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DU-41165

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
DU-41165
Clinical data
Other names6-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 classProgestin;Progestogen
Identifiers
  • [(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
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC24H29FO4
Molar mass400.490 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 as6-fluoro-16-methylene-17α-acetoxy-δ6-retroprogesterone, is aprogestin which was developed byPhilips-Duphar in the 1970s and was never marketed.[1][2] It is a combinedderivative of17α-hydroxyprogesterone andretroprogesterone.[1][2] The drug shows extremely highpotency as a progestogen in animals.[1] It has been found to possess 158% of therelative binding affinity ofpromegestone for theprogesterone receptor expressed in rat uterus (relative to 74% for the closely related progestinDU-41164).[1] DU-41165 also showed 28% of the affinity ofRU-28362 for theglucocorticoid receptor expressed in ratliver, but no affinity for themineralocorticoid receptor expressed in ratkidney (<0.003% of that ofRU-26752).[1] The drug showed noandrogenic,anabolic, orestrogenic activity in animals, but did show someantiandrogenic andglucocorticoid 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 potentialphotoaffinity label for the progesterone receptor.[1]

References

[edit]
  1. ^abcdefghMorsink 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.
  2. ^abPinney 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.


ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
GRTooltip Glucocorticoid receptor
Agonists
Mixed
(SEGRMsTooltip Selective glucocorticoid receptor agonists)
Antagonists
Others
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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