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

Details

Stereochemistry ACHIRAL
Molecular Formula C29H27F2N7O5S
Molecular Weight 623.6326
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RELUGOLIX

SMILES

CN(C)Cc1c2c(=O)n(-c3ccc(nn3)OC)c(=O)n(Cc4c(cccc4F)F)c2sc1-c5ccc(cc5)NC(=NOC)O

InChI

InChIKey=AOMXMOCNKJTRQP-UHFFFAOYSA-N
InChI=1S/C29H27F2N7O5S/c1-36(2)14-19-24-26(39)38(22-12-13-23(42-3)34-33-22)29(41)37(15-18-20(30)6-5-7-21(18)31)27(24)44-25(19)16-8-10-17(11-9-16)32-28(40)35-43-4/h5-13H,14-15H2,1-4H3,(H2,32,35,40)

HIDE SMILES / InChI

Molecular Formula C29H27F2N7O5S
Molecular Weight 623.6326
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Relugolix (TAK-385) is an orally active nonpeptide gonadotropin-releasing hormone (GnRH) that binds to human GnRH receptors with subnanomolar affinity. Relugolix was demonstrated to act as a classic competitive antagonist of GnRH binding, but the exact molecular mechanism of that antagonism remains unknown. This drug is being developed as a treatment for various sex hormone related disorders. Clinical trials have been conducted to study safety and efficacy of relugolix as a treatment in endometriosis, uterine fibroids (noncancerous growths of the uterus), and prostate cancer. Two phase III trials evaluating the efficacy of Relugolix in patients with uterine fibroids were completed in 2019. No serious adverse events were reported.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.0800000000000000017 nM [IC50]
PubMed

PubMed

TitleDatePubMed
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
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:29:10 UTC 2021
Edited
by admin
on Fri Jun 25 21:29:10 UTC 2021
Record UNII
P76B05O5V6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RELUGOLIX
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
MYFEMBREE COMPONENT RELUGOLIX
Brand Name English
RELUGOLIX COMPONENT OF MYFEMBREE
Brand Name English
RELUGOLIX [JAN]
Common Name English
TAK-385
Code English
RELUGOLIX [INN]
Common Name English
RELUGOLIX [WHO-DD]
Common Name English
UREA, N-(4-(1-((2,6-DIFLUOROPHENYL)METHYL)-5-((DIMETHYLAMINO)METHYL)-1,2,3,4-TETRAHYDRO-3-(6-METHOXY-3-PYRIDAZINYL)-2,4-DIOXOTHIENO(2,3-D)PYRIMIDIN-6-YL)PHENYL)-N'-METHOXY-
Systematic Name English
ORGOVYX
Brand Name English
1-(4-(1-((2,6-DIFLUOROPHENYL)METHYL)-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
Systematic Name English
RELUGOLIX [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C63347
Created by admin on Fri Jun 25 21:29:10 UTC 2021 , Edited by admin on Fri Jun 25 21:29:10 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C114498
Created by admin on Fri Jun 25 21:29:10 UTC 2021 , Edited by admin on Fri Jun 25 21:29:10 UTC 2021
PRIMARY
INN
9628
Created by admin on Fri Jun 25 21:29:10 UTC 2021 , Edited by admin on Fri Jun 25 21:29:10 UTC 2021
PRIMARY
ChEMBL
CHEMBL1800159
Created by admin on Fri Jun 25 21:29:10 UTC 2021 , Edited by admin on Fri Jun 25 21:29:10 UTC 2021
PRIMARY
WIKIPEDIA
RELUGOLIX
Created by admin on Fri Jun 25 21:29:10 UTC 2021 , Edited by admin on Fri Jun 25 21:29:10 UTC 2021
PRIMARY
PUBCHEM
10348973
Created by admin on Fri Jun 25 21:29:10 UTC 2021 , Edited by admin on Fri Jun 25 21:29:10 UTC 2021
PRIMARY
EPA CompTox
737789-87-6
Created by admin on Fri Jun 25 21:29:10 UTC 2021 , Edited by admin on Fri Jun 25 21:29:10 UTC 2021
PRIMARY
DRUG BANK
DB11853
Created by admin on Fri Jun 25 21:29:10 UTC 2021 , Edited by admin on Fri Jun 25 21:29:10 UTC 2021
PRIMARY
FDA UNII
P76B05O5V6
Created by admin on Fri Jun 25 21:29:10 UTC 2021 , Edited by admin on Fri Jun 25 21:29:10 UTC 2021
PRIMARY
CAS
737789-87-6
Created by admin on Fri Jun 25 21:29:10 UTC 2021 , Edited by admin on Fri Jun 25 21:29:10 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> INDUCER
METABOLIC ENZYME -> INDUCER
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
Plasma protein binding of relugolix is 68 to 71%, primarily to albumin and to a lesser extent to ?1-acid glycoprotein.
EXCRETED UNCHANGED
URINE
EXCRETED UNCHANGED
FECAL
METABOLIC ENZYME -> SUBSTRATE
Co-administration with rifampin (P-gp and strong CYP3A inducer) decreased the AUC and Cmax of relugolix by 55% and 23%, respectively.
MAJOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
Relugolix is a substrate for intestinal P-gp.Co-administration with rifampin (P-gp and strong CYP3A inducer) decreased the AUC and Cmax of relugolix by 55% and 23%, respectively.
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
terminal elimination half-life PHARMACOKINETIC
blood-to-plasma ratio PHARMACOKINETIC
effective half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC