Evaluating the Efficacy and Safety of PD 0332334 for the Treatment of Generalized Anxiety Disorder". Archived from the original on 2021-03-31. Retrieved 2020-09-08.

[6] Pfizer (2012-11-09). "A 52-Week Open-Label Safety Study of PD 0332334 in Subjects With Generalized Anxiety Disorder". Archived from the original on 2021-04-01. Retrieved 2020-09-08.

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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

See also

References