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Relugolix

CAT: 0804-HY-16474-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-16474-02Size:10 mM - 1 mL
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Description
Relugolix (TAK-385) is a potent, orally active, nonpeptidic gonadotropin-releasing hormone (GnRH) antagonist. Relugolix possesses high affinity and potent antagonistic activity for human receptor (binding IC50=0.33 nM) and monkey receptor (IC50=0.32 nM) compared with TAK-013. Relugolix is used for the study of sex-hormone-dependent diseases, such as including endometriosis, uterine fibroids and prostate cancer et al[2].
CAS Number
737789-87-6
Product Name Alternative
TAK-385
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
GnRH Receptor
Type
Reference compound
Related Pathways
GPCR/G Protein
Applications
Cancer-programmed cell death
Field of Research
Cancer; Endocrinology
Assay Protocol
https://www.medchemexpress.com/Relugolix.html
Purity
99.95
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C(NOC)NC1=CC=C(C(S2)=C(CN(C)C)C(C(N3C4=NN=C(OC)C=C4)=O)=C2N(CC5=C(F)C=CC=C5F)C3=O)C=C1
Molecular Formula
C29H27F2N7O5S
Molecular Weight
623.63
Precautions
H302, H315, H319, H335
References & Citations
[1]Kazuhiro Miwa, et al. 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. doi/10.1021/jm200216q|[2]Daisuke Nakata, et al. Suppression of the hypothalamic-pituitary-gonadal axis by TAK-385 (relugolix), a novel, investigational, orally active, small molecule gonadotropin-releasing hormone (GnRH) antagonist: studies in human GnRH receptor knock-in mice. Eur J Pharmacol. 2014 Jan 15;723:167-74.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Relugolix

Relugolix is a gonadotropin-releasing hormone (GnRH) receptor antagonist used in the treatment of several hormone-responsive conditions. It was first approved in Japan in 2019, under the brand name Relumina, for the symptomatic treatment of uterine fibroids, and more recently by the United States' FDA in 2020, under the brand name Orgovyx, for the treatment of advanced prostate cancer. This branded product was later approved by the European Commission on April 29, 2022. Relugolix has also been studied in the symptomatic treatment of endometriosis. Relugolix is the first (and currently only) orally-administered GnRH receptor antagonist approved for the treatment of prostate cancer - similar therapies such as [degarelix] require subcutaneous administration - and therefore provides a less burdensome therapeutic option for patients who might otherwise require clinic visits for administration by healthcare professionals. In addition to its relative ease-of-use, relugolix was shown to be superior in the depression of testosterone levels when compared to [leuprolide], another androgen deprivation therapy used in the treatment of prostate cancer. In May 2021, the FDA approved the combination product made up of relugolix, [estradiol], and [norethindrone] under the market name Myfembree for the first once-daily treatment for the management of heavy menstrual bleeding associated with uterine fibroids in premenopausal women.

CAS Number737789-87-6
PubChem CID10348973
IUPAC Name1-[4-[1-[(2,6-difluorophenyl)methyl]-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxothieno[2,3-d]pyrimidin-6-yl]phenyl]-3-methoxyurea
Molecular FormulaC29H27F2N7O5S
Molecular Weight623.6
XLogP3.2
Topological Polar Surface Area157
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count11
Rotatable Bond Count9
Heavy Atom Count44
Formal Charge0
Complexity1010
SMILES
CN(C)CC1=C(SC2=C1C(=O)N(C(=O)N2CC3=C(C=CC=C3F)F)C4=NN=C(C=C4)OC)C5=CC=C(C=C5)NC(=O)NOC
InChI
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)
InChIKey
AOMXMOCNKJTRQP-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Relugolix
CAS: 737789-87-6
CID: 10348973
Formula: C29H27F2N7O5S
MW: 623.6
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight623.6
XLogP33.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count11
Rotatable Bond Count9
Exact Mass623.17624448
Monoisotopic Mass623.17624448
Topological Polar Surface Area157 Ų
Heavy Atom Count44
Formal Charge0
Complexity1010
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes