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Cinacalcet hydrochloride

CAS No.
364782-34-3
Chemical Name:
Cinacalcet hydrochloride
Synonyms
CS-502;AMG-073 HCl;calcimimetics;Cinacalcet HCl;MIMPARA; SENSIPAR;Cinacalcet HCl D3;Cinacalcet R-isomer;Cinacalcet HCl,AMG073;nacalcet hydrochloride;AMG 073 (Hydrochloride)
CBNumber:
CB71176208
Molecular Formula:
C22H23ClF3N
Formula Weight:
393.88
MOL File:
364782-34-3.mol

Cinacalcet hydrochloride Properties

Melting point
175-177°C
storage temp.
Inert atmosphere,2-8°C
CAS DataBase Reference
364782-34-3(CAS DataBase Reference)
FDA UNII
1K860WSG25
NCI Drug Dictionary
cinacalcet hydrochloride

SAFETY

Risk and Safety Statements

Safety Statements  24/25
HS Code  29214990

Cinacalcet hydrochloride price More Price(56)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML2012 Cinacalcet hydrochloride ≥98% (HPLC) 364782-34-3 10MG $71.4 2022-05-15 Buy
Sigma-Aldrich SML2012 Cinacalcet hydrochloride ≥98% (HPLC) 364782-34-3 50MG $289 2022-05-15 Buy
Sigma-Aldrich 1133977 Cinacalcet hydrochloride United States Pharmacopeia (USP) Reference Standard 364782-34-3 250MG $639 2022-05-15 Buy
Cayman Chemical 16042 Cinacalcet (hydrochloride) ≥95% 364782-34-3 10mg $71 2022-04-27 Buy
Cayman Chemical 16042 Cinacalcet (hydrochloride) ≥95% 364782-34-3 25mg $159 2022-04-27 Buy
Product number Packaging Price Buy
SML2012 10MG $71.4 Buy
SML2012 50MG $289 Buy
1133977 250MG $639 Buy
16042 10mg $71 Buy
16042 25mg $159 Buy

Cinacalcet hydrochloride Chemical Properties,Uses,Production

Description

Cinacalcet is the first entry in a new class of therapeutic agents called the calcimimetics. It was launched as an oral treatment for secondary hyperparathyroidism (SHPT) in patients with chronic kidney disease on dialysis and for hypercalcemia in patients with parathyroid carcinoma. SHPT is associated with increased parathyroid hormone (PTH) secretion, which is triggered by low serum levels of calcium resulting from the failure of the kidney to clear phosphorous from the body and its inability to produce sufficient quantities of vitamin D. The consequences of increased PTH include stimulation of osteoclastic activity, cortical bone resorption and marrow fibrosis. PTH secretion is primarily regulated by the calcium-sensing receptor (CaR), which is located on the surface of the chief cell of the parathyroid gland. Calcimimetics bind to CaR and increase the sensitivity of CaR to extracellular calcium, thereby enabling its activation at subnormal levels of serum calcium. As a result, in the presence of these agents, the low levels of endogenous calcium in patients with renal failure are able to exert a suppressive effect on PTH secretion. Parathyroid carcinoma is also associated with elevated PTH levels, which are driven by autonomous parathyroid gland activity and subsequently lead to hypercalcemia. Although surgical resection is the primary therapy for treating hypercalcemia in parathyroid carcinoma patients, calcimimetics offer a nonsurgical alternative for patients with failed parathyroidectomy, metastatic parathyroid carcinoma, or high surgical risk. The recommended dosage of cinacalcet for the treatment of SHPT in chronic kidney disease is 30mg once daily at start and subsequent titration to 60, 90, 120 or 180 mg once daily. The dosage for the treatment of hypercalcemia in patients with parathyroid carcinoma is 30 mg twice daily at start and subsequent titration to 60 or 90 mg twice daily, or 90mg three or four times daily as necessary to normalize serum calcium level. After oral administration of cinacalcet, maximum plasma concentration is achieved in approximately 2 to 6 hours. It has a terminal half-life of 30 to 40 hours and steady-state drug levels are reached within 7 days. Cinacalcet has a high volume of distribution (1000 L) and high protein binding (93%–97%). It is extensively metabolized in the liver, mainly by CYP3A4, CYP2D6 and CYP1A2. The primary routes of elimination are in the urine (80%) and in the feces (15%). In Phase III clinical trials involving 1136 patients with SHPT, administration of cinacalcet at 30–180 mg/day doses for 6 months produced 38–48% decrease in intact PTH. Overall, 64% of patients given cinacalcet achieved at least a 30% reduction in PTH, versus 11% of placebo patients. Calcium-phosphorous product was reduced 14% by the active treatment and did not change in the placebo group. In a much smaller clinical study involving 21 hypercalcemic patients with parathyroid carcinoma, administration of 60–360 mg/day doses of cinacalcet resulted in 71% of patients achieving a target reduction of ≥1 mg/dL in serum calcium. The most common adverse events in these trials were nausea and vomiting. In vitro, cinacalcet is a strong inhibitor of CYP2D6; therefore, dose adjustments may be required when coadministered with medications that are predominantly metabolized by CYP2D6 and have a narrow therapeutic index (e.g. flecainide, vinblastine, thioridazine and most tricyclic antidepressants). Cinacalcet is prepared in a two-step synthesis starting from 3-[3-(trifluoromethyl)phenyl]propionaldehyde, by first condensing with (R)-(1-naphthyl)ethylamine to form the corresponding imine and subsequent reduction of the imine with sodium cyanoborohydride.

Chemical Properties

Off-White to Tan Solid

Originator

NPS pharmaceuticals (US)

Uses

Cinacalcet hydrochloride can be used in clinical trial in secondary hyperparathyroidism.

Definition

ChEBI: A hydrochloride derived from equimolar amounts of cinacalcet and hydrogen chloride.

brand name

Sensipar (Amgen).

Chemical Synthesis

General syntheses of this class of compounds have been published, however, the specific synthesis of cinacalcet (III) has not been available to date. The synthesis of cinacalcet, based on a patented procedure, is depicted in Scheme 3. A mixture of 1-acetonaphthone (21), 3-trifluoromethyl-1-propylamine (22) and titanium (IV) isopropoxide were stirred at rt to form the enamine intermediate which was reduced with methanolic sodium cyanoborohydride at rt to give corresponding racemic a-methyl amine (23). Compound 23 was resolved and then treated with HCl etherate to give cinacalcet hydrochloride (III) as a white solid.

1201910-95-3
364782-34-3
Synthesis of Cinacalcet hydrochloride from 1-Naphthalenemethanamine, α-methyl-N-[3-[3-(trifluoromethyl)phenyl]-2-propen-1-ylidene]-, (αR)-
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View Lastest Price from Cinacalcet hydrochloride manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2022-02-25 Cinacalcet hydrochloride CAS NO.364782-34-3
364782-34-3
US $1.00 / G 100G 99.9% 50000 tons Wuhan Boyuan Import & Export Co., LTD
2022-02-24 Cinacalcet hydrochloride
364782-34-3
US $30.00 / KG 1KG 99.9% 1000kg/month Shanxi Lianxu New Material Co., LTD
2022-01-14 Cinacalcet hydrochloride
364782-34-3
US $50.00 / ASSAYS 1ASSAYS 99% 500ton Shanghai Yunao International Trade Co., Ltd
(aR)-a-Methyl-N-[3-[3-(trifluoromethyl)phenyl)propyl]-1-napthalenemethanamine Hydrochloride (R)-N-(3-(3-(trifluoromethyl)phenyl)propyl)-1- -(1-napthyl)ethylamine Hydrochloride calcimimetics (R)-Cinacalcet Hydrochloride Cinacalcet Hydrochloride N-[(1R)-1-naphthalen-1-ylethyl]-3-[3-(trifluoromethyl)phenyl]propan-1-amine hydrochloride N-((1R)-1-(1-Naphthyl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine hydrochloride -Naphthalenemethanamine, .alpha.-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-, hydrochloride (1:1), (.alpha.R)- (aR)-α-Methyl-N-[3-[3-(trifluoromethyl)phenyl)propyl]-1-napthalenemethanamine Hydrochloride N-[(1R)-1-naphthalen-1-yleth [(1R)-1-(naphthalen-1-yl)ethyl]({3-[3-(trifluoroMethyl)phenyl]propyl})aMine hydrochloride AMG-073 HCl (Cinacalcet hydrochloride) (αR)-α-Methyl-N-[3-[3-(trifluoroMethyl)phenyl)propyl]-1-napthaleneMethanaMine Hydrochloride AMG 073 (Hydrochloride) Cinacalcet HCl AMG-073 (Cinacalcet hydrochloride) (R)-N-(1-(Naphthalen-1-yl)ethyl)-3-(3-(trifluoroMethyl)phenyl)propan-1-aMine hydrochloride rac Cinacalcet-d3 (Methyl-d3) Hydrochloride Cinacalcet (R-EnantioMer) HCl 1-NaphthaleneMethanaMine,a-Methyl-N-[3-[3-(trifluoroMethyl)phenyl]propyl]-,hydrochloride (1:1), (aR)- Cinacalcet (AMG-073) HCl MIMPARA; SENSIPAR (R)-N-(1-(naphthalen-1-yl)ethyl)- CS-502 AMG-073 HCl Cinacalcet hydrochloride N-((1R)-1-(1-Naphthyl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine hydrochloride Cinacalcet(AMG-073) Hydrochloride Cinacalcet hydrochloride, >=99% Cinacalcet hydrochloride CAS NO.364782-34-3 Hot sale Cinacalcet hydrochloride 99%min Top quality Cinacalcet hydrochloride with best price Cinacalcet hydrochloride CAS:364782-34-3 with fast delivery 1-Naphthalenemethanamine, alpha-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-, hydrochloride (1:1), (alphaR)- Cinacalcet hydrochlodide AMG-073 HCl (Cinacalcet HCl) Cinacalcet HCl,AMG073 CINACALCET HCL;MIMPARA; SENSIPAR Cinacalcet HCl D3 Cinacalcet Hydrochloride (250 mg) 1-Naphthalenemethanamine,a-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-, hydrochloride, (aR)- Cinacalcet hydrochloride USP/EP/BP Cinacalcet R-isomer Cinacalcet Hydrochkoride (cGMP) (R)-CINACALCET-D3 HYDROCHLORIDE nacalcet hydrochloride Cinacalcet HydrochlorideQ: What is Cinacalcet Hydrochloride Q: What is the CAS Number of Cinacalcet Hydrochloride Q: What is the storage condition of Cinacalcet Hydrochloride Q: What are the applications of Cinacalcet Hydrochloride TIANFU CHEM--Cinacalcet hydrochloride Cinacalcet Hydrochkoride 364782-34-3 C22H23ClF3N C22H22F3NHCl C22H22F3NClH Inhibitors Mimpara, Sensipar Cinacalcet API Aromatics Chiral Reagents