Chemistry:Arbaclofen placarbil

Short description: Chemical 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
PubChem CID	11281011
ChemSpider	9456008
UNII	W89H91R7VX
KEGG	D08861 Y
ChEMBL	ChEMBL2107312 Y
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 (/ɑːrˈbækloʊfɛn pləˈkɑːrbɪl/ ar-BAK-loh-fen plə-KAR-bil, also known as XP19986) is a prodrug of R-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 with GERD and spasticity due to multiple sclerosis; however, in May 2013 XenoPort announced the termination of development because of unsuccessful results in phase III clinical trials.

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

See also

• Gabapentin enacarbil
• Lesogaberan

References

{{Navbox | name = GABA receptor modulators | title = GABA receptor modulators | state = collapsed | bodyclass = hlist | groupstyle = text-align:center;

 | group1 = Ionotropic
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   | group1 = GABAA
   | list1  = 

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

• Positive modulators (abridged; see here for a full list): α-EMTBL
• Alcohols (e.g., ethanol)
• 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)<!--PMID: 9776662-->
• Lanthanum
• Loreclezole
• Monastrol
• Neuroactive steroids (e.g., allopregnanolone, [[Chemistry:Cholecholesterol]], THDOC)
• Niacin
• Nicotinamide (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, [[Chemistry:Diethyl diethyl ether, Parparaldehyde]], sevoflurane)

• Antagonists: Bicuculline
• Coriamyrtin
• Dihydrosecurinine
• Gabazine (SR-95531)
• Hydrastine
• Hyenachin (mellitoxin)
• PHP-501
• Pitrazepin
• Securinine
• Sinomenine
• SR-42641
• SR-95103
• Thiocolchicoside
• Tutin

• Negative modulators: 1,3M1B
• 3M2B
• 11-Ketoprogesterone
• 17-Phenylandrostenol
• α5IA (LS-193,268)
• β-CCB
• β-CCE
• β-CCM
• β-CCP
• β-EMGBL
• Anabolic steroids
• Amiloride
• Anisatin
• β-Lactams (e.g., penicillins, cephalosporins, carbapenems)
• Basmisanil
• Bemegride
• Bicyclic phosphates (TBPS, TBPO, IPTBO)
• BIDN
• Bilobalide
• Bupropion
• CHEB
• Chlorophenylsilatrane
• Cicutoxin
• Cloflubicyne
• Cyclothiazide
• DHEA
• DHEA-S
• Dieldrin
• (+)-DMBB
• DMCM
• DMPC
• EBOB
• Etbicyphat
• FG-7142 (ZK-31906)
• Fiproles (e.g., fipronil)
• Flavonoids (e.g., amentoflavone, oroxylin A)
• Flumazenil
• Fluoroquinolones (e.g., ciprofloxacin)
• Flurothyl
• Furosemide
• Golexanolone
• Iomazenil (¹²³I)
• IPTBO
• Isopregnanolone (sepranolone)
• L-655,708
• Laudanosine
• Leptazol
• Lindane
• MaxiPost
• Morphine
• Morphine-3-glucuronide
• MRK-016
• Naloxone
• Naltrexone
• Nicardipine
• Nonsteroidal antiandrogens (e.g., [[apalutamide, [[Chemistry:Bicalutbicalutamide, Enzalutenzalutamide, Chemistry:Flutamide|flut]]amide]], nilutamide)
• Oenanthotoxin
• Pentylenetetrazol (pentetrazol)
• Phenylsilatrane
• Picrotoxin (i.e., picrotin, picrotoxinin and dihydropicrotoxinin)
• Pregnenolone sulfate
• Propybicyphat
• PWZ-029
• Radequinil
• Ro 15-4513
• Ro 19-4603
• RO4882224
• RO4938581
• Sarmazenil
• SCS
• Suritozole
• TB-21007
• TBOB
• TBPS
• TCS-1105
• Terbequinil
• TETS
• Thujone
• U-93631
• Zinc
• ZK-93426

   | group2 = GABAA-ρ
   | list2  = 

• Agonists: BL-1020
• CACA
• CAMP
• Homohypotaurine
• GABA
• GABOB
• Ibotenic acid
• Isoguvacine
• Muscimol
• N⁴-Chloroacetylcytosine arabinoside
• Picamilon
• Progabide
• TACA
• TAMP
• Thiomuscimol
• Tolgabide

• Positive modulators: Allopregnanolone
• Alphaxolone
• ATHDOC
• Lanthanides

• Antagonists: (S)-2-MeGABA
• (S)-4-ACPBPA
• (S)-4-ACPCA
• 2-MeTACA
• 3-APMPA
• 4-ACPAM
• 4-GBA
• cis-3-ACPBPA
• CGP-36742 (SGS-742)
• DAVA
• Gabazine (SR-95531)
• Gaboxadol (THIP)
• I4AA
• Isonipecotic acid
• Loreclezole
• P4MPA
• P4S
• SKF-97541
• SR-95318
• SR-95813
• TPMPA
• trans-3-ACPBPA
• ZAPA

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

 }}

 | group2 = Metabotropic

| list2 =

GABAB

Agonists: 1,4-Butanediol 4-Fluorophenibut Aceburic acid Arbaclofen Arbaclofen placarbil Baclofen BL-1020 GABA Gabamide GABOB GBL GHB GHBAL GHV GVL Isovaline Lesogaberan Phenibut Picamilon Progabide Sodium oxybate SKF-97,541 SL 75102 Tolgabide Tolibut Positive modulators: ADX-71441 BHF-177 BHFF BSPP CGP-7930 CGP-13501 GS-39783 rac-BHFF KK-92A Antagonists: 2-Hydroxysaclofen CGP-35348 CGP-46381 CGP-52432 CGP-54626 CGP-55845 CGP-64213 DAVA Homotaurine (tramiprosate, 3-APS) Phaclofen Saclofen SCH-50911 SKF-97541 Negative modulators: Compound 14

 | below = 

See also

Receptor/signaling modulators

GABA_A receptor positive modulators

GABA metabolism/transport modulators

}}