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SML0362

Sigma-Aldrich

NPS2143 hydrochloride

≥98% (HPLC)

Synonym(s):

2-Chloro-6-[(2R)-3-[[1,1-dimethyl-2-(2-naphthalenyl)ethyl]amino]-2-hydroxypropoxy]-benzonitrile hydrochloride (1:1), NPS-2143 hydrochloride, SB-262470-A hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C24H25ClN2O2 · HCl
CAS Number:
324523-20-8
Molecular Weight:
445.38
MDL number:
MFCD16038896
UNSPSC Code:
12352200
PubChem Substance ID:
329825364
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

optical activity

[α]20/D +20 to +24°, c = 1.0 in methanol

storage condition

desiccated

color

white to beige

solubility

DMSO: >10 mg/mL

storage temp.

2-8°C

SMILES string

Cl.CC(C)(Cc1ccc2ccccc2c1)NC[C@@H](O)COc3cccc(Cl)c3C#N

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

InChI key

ZEBNDUQLNGYBNL-VEIFNGETSA-N

Application

NPS2143 hydrochloride has been used to study the function of calcium-sensing receptor :
  • In the regulation of intestinal calcium transport.
  • In the regulation of local negative feedback of intestinal calcium absorption.
  • In sensorimotor decision making during development.

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.
NPS2143 is a selective calcium-sensing receptor (CaR) antagonist. The compound blocks increases in cytoplasmic calcium concentrations with an IC50 of 43 nM, and stimulates parathyroid hormone (PTH) secretion from bovine parathyroid cells over a wide range of extracellular calcuim concentrations.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Novel activating mutations of the calcium-sensing receptor: the calcilytic NPS-2143 mitigates excessive signal transduction of mutant receptors
Letz S, et al.
The Journal of Clinical Endocrinology and Metabolism, 95(10), E229-E233 (2010)
Activation of calcium-sensing receptor by allosteric agonists cinacalcet and AC-265347 abolishes the 1, 25 (OH) 2D3-induced Ca2+ transport: Evidence that explains how the intestine prevents excessive Ca2+ absorption
Wongdee K, et al.
Archives of Biochemistry and Biophysics, 657, 15-22 (2018)
Progress in Medicinal Chemistry, 57 (2018)
The calcilytic agent NPS 2143 rectifies hypocalcemia in a mouse model with an activating calcium-sensing receptor (CaSR) mutation: relevance to autosomal dominant hypocalcemia type 1 (ADH1)
Hannan FM, et al.
Endocrinology, 156(9), 3114-3121 (2015)
A Forward Genetic Screen in Zebrafish Identifies the G-Protein-Coupled Receptor CaSR as a Modulator of Sensorimotor Decision Making
Jain RA, et al.
Current Biology, 28(9), 1357-1369 (2018)
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