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Details

Stereochemistry ABSOLUTE
Molecular Formula C32H30F5N3O5
Molecular Weight 631.5897
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELAGOLIX

SMILES

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=HEAUOKZIVMZVQL-VWLOTQADSA-N
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

HIDE SMILES / InChI

Molecular Formula C32H30F5N3O5
Molecular Weight 631.5897
Charge 0
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
5B2546MB5Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ELAGOLIX
INN   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
ELAGOLIX [INN]
Common Name English
ELAGOLIX [USAN]
Common Name English
ELAGOLIX [WHO-DD]
Common Name English
NBI-56418
Code English
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)BUTANOIC ACID
Systematic Name English
ELAGOLIX [MI]
Common 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)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C241
Created by admin on Mon Oct 21 23:54:24 UTC 2019 , Edited by admin on Mon Oct 21 23:54:24 UTC 2019
NCI_THESAURUS C2092
Created by admin on Mon Oct 21 23:54:24 UTC 2019 , Edited by admin on Mon Oct 21 23:54:24 UTC 2019
Code System Code Type Description
CAS
834153-87-6
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
EPA CompTox
834153-87-6
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
WIKIPEDIA
Elagolix
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
NCI_THESAURUS
C153373
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
PUBCHEM
11250647
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
MESH
C539351
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
INN
8983
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
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
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TARGET -> INHIBITOR
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TRANSPORTER -> INHIBITOR
TARGET -> INDUCER
SALT/SOLVATE -> PARENT
TARGET -> INDUCER
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TARGET -> INDUCER
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
EXCRETED UNCHANGED
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EXCRETED UNCHANGED
FECAL
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TRANSPORTER -> INHIBITOR
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METABOLIC ENZYME -> SUBSTRATE
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BINDER->LIGAND
METABOLIC ENZYME -> SUBSTRATE
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC DOSE

Biological Half-life PHARMACOKINETIC DOSE

Tmax PHARMACOKINETIC DOSE