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.
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2D Structure
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Physico-chemical Properties
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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
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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
References
1. Cook AE, Mistry SN, Gregory KJ, Furness SG, Sexton PM, Scammells PJ, Conigrave AD, Christopoulos A, Leach K. (2015)
Biased allosteric modulation at the CaS receptor engendered by structurally diverse calcimimetics.
Br J Pharmacol, 172 (1): 185-200. [PMID:25220431]
2. Davey AE, Leach K, Valant C, Conigrave AD, Sexton PM, Christopoulos A. (2012)
Positive and negative allosteric modulators promote biased signaling at the calcium-sensing receptor.
Endocrinology, 153 (3): 1232-41. [PMID:22210744]
3. Hellyer SD, Albold S, Wang T, Chen ANY, May LT, Leach K, Gregory KJ. (2018)
"Selective" Class C G Protein-Coupled Receptor Modulators Are Neutral or Biased mGlu5 Allosteric Ligands.
Mol Pharmacol, 93 (5): 504-514. [PMID:29514854]
4. Leach K, Gregory KJ, Kufareva I, Khajehali E, Cook AE, Abagyan R, Conigrave AD, Sexton PM, Christopoulos A. (2016)
Towards a structural understanding of allosteric drugs at the human calcium-sensing receptor.
Cell Res, 26 (5): 574-92. [PMID:27002221]
5. Leach K, Wen A, Cook AE, Sexton PM, Conigrave AD, Christopoulos A. (2013)
Impact of clinically relevant mutations on the pharmacoregulation and signaling bias of the calcium-sensing receptor by positive and negative allosteric modulators.
Endocrinology, 154 (3): 1105-16. [PMID:23372019]
6. Levi R, Ben-Dov IZ, Lavi-Moshayoff V, Dinur M, Martin D, Naveh-Many T, Silver J. (2006)
Increased parathyroid hormone gene expression in secondary hyperparathyroidism of experimental uremia is reversed by calcimimetics: correlation with posttranslational modification of the trans acting factor AUF1.
J Am Soc Nephrol, 17 (1): 107-12. [PMID:16291838]
7. Nemeth EF, Heaton WH, Miller M, Fox J, Balandrin MF, Van Wagenen BC, Colloton M, Karbon W, Scherrer J, Shatzen E et al.. (2004)
Pharmacodynamics of the type II calcimimetic compound cinacalcet HCl.
J Pharmacol Exp Ther, 308 (2): 627-35. [PMID:14593085]