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Arbaclofen placarbil

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Chemical compound

Pharmaceutical compound

Arbaclofen placarbil
Clinical data

Pregnancy category	N/A
ATC code	none
Legal status
Legal status	Development terminated
Identifiers
IUPAC name (3R)-3-(4-chlorophenyl)-4-[[[(1S)-2-methyl-1-[(2-methylpropanoyl)oxy]propoxy]carbonyl]amino]butanoic acid
CAS Number	847353-30-4
PubChemCID	11281011
ChemSpider	9456008
UNII	W89H91R7VX
KEGG	D08861^Y
ChEMBL	ChEMBL2107312^Y
CompTox Dashboard(EPA)	DTXSID40233754
ECHA InfoCard	100.221.150
Chemical and physical data
Formula	C₁₉H₂₆ClNO₆
Molar mass	399.87 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(C)C(=O)O[C@@H](OC(=O)NC[C@H](CC(=O)O)c1ccc(Cl)cc1)C(C)C
InChI InChI=1S/C19H26ClNO6/c1-11(2)17(24)26-18(12(3)4)27-19(25)21-10-14(9-16(22)23)13-5-7-15(20)8-6-13/h5-8,11-12,14,18H,9-10H2,1-4H3,(H,21,25)(H,22,23)/t14-,18-/m0/s1 Key:JXTAALBWJQJLGN-KSSFIOAISA-N

Arbaclofen placarbil (/ɑːrˈbækloʊfɛnpləˈkɑːrbɪl/ar-BAK-loh-fen plə-KAR-bil, also known asXP19986) is aprodrug ofR-baclofen. Arbaclofen placarbil possesses more favorable pharmacokinetic profile than baclofen, with less fluctuations in plasma drug levels. It was being developed as a potential treatment for patients withGERD and spasticity due tomultiple sclerosis; however, in May 2013 XenoPort announced the termination of development because of unsuccessful results inphase III clinical trials.^[1]

It is being developed as an addiction medicine to treat alcoholism.^[2] It is also studied as a potential therapeutic for some autistic subjects.^[3]

References

[edit]

^"XenoPort Reports Top-Line Results of Phase 3 Trial of Arbaclofen Placarbil for Spasticity in Multiple Sclerosis Patients".XenoPort, Inc. May 20, 2013. Archived from the original on 2013-12-02. Retrieved2013-06-03.
^Anderson E (3 July 2020)."Pill that replaces alcohol aims to end 'glass of wine' craving".The i newspaper. Associated Newspapers Limited.
^Huang Q, Pereira AC, Velthuis H, Wong NM, Ellis CL, Ponteduro FM, et al. (January 2022)."GABA_B receptor modulation of visual sensory processing in adults with and without autism spectrum disorder"(PDF).Science Translational Medicine.14 (626) eabg7859.doi:10.1126/scitranslmed.abg7859.PMID 34985973.S2CID 245771626.

Skeletalmuscle relaxants (M03)

Peripherally acting
(primarilyantinicotinic,
NMJ block)

Non-depolarizing

Curare alkaloids	Alcuronium Dimethyltubocurarine Tubocurarine
4° ammonium agents	ultra-short duration:Gantacurium short duration:Rapacuronium Mivacurium Chandonium intermediate duration:Atracurium Cisatracurium Fazadinium Rocuronium Vecuronium long duration:Doxacurium Dimethyltubocurarine Pancuronium Pipecuronium Laudexium Gallamine unsorted:Hexafluronium (Hexafluorenium)

Depolarizing

Choline derivatives:Suxamethonium (Succinylcholine)

Polyalkylene derivatives:Hexamethonium

ACh release inhibitors

Botulinum toxin

Centrally acting

Carbamic acid esters	Carisoprodol Cyclarbamate Difebarbamate Febarbamate Meprobamate Phenprobamate Styramate Tybamate
Benzodiazepines	Bromazepam Diazepam Clonazepam Flunitrazepam Lorazepam Nitrazepam Temazepam Tetrazepam
Nonbenzodiazepines	Eszopiclone
Thienodiazepines	Etizolam
Quinazolines	Methaqualone
Anticholinergics (Antimuscarinics)	Cyclobenzaprine Orphenadrine
Other	Arbaclofen placarbil Baclofen Chlormezanone Chlorphenesin Chlorzoxazone Eperisone Fenyramidol Flopropione Gabapentin GHB Inaperisone Lanperisone Mephenesin Mephenoxalone Metaxalone Methocarbamol Phenibut Pregabalin Pridinol Promoxolane Quinine Silperisone Thiocolchicoside Tizanidine Tolperisone Zoxazolamine

Directly acting

Dantrolene

v t e Drugs forpeptic ulcer andGERD/GORD (A02B)
H₂ antagonists ("-tidine")	Cimetidine Famotidine Lafutidine Lavoltidine (loxtidine) Niperotidine Nizatidine Ranitidine^#‡ Roxatidine
Prostaglandins (E)/ analogues ("-prost-")	Misoprostol Enprostil
Proton-pump inhibitors ("-prazole")	Anaprazole Azeloprazole Dexlansoprazole Dexrabeprazole Esomeprazole Ilaprazole Lansoprazole Omeprazole^# Pantoprazole Picoprazole Rabeprazole Tenatoprazole Timoprazole
Potassium-competitive acid blockers ("-prazan")	Fexuprazan Linaprazan Revaprazan Soraprazan Tegoprazan Vonoprazan Zastaprazan
Others	Aceglutamide aluminum Acetoxolone Alginic acid Arbaclofen placarbil Bismuth subcitrate Carbenoxolone Cetraxate Gefarnate Irsogladine Lesogaberan Pirenzepine Proglumide Rebamipide Sucralfate Sulglicotide Telenzepine Teprenone Troxipide Zinc L-carnosine Zolimidine
Combinations	Bismuth subcitrate/metronidazole/tetracycline Omeprazole/amoxicillin/rifabutin Vonoprazan/amoxicillin Vonoprazan/amoxicillin/clarithromycin
See also:Helicobacter pylori* eradication protocols*
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

GABA receptor modulators

Ionotropic

GABA_ATooltip γ-Aminobutyric acid A receptor

Agonists:4-AHP
(+)-Catechin
Bamaluzole
Barbiturates (e.g.,phenobarbital)
Beta-Alanine
BL-1020
DAVA
DH-P4S
Dihydromuscimol
GABA
Gabamide
GABOB
Gaboxadol (THIP)
Homotaurine (tramiprosate, 3-APS)
IAA (IMA)
Ibotenic acid
iso-THAZ
Isoguvacine
Isonipecotic acid
Kojic amine
L-838,417
Lignans (e.g.,honokiol)
Methylglyoxal
Monastrol
Muscimol
Nefiracetam
Neuroactive steroids (e.g.,allopregnanolone)
Org 20599
PF-6372865
Phenibut
Picamilon
4-PIOL
P4S
Progabide
Propofol
Quisqualamine
SL-75102
Taurine
TACA
TAMP
Terpenoids (e.g.,borneol)
Thio-4-PIOL
Thiomuscimol
Tolgabide
ZAPA

Positive modulators (abridged; seehere for a full list):α-EMTBL
Alcohols (e.g.,drinking alcohol,2M2B)
Anabolic steroids
Avermectins (e.g.,ivermectin)
Barbiturates (e.g.,phenobarbital)
Benzodiazepines (e.g.,diazepam)
Bromide compounds (e.g.,potassium bromide)
Carbamates (e.g.,meprobamate)
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
Dihydroergolines (e.g.,ergoloid (dihydroergotoxine))
Etazepine
Etifoxine
Fenamates (e.g.,mefenamic acid)
Flavonoids (e.g.,apigenin,hispidulin)
Fluoxetine
Flupirtine
Imidazoles (e.g.,etomidate)
Kava constituents (e.g.,kavain)
Lanthanum
Loreclezole
Monastrol
Neuroactive steroids (e.g.,allopregnanolone,cholesterol,THDOC)
Niacin
Niacinamide
Nonbenzodiazepines (e.g.,β-carbolines (e.g.,abecarnil),cyclopyrrolones (e.g.,zopiclone),imidazopyridines (e.g.,zolpidem),pyrazolopyrimidines (e.g.,zaleplon))
Norfluoxetine
Petrichloral
Phenols (e.g.,propofol)
Phenytoin
Piperidinediones (e.g.,glutethimide)
Propanidid
Pyrazolopyridines (e.g.,etazolate)
Quinazolinones (e.g.,methaqualone)
Retigabine (ezogabine)
ROD-188
Skullcap constituents (e.g.,baicalin)
Stiripentol
Sulfonylalkanes (e.g.,sulfonmethane (sulfonal))
Topiramate
Valerian constituents (e.g.,valerenic acid)
Volatiles/gases (e.g.,chloral hydrate,chloroform,diethyl ether,paraldehyde,sevoflurane)

GABA_A-ρTooltip γ-Aminobutyric acid A-rho receptor

Negative modulators:5α-Dihydroprogesterone
Bilobalide
Loreclezole
Picrotoxin (picrotin,picrotoxinin)
Pregnanolone
ROD-188
THDOC
Zinc

Metabotropic

GABA_BTooltip γ-Aminobutyric acid B receptor

Negative modulators:Compound 14

See also: Receptor/signaling modulators; GABA_A receptor positive modulators; GABA metabolism/transport modulators

Ion channel modulators

Calcium

VDCCsTooltip Voltage-dependent calcium channels

Blockers

R-type-selective:SNX-482

Activators

L-type-selective:Bay K8644

Potassium

VGKCsTooltip Voltage-gated potassium channels

Blockers

Activators

KCNQ (K_v7)-specific:Flupirtine
Retigabine

IRKsTooltip Inwardly rectifying potassium channel

Blockers

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

Activators

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

Sodium

VGSCsTooltip Voltage-gated sodium channels

Blockers

Antianginals:Ranolazine

Activators

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

Chloride

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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