Cinacalcet

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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]

Clinical uses[edit]

Cinacalcet is indicated for the treatment of secondary hyperparathyroidism in patients with chronic kidney disease on dialysis and hypercalcemia in patients with parathyroid carcinoma.[4]

Mechanism of action[edit]

Cinacalcet increases the sensitivity of calcium receptors on parathyroid cells to reduce parathyroid hormone (PTH) levels and thus decrease serum calcium levels. [4]

Synthesis[edit]

Cinacalcet scheme.png

B.C. Van Wagenen, S.T. Moe, M.F. Balandrin, E.G. DelMar, E.F. Nemeth, U.S. Patent 6,211,244 (2001).

References[edit]

  1. ^ Torres PU (2006). "Cinacalcet HCl: a novel treatment for secondary hyperparathyroidism caused by chronic kidney disease". Journal of renal nutrition : the official journal of the Council on Renal Nutrition of the National Kidney Foundation 16 (3): 253–8. doi:10.1053/j.jrn.2006.04.010. PMID 16825031. 
  2. ^ "Sensipar for Parathyroid Carcinoma". Amgen. 2009. Retrieved 25 September 2009. 
  3. ^ Edney, Anna (February 26, 2013). "Amgen Pediatric Trials of Sensipar Halted by FDA After Death". Businessweek. 
  4. ^ a b 2014 Nurses Drug Handbook (13th ed.). Burlington, MA: Jones & Bartlett Learning. 2014. pp. 245–6. ISBN 978-1-284-03115-7. 

External links[edit]