2-Chloro-6-[(2R)-3-[[1,1-dimethyl-2-(2-naphthalenyl)ethyl]amino]-2-hydroxypropoxy]benzonitrile hydrochloride

Product Name2-Chloro-6-[(2R)-3-[[1,1-dimethyl-2-(2-naphthalenyl)ethyl]amino]-2-hydroxypropoxy]benzonitrile hydrochloride
CAS324523-20-8
MFC24H26Cl2N2O2
MW445.38
EINECS
MOL File324523-20-8.mol

Chemical Properties

storage temp.	2-8°C
solubility	DMSO: >10mg/mL
form	powder
color	white to beige
optical activity	[α]20/D +20 to +24°, c = 1.0 in methanol
InChI	1S/C24H25ClN2O2.ClH/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;1H/t20-;/m1./s1
InChIKey	ZEBNDUQLNGYBNL-VEIFNGETSA-N
SMILES	Cl.CC(C)(Cc1ccc2ccccc2c1)NC[C@@H](O)COc3cccc(Cl)c3C#N

Safety Information

Hazard Codes	Xn,N
Risk Statements	20/21/22-50/53
Safety Statements	36/37-60-61
RIDADR	UN 3077 9 / PGIII
WGK Germany	3
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Dermal Acute Tox. 4 Inhalation Acute Tox. 4 Oral Aquatic Acute 1 Aquatic Chronic 1

Usage And Synthesis

Description

Calcium-sensing receptor (CaSR) is a G protein-coupled receptor that is involved in calcium homeostasis. Activation of CaSR on parathyroid cells decreases the secretion of parathyroid hormone (PTH), which in turn reduces blood calcium concentration. NPS 2143 is a potent and selective antagonist of CaSR (IC₅₀ = 43 nM) that stimulates PTH secretion from parathyroid cells in vitro (EC₅₀ = 39 nM). It is effective in vivo, causing a sustained increase in plasma PTH in rats when given intravenously. Daily oral administration of NPS 2143 to osteopenic ovariectomized rats results in a dramatic increase in bone turnover, as well as increased circulating PTH levels.

Uses

NPS 2143 acts as a potent and selective antagonist for CaSR (Calcium-sensing receptor) which is involved in calcium blood concentration homeostasis.

Biochem/physiol Actions

NPS2143 is a phenylalkylamine calcilytic compound, and might be useful in treating autosomal dominant hypocalcemia. It serves as a blocking agent for hERG (human ether-a-go-go-related gene ) channel, CYP2D6 (cytochrome P450 2D6 ) and monoamine transporters.

in vivo

When infused intravenously in normal rats, NPS-2143 hydrochloride (SB-262470A hydrochloride) causes a rapid and large increase in plasma levels of PTH. Ca²⁺ receptor antagonists are termed calcilytics and NPS-2143 is the first substance (either atomic or molecular) shown to possess such activity^[1].
When administered together with an antiresorptive agent (estradiol), NPS 2143 causes an increase in trabecular bone volume and bone mineral density in osteopenic rats^[2].

storage

Desiccate at RT

References

[1] M GOWEN. Antagonizing the parathyroid calcium receptor stimulates parathyroid hormone secretion and bone formation in osteopenic rats.[J]. Journal of Clinical Investigation, 2000, 105 11: 1595-1604. DOI: 10.1172/jci9038
[2] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.

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