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Imagabalin

From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

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)
PubChemCID	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 investigationaldrug that acts as aligand for theα₂δ subunit of thevoltage-dependent calcium channel,^[1] with someselectivity for theα₂δ₁ subunit overα₂δ₂.^[2] It was under development byPfizer as apharmaceutical medication due to its hypothesizedanxiolytic,analgesic,hypnotic, andanticonvulsant-like activity. It reachedphase-III clinical trials for treatment ofgeneralized anxiety disorder; however, the trials were terminated by the manufacturer.^[3]^[4]^[5]^[6] The drug is no longer under development.

Synthesis

Protein engineering has been used to modify theVibrio fluvialisaminotransferase to catalyze the asymmetric transamination of a synthetic intermediate.^[7]

See also

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.
^Ereshefsky L (2008)."Therapies in the Pipeline for Sleep Disorders: Focus on Novel Mechanisms and Disease Models"(PDF) (Press release). p. 11. Retrieved2012-04-22.
^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. Retrieved2020-09-08.
^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. Retrieved2020-09-08.
^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. Retrieved2020-09-08.
^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. Retrieved2020-09-08.
^Midelfort KS, Kumar R, Han S, Karmilowicz MJ, McConnell K, Gehlhaar DK, et al. (January 2013). "Redesigning and characterizing the substrate specificity and activity of Vibrio fluvialis aminotransferase for the synthesis of imagabalin".Protein Engineering, Design & Selection.26 (1):25–33.doi:10.1093/protein/gzs065.PMID 23012440.

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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Ion channel modulators

VDCCsTooltip Voltage-dependent calcium channels

R-type-selective:SNX-482

L-type-selective:Bay K8644

VGKCsTooltip Voltage-gated potassium channels

KCNQ (K_v7)-specific:Flupirtine
Retigabine

IRKsTooltip Inwardly rectifying potassium channel

K_ATPTooltip ATP-sensitive potassium channel-specific:Acetohexamide
Carbutamide
Chlorpropamide
Glibenclamide (glyburide)
Glibornuride
Glicaramide
Gliclazide
Glimepiride
Glipizide
Gliquidone
Glisoxepide
Glyclopyramide
Glycyclamide
Metahexamide
Mitiglinide
Nateglinide
Repaglinide
Tolazamide
Tolbutamide

GIRKTooltip G protein-coupled inwardly rectifying potassium channel-specific:Barium
Caramiphen
Cloperastine
Clozapine
Dextromethorphan
Ethosuximide
Ifenprodil
Tertiapin
Tipepidine

K_ATPTooltip ATP-sensitive potassium channel-specific:Aprikalim
Bimakalim
Cromakalim
Diazoxide
Emakalim
Levcromakalim
Mazokalim
Minoxidil
Minoxidil sulfate
Naminidil
Nicorandil
Pinacidil
Rilmakalim
Sarakalim

GIRKTooltip G protein-coupled inwardly rectifying potassium channel-specific:ML-297 (VU0456810)

K_CaTooltip Calcium-activated potassium channel

Blockers	BK_Ca-specific:Ethanol (alcohol) GAL-021
Activators	BK_Ca-specific:Flufenamic acid Meclofenamic acid Niflumic acid Nimesulide Rottlerin (mallotoxin) Tolfenamic acid

K2PsTooltip Tandem pore domain potassium channel

Blockers	12-O-Tetradecanoylphorbol-13-acetate Arachidonic acid Fluoxetine Norfluoxetine
Activators	Riluzole

VGSCsTooltip Voltage-gated sodium channels

Antianginals:Ranolazine

Aconitine
Atracotoxins (ω-Atracotoxin,Robustoxin,Versutoxin)
Batrachotoxin
Ciguatoxins
Grayanotoxins
Poneratoxin

ENaCTooltip Epithelial sodium channel

Blockers	Amiloride Benzamil Triamterene
Activators	Solnatide

ASICsTooltip Acid-sensing ion channel

Blockers	A-317567 Amiloride Aspirin Ibuprofen PcTX1

CaCCsTooltip Calcium-activated chloride channel

Blockers	Crofelemer DIDS Ethacrynic acid Flufenamic acid Fluoxetine Furosemide Glibenclamide Mefloquine Mibefradil Niflumic acid
Activators	Carbachol

CFTRTooltip Cystic fibrosis transmembrane conductance regulator

Blockers	Glibenclamide Lonidamine Piretanide
Activators	1,7-Phenanthroline 1,10-Phenanthroline 4,7-Phenanthroline 7,8-Benzoquinoline Ivacaftor Phenanthridine

Unsorted

Blockers	Bumetanide Flufenamic acid Meclofenamic acid Mefenamic acid Mepacrine Niflumic acid Talniflumate Tolfenamic acid Trifluoperazine

Others

TRPsTooltip Transient receptor potential channels	Seehere instead.
LGICsTooltip Ligand gated ion channels	Seehere instead.

See also:Receptor/signaling modulators •Transient receptor potential channel modulators

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