17α-Bromoprogesterone

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]

17α-Bromoprogesterone

Clinical data
Other names	17α-BP; 17α-Bromopregn-4-ene-3,20-dione
Drug class	Progestogen; Progestin
Identifiers
IUPAC name (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	28449-24-3
PubChem CID	68524848
Chemical and physical data
Formula	C21H29BrO2
Molar mass	393.365 g·mol^−1
3D model (JSmol)	Interactive image
SMILES 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 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

See also

• 17α-Hydroxyprogesterone
• 17α-Methylprogesterone
• 19-Norprogesterone

References

1. Engel CR, Jahnke H (November 1957). "Steroids and related products. X. 17 alpha-Bromoprogesterone, a new potent gestogen". Can J Biochem Physiol. 35 (11): 1047–55. 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". J. Biol. Chem. 257 (22): 13359–66. 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". Z. Naturforsch. C. 42 (7–8): 935–40. doi:10.1515/znc-1987-7-834. PMID 2961153.
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. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 179, 620. ISBN 978-1-4757-2085-3.