DU-41165

Today we are going to talk about DU-41165, a topic that has captured the attention of many people in recent times. DU-41165 is a topic that covers several aspects and can be interpreted in different ways depending on the approach given to it. From its impact on society to its relevance in history, DU-41165 has aroused widespread interest and that is why we want to delve into this topic in order to better understand it and be aware of all the implications it entails.

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
  • phenanthren-17-yl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H29FO4
Molar mass400.490 g·mol−1
3D model (JSmol)
  • CC(=O)1(C(=C)C21(CC32C=C(C4=CC(=O)CC34C)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

  1. ^ 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.
  2. ^ a b Pinney KG, Carlson KE, Katzenellenbogen JA (February 1990). "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.