etelcalcetide   Click here for help

GtoPdb Ligand ID: 8375

Synonyms: AMG 416 | AMG-416 | KAI-4169 | Parsabiv® | velcalcetide
Approved drug
etelcalcetide is an approved drug (EMA (2016), FDA (2017))
Compound class: Peptide or derivative
Comment: Etelcalcetide is a novel calcimimetic, peptidic agonist of the human cell surface calcium-sensing receptor (CaSR) [1]. The chemical structure shown here was generated using the SMILES from PubChem CID 71511839.
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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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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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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 NC(=NCCC[C@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N)CCCN=C(N)N)C)CCCN=C(N)N)NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](NC(=O)C)CSSC[C@@H](C(=O)O)N)C)CCCN=C(N)N)N
Isomeric SMILES C[C@H](C(=O)N[C@H](CCCN=C(N)N)C(=O)N)NC(=O)[C@@H](CCCN=C(N)N)NC(=O)[C@@H](CCCN=C(N)N)NC(=O)[C@@H](CCCN=C(N)N)NC(=O)[C@@H](C)NC(=O)[C@@H](CSSC[C@@H](C(=O)O)N)NC(=O)C
InChI InChI=1S/C38H73N21O10S2/c1-18(28(62)56-22(27(40)61)8-4-12-49-35(41)42)53-30(64)23(9-5-13-50-36(43)44)58-32(66)25(11-7-15-52-38(47)48)59-31(65)24(10-6-14-51-37(45)46)57-29(63)19(2)54-33(67)26(55-20(3)60)17-71-70-16-21(39)34(68)69/h18-19,21-26H,4-17,39H2,1-3H3,(H2,40,61)(H,53,64)(H,54,67)(H,55,60)(H,56,62)(H,57,63)(H,58,66)(H,59,65)(H,68,69)(H4,41,42,49)(H4,43,44,50)(H4,45,46,51)(H4,47,48,52)/t18-,19-,21+,22-,23-,24-,25-,26-/m1/s1
InChI Key ANIAZGVDEUQPRI-ZJQCGQFWSA-N
No information available.
Summary of Clinical Use Click here for help
Etelcalcetide (AMG 416) was approved by the EMA in 2016, and later by the US FDA in Feb. 2017 for the treatment of secondary hyperparathyroidism (HPT) in adult patients with chronic kidney disease (CKD) on hemodialysis. Click here to link to ClinicalTrials.gov's listing of Phase 3 AMG 416 trials.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The calcimimetic mechanism of etelcalcetide is distinct from that of the approved drug cinacalcet which is an allosteric modulator of the CaSR.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)