Cinacalcet

Title: Cinacalcet
CAS Registry Number: 226256-56-0
CAS Name: (aR)-a-Methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-1-napthalenemethanamine
Additional Names: (R)-N-(3-(3-(trifluoromethyl)phenyl)propyl)-1-(1-napthyl)ethylamine
Manufacturers' Codes: AMG-073; KRN-1493
Molecular Formula: C22H22F3N
Molecular Weight: 357.41
Percent Composition: C 73.93%, H 6.20%, F 15.95%, N 3.92%
Literature References: Calcimimetic. Prepn: B. C. Van Wagenen et al., US 6211244 (2001 to NPS Pharmaceuticals). Review of pharmacology and mechanism of action: M. Wada, N. Nagano, Nephrol. Dial. Transplant. 18, Suppl. 3, iii13-iii17 (2003); of clinical development: N. Franceschini et al., Expert Opin. Invest. Drugs 12, 1413-1421 (2003). Clinical trial in secondary hyperparathyroidism: G. A. Block et al., N. Engl. J. Med. 350, 1516 (2004).
Derivative Type: Hydrochloride
CAS Registry Number: 364782-34-3
Trademarks: Mimpara (Amgen); Sensipar (Amgen)
Molecular Formula: C22H22F3N.HCl
Molecular Weight: 393.87
Percent Composition: C 67.09%, H 5.89%, F 14.47%, N 3.56%, Cl 9.00%
Properties: White to off-white, crystalline solid. Sol in methanol, 95% ethanol; slightly sol in water.
Therap-Cat: Antihyperparathyroid.
Keywords: Antihyperparathyroid.
Cinametic Acid Cinchomeronic Acid Cinchona Cinchonamine Cinchonidine

Cinacalcet
Cinacalcet Structural Formulae.png
Cinacalcet ball-and-stick.png
Systematic (IUPAC) name
(R)-N-[1-(1-naphthyl)ethyl]-3-
[3-(trifluoromethyl)phenyl]propan-1-amine
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a605004
Licence data EMA:Link, US FDA:link
Pregnancy cat. B3 (AU) C (US)
Legal status Prescription only
Routes Oral
Pharmacokinetic data
Bioavailability 20 to 25%
Increases if taken with food
Protein binding 93 to 97%
Metabolism Hepatic (CYP3A4-, CYP2D6- and CYP1A2-mediated)
Half-life 30 to 40 hours
Excretion Renal (80%) and fecal (15%)
Identifiers
CAS number 226256-56-0 YesY
ATC code H05BX01
PubChem CID 156419
IUPHAR ligand 3308
DrugBank DB01012
ChemSpider 137743 YesY
UNII UAZ6V7728S YesY
KEGG D03504 YesY
ChEBI CHEBI:48390 YesY
ChEMBL CHEMBL1201284 N
Chemical data
Formula C22H22F3N 
Mol. mass 357.412 g/mol
 N (what is this?)  (verify)

Cinacalcet (INN) is a drug that acts as a calcimimetic (i.e. it mimics the action of calcium on tissues) by allosteric activation of the calcium-sensing receptor that is expressed in various human organ tissues. It is sold by Amgen under the trade name Sensipar in North America and Australia and as Mimpara in Europe. Cinacalcet is used to treat secondary hyperparathyroidism (elevated parathyroid hormone levels), a consequence of end-stage renal disease.[1] Cinacalcet is also indicated for the treatment of hypercalcemia in patients with parathyroid carcinoma.[2]

Clinical trials conducted in the United States by Amgen to determine whether the drug is safe for children were halted by the FDA in February 2013 following the death of a 14-year-old patient.[3]