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Chemical compound
DU-41165 Other names 6-Fluoro-16-methylene-17α あるふぁ -acetoxy-δ でるた 6 -retroprogesterone; 6-Fluoro-16-methylene-17α あるふぁ -hydroxy-9β べーた ,10α あるふぁ -pregna-4,6-diene-3,20-dione 17α あるふぁ -acetate; 6-Fluoro-16-methylene-3,20-dioxo-9β べーた ,10α あるふぁ -pregna-4,6-dien-17α あるふぁ -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 あるふぁ -acetoxy-δ でるた 6 -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 あるふぁ -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 μ みゅー g/day in women, suggesting major species differences.[ 1] DU-41165 has been studied as a potential photoaffinity label for the progesterone receptor.[ 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 .
^ 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 .
AR Tooltip Androgen receptor
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GPRC6A
GR Tooltip Glucocorticoid receptor
PR Tooltip Progesterone receptor
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Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone
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Mixed (SPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor (PAQR Tooltip Progestin and adipoQ receptor )