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| Clinical data | |
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| Other names | 1,2β-Methylene-6-fluoro-17α-acetoxy-δ6-retroprogesterone; 6-Fluoro-17α-hydroxy-1,2β-methylene-9β,10α-pregna-4,6-diene-3,20-dione 17α-acetate; 6-Fluoro-1,2β-methylene-3,20-dioxo-9β,10α-pregna-4,6-dien-17α-yl acetate; (1α,2α,9β,10α)-17-Acetoxy-6-fluoro-1,2-dihydro-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione |
| Routes of administration | By mouth |
| Drug class | Progestin;Progestogen |
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| CAS Number | |
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| Chemical and physical data | |
| Formula | C24H29FO4 |
| Molar mass | 400.490 g·mol−1 |
| 3D model (JSmol) | |
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DU-41164, also known as1,2β-methylene-6-fluoro-17α-acetoxy-δ6-retroprogesterone, is aprogestin which was developed byPhilips-Duphar in the 1970s and was never marketed.[1][2][3][4][5] It is a combinedderivative of17α-hydroxyprogesterone andretroprogesterone.[1][2][3][4] The drug shows extremely highpotency as a progestogen in animals; it was reported to possess 500 times theaffinity ofprogesterone for theprogesterone receptor expressed in rabbituterus (Ki = 0.87 pM and 0.41 nM, respectively), and showed 600 times the progestogenic potency ofsubcutaneous progesterone when givenorally in animals.[1][2] The affinity of DU-41164 for the progesterone receptor was described in 1974 as "probably the highest reported for any steroid-receptor interaction".[2] The drug showed noandrogenic,anabolic,antiandrogenic,estrogenic, orcorticosteroid activity in animals.[3] Although highly potent in animals, DU-41164 produced little or no progestogenic effect at dosages of 50 and 200 μg/day in women, suggesting major species differences.[3] A closely related compound,DU-41165, has been developed as aphotoaffinity label for the progesterone receptor.[3]
