Progesterone 3-acetyl enol ether

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Progesterone 3-acetyl enol ether

Progesterone 3-acetyl enol ether, also known as progesterone acetate,[1] as well as 3-acetoxypregna-3,5-dien-20-one, is a progestin which was never marketed.[2][3][4][5] It was reported to possess similar potency to progesterone and hydroxyprogesterone caproate in the rabbit endometrial carbonic anhydrase test, a bioassay of progestogenic activity.[2][3] In addition, it was able to maintain pregnancy in animals.[2] Progesterone 3-acetyl enol ether is closely related to quingestrone, which is also known as progesterone 3-cyclopentyl enol ether and was formerly marketed as an oral contraceptive.[6]

Quick Facts Clinical data, Other names ...
Progesterone 3-acetyl enol ether
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Clinical data
Other namesProgesterone acetate; Progesterone 3-acetate; 3-Acetoxypregna-3,5-diene-20-one; 20-Oxopregna-3,5-dien-3-yl acetate; 3,5-Progesterol acetate; NSC-124740
Drug classProgestogen; Progestogen ether
Identifiers
  • [(8S,9S,10R,13S,14S,17S)-17-Acetyl-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC23H32O3
Molar mass356.506 g·mol−1
3D model (JSmol)
  • CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CCC(=C4)OC(=O)C)C)C
  • InChI=1S/C23H32O3/c1-14(24)19-7-8-20-18-6-5-16-13-17(26-15(2)25)9-11-22(16,3)21(18)10-12-23(19,20)4/h5,13,18-21H,6-12H2,1-4H3/t18-,19+,20-,21-,22-,23+/m0/s1
  • Key:YIPYJRPRHUJJDP-WKOLOUIMSA-N
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The 3-acetyl ether may be cleaved from progesterone 3-acetyl enol ether in vivo and, based on its chemical structure, this may result in the transformation of progesterone 3-acetyl enol ether into 3α-dihydroprogesterone and/or 3β-dihydroprogesterone. 3β-Dihydroprogesterone has been reported to possess about the same progestogenic potency as progesterone in the Clauberg test, whereas 3α-dihydroprogesterone was not assessed.[7]

The C3 enol ethers of progesterone are less suited for use via depot injection relative to progestogen esters like hydroxyprogesterone caproate due to their susceptibility to oxidative metabolism.[8]

See also

References

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