cinacalcet   Click here for help

GtoPdb Ligand ID: 3308

Synonyms: AMG-073 | Mimpara® | Sensipar®
Approved drug PDB Ligand
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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: cinacalcet

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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]