SUFUGOLIX

Details

Stereochemistry	ACHIRAL
Molecular Formula	C36H31F2N5O4S
Molecular Weight	667.724
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CONC(=O)NC1=CC=C(C=C1)C2=C(CN(C)CC3=CC=CC=C3)C4=C(S2)N(CC5=C(F)C=CC=C5F)C(=O)N(C4=O)C6=CC=CC=C6

InChI

InChIKey=UCQSBGOFELXYIN-UHFFFAOYSA-N

InChI=1S/C36H31F2N5O4S/c1-41(20-23-10-5-3-6-11-23)21-28-31-33(44)43(26-12-7-4-8-13-26)36(46)42(22-27-29(37)14-9-15-30(27)38)34(31)48-32(28)24-16-18-25(19-17-24)39-35(45)40-47-2/h3-19H,20-22H2,1-2H3,(H2,39,40,45)

HIDE SMILES / InChI

Molecular Formula	C36H31F2N5O4S
Molecular Weight	667.724
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12502365 | https://www.ncbi.nlm.nih.gov/pubmed/12679460 | http://adisinsight.springer.com/drugs/800017215 | https://www.clinicaltrialsregister.eu/ctr-search/trial/2004-001721-13/GB

Sufugolix (TAK-013 or 5-(N-benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-6-[4-(3-methoxyureido)phenyl]-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione) is a highly potent and orally active non-peptide antagonist of luteinizing hormone-releasing hormone (LHRH) receptor. Sufugolix by oral administration suppresses a pituitary-ovarian axis continuously and reversibly in cynomolgus monkeys. Takeda studied Sufugolix in the trials for the treatment of endometriosis and uterine leiomyoma however development was discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Gonadotropin-releasing hormone receptor 41 Target ID: CHEMBL1855 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12502365	Antagonist 2778		0.06 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Endometriosis 32 Sources: http://adisinsight.springer.com/drugs/800017215	Primary		Phase III 656	Unknown Approved Use Unknown
Uterine leiomyomata 8 Sources: http://adisinsight.springer.com/drugs/800017215	Primary		Phase I 428	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/21657270/	weak [Inhibition 10 uM]

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00BJPO	https://www.1pchem.com/search?query=1P00BJPO
AChemBlock	O33753	http://www.achemblock.com/catalogsearch/result/?q=O33753
Alfa Chemistry	ACM308831610	http://www.alfa-chemistry.com/search.aspx?q=ACM308831610
AstaTech	44351	http://astatechinc.com/CPSResult.php?CRNO=44351
BOC Sciences	308831-61-0	http://www.bocsci.com/description.asp?cas=308831-61-0
Chem Scene	CS-6434	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-6434
ChemShuttle	153272	https://www.chemshuttle.com/catalogsearch/result/?q=153272
KeyOrganics	AS-35342	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-35342
MedChem Express	HY-100209	https://www.medchemexpress.com/search.html?q=HY-100209&ft=&fa=&fp=
MolPort	MolPort-046-033-569	https://www.molport.com/shop/molecule-link/MolPort-046-033-569
Molnova	M13986	https://www.molnova.com/en/serch-list.html?keywords=M13986
MuseChem	I009627	https://www.musechem.com/product/I009627.html
TargetMol	T3538	https://www.targetmol.com/search?keyword=T3538
eMolecules	95536585	https://orderbb.emolecules.com/search/#?query=95536585
eNovation Chemicals	D544523	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D544523&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-2604591732	https://mcule.com/MCULE-2604591732/

PubMed

Title	Date	PubMed
Amiloride derivatives and a nonpeptidic antagonist bind at two distinct allosteric sites in the human gonadotropin-releasing hormone receptor.	2008 Jun	18344315
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	21657270

Patents

Sample Use Guides

In Vivo Use Guide

In a Phase III study the efficacy and safety of 50 mg and 100 mg of sufugolix (TAK-013) tablets administered twice daily versus placebo for 12 weeks were evaluated in subjects with symptomatic endometriosis.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:58:01 GMT 2023` Edited by `admin` on `Fri Dec 15 15:58:01 GMT 2023`
Record UNII	56S17Z6X9M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SUFUGOLIX

Official Name

English

5-((BENZYL(METHYL)AMINO)METHYL)-1-(2,6-DIFLUOROBENZYL)-6-(4-(3-METHOXYUREIDO)PHENYL)-3-PHENYLTHIENO(2,3-D)PYRIMIDINE-2,4(1H,3H)-DIONE

Systematic Name

English

sufugolix [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C63347