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Merck

SML2012

Cinacalcet hydrochloride

≥98% (HPLC)

Sinónimos:

AMG 073 hydrochloride, KRN 1493 hydrochloride, N-[1-(R)-(-)-(1-naphthyl)ethyl]-3-[3(trifluoromethyl)phenyl]-1-aminopropane hydrochloride, NPS 1493 hydrochloride

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Fórmula empírica (notación de Hill):
C22H22F3N·HCl
Número CAS:
364782-34-3
Peso molecular:
393.87
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
Storage condition:
desiccated

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SMILES string

FC(F)(F)c1cc(ccc1)CCCN[C@H](C)c2c3c(ccc2)cccc3.Cl

InChI

1S/C22H22F3N.ClH/c1-16(20-13-5-10-18-9-2-3-12-21(18)20)26-14-6-8-17-7-4-11-19(15-17)22(23,24)25;/h2-5,7,9-13,15-16,26H,6,8,14H2,1H3;1H/t16-;/m1./s1

InChI key

QANQWUQOEJZMLL-PKLMIRHRSA-N

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -24 to -32°, c = 0.5 in methanol

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

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Application

Cinacalcet hydrochloride has been used:
  • to stimulate calcium-sensing receptor (CaSR) in thick ascending limb (TAL) of the male Sprague-Dawley rats to study the effect of altered claudins levels on calciuria and magnesiuria in metabolic acidosis
  • as a calcimimetic positive allosteric modulator (PAM) of CaSR to determine the structural rearrangements of human CaSR upon activation
  • as a calcium-sensing receptor (CaSR) agonist to study the effect of CaSR on tumor cell proliferation in lung adenocarcinoma (LUAD) cell line

Biochem/physiol Actions

Calcimimetic; Calcium Sensing Receptor (CaSR) positive allosteric modulator
Cinacalcet is a positive allosteric modulator of the Calcium Sensing Receptor (CaSR) that acts as a calcimimetic. It increases the sensitivity of the calcium-sensing receptor to extracellular calcium resulting in a decrease in serum calcium levels.
Studies show that oral administration of cinacalcet hydrochloride aids in treating secondary hyperparathyroidism in patients with chronic kidney disease on dialysis. It may also be a potential therapeutic to treat hypercalcemia in patients with parathyroid carcinoma.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 4 - Eye Dam. 1 - Skin Corr. 1A - Skin Sens. 1B - STOT RE 2

target_organs

eye - retina

Clase de almacenamiento

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000183830
0000181994
0000181994
0000183830
0000123266

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Yang Gao et al.
Nature, 595(7867), 455-459 (2021-07-02)
The calcium-sensing receptor (CaSR), a cell-surface sensor for Ca2+, is the master regulator of calcium homeostasis in humans and is the target of calcimimetic drugs for the treatment of parathyroid disorders1. CaSR is a family C G-protein-coupled receptor2 that functions
Jordi Bover et al.
Clinical journal of the American Society of Nephrology : CJASN, 11(1), 161-174 (2015-08-01)
CKD and CKD-related mineral and bone disorders (CKD-MBDs) are associated with high cardiovascular and mortality risks. In randomized clinical trials (RCTs), no single drug intervention has been shown to reduce the high mortality risk in dialysis patients, but several robust
Gamal A E Mostafa et al.
Profiles of drug substances, excipients, and related methodology, 42, 1-90 (2017-04-23)
Cinacalcet hydrochloride is a calcimimetic agent that increases the sensitivity to the extracellular calcium of the calcium-sensing receptors of the parathyroid gland which regulates parathyroid hormone secretion. This comprehensive profile on cinacalcet hydrochloride starts with a description: nomenclature, formulae, chemical
Il Hwan Oh et al.
American journal of physiology. Renal physiology, 320(3), F418-F428 (2021-02-02)
Urinary calcium and magnesium wasting is a characteristic feature of metabolic acidosis, and this study focused on the role of the thick ascending limb of Henle's loop in metabolic acidosis-induced hypercalciuria and hypermagnesiuria because thick ascending limb is an important
Cecelia A Byrnes et al.
Pharmacotherapy, 25(5), 709-716 (2005-05-19)
Cinacalcet is the first calcimimetic drug approved by the United States Food and Drug Administration for the treatment of secondary hyperparathyroidism in patients with chronic kidney disease. A literature search, performed by using PubMed and MEDLINE from January 1997-June 2004
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