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    Norelgestromin

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    FINISHED DOSAGE FORMULATIONS

    RELATED EXCIPIENT COMPANIES

    GLOBAL SALES INFORMATION

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    2D Structure
    Also known as: Levonorgestrel oxime, Norplant 3-oxime, D-norgestrel 3-oxime, 18-methylnorethindrone oxime, 17-deacetylnorgestimate, 53016-31-2
    Molecular Formula
    C21H29NO2
    Molecular Weight
    327.5  g/mol
    InChI Key
    ISHXLNHNDMZNMC-XUDSTZEESA-N
    Norelgestromin is a drug used in contraception. Norelgestromin is the active progestin responsible for the progestational activity that occurs in women after application of ORTHO EVRA patch.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
    2.1.2 InChI
    InChI=1S/C21H29NO2/c1-3-20-11-9-17-16-8-6-15(22-24)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23-24H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
    2.1.3 InChI Key
    ISHXLNHNDMZNMC-XUDSTZEESA-N
    2.1.4 Canonical SMILES
    CCC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=NO)CCC34
    2.1.5 Isomeric SMILES
    CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=NO)CC[C@H]34
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. 17-deacetylnorgestimate

    2. 18,19-dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, Oxime, (17alpha)-

    3. Levonorgestrel Oxime

    4. Levonorgestrel Oxime, (3e,17alpha)-isomer

    5. Levonorgestrel Oxime, (3z,17alpha)-isomer

    6. Lngo

    7. Progestin Norelgestromin

    2.2.2 Depositor-Supplied Synonyms

    1. Levonorgestrel Oxime

    2. Norplant 3-oxime

    3. D-norgestrel 3-oxime

    4. 18-methylnorethindrone Oxime

    5. 17-deacetylnorgestimate

    6. 53016-31-2

    7. 17-deacylnorgestimate

    8. (8r,9s,10r,13s,14s,17r)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol

    9. Deacetylnorgestimate

    10. Norgestimate Metabolite Norelgestromin

    11. Norelgestromin (17-deacetylnorgestimate)

    12. Brn 4202099

    13. Unii-r0tay3x631

    14. Norelgestromin [usan:inn:ban]

    15. Rwj 10553

    16. Levonorgestrel 3-oxime

    17. 17-deacetyl Norgestimate

    18. 18,19-dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, Oxime, (17alpha)-

    19. R0tay3x631

    20. Chembl4791392

    21. Dtxsid9046788

    22. 13-ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one Oxime

    23. Db06713

    24. 18,19-dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, Oxime, (8-alpha,9-beta,10-alpha,13-alpha,14-beta)-

    25. 17-deacylnorgestimate17-deacetyl Norgestimate

    2.3 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 327.5 g/mol
    Molecular Formula C21H29NO2
    XLogP33.6
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count2
    Exact Mass327.219829168 g/mol
    Monoisotopic Mass327.219829168 g/mol
    Topological Polar Surface Area52.8 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity642
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count1
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Norelgestromin is used for contraception and menopausal hormonal therapy. Norelgestromin may potentially be used in breast cancer treatment due to its inhibitory effect on estrone sulfatase . They convert sulfated steroid precursors to estrogen during pregnancy.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Norelgestromin is used for contraception and menopausal hormonal therapy transdermally or in combination with ethinyl estradiol as a vaginal ring. Norelgestromin, in combination with ethinyl estradiol inhibits ovulation by suppressing gonadotropins.

    5.2 MeSH Pharmacological Classification

    Contraceptive Agents, Hormonal

    Contraceptive agents that act on the ENDOCRINE SYSTEM. (See all compounds classified as Contraceptive Agents, Hormonal.)

    5.3 ATC Code

    G03AA13

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    5.4 Mechanism of Action

    Norelgestromin inhibits estrone sulfatase, which converts sulfated steroid precursors to estrogen during pregnancy. Norgelgestromin/ethinylestradiol suppresses follicular development, induces changes to the endometrium, which decreases chances of implantation and thickens the cervical mucus, impeding sperm swimming into the uterus. It also has similar agonisting binding affinities as its parent compound, Norgestimate, for progesterone and estrogen receptors.