DU-41165 Article

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DU-41165
DU-41165.svg
Clinical data
Synonyms6-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
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC24H29FO4
Molar mass400.49 g/mol
3D model ( JSmol)

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). "[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.