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Chemical compound
DU-41165
Other names 6-Fluoro-16-methylene-17α-acetoxy-δ6 -retroprogesterone; 6-Fluoro-16-methylene-17α-hydroxy-9β,10α-pregna-4,6-diene-3,20-dione 17α-acetate; 6-Fluoro-16-methylene-3,20-dioxo-9β,10α-pregna-4,6-dien-17α-yl acetate
Routes of administration
By mouth
Drug class
Progestin ;
Progestogen
[(8R ,9R ,10S ,13S ,14S ,17R )-17-Acetyl-6-fluoro-10,13-dimethyl-16-methylidene-3-oxo-1,2,8,9,11,12,14,15-octahydrocyclopenta[a ]phenanthren-17-yl] acetate
CAS Number
PubChem
CID
ChemSpider
UNII
CompTox Dashboard (
EPA )
Formula C 24 H 29 F O 4
Molar mass 400.490 g·mol−1 3D model (
JSmol )
CC(=O)[C@]1(C(=C)C[C@@H]2[C@@]1(CC[C@@H]3[C@H]2C=C(C4=CC(=O)CC[C@@]34C)F)C)OC(=O)C
InChI=1S/C24H29FO4/c1-13-10-19-17-12-21(25)20-11-16(28)6-8-22(20,4)18(17)7-9-23(19,5)24(13,14(2)26)29-15(3)27/h11-12,17-19H,1,6-10H2,2-5H3/t17-,18-,19+,22+,23+,24+/m1/s1
Key:XSSIGSNQDKHHLD-JBARXXBASA-N
DU-41165 , also known as 6-fluoro-16-methylene-17α-acetoxy-δ6 -retroprogesterone , is a
progestin which was developed by
Philips-Duphar in the 1970s and was never marketed.
[1]
[2] It is a combined
derivative of
17α-hydroxyprogesterone and
retroprogesterone .
[1]
[2] The drug shows extremely high
potency as a progestogen in animals.
[1] It has been found to possess 158% of the
relative binding affinity of
promegestone for the
progesterone receptor expressed in rat uterus (relative to 74% for the closely related progestin
DU-41164 ).
[1] DU-41165 also showed 28% of the affinity of
RU-28362 for the
glucocorticoid receptor expressed in rat
liver , but no affinity for the
mineralocorticoid receptor expressed in rat
kidney (<0.003% of that of
RU-26752 ).
[1] The drug showed no
androgenic ,
anabolic , or
estrogenic activity in animals, but did show some
antiandrogenic and
glucocorticoid activity at high doses.
[1] Although highly potent in animals, DU-41165 produced little or no progestogenic effect at dosages of 50 and 200 μg/day in women, suggesting major species differences.
[1] DU-41165 has been studied as a potential
photoaffinity label for the progesterone receptor.
[1]
References
^
a
b
c
d
e
f
g
h Morsink L, de Wachter AM, Brenner P, Cekan SZ, Guerrero R, Hagenfeldt K, Diczfalusy E (May 1976). "Endocrine effects of two new retro-steroids in animal models and in women". Acta Endocrinol . 82 (1): 193–212.
doi :
10.1530/acta.0.0820193 .
PMID
57688 .
^
a
b Pinney KG, Carlson KE, Katzenellenbogen JA (February 1990). "[3H]DU41165: a high affinity ligand and novel photoaffinity labeling reagent for the progesterone receptor". J. Steroid Biochem . 35 (2): 179–89.
doi :
10.1016/0022-4731(90)90272-T .
PMID
2308335 .
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