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17α-Bromoprogesterone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
17α-Bromoprogesterone
Clinical data
Other names17α-BP; 17α-Bromopregn-4-ene-3,20-dione
Drug classProgestogen;Progestin
Identifiers
  • (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
PubChemCID
ChemSpider
UNII
Chemical and physical data
FormulaC21H29BrO2
Molar mass393.365 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 aprogestin which was first described in 1957 and was never marketed.[1][2][3][4] It is about twice aspotent asprogesterone in terms ofprogestogenic activity in animalbioassays.[1] 17α-BP is aparent compound ofhaloprogesterone (6α-fluoro-17α-bromoprogesterone) and6α-methyl-17α-bromoprogesterone.[5]

See also

[edit]

References

[edit]
  1. ^abEngel 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.
  2. ^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.
  3. ^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.
  4. ^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.
  5. ^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.
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists

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