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    Chemistry

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    Also known as: 935283-04-8, Linzagolix [inn], Linzagolix [usan], Obe-2109, 7cdw97huex, Obe2109
    Molecular Formula
    C22H15F3N2O7S
    Molecular Weight
    508.4  g/mol
    InChI Key
    BMAAMIIYNNPHAB-UHFFFAOYSA-N
    FDA UNII
    7CDW97HUEX
    Linzagolix
    Linzagolix is an orally bioavailable gonadotropin-releasing hormone (GnRH or LHRH) receptor antagonist, with potential hormone production inhibitory activity. Upon oral administration of linzagolix, this agent competes with GnRH for receptor binding and inhibits GnRH receptor signaling in the anterior pituitary gland, thereby inhibiting the secretion and release of luteinizing hormone (LH) and follicle stimulating hormone (FSH). In males, the inhibition of LH secretion prevents the release of testosterone. As a result, this may relieve symptoms associated with hormonally dependent disease states such as hormone-dependent prostate cancer. In women, this prevents the production of estrogen by the ovaries and may relieve symptoms from sex-hormone dependent diseases, such as pain associated with endometriosis, heavy menstrual bleeding or uterine fibroids.
    1 2D Structure

    Linzagolix

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-[5-[(2,3-difluoro-6-methoxyphenyl)methoxy]-2-fluoro-4-methoxyphenyl]-2,4-dioxo-1H-thieno[3,4-d]pyrimidine-5-carboxylic acid
    2.1.2 InChI
    InChI=1S/C22H15F3N2O7S/c1-32-14-4-3-10(23)18(25)9(14)7-34-16-6-13(11(24)5-15(16)33-2)27-20(28)17-12(26-22(27)31)8-35-19(17)21(29)30/h3-6,8H,7H2,1-2H3,(H,26,31)(H,29,30)
    2.1.3 InChI Key
    BMAAMIIYNNPHAB-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    COC1=C(C(=C(C=C1)F)F)COC2=C(C=C(C(=C2)N3C(=O)C4=C(SC=C4NC3=O)C(=O)O)F)OC
    2.2 Other Identifiers
    2.2.1 UNII
    7CDW97HUEX
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 3-(5-((2,3-difluoro-6-methoxyphenyl)methoxy)-2-fluoro-4-methoxyphenyl)-2,4-dioxo-1h-thieno(3,4-d)pyrimidine-5-carboxylic Acid

    2. Klh-2109

    3. Klh2109

    4. Obe-2109

    5. Obe2109

    2.3.2 Depositor-Supplied Synonyms

    1. 935283-04-8

    2. Linzagolix [inn]

    3. Linzagolix [usan]

    4. Obe-2109

    5. 7cdw97huex

    6. Obe2109

    7. Klh-2109

    8. Klh-2109; Obe-2109

    9. 3-{5-[(2,3-difluoro-6-methoxyphenyl)methoxy]-2-fluoro-4-methoxyphenyl}-2,4-dioxo-1,2,3,4-tetrahydrothieno[3,4-d]pyrimidine-5-carboxylic Acid

    10. Thieno(3,4-d)pyrimidine-5-carboxylic Acid, 3-(5-((2,3-difluoro-6-methoxyphenyl)methoxy)-2-fluoro-4-methoxyphenyl)-1,2,3,4-tetrahydro-2,4-dioxo-

    11. 3-(5-((2,3-difluoro-6-methoxyphenyl)methoxy)-2-fluoro-4-methoxyphenyl)-2,4-dioxo-1,2,3,4-tetrahydrothieno(3,4-d)pyrimidine-5-carboxylic Acid

    12. Linzagolix (usan/inn)

    13. Linzagolix [usan:inn]

    14. Unii-7cdw97huex

    15. Linzagolix [who-dd]

    16. Schembl2333748

    17. Chembl3668014

    18. Bdbm160329

    19. Dtxsid801337395

    20. Bcp30444

    21. Who 10711

    22. Hy-109093

    23. D11608

    24. Us9040693, 233

    25. 3-[5-(2,3-difluoro-6-methoxybenzyloxy)-2-fluoro-4-methoxyphenyl]-2,4-dioxo-1,2,3,4-tetrahydrothieno[3,4-d]pyrimidine-5-carboxylic Acid

    26. 3-[5-[(2,3-difluoro-6-methoxyphenyl)methoxy]-2-fluoro-4-methoxyphenyl]-2,4-dioxo-1h-thieno[3,4-d]pyrimidine-5-carboxylic Acid

    2.4 Create Date
    2007-08-09
    3 Chemical and Physical Properties
    Molecular Weight 508.4 g/mol
    Molecular Formula C22H15F3N2O7S
    XLogP33.4
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count7
    Exact Mass508.05520648 g/mol
    Monoisotopic Mass508.05520648 g/mol
    Topological Polar Surface Area143 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity826
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 ATC Code

    H - Systemic hormonal preparations, excl. sex hormones and insulins

    H01 - Pituitary and hypothalamic hormones and analogues

    H01C - Hypothalamic hormones

    H01CC - Anti-gonadotropin-releasing hormones

    H01CC04 - Linzagolix

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