:Atagabalin

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477351069

| IUPAC_name = [(3S,4S)-1-(aminomethyl)-3,4-dimethylcyclopentyl]acetic acid

| image = Atagabalin.svg

| tradename =

| pregnancy_AU =

| pregnancy_US =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 223445-75-8

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 593430

| PubChem = 9794485

| ATC_prefix = none

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

| UNII = JT7957Q2FB

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 7970252

| C=10 | H=19 | N=1 | O=2

| smiles = C[C@H]1CC(C[C@@H]1C)(CC(=O)O)CN

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C10H19NO2/c1-7-3-10(6-11,4-8(7)2)5-9(12)13/h7-8H,3-6,11H2,1-2H3,(H,12,13)/t7-,8-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = IUVMAUQEZFTTFB-YUMQZZPRSA-N

}}

Atagabalin (PD-0200,390) is a drug developed by Pfizer and related to gabapentin, which similarly binds to the α₂δ calcium channels (1 and 2).{{cite journal |vauthors=Blakemore DC, Bryans JS, Carnell P, Carr CL, Chessum NE, Field MJ, Kinsella N, Osborne SA, Warren AN, Williams SC |title=Synthesis and in vivo evaluation of bicyclic gababutins |journal=Bioorganic & Medicinal Chemistry Letters |volume=20 |issue=2 |pages=461–4 |date=January 2010 |pmid=20005103 |doi=10.1016/j.bmcl.2009.11.118 }} It was under development as a treatment for insomnia,{{cite journal |vauthors=Corrigan B, Feltner DE, Ouellet D, Werth JL, Moton AE, Gibson G |title=Effect of renal impairment on the pharmacokinetics of PD 0200390, a novel ligand for the voltage-gated calcium channel alpha-2-delta subunit |journal=British Journal of Clinical Pharmacology |volume=68 |issue=2 |pages=174–80 |date=August 2009 |pmid=19694735 |pmc=2767279 |doi=10.1111/j.1365-2125.2009.03444.x }}{{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=May 2011 |pmid=21664606 |doi=10.1016/j.brainres.2011.05.025 |pmc=3197737}}{{cite journal |vauthors=Kjellsson MC, Ouellet D, Corrigan B, Karlsson MO |title=Modeling Sleep Data for a New Drug in Development using Markov Mixed-Effects Models |journal=Pharmaceutical Research |volume= 28|issue= 10|pages= 2610–27|date=June 2011 |pmid=21681607 |doi=10.1007/s11095-011-0490-x |s2cid=22241527 }} but was discontinued following unsatisfactory trial results.