| 词条 | Bromoketoprogesterone |
| 释义 |
| Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = (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 | image = Braxarone.svg | width = 225px | tradename = Braxarone | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = By mouth | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 2527-11-9 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 197766 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 196517 | UNII = | KEGG = | ChEBI = 34585 | ChEMBL = | synonyms = BKP; BOP; NSC-15990; 9α-Bromo-11-oxoprogesterone; Braxarone; Bromo-oxy-progesterone; BOP; 9α-Bromopregn-4-en-3,11,20-trione; Bromopregnenetrione | C=21 | H=27 | Br=1 | O=3 | SMILES = CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC(=O)C3([C@H]2CCC4=CC(=O)CC[C@@]43C)Br)C | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = NWFOHSCPTMLQIH-WHJJYKQUSA-N }}Bromoketoprogesterone (BKP), also known as 9α-bromo-11-oxoprogesterone (BOP), also known as Braxarone (Squibb), is an orally active progestin.[1][2][3][4][5] 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.[3] Similarly to various other progestogens, BKP has been studied in the treatment of breast cancer in women.[6][7] Evaluated in 1959, it was the first oral progestin to be found effective in the treatment of breast cancer.[7][8][9] PharmacologyPharmacodynamicsWhereas 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.[10][11] In contrast, 9α-fluoro-11β-hydroxyprogesterone has much lower progestogenic activity with only about 8 times that of 11β-hydroxyprogesterone.[11] In addition, whereas 9α-fluoro-11β-hydroxyprogesterone has pronounced mineralocorticoid effects, BKP lacks such effects.[3] BKP has been described as a weaker progestogen.[12] It has been used at doses of up to 150 mg orally per day.[12] PharmacokineticsThe pharmacokinetics of BKP have been reviewed.[18] ChemistrySynthesisChemical syntheses of BKP have been published.[13]See also
References1. ^{{cite book|author1=Martin Negwer|author2=Hans-Georg Scharnow|title=Organic-chemical drugs and their synonyms: (an international survey)|url=https://books.google.com/books?id=zmpqAAAAMAAJ|year=2001|publisher=Wiley-VCH|isbn=978-3-527-30247-5|page=2134}} {{Progesterone receptor modulators}}{{DEFAULTSORT:Bromo-11-ketoprogesterone, 9α-}}{{Steroid-stub}}{{Genito-urinary-drug-stub}}2. ^{{cite journal | vauthors = TYLER ET, OLSON HJ | title = Clinical use of new progestational steroids in fertility | journal = Ann. N. Y. Acad. Sci. | volume = 71 | issue = 5 | pages = 704–9 | year = 1958 | pmid = 13583825 | doi = | url = }} 3. ^1 2 {{cite journal | vauthors = WIED GL, DAVIS ME | title = 9 alpha-Bromo-11-ketoprogesterone; another new orally effective substance with progestational activity | journal = Obstet Gynecol | volume = 10 | issue = 4 | pages = 411–7 | year = 1957 | pmid = 13477602 | doi = | url = }} 4. ^{{cite journal|last1=Tyler|first1=Edward T.|title=FERTILITY PROMOTING AND INHIBITING EFFECTS OF NEW STEROID HORMONAL SUBSTANCES|journal=Journal of the American Medical Association|volume=169|issue=16|year=1959|pages=1843|issn=0002-9955|doi=10.1001/jama.1959.03000330015003}} 5. ^{{cite book|author=Norman Applezweig|title=Steroid Drugs|url=https://books.google.com/books?id=h-1sAAAAMAAJ|year=1962|publisher=Blakiston Division, McGraw-Hill|page=444}} 6. ^{{cite book|author1=Alan C. Sartorelli|author2=David G. Johns|title=Antineoplastic and Immunosuppressive Agents|url=https://books.google.com/books?id=aU_oCAAAQBAJ&pg=PA185|date=27 November 2013|publisher=Springer Science & Business Media|isbn=978-3-642-65806-8|pages=185–}} 7. ^1 {{cite journal | vauthors = GOLDENBERG IS, HAYES MA | title = Hormonal therapy of metastatic female breast carcinoma. I. 9 alpha-Bromo-11-ketoprogesterone | journal = Cancer | volume = 12 | issue = 4 | pages = 738–40 | year = 1959 | pmid = 13663018 | doi = | url = }} 8. ^{{cite journal | vauthors = Carpenter JT | title = Progestational agents in the treatment of breast cancer | journal = Cancer Treat. Res. | volume = 39 | issue = | pages = 147–56 | date = 1988 | pmid = 2908605 | doi = | url = }} 9. ^{{cite journal | vauthors = Kaufman RJ | title = Advanced breast cancer - additive hormonal therapy | journal = Cancer | volume = 47 | issue = 10 | pages = 2398–403 | date = May 1981 | pmid = 7272894 | doi = | url = }} 10. ^{{cite book|title=Veterinary Medicine|url=https://books.google.com/books?id=PVQmAQAAMAAJ|year=1953|publisher=American Veterinary Publishing Company|quote=Ketogestin [(11-ketoprogesterone)] is devoid of androgenic, estrogenic, or progestational activity and is nontoxic in amounts greatly exceeding pharmacological dosage.}} 11. ^1 {{cite book|author=Otto Hoffmann-Ostenhof|title=Proceedings of the Fourth International Congress of Biochemistry, Vienna, 1-6 September, 1958|url=https://books.google.com/books?id=250hAQAAMAAJ|year=1959|publisher=and|page=269|quote=In addition, it had been previously reported that 11β-hydroxyprogesterone was devoid of progestational action. However, we found that it does possess about 1% of the activity of progesterone. This trace activity is substantially enhanced by fluorination, since 9α-fluoro-11β-hydroxyprogesterone is eight times as active as the non-halogenated analogue.6 Concomitantly, Fried et al.7 described the relatively high progestational activity of 9α-bromo-11-ketoprogesterone as well.}} 12. ^1 {{cite book|author1=Henryk Nowakowski|author2=Deutsche Gesellschaft für Endokrinologie|title=Moderne Entwicklungen auf dem Gestagengebiet: Hormone in der Veterinärmedizin|url=https://books.google.com/books?id=ms-1BgAAQBAJ&pg=PA65|date=2 July 2013|publisher=Springer-Verlag|isbn=978-3-662-25301-4|pages=65–}} 13. ^1 {{cite book|title=Die Gestagene|url=https://books.google.com/books?id=t8GpBgAAQBAJ&pg=PA9|date=27 November 2013|publisher=Springer-Verlag|isbn=978-3-642-99941-3|pages=9–,276}} 5 : Abandoned drugs|Organobromides|Pregnanes|Progestogens|Triketones |
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