Cannabaceae

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DU-41164
Clinical data
Other names1,2β-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 classProgestin; Progestogen
Identifiers
  • (2aS,3aR,3bR,3cR,5aS,6R,8aS,8bR)-6-Acetyl-10-fluoro-3b,5a-dimethyl-2-oxo-2,2a,3,3a,3b,3c,4,5,5a,6,7,8,8a,8b-tetradecahydrocyclopenta[a]cyclopropa[g]phenanthren-6-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)[C@]1(CC[C@@H]2[C@@]1(CC[C@@H]3[C@H]2C=C(C4=CC(=O)[C@H]5C[C@H]5[C@@]34C)F)C)OC(=O)C
  • InChI=1S/C24H29FO4/c1-12(26)24(29-13(2)27)8-6-16-14-10-20(25)19-11-21(28)15-9-18(15)23(19,4)17(14)5-7-22(16,24)3/h10-11,14-18H,5-9H2,1-4H3/t14-,15-,16-,17+,18+,22-,23+,24-/m0/s1
  • Key:WJSHHKQEKQVLOP-QHAUNDHQSA-N

DU-41164, also known as 1,2β-methylene-6-fluoro-17α-acetoxy-δ6-retroprogesterone, is a progestin which was developed by Philips-Duphar in the 1970s and was never marketed.[1][2][3][4][5] It is a combined derivative of 17α-hydroxyprogesterone and retroprogesterone.[1][2][3][4] The drug shows extremely high potency as a progestogen in animals; it was reported to possess 500 times the affinity of progesterone for the progesterone receptor expressed in rabbit uterus (Ki = 0.87 pM and 0.41 nM, respectively), and showed 600 times the progestogenic potency of subcutaneous progesterone when given orally 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 no androgenic, anabolic, antiandrogenic, estrogenic, or corticosteroid 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 a photoaffinity label for the progesterone receptor.[3]

References[edit]

  1. ^ a b c Halkes SJ, Hartog J, Morsink L, de Wachter AM (December 1972). "Investigations on sterols. 38. Synthesis of 1,2β-methylene-17α-acetoxy-9β,10α-pregnanes, a class of potent progestational agents". J. Med. Chem. 15 (12): 1288–92. doi:10.1021/jm00282a022. PMID 4635976.
  2. ^ a b c d Terenius L (June 1974). "Affinities of progestogen and estrogen receptors in rabbit uterus for synthetic progestogens". Steroids. 23 (6): 909–919. doi:10.1016/0039-128X(74)90063-4. PMID 4134774.
  3. ^ a b c d e 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.
  4. ^ 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.
  5. ^ AdrainD. Nunn (27 April 2018). Radiopharmaceuticals: Chemistry and Pharmacology. CRC Press. pp. 1–. ISBN 978-1-351-41989-5.


source: https://en.wikipedia.org/wiki/DU-41164

One thought on “Cannabaceae”

  1. Well, that’s interesting to know that Psilotum nudum are known as whisk ferns. Psilotum nudum is the commoner species of the two. While the P. flaccidum is a rare species and is found in the tropical islands. Both the species are usually epiphytic in habit and grow upon tree ferns. These species may also be terrestrial and grow in humus or in the crevices of the rocks.
    View the detailed Guide of Psilotum nudum: Detailed Study Of Psilotum Nudum (Whisk Fern), Classification, Anatomy, Reproduction

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