Cinacalcet

Base Information

• Chemical Name: Cinacalcet
• CAS No.: 226256-56-0
• Molecular Formula: C22H22F3N
• Molecular Weight: 357.419
• Hs Code.: 2921499090
• European Community (EC) Number: 682-701-7
• UNII: UAZ6V7728S
• DSSTox Substance ID: DTXSID8048286
• Nikkaji Number: J1.645.239D
• Wikipedia: Cinacalcet
• Wikidata: Q193978
• NCI Thesaurus Code: C74100
• RXCUI: 407990
• Pharos Ligand ID: QVAZDS6A5DRX
• Metabolomics Workbench ID: 43258
• ChEMBL ID: CHEMBL1201284
• Mol file: 226256-56-0.mol

Synonyms:alpha-methyl-N-(3-(3-(trifluoromethyl)phenyl)propyl)-1-naphthalenemethanamine, (alphaR)-hydrochloride;AMG 073;AMG073;cinacalcet;cinacalcet hydrochloride;KRN 1493;Sensipar

Chemical Property of Cinacalcet

Chemical Property:

• Appearance/Colour: yellow oil
• Vapor Pressure: 5.67E-08mmHg at 25°C
• Refractive Index: 1.563
• Boiling Point: 440.9 °C at 760 mmHg
• PKA: 9.19±0.29(Predicted)
• Flash Point: 220.5 °C
• PSA: 12.03000
• Density: 1.154 g/cm³
• LogP: 6.53290
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 357.17043419
• Heavy Atom Count: 26
• Complexity: 422

Purity/Quality:

99% ^*data from raw suppliers

Cinacalcet ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=CC2=CC=CC=C21)NCCCC3=CC(=CC=C3)C(F)(F)F
• Isomeric SMILES: C[C@H](C1=CC=CC2=CC=CC=C21)NCCCC3=CC(=CC=C3)C(F)(F)F
• Recent ClinicalTrials: Evaluating Alternative Medical Therapies in Primary Hyperparathyroidism
• Recent EU Clinical Trials: Treatment of Primary Hyperparathyroidism with Denosumab and Cinacalcet
• Recent NIPH Clinical Trials: Switching from cinacalcet to ebocalcet in secondary hyperparathyroidism patients during hemodialysis.
• Description: Cinacalcet is the first type II calcimimet ic agent approved that improves CaSR sensi Tivity to calcium . When calcium is bound to the CaSR, phospholipase C is act ivated, and the secretion of PTH is inhibited. In the presence of cinacalcet , not only is a drop in PTH levels observed but also a decrease in serum calcium and phosphorous levels.
• Uses: 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 macular degeneration therapy Labeled Cinacalcet, intended for use as an internal standard for the quantification of Cinacalcet by GC- or LC-mass spectrometry.
• Clinical Use: Cinacalcet hydrochloride is a second-generat ion calcimimetic approved for the treatment of secondary hyperparathyroidism in patients wi th chronic kidney disease on dialysis and for the treatment of hypercalcemia in patients with parathyroid cancer . It can be used alone, with vitamin D, and/or with a phosphate binder .
• Drug interactions: Potentially hazardous interactions with other drugs Antifungals: metabolism inhibited by ketoconazole. Hormone antagonists: metabolism of tamoxifen to active metabolite inhibited - avoid. Tobacco: metabolism increased by tobacco.

Technology Process of Cinacalcet

There total 90 articles about Cinacalcet which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(1R)-1-(naphthalen-1-yl)ethanamine (R)-mandelate (1073144-62-3) + methylsulfonyl-3-(3-trifluoromethylphenyl)propyl ester (21172-43-0) → cinacalcet (226256-56-0,694495-47-1)

Guidance literature:

With potassium carbonate; In water; at 60 - 65 ℃; for 20h;

Reference yield: 96.0%

cinacalcet hydrochloride (364782-34-3,1217809-88-5) → cinacalcet (226256-56-0,694495-47-1)

Guidance literature:

With sodium carbonate; In dichloromethane; water;

Reference yield: 96.0%

(R)-cinacalcet (-)-di-para-D-toluoyl tartrate → cinacalcet (226256-56-0,694495-47-1)

Guidance literature:

With sodium hydroxide; In dichloromethane; water; for 0.5h; pH=9 - 10;

upstream raw materials:

(2E)-N-[(1R)-1-(1-naphthyl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine

(R)‐N‐(1‐(naphthalen‐1‐yl)ethyl)‐3‐(3‐trifluoromethylphenyl)propanamide

cinacalcet hydrochloride

(R)-1-(1-Naphthyl)ethylamine

Downstream raw materials:

cinacalcet hydrochloride

N-[1-(R)-(-)-(1-naphthyl)ethyl]-3-[3-(trifluoromethyl)phenyl]-1-aminopropane acetate

(R)-tert-butyl (1-(naphthalen-1-yl)ethyl)(3-(3-(trifluoromethyl)phenyl)propyl)carbamate

(R)-α-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-1-(5,6,7,8-tetrahydronaphthalene)methane amine

Refernces

• 1、 Fan, Qing-Hua,Liu, Xintong,Luo, Zhenli,Pan, Yixiao,Xu, Lijin,Yang, Ji,Yao, Zhen,Zhang, Xin. "BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant". supporting information. p. 5205 - 5211. Retrieved 2021/07/29.
• 2、 Cheng, Jiang-Tao,Dong, Xiao-Yang,Gu, Qiang-Shuai,Li, Zhong-Liang,Liu, Juan,Liu, Xin-Yuan,Luan, Cheng,Wang, Fu-Li,Wang, Li-Lei,Yang, Ning-Yuan,Zhang, Yu-Feng. "Enantioconvergent Cu-Catalyzed Radical C-N Coupling of Racemic Secondary Alkyl Halides to Access α-Chiral Primary Amines". supporting information. p. 15413 - 15419. Retrieved 2021/09/30.