Imagabalin

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Infobox drug

| IUPAC_name = (3S,5R)-3-amino-5-methyloctanoic acid

| image = Imagabalin.svg

| CAS_number = 610300-07-7

| CAS_supplemental =
610300-00-0 (hydrochloride)

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = NDG6931B7H

| ATC_prefix = None

| ATC_suffix =

| KEGG = D09627

| C = 9 | H = 19 | N = 1 | O = 2

| synonyms = PD-0332334; PD-332,334

| PubChem = 10236037

| ChemSpiderID = 8411525

| smiles = O=C(O)C[C@@H](N)C[C@@H](CCC)C

| StdInChI = 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

| StdInChIKey = JXEHXYFSIOYTAH-SFYZADRCSA-N

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

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| pregnancy_category =

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}}

Imagabalin (INN, USAN; PD-0332334) was an investigational drug that acts as a ligand for the α₂δ subunit of the voltage-dependent calcium channel,{{cite journal | vauthors = Quintero JE, Pomerleau F, Huettl P, Johnson KW, Offord J, Gerhardt GA | title = Methodology for rapid measures of glutamate release in rat brain slices using ceramic-based microelectrode arrays: basic characterization and drug pharmacology | journal = Brain Research | volume = 1401 | pages = 1–9 | date = July 2011 | pmid = 21664606 | pmc = 3197737 | doi = 10.1016/j.brainres.2011.05.025 }} with some selectivity for the α₂δ₁ subunit over α₂δ₂.{{cite press release | vauthors = Ereshefsky L | title = Therapies in the Pipeline for Sleep Disorders: Focus on Novel Mechanisms and Disease Models | pages = 11 | year = 2008 | url = http://www.cmellc.com/psychcongress/images/08pdf/43-5%20Ereshefsky.pdf | access-date = 2012-04-22 }} 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.{{Cite web | author = Pfizer | title = 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 | date = 2012-11-09 | url = https://clinicaltrials.gov/ct2/show/NCT00658008 | access-date = 2020-09-08 | archive-date = 2021-03-28 | archive-url = https://web.archive.org/web/20210328220724/https://www.clinicaltrials.gov/ct2/show/NCT00658008 | url-status = live }}{{Cite web | author = Pfizer | title = 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 | date = 2012-11-09 | url = https://clinicaltrials.gov/ct2/show/NCT00658372 | access-date = 2020-09-08 | archive-date = 2021-03-30 | archive-url = https://web.archive.org/web/20210330075157/https://www.clinicaltrials.gov/ct2/show/NCT00658372 | url-status = live }}{{Cite web | author = Pfizer | title = 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 | date = 2012-11-09 | url = https://clinicaltrials.gov/ct2/show/NCT00658762 | access-date = 2020-09-08 | archive-date = 2021-03-31 | archive-url = https://web.archive.org/web/20210331014217/https://www.clinicaltrials.gov/ct2/show/NCT00658762 | url-status = live }}{{Cite web | author = Pfizer | title = A 52-Week Open-Label Safety Study of PD 0332334 in Subjects With Generalized Anxiety Disorder | date = 2012-11-09 | url = https://clinicaltrials.gov/ct2/show/NCT00735267 | access-date = 2020-09-08 | archive-date = 2021-04-01 | archive-url = https://web.archive.org/web/20210401114311/https://www.clinicaltrials.gov/ct2/show/NCT00735267 | url-status = live }} The drug is no longer under development.