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Abandoned drugs
Bromoketoprogesterone
Другие языки:

    Bromoketoprogesterone

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    Bromoketoprogesterone
    Braxarone.svg
    Clinical data
    Trade names Braxarone
    Other names BKP; BOP; NSC-15990; 9α-Bromo-11-oxoprogesterone; Braxarone; Bromo-oxy-progesterone; BOP; 9α-Bromopregn-4-en-3,11,20-trione; Bromopregnenetrione
    Routes of
    administration    		 By mouth
    Identifiers
    • (8S,10S,13S,14S,17S)-17-Acetyl-9-bromo-10,13-dimethyl-1,2,6,7,8,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,11-dione
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    ChEBI
    Chemical and physical data
    Formula C21H27BrO3
    Molar mass 407.348 g·mol−1
    3D model (JSmol)
    • CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC(=O)C3([C@H]2CCC4=CC(=O)CC[C@@]43C)Br)C
    • InChI=1S/C21H27BrO3/c1-12(23)15-6-7-16-17-5-4-13-10-14(24)8-9-20(13,3)21(17,22)18(25)11-19(15,16)2/h10,15-17H,4-9,11H2,1-3H3/t15-,16+,17+,19-,20+,21?/m1/s1
    • Key:NWFOHSCPTMLQIH-WHJJYKQUSA-N

    Bromoketoprogesterone (BKP), also known as 9α-bromo-11-oxoprogesterone (BOP), and known by the tentative brand name Braxarone (Squibb), is an orally active progestin which does not appear to have been marketed.

    Pharmacology

    Pharmacodynamics

    Whereas 11-ketoprogesterone and 11β-hydroxyprogesterone are virtually devoid of progestogenic activity (although 11β-hydroxyprogesterone has been reported to possess about 1% of the progestogenic activity of progesterone), the progestogenic activity of BKP is restored and is in fact relatively high. In contrast, 9α-fluoro-11β-hydroxyprogesterone has much lower progestogenic activity with only about 8 times that of 11β-hydroxyprogesterone. In addition, whereas 9α-fluoro-11β-hydroxyprogesterone has pronounced mineralocorticoid effects, BKP lacks such effects.

    BKP has been described as a weaker progestogen. It has been used at doses of as much as 300 mg orally per day.

    In addition to its activity as a progestogen, BKP has glucocorticoid activity.

    Pharmacokinetics

    The pharmacokinetics of BKP have been reviewed.

    Chemistry

    Synthesis

    Chemical syntheses of BKP have been published.

    History

    It was developed in the 1950s and, along with the testosterone derivatives ethisterone, norethisterone, normethandrone, and norethandrolone and the progesterone derivative hydroxyprogesterone acetate, was one of the first orally active progestogens to be developed. Similarly to various other progestogens, BKP has been studied in the treatment of breast cancer in women. Evaluated in 1959, it was the first oral progestin to be found effective in the treatment of breast cancer. It induced regression in 20% of women with advanced breast cancer at a dosage of 300 mg/day orally.

    See also


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