Cinacalcet (CED0004412)

Record Information

Version

1.0

Creation Date

2016-05-25 18:24:20 UTC

Update Date

2026-08-21 21:48:41 UTC

Accession Number

CHEM022218

Identification

Common Name

Cinacalcet

Class

Small Molecule

Description

Cinacalcet is an organic compound with the formula C22H22F3N and an average molecular weight of 357.41 g/mol. Cinacalcet belongs to the naphthalenes, a class of benzenoids within the organic compounds. It acts as an agonist of the extracellular calcium-sensing receptor (CASR). The compound is found in or released from three recorded sources, including healthcare, pharmaceuticals, and veterinary products as anti-parathyroid agents, as well as household cleaning and consumer products such as other smoking requisites and non-electric simulated smoking devices. The recorded route of exposure for this compound is oral.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R)-alpha-Methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-1-naphthalenemethane amine	ChEBI
CNC	ChEBI
Mimpara	ChEBI
N-((1R)-1-(Naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine	ChEBI
(R)-a-Methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-1-naphthalenemethane amine	Generator
(R)-Α-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-1-naphthalenemethane amine	Generator
alpha-Methyl-N-(3-(3-(trifluoromethyl)phenyl)propyl)-1-naphthalenemethanamine, (alphar)-hydrochloride	HMDB
Hydrochloride, cinacalcet	HMDB
Sensipar	HMDB
073, AMG	HMDB
AMG 073	HMDB
1493, KRN	HMDB
Cinacalcet hydrochloride	HMDB

Chemical Formula

C₂₂H₂₂F₃N

Average Molecular Mass

357.412 g/mol

Monoisotopic Mass

357.170 g/mol

CAS Registry Number

226256-56-0

IUPAC Name

[(1R)-1-(naphthalen-1-yl)ethyl]({3-[3-(trifluoromethyl)phenyl]propyl})amine

Traditional Name

cinacalcet

SMILES

C[C@@H](NCCCC1=CC(=CC=C1)C(F)(F)F)C1=CC=CC2=CC=CC=C12

InChI Identifier

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

InChI Key

VDHAWDNDOKGFTD-MRXNPFEDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Phenylpropylamine
Trifluoromethylbenzene
Aralkylamine
Monocyclic benzene moiety
Secondary amine
Secondary aliphatic amine
Organopnictogen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organic nitrogen compound
Alkyl fluoride
Amine
Alkyl halide
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

secondary amino compound (CHEBI:48390 )
naphthalenes (CHEBI:48390 )
(trifluoromethyl)benzenes (CHEBI:48390 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	5.6e-05 g/L	ALOGPS
logP	5.57	ALOGPS
logP	6.27	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Basic)	10.3	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	100.12 m³·mol⁻¹	ChemAxon
Polarizability	37.9 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0a4i-1900000000-ff50504d0f6ffef59a7b	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0309000000-579cbf32d5eedf61db7a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4r-0914000000-acecef19519978f625ea	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0900000000-a207a28d48eb7ba6a89d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0109000000-18e95e1ee96e200ba3da	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0219000000-772e71699ff5f6ac691b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fi0-0911000000-4f5a6d4d922a64e42dd5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0009000000-96ce8755309529c03984	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0946000000-38ac52900348ce1c2113	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ar0-0900000000-d38c260d0a40e276b403	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0009000000-51ca816804eb82452154	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-056r-0619000000-6341e0b66d001c34dba5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0921000000-6fdee7d0fae14f3499b2	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
610.0	Log mg/kg	[340:1100]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
337	Anti-parathyroid agents	Healthcare, pharmaceuticals & veterinary products	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available

Pathways

1 pathway

Cinacalcet Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Extracellular calcium-sensing receptor	P41180	Humans	Predicted (SEA)	0.233548
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	9.88685
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	51.9254
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	46.8652
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	71.5434
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	106.108
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	48.6558
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	106.031
Click to view 3D structure	Sigma intracellular receptor 2	Q5BJF2	Humans	Predicted (SEA)	21.4085
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	66.2497
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	32.3074
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	108.522
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Predicted (SEA)	153.207
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	170.801
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	32.9302
Click to view 3D structure	Histamine H2 receptor	P25021	Humans	Predicted (SEA)	24.3668
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	93.964
Click to view 3D structure	G-protein coupled receptor 65	Q8IYL9	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Replicase polyprotein 1ab	P0DTD1	SARS-CoV-2	Predicted (SEA)	42.1943
Click to view 3D structure	5-hydroxytryptamine receptor 5A	P47898	Humans	Predicted (SEA)	29.1935
Click to view 3D structure	5-hydroxytryptamine receptor 1D	P28221	Humans	Predicted (SEA)	52.0811
Click to view 3D structure	Alpha-1B adrenergic receptor	P35368	Humans	Predicted (SEA)	57.0635
Click to view 3D structure	G-protein coupled receptor 35	Q9HC97	Humans	Predicted (SEA)	4.04816
Click to view 3D structure	N-formyl peptide receptor 3	P25089	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	G-protein coupled receptor 183	P32249	Humans	Predicted (SEA)	2.17978