NPS-2143

NPS-2143
Identifiers
	IUPAC name 2-chloro-6-[(2R)-3-([1,1-dimethyl-2-(2-naphthalenyl)ethyl]amino)-2-hydroxypropoxy]benzonitrile;
CAS Number	284035-33-2 ; hydrochloride: 324523-20-8 ;
PubChem CID	6918446;
IUPHAR/BPS	716;
ChemSpider	5293643;
UNII	Z25PJ77W7V; hydrochloride: U48SZ6EBB3 ;
CompTox Dashboard (EPA)	DTXSID10426075 ;
Chemical and physical data
Formula	C24H25ClN2O2
Molar mass	408.93 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES N#Cc2c(Cl)cccc2OCC(O)CNC(C)(C)Cc3ccc1ccccc1c3;
	InChI InChI=1S/C24H25ClN2O2/c1-24(2,13-17-10-11-18-6-3-4-7-19(18)12-17)27-15-20(28)16-29-23-9-5-8-22(25)21(23)14-26/h3-12,20,27-28H,13,15-16H2,1-2H3/t20-/m1/s1; Key:PZUJQWHTIRWCID-HXUWFJFHSA-N;

NPS-2143 (SB-262,470A) is a calcilytic drug which acts as an antagonist at the Calcium-sensing receptor (CaSR), and consequently stimulates release of parathyroid hormone.^[1] Calcilytic drugs have been researched as potential treatments for osteoporosis, and as the first such compound developed, NPS-2143 is still widely used in research into the CaSR receptor as well as design of newer calcilytic agents.^[2]^[3]^[4]

References

^ Nemeth EF, Delmar EG, Heaton WL, Miller MA, Lambert LD, Conklin RL, et al. (October 2001). "Calcilytic compounds: potent and selective Ca2+ receptor antagonists that stimulate secretion of parathyroid hormone". The Journal of Pharmacology and Experimental Therapeutics. 299 (1): 323–31. PMID 11561095.
^ Marquis RW, Lago AM, Callahan JF, Trout RE, Gowen M, DelMar EG, et al. (July 2009). "Antagonists of the calcium receptor I. Amino alcohol-based parathyroid hormone secretagogues". Journal of Medicinal Chemistry. 52 (13): 3982–93. doi:10.1021/jm900364m. PMID 19492813.
^ Kiefer L, Leiris S, Dodd RH (May 2011). "Novel calcium sensing receptor ligands: a patent survey". Expert Opinion on Therapeutic Patents. 21 (5): 681–98. doi:10.1517/13543776.2011.568479. PMID 21406038. S2CID 27608531.
^ Breitwieser GE (May 2014). "Pharmacoperones and the calcium sensing receptor: exogenous and endogenous regulators". Pharmacological Research. 83: 30–7. doi:10.1016/j.phrs.2013.11.006. PMID 24291533.

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[1] Nemeth EF, Delmar EG, Heaton WL, Miller MA, Lambert LD, Conklin RL, et al. (October 2001). "Calcilytic compounds: potent and selective Ca2+ receptor antagonists that stimulate secretion of parathyroid hormone". The Journal of Pharmacology and Experimental Therapeutics. 299 (1): 323–31. PMID 11561095.

[2] Marquis RW, Lago AM, Callahan JF, Trout RE, Gowen M, DelMar EG, et al. (July 2009). "Antagonists of the calcium receptor I. Amino alcohol-based parathyroid hormone secretagogues". Journal of Medicinal Chemistry. 52 (13): 3982–93. doi:10.1021/jm900364m. PMID 19492813.

[3] Kiefer L, Leiris S, Dodd RH (May 2011). "Novel calcium sensing receptor ligands: a patent survey". Expert Opinion on Therapeutic Patents. 21 (5): 681–98. doi:10.1517/13543776.2011.568479. PMID 21406038. S2CID 27608531.

[4] Breitwieser GE (May 2014). "Pharmacoperones and the calcium sensing receptor: exogenous and endogenous regulators". Pharmacological Research. 83: 30–7. doi:10.1016/j.phrs.2013.11.006. PMID 24291533.

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Identifiers

IUPAC name 2-chloro-6-[(2R)-3-([1,1-dimethyl-2-(2-naphthalenyl)ethyl]amino)-2-hydroxypropoxy]benzonitrile
CAS Number	284035-33-2^Y hydrochloride: 324523-20-8^Y
PubChem CID	6918446
IUPHAR/BPS	716
ChemSpider	5293643
UNII	Z25PJ77W7V hydrochloride: U48SZ6EBB3^Y
CompTox Dashboard (EPA)	DTXSID10426075
Chemical and physical data
Formula	C₂₄H₂₅ClN₂O₂
Molar mass	408.93 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES N#Cc2c(Cl)cccc2OCC(O)CNC(C)(C)Cc3ccc1ccccc1c3
InChI InChI=1S/C24H25ClN2O2/c1-24(2,13-17-10-11-18-6-3-4-7-19(18)12-17)27-15-20(28)16-29-23-9-5-8-22(25)21(23)14-26/h3-12,20,27-28H,13,15-16H2,1-2H3/t20-/m1/s1 Key:PZUJQWHTIRWCID-HXUWFJFHSA-N

NPS-2143

See also

References