Progesterone 3-acetyl enol ether

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Progesterone 3-acetyl enol ether
Progesterone 3-acetyl enol ether.svg
Clinical data
Synonyms Progesterone 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
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C23H32O3
Molar mass 356.506 g/mol
3D model (JSmol)

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]

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]

See also[edit]

References[edit]

  1. ^ https://chem.nlm.nih.gov/chemidplus/sid/0004954067
  2. ^ a b c Lutwak-Mann C, Adams CE (April 1957). "Carbonic anhydrase in the female reproductive tract. II. Endometrial carbonic anhydrase as indicator of luteoid potency: correlation with progestational proliferation". J. Endocrinol. 15 (1): 43–55. doi:10.1677/joe.0.0150043. PMID 13439082. 
  3. ^ a b Pincus G, Miyake T, Merrill AP, Longo P (November 1957). "The bioassay of progesterone". Endocrinology. 61 (5): 528–33. doi:10.1210/endo-61-5-528. PMID 13480263. 
  4. ^ Ralph I. Dorfman (3 February 2016). Bioassay. Elsevier. pp. 153–. ISBN 978-1-4832-7276-4. 
  5. ^ Rao, P. N., & Edwards, B. E. (1967). U.S. Patent No. 3,321,495. Washington, DC: U.S. Patent and Trademark Office.
  6. ^ Gaunt R, Steinetz BG, Chart JJ (1968). "Pharmacologic alteration of steroid hormone functions". Clin. Pharmacol. Ther. 9 (5): 657–81. doi:10.1002/cpt196895657. PMID 4175595. An interesting substance which has received little attention is the 3-cyclopentyl enol ether of progesterone (quingestrone). [...] 
  7. ^ Junkermann H, Runnebaum B, Lisboa BP (July 1977). "New progesterone metabolites in human myometrium". Steroids. 30 (1): 1–14. doi:10.1016/0039-128X(77)90131-3. PMID 919010. In the Clauberg bioassay the 3β-hydroxy-4-pregnen-20-one shows about the same potency as progesterone (34). In regard to the biological activity of the 3α epimer no data are available.