U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C32H29F5N3O5.Na
Molecular Weight 653.5715
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELAGOLIX SODIUM

SMILES

[Na+].COC1=CC=CC(=C1F)C2=C(C)N(CC3=C(C=CC=C3F)C(F)(F)F)C(=O)N(C[C@H](NCCCC([O-])=O)C4=CC=CC=C4)C2=O

InChI

InChIKey=DQYGXRQUFSRDCH-UQIIZPHYSA-M
InChI=1S/C32H30F5N3O5.Na/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);/q;+1/p-1/t25-;/m0./s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C32H29F5N3O5
Molecular Weight 630.5818
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Elagolix (ABT-620) is an oral gonadotropin-releasing hormone antagonist being studied for the treatment of endometriosis and uterine fibroids. The U.S. Food and Drug Administration (FDA) approved AbbVie's elagolix under the brand name Orilissa as the first and only oral gonadotropin-releasing hormone (GnRH) antagonist specifically developed for women with moderate to severe endometriosis pain.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.9 nM [Ki]
Conditions
PubMed

PubMed

TitleDatePubMed
Discovery of sodium R-(+)-4-{2-[5-(2-fluoro-3-methoxyphenyl)-3-(2-fluoro-6-[trifluoromethyl]benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenylethylamino}butyrate (elagolix), a potent and orally available nonpeptide antagonist of the human gonadotropin-releasing hormone receptor.
2008 Dec 11
Discovery of 1-{4-[1-(2,6-difluorobenzyl)-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea (TAK-385) as a potent, orally active, non-peptide antagonist of the human gonadotropin-releasing hormone receptor.
2011 Jul 28
Patents

Sample Use Guides

In Vivo Use Guide
Normal liver function or mild hepatic impairment : 150 mg once daily for up to 24 months or 200 mg twice daily for up to 6 months. (2.1) Moderate hepatic impairment: 150 mg once daily for up to 6 months. (2.1) Oral tablets: 150 mg and 200 mg
Route of Administration: Oral
In Vitro Use Guide
Elagolix displays high affinity in a competition binding assay for hGnRH-R (Ki = 0.90 nM) and low CYP3A4 inhibition (IC50 = 56 uM). It is a slowly disassociating antagonist exhibiting very high affinity (KD = 54 pM) and insurmountable antagonism. Elagolix is highly selective at hGnRH-R, its wider receptor selectivity is tested at a concentration of 10 uM in a panel of radioligand binding assays for 100 off-target receptors, ion channels, enzymes, and transporters, and significant activity is not observed (inhibition <50%). It does not stimulate histamine release from cultured rat peritoneal mast cells.
Substance Class Chemical
Created
by admin
on Mon Oct 21 23:54:24 UTC 2019
Edited
by admin
on Mon Oct 21 23:54:24 UTC 2019
Record UNII
5948VUI423
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ELAGOLIX SODIUM
USAN   WHO-DD  
USAN  
Official Name English
BUTANOIC ACID, 4-(((1R)-2-(5-(2-FLUORO-3-METHOXYPHENYL)-3-((2-FLUORO-6-(TRIFLUOROMETHYL)PHENYL)METHYL)-3,6-DIHYDRO-4-METHYL-2,6-DIOXO-1(2H)-PYRIMIDINYL)-1- PHENYLETHYL)AMINO)-, MONOSODIUM SALT
Common Name English
SODIUM 4-(((1R)-2-(5-(2-FLUORO-3-METHOXYPHENYL)-3-((2-FLUORO-6- (TRIFLUOROMETHYL)PHENYL)METHYL)-4-METHYL-2,6-DIOXO-3,6-DIHYDROPYRIMIDIN-1(2H)-YL)-1- PHENYLETHYL)AMINO)BUTANOATE
Systematic Name English
ORLISSA
Brand Name English
ELAGOLIX SODIUM [WHO-DD]
Common Name English
ELAGOLIX SODIUM SALT [MI]
Common Name English
NBI-56418-NA
Code English
ELAGOLIX SODIUM [USAN]
Common Name English
NBI-56418 NA
Code English
Code System Code Type Description
PUBCHEM
24785956
Created by admin on Mon Oct 21 23:54:24 UTC 2019 , Edited by admin on Mon Oct 21 23:54:24 UTC 2019
PRIMARY
CAS
832720-36-2
Created by admin on Mon Oct 21 23:54:24 UTC 2019 , Edited by admin on Mon Oct 21 23:54:24 UTC 2019
PRIMARY
MERCK INDEX
M4850
Created by admin on Mon Oct 21 23:54:24 UTC 2019 , Edited by admin on Mon Oct 21 23:54:24 UTC 2019
PRIMARY Merck Index
ChEMBL
CHEMBL1208155
Created by admin on Mon Oct 21 23:54:24 UTC 2019 , Edited by admin on Mon Oct 21 23:54:24 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY