CHEBI:48390 - cinacalcet

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ChEBI Name cinacalcet
ChEBI ID CHEBI:48390
Definition A secondary amino compound that is (1R)-1-(naphthalen-1-yl)ethanamine in which one of the hydrogens attached to the nitrogen is substituted by a 3-[3-(trifluoromethyl)phenyl]propyl group.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C22H22F3N
Net Charge 0
Average Mass 357.41203
Monoisotopic Mass 357.170
InChI InChI=1S/C22H22F3N/c1-16(20-13-5-10-18-9-2-3-12-21(18)20)26-14-6-8-17-7-4-11-19(15-17)22(23,24)25/h2-5,7,9-13,15-16,26H,6,8,14H2,1H3/t16-/m1/s1
InChIKey VDHAWDNDOKGFTD-MRXNPFEDSA-N
SMILES C[C@@H](NCCCc1cccc(c1)C(F)(F)F)c1cccc2ccccc12
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): P450 inhibitor
An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.
Application(s): calcimimetic
A drug that it mimics the action of calcium on tissues.
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ChEBI Ontology
Outgoing cinacalcet (CHEBI:48390) has role calcimimetic (CHEBI:48525)
cinacalcet (CHEBI:48390) has role P450 inhibitor (CHEBI:50183)
cinacalcet (CHEBI:48390) is a (trifluoromethyl)benzenes (CHEBI:83565)
cinacalcet (CHEBI:48390) is a naphthalenes (CHEBI:25477)
cinacalcet (CHEBI:48390) is a secondary amino compound (CHEBI:50995)
Incoming cinacalcet carbamate (CHEBI:48392) has functional parent cinacalcet (CHEBI:48390)
cinacalcet hydrochloride (CHEBI:48391) has functional parent cinacalcet (CHEBI:48390)
IUPAC Name
N-[(1R)-1-(1-naphthyl)ethyl]-3-[3-(trifluoromethyl)phenyl]propan-1-amine
INN Source
cinacalcet ChemIDplus
Synonyms Sources
(R)-α-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-1-naphthalenemethane amine Patent
CNC Patent
N-((1R)-1-(Naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine ChemIDplus
Brand Name Source
Mimpara DrugBank
Manual Xrefs Databases
647 DrugCentral
Cinacalcet Wikipedia
D03504 KEGG DRUG
DB01012 DrugBank
LSM-5815 LINCS
US2007060645 Patent
US6011068 Patent
US6211244 Patent
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Registry Numbers Types Sources
10191346 Reaxys Registry Number Reaxys
226256-56-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
16680561 PubMed citation Europe PMC
17652181 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2011-07-12 Cinacalcet acts as a calcimimetic, i.e. it mimics the action of calcium on tissues. It is used (generally as the hydrochloride salt) for the treatment of secondary hyperparathyroidism in patients with chronic kidney disease who are on haemodialysis or peritoneal dialysis, and for the treatment of hypercalcaemia in patients with parathyroid carcinoma.