cinacalcet   Click here for help

GtoPdb Ligand ID: 3308

Synonyms: AMG-073 | Mimpara® | Sensipar®
Approved drug
cinacalcet is an approved drug (EMA & FDA (2004))
Compound class: Synthetic organic
Comment: Cinacalcet is a positive allosteric activator of the calcium-sensing receptor (CaSR), thus improving the effect of calcium on tissues expressing this receptor.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: cinacalcet

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 12.03
Molecular weight 357.17
XLogP 6.48
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES CC(c1cccc2c1cccc2)NCCCc1cccc(c1)C(F)(F)F
Isomeric SMILES C[C@H](c1cccc2c1cccc2)NCCCc1cccc(c1)C(F)(F)F
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
InChI Key VDHAWDNDOKGFTD-MRXNPFEDSA-N
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
CaS receptor Primary target of this compound Hs Allosteric modulator Positive 5.9 – 6.6 pKB - 1-2,4-5
pKB 5.9 – 6.6 [1-2,4-5]
Description: Ca2+i release
mGlu5 receptor Rn Allosteric modulator Positive 4.3 pKi - 3
pKi 4.3 [3]
CaS receptor Primary target of this compound Hs Allosteric modulator Positive 7.3 pEC50 - 7
pEC50 7.3 (EC50 5.1x10-8 M) [7]