1025064-33-8

Basic information

• Product Name: rac Cinacalcet HCl
• Synonyms: rac Cinacalcet HCl;rac Cinacalcet;rac-Cinacalcet Hydrochloride;N-(1-(naphthalen-2-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine hydrochloride
• CAS NO: 1025064-33-8
• Molecular Formula: C₂₂H₂₂F₃N
• Molecular Weight: 357.41
• EINECS: -0
• Mol File: 1025064-33-8.mol

Chemical Properties

• Boiling Point: 440.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.154±0.06 g/cm3(Predicted)
• PKA: 9.19±0.29(Predicted)
• CAS DataBase Reference: rac Cinacalcet HCl(CAS DataBase Reference)
• NIST Chemistry Reference: rac Cinacalcet HCl(1025064-33-8)
• EPA Substance Registry System: rac Cinacalcet HCl(1025064-33-8)

Safety Data

• Hazardous Substances Data: 1025064-33-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Rac Cinacalcet HCl is used as a therapeutic agent for the treatment of secondary hyperparathyroidism in patients with chronic kidney disease. It helps manage the condition by reducing the secretion of parathyroid hormone and lowering serum calcium levels, thus alleviating the symptoms and complications associated with the disease.
Used in Oncology:
Rac Cinacalcet HCl is used as a treatment option for hypercalcemia in patients with parathyroid carcinoma. It effectively lowers serum calcium levels, providing relief from the symptoms and complications caused by the excessive calcium in the blood.
Used in Endocrinology:
Rac Cinacalcet HCl is used as a management tool for primary hyperparathyroidism. It helps regulate the calcium levels in the blood by reducing the secretion of parathyroid hormone, thereby controlling the symptoms and preventing complications related to the condition.
Common side effects of Rac Cinacalcet HCl may include nausea, vomiting, and diarrhea. Patients with a history of seizures or those taking other medications that can prolong the QT interval should exercise caution when using rac Cinacalcet HCl. Despite these potential side effects, Rac Cinacalcet HCl remains a valuable therapeutic option for the management of various hypercalcemic conditions.

Upstream product

• 1025064-44-1 N-[1-(naphthalen-1-yl)ethyl]-3-(3-trifluoromethylphenyl)propanamide 
• 1206633-34-2 C₂₃H₂₄F₃N 

Downstream Products

• 1025064-35-0 (R)-N-[1-(1-naphthyl)ethyl]-3-[3-(trifluoromethyl)phenyl]-1-aminopropane (-)-di-p-toluoyl-D-tartrate 

Relevant articles and documents

A PROCESS FOR THE PREPARATION OF CINACALCET AND ITS SALTS

A process for preparing (cinacalcet) α-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-l- naphthalenemethanamine (formula I): or a pharmaceutically acceptable salt thereof which comprises: a) reacting 1-acetonaphthone with an alkyl amine or a substituted or non-substituted aralkyl amine in presence of a suitable solvent to form imine compound (formula III), which on reduction using suitable reducing agent yields N-substituted naphthyl ethyl amine (formula IV). b) Optionally resolving the N-substituted naphthyl ethyl amine (formula (IV) into its corresponding (R) or (S) isomer (formula IVa and IVb). c) Further reacting the (R,S) or (R) or (S)-N-substituted naphthyl ethyl amine (formula IV, IVa, or IVb) with trifluoromethyl aryl alkyl compound (formula V) in presence of a base and in a suitable solvent to form an intermediate corresponding to (R5S), (R) or (S)-N-substituted- methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-l-naphthalenemethanamine (N-substituted- cinacalcet) (formula VI, Via or VIb). d) Optionally resolving (R,S)-N-substituted cinacalcet (formula VI) into its corresponding (R) and (S) isomers (formula Via or VIb). e) Converting (R5S) or (R) or (S)-N-substituted-cinacalcet (formula VI, Via or VIb) to the corresponding (R5S) or (R) or (S)-α-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-l- naphthalenemethanamine (cinacalcet) (formula, I5 Ia or Ib)) by dealkylation or debenzylation, f) Optionally resolving (R,S)-α-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-l- naphthalenemethanamine (cincacalcet, formula I) into (R) and (S)-α-methyl-N-[3-[3- (trifluoromethyl)phenyl]propyl]-l-naphthalenemethanamine (formula Ia and Ib) using a suitable resolving agent.

PROCESSES FOR THE PREPARATION OF CINACALCET

There are described several processes for making a free base of cinacalcet. One of the described processes goes through an intermediate of the formula (II) where R1 and R2 are both hydrogen, or R1 and R2, together, form a double bond.