BMS-466442

BMS-466442
Identifiers
	IUPAC name methyl (2S)-3-(1-benzylimidazol-4-yl)-2-[(5-methoxy-6-phenylmethoxy-1H-indole-2-carbonyl)amino]propanoate;
CAS Number	1598424-76-0;
PubChem CID	124082063;
ChemSpider	57582778;
Chemical and physical data
Formula	C31H30N4O5
Molar mass	538.604 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=C(C=C2C(=C1)C=C(N2)C(=O)N[C@@H](CC3=CN(C=N3)CC4=CC=CC=C4)C(=O)OC)OCC5=CC=CC=C5;
	InChI InChI=1S/C31H30N4O5/c1-38-28-14-23-13-26(33-25(23)16-29(28)40-19-22-11-7-4-8-12-22)30(36)34-27(31(37)39-2)15-24-18-35(20-32-24)17-21-9-5-3-6-10-21/h3-14,16,18,20,27,33H,15,17,19H2,1-2H3,(H,34,36)/t27-/m0/s1; Key:UUCAHZCMRZOTNF-MHZLTWQESA-N;

BMS-466442 is an experimental drug that acts as a selective inhibitor of the amino acid transporter alanine serine cysteine transporter-1 (ASC-1). It indirectly increases activation of the NMDA receptor by boosting intracellular levels of the endogenous ligands glycine and D-serine. It was developed as a potential treatment for schizophrenia.^[1]^[2]^[3]

References

^ Brown JM, Hunihan L, Prack MM, Harden DG, Bronson J, Dzierba CD, et al. (April 2014). "In vitro Characterization of a small molecule inhibitor of the alanine serine cysteine transporter -1 (SLC7A10)". Journal of Neurochemistry. 129 (2): 275–283. doi:10.1111/jnc.12618. PMID 24266811.
^ Torrecillas IR, Conde-Ceide S, de Lucas AI, Garcı A Molina A, Trabanco AA, Lavreysen H, et al. (May 2019). "Inhibition of the Alanine-Serine-Cysteine-1 Transporter by BMS-466442". ACS Chemical Neuroscience. 10 (5): 2510–2517. doi:10.1021/acschemneuro.9b00019. PMID 30821959.
^ Arianti R, Vinnai BÁ, Tóth BB, Shaw A, Csősz É, Vámos A, et al. (August 2021). "ASC-1 transporter-dependent amino acid uptake is required for the efficient thermogenic response of human adipocytes to adrenergic stimulation". FEBS Letters. 595 (16): 2085–2098. doi:10.1002/1873-3468.14155. hdl:2437/321362. PMID 34197627.

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[Brown_2014-1] Brown JM, Hunihan L, Prack MM, Harden DG, Bronson J, Dzierba CD, et al. (April 2014). "In vitro Characterization of a small molecule inhibitor of the alanine serine cysteine transporter -1 (SLC7A10)". Journal of Neurochemistry. 129 (2): 275–283. doi:10.1111/jnc.12618. PMID 24266811.

[Torrecillas_2019-2] Torrecillas IR, Conde-Ceide S, de Lucas AI, Garcı A Molina A, Trabanco AA, Lavreysen H, et al. (May 2019). "Inhibition of the Alanine-Serine-Cysteine-1 Transporter by BMS-466442". ACS Chemical Neuroscience. 10 (5): 2510–2517. doi:10.1021/acschemneuro.9b00019. PMID 30821959.

[Arianti_2021-3] Arianti R, Vinnai BÁ, Tóth BB, Shaw A, Csősz É, Vámos A, et al. (August 2021). "ASC-1 transporter-dependent amino acid uptake is required for the efficient thermogenic response of human adipocytes to adrenergic stimulation". FEBS Letters. 595 (16): 2085–2098. doi:10.1002/1873-3468.14155. hdl:2437/321362. PMID 34197627.

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