elagolix   Click here for help

GtoPdb Ligand ID: 8362

Synonyms: compound 10b [PMID 19006286] | NBI-56418 | NBI56418 | Orilissa®
Approved drug PDB Ligand
elagolix is an approved drug (FDA (2018))
Compound class: Synthetic organic
Comment: Elagolix is a non-peptide gonadotrophin receptor (GnRHR) antagonist [1]. As of July 2018, it is the first and only FDA-approved oral GnRH antagonist available for the treatment of moderate to severe endometriosis pain.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 13
Topological polar surface area 102.56
Molecular weight 631.21
XLogP 7.35
No. Lipinski's rules broken 2
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Canonical SMILES COc1cccc(c1F)c1c(=O)n(CC(c2ccccc2)NCCCC(=O)O)c(=O)n(c1C)Cc1c(F)cccc1C(F)(F)F
Isomeric SMILES COc1cccc(c1F)c1c(=O)n(C[C@@H](c2ccccc2)NCCCC(=O)O)c(=O)n(c1C)Cc1c(F)cccc1C(F)(F)F
InChI InChI=1S/C32H30F5N3O5/c1-19-28(21-11-6-14-26(45-2)29(21)34)30(43)40(18-25(20-9-4-3-5-10-20)38-16-8-15-27(41)42)31(44)39(19)17-22-23(32(35,36)37)12-7-13-24(22)33/h3-7,9-14,25,38H,8,15-18H2,1-2H3,(H,41,42)/t25-/m0/s1
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2018))
IUPAC Name Click here for help
4-[[(1R)-2-[5-(2-fluoro-3-methoxyphenyl)-3-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-4-methyl-2,6-dioxopyrimidin-1-yl]-1-phenylethyl]amino]butanoic acid
International Nonproprietary Names Click here for help
INN number INN
8983 elagolix
Synonyms Click here for help
compound 10b [PMID 19006286] | NBI-56418 | NBI56418 | Orilissa®
Database Links Click here for help
Specialist databases
GPCRdb Ligand elagolix
Other databases
CAS Registry No. 834153-87-6
ChEMBL Ligand CHEMBL1208155
DrugCentral Ligand 5293
GtoPdb PubChem SID 252166574
PubChem CID 11250647
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UniChem Compound Search for chemical match using the InChIKey HEAUOKZIVMZVQL-VWLOTQADSA-N
UniChem Connectivity Search for chemical match using the InChIKey HEAUOKZIVMZVQL-VWLOTQADSA-N