From Wikipedia, the free encyclopedia
Chemical compound
17α-Bromoprogesterone
Other names 17α-BP; 17α-Bromopregn-4-ene-3,20-dione
Drug class
Progestogen ;
Progestin
(8R ,9S ,10R ,13S ,14S ,17R )-17-Acetyl-17-bromo-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H -cyclopenta[a ]phenanthren-3-one
CAS Number
PubChem
CID
UNII
Formula C 21 H 29 Br O 2
Molar mass 393.365 g·mol−1 3D model (
JSmol )
CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)Br
InChI=1S/C21H29BrO2/c1-13(23)21(22)11-8-18-16-5-4-14-12-15(24)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1
Key:IENASMFTJRLBJP-CEGNMAFCSA-N
17α-Bromoprogesterone (17α-BP ) is a
progestin which was first described in 1957 and was never marketed.
[1]
[2]
[3]
[4] It is about twice as
potent as
progesterone in terms of
progestogenic activity in animal
bioassays .
[1] 17α-BP is a
parent compound of
haloprogesterone (6α-fluoro-17α-bromoprogesterone) and
6α-methyl-17α-bromoprogesterone .
[5]
See also
References
^
a
b Engel CR, Jahnke H (November 1957). "Steroids and related products. X. 17 alpha-Bromoprogesterone, a new potent gestogen". Canadian Journal of Biochemistry and Physiology . 35 (11): 1047–1055.
doi :
10.1139/o57-120 .
PMID
13479803 .
^ Seeley DH, Wang WY, Salhanick HA (November 1982).
"Molecular interactions of progesterone analogues with rabbit uterine cytoplasmic receptor" . The Journal of Biological Chemistry . 257 (22): 13359–13366.
doi :
10.1016/S0021-9258(18)33456-2 .
PMID
7142152 .
^ Bohl M, Simon Z, Vlad A, Kaufmann G, Ponsold K (1987).
"MTD calculations on quantitative structure-activity relationships of steroids binding to the progesterone receptor" . Zeitschrift für Naturforschung C . 42 (7–8): 935–940.
doi :
10.1515/znc-1987-7-834 .
PMID
2961153 .
S2CID
22962904 .
^ Simon Z, Bohl M (1992). "Structure-activity Relations in Gestagenic Steroids by the MTD Method. The Case of Hard Molecules and Soft Receptors". Quantitative Structure-Activity Relationships . 11 (1): 23–28.
doi :
10.1002/qsar.19920110104 .
ISSN
0931-8771 .
^ Elks J (14 November 2014).
The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer. pp. 179, 620.
ISBN
978-1-4757-2085-3 .
PR Tooltip Progesterone receptor
Agonists
Testosterone derivatives: Progestins:
6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
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Norethisterone esters (e.g.,
norethisterone acetate ,
norethisterone enanthate )
Noretynodrel
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Norgestimate
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Norgestrienone
Norvinisterone
Oxendolone
Quingestanol
Quingestanol acetate
Tibolone
Tigestol
Tosagestin ; Anabolic–androgenic steroids:
11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
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Bolandione
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RU-2309
Tetrahydrogestrinone
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Trendione
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Mixed (
SPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor (
PAQR Tooltip Progestin and adipoQ receptor )