Sufugolix

Sufugolix
Clinical data

Synonyms	TAK-013
Routes of administration	Oral
ATC code	none
Identifiers
IUPAC name 1-[4-[5-[[benzyl(methyl)amino]methyl]-1-[(2,6-difluorophenyl)methyl]-2,4-dioxo-3-phenylthieno[2,3-d]pyrimidin-6-yl]phenyl]-3-methoxyurea
CAS Number	308831-61-0
PubChem CID	3038517
ChemSpider	2302081
UNII	56S17Z6X9M
Chemical and physical data
Formula	C₃₆H₃₁F₂N₅O₄S
Molar mass	667.724246 g/mol
3D model (JSmol)	Interactive image
SMILES CN(CC1=CC=CC=C1)CC2=C(SC3=C2C(=O)N(C(=O)N3CC4=C(C=CC=C4F)F)C5=CC=CC=C5)C6=CC=C(C=C6)NC(=O)NOC
InChI 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) Key:UCQSBGOFELXYIN-UHFFFAOYSA-N

Sufugolix (INN, BAN) (developmental code name TAK-013) is a non-peptide, orally-active, selective antagonist of the gonadotropin-releasing hormone receptor (GnRHR) (IC₅₀ = 0.1 and 0.06 nM for affinity and in vitro inhibition, respectively). It was under development by Takeda for the treatment of endometriosis and uterine leiomyoma and reached phase II clinical trials for both of these indications, but was subsequently discontinued.[1] It seems to have been supplanted by relugolix (TAK-385), which is also under development by Takeda for the treatment of these conditions and has a more favorable drug profile (including reduced inhibition and improved in vivo GnRHR antagonistic activity) in comparison.

Oral administration of sufugolix at a dose of 30 mg/kg to castrated male cynomolgus monkeys resulted in nearly complete suppression of luteinizing hormone levels. The duration of action was more than 24 hours, indicating a long half-life of the drug. The suppressive effects of sufugolix on gonadotropin and sex hormone levels are rapidly reversible with discontinuation.

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