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SML0129

Sigma-Aldrich

AC-265347

≥98% (HPLC)

Synonym(s):

1-(1,3-benzothiazol-2-yl)-1-(2,4-dimethylphenyl)ethanol, a-(2,4-Dimethylphenyl)-a-methyl-2-benzothiazolemethanol.

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About This Item

Empirical Formula (Hill Notation):
C17H17NOS
CAS Number:
1253901-26-6
Molecular Weight:
283.39
MDL number:
MFCD20527324
UNSPSC Code:
12352200
PubChem Substance ID:
329825179
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO: ≥19 mg/mL

storage temp.

2-8°C

SMILES string

Cc1ccc(c(C)c1)C(C)(O)c2nc3ccccc3s2

InChI

1S/C17H17NOS/c1-11-8-9-13(12(2)10-11)17(3,19)16-18-14-6-4-5-7-15(14)20-16/h4-10,19H,1-3H3

InChI key

IGSZVEPQZANNAB-UHFFFAOYSA-N

Application

AC-265347 may be used in calcium-sensing receptor-mediated signaling.

Biochem/physiol Actions

AC-265347 is a calcimimetic that acts as agonist to calcium-sensing receptor. It reduces serum parathyroid hormone and plasma ionizable calcium.
AC-265347 is a human calcium-sensing receptor (CaSR) allosteric agonist. AC-265347 activates CaSR signaling in cellular proliferation and phosphatidyl inositol (PI) hydrolysis assays.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

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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Jian-Nong Ma et al.
The Journal of pharmacology and experimental therapeutics, 337(1), 275-284 (2011-01-18)
We discovered structurally novel human calcium-sensing receptor (CaSR) allosteric agonists and compared their pharmacology to phenylalkylamine calcimimetics. 1-Benzothiazol-2-yl-1-(2,4-dimethyl-phenyl)-ethanol (AC-265347) activated CaSR signaling in cellular proliferation and phosphatidylinositol (PI) hydrolysis assays with potencies of 30 and 10 nM, respectively. (S)-1-Benzothiazol-2-yl-1-(2,4-dimethyl-phenyl)-ethanol) [(S)-AC-265347]
Pablo A Ureña Torres et al.
Kidney international, 82(1), 19-25 (2012-03-23)
Renal function impairment goes along with a disturbed calcium, phosphate, and vitamin D metabolism, resulting in secondary hyperparathyroidism (sHPT). These mineral metabolism disturbances are associated with soft tissue calcifications, particularly arteries, cardiac valves, and myocardium, ultimately associated with increased risk
Shane D Hellyer et al.
Molecular pharmacology, 93(5), 504-514 (2018-03-09)
Numerous positive and negative allosteric modulators (PAMs and NAMs) of class C G protein-coupled receptors (GPCRs) have been developed as valuable preclinical pharmacologic tools and therapeutic agents. Although many class C GPCR allosteric modulators have undergone subtype selectivity screening, most

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