Arbaclofen placarbil

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 ;
ChEMBL	ChEMBL2107312 ;
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 (/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.^[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

^ "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. Retrieved 2013-06-03.
^ 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.

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[Results-1] "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. Retrieved 2013-06-03.

[2] Anderson E (3 July 2020). "Pill that replaces alcohol aims to end 'glass of wine' craving". The i newspaper. Associated Newspapers Limited.

[3] 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.

[1]

[2]

[3]

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
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

See also

References