Bromoketoprogesterone
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| 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 | |
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JSmol) | |
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Bromoketoprogesterone (BKP), also known as 9α-bromo-11-oxoprogesterone (BOP), and known by the tentative brand name Braxarone (
Pharmacology
Pharmacodynamics
Whereas
BKP has been described as a weaker progestogen.[8] It has been used at doses of as much as 300 mg orally per day.[9][8]
In addition to its activity as a progestogen, BKP has glucocorticoid activity.[9]
Pharmacokinetics
The pharmacokinetics of BKP have been reviewed.[10]
Chemistry
Synthesis
Chemical syntheses of BKP have been published.[10]
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.[3] Similarly to various other progestogens, BKP has been studied in the treatment of breast cancer in women.[11][12][9]: 185 Evaluated in 1959, it was the first oral progestin to be found effective in the treatment of breast cancer.[12][13][14][9] It induced regression in 20% of women with advanced breast cancer at a dosage of 300 mg/day orally.[9]
See also
References
- ISBN 978-3-527-30247-5.
- PMID 13583825.
- ^ PMID 13477602.
- PMID 13640942.
- ^ Applezweig N (1962). Steroid Drugs. Blakiston Division, McGraw-Hill. p. 444.
- ^ Veterinary Medicine. American Veterinary Publishing Company. 1953.
Ketogestin [(11-ketoprogesterone)] is devoid of androgenic, estrogenic, or progestational activity and is nontoxic in amounts greatly exceeding pharmacological dosage.
- ^ a b Hoffmann-Ostenhof O (1959). Proceedings of the Fourth International Congress of Biochemistry, Vienna, 1-6 September, 1958. and. p. 269.
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.
- ^ ISBN 978-3-662-25301-4.
- ^ ISBN 978-3-642-65806-8.
Halogenated progestogens have also been studied in patients with breast cancer. 9α-Bromo-11-oxoprogesterone (bromoketoprogesterone) given in a dose of 300 mg orally daily in patients with advanced breast cancer induced a 20 % regression rate. Regression of cancer occurs mainly in soft tissue and osseous metastases. [...] Both of these progestational compounds possess corticoid activity, particularly oxylone acetate, which, in 50 mg doses, causes Cushingoid symptoms, hypertension, and osteoporosis. On withdrawal of the drug, vaginal bleeding occurs frequently. [...] Progesterone-like compounds with glucocorticoid activity, such as oxylone, induce severe Cushingoid symptoms such as plethora, moonface, glycosuria, marked weight gain, and hypertension, requiring discontinuation of the drug.
- ^ ISBN 978-3-642-99941-3.
- ISBN 978-3-642-65806-8.
- ^ PMID 13663018.
- PMID 2908605.
- PMID 7272894.