Chemistry:Gestonorone acetate

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Short description: Chemical compound
Gestonorone acetate
Gestonorone acetate.svg
Clinical data
Other namesGestronol acetate; Norhydroxyprogesterone acetate; 17α-Hydroxy-19-norprogesterone 17α-acetate; 17α-Acetoxy-19-norprogesterone; 17α-Hydroxy-19-norpregn-4-ene-3,20-dione 17α-acetate
Drug classProgestin; Progestogen
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC22H30O4
Molar mass358.478 g·mol−1
3D model (JSmol)

Gestonorone acetate, or gestronol acetate, also known as norhydroxyprogesterone acetate, is a progestin of the 19-norprogesterone and 17α-hydroxyprogesterone groups which was developed in the early 1960s but was never marketed.[1][2][3][4][5][6][7][8][9][10][11][12][13][14] It is the C17α acetate ester of gestronol (17α-hydroxy-19-norprogesterone).

Gestonorone acetate has been found to consistently inhibit ovulation at an oral dosage of 10 mg/day in combination with 50 μg/day oral ethinylestradiol.[15] Weak or no endometrial effects were observed at an oral dosage of 100 mg/day, basal vacuoles appeared at 130 to 140 mg/day, and full endometrial secretory transformation occurred at 220 mg/day.[16]

See also

References

  1. ↑ "Steroids. XX. Hydrolysis of steroidal esters by malt enzyme. 1. Selective hydrolysis of steroidal acetates". Yakugaku Zasshi 81 (3): 369–373. 1961. doi:10.1248/yakushi1947.81.3_369. ISSN 0031-6903. 
  2. ↑ "Steroids. XXIII Hydrolysis of steroidal esters by malt enzyme. 4. Synthesis of 17α,19-dihydroxyprogesterone and 17α-hydroxy-19-norprogesterone". Yakugaku Zasshi 81 (3): 381–384. 1961. doi:10.1248/yakushi1947.81.3_381. ISSN 0031-6903. 
  3. ↑ "Steroid anti-estrogens". Steroids 1 (2): 185–209. 1963. doi:10.1016/S0039-128X(63)80136-1. ISSN 0039-128X. 
  4. ↑ "Pregnancy-maintaining effect of synthetic progestogens in the rat". Acta Endocrinologica 42 (4): 533–536. April 1963. doi:10.1530/acta.0.0420533. PMID 13979052. 
  5. ↑ "Steroids. CXCVI. 19-Norsteroids. III. Synthesis of 19-norprogesterones". Helvetica Chimica Acta 46: 1017–1029. 1963. doi:10.1002/hlca.19630460332. ISSN 0018-019X. 
  6. ↑ "[Experimental viewpoints in the testing of synthetic gestagens]". Deutsche Medizinische Wochenschrift 88 (13): 629–638. March 1963. doi:10.1055/s-0028-1111990. PMID 13958089. 
  7. ↑ "Orally active steroidal ovulation inhibitors in the adult estrus rabbit". Steroids 2 (5): 521–525. 1963. doi:10.1016/0039-128X(63)90029-1. ISSN 0039-128X. 
  8. ↑ "Inhibition of ovulation by steroids". Journal of the Egyptian Medical Association 1962-1963: 67–73. 1963. ISSN 0013-2411. 
  9. ↑ "The pharmacology of new gestational and anabolic steroids". Deutsch-Englische Medizinische Rundschau 1 (4): 385–399. 1962. ISSN 0003-3332. 
  10. ↑ "Relationship Between Progestational Activity and Chemical Structure of Synthetic Steroids". The Journal of Endocrinology 30 (2): 159–170. September 1964. doi:10.1677/joe.0.0300159. PMID 14207040. 
  11. ↑ "Inhibition of ovulation determined by estimation of pregnanediol excretion". International Journal of Fertility 9: 57–67. 1964. PMID 14106269. https://www.popline.org/node/473877. 
  12. ↑ "[The effect of various gestagens on the development of the fetus and rate of mortality in animal experiments]". Archiv Fur Gynakologie 204 (1): 68–77. 1967. doi:10.1007/BF00668265. PMID 5630697. 
  13. ↑ "The progestational and anti-estrogenic activities of some novel 11beta-substituted steroids". Steroids 23 (4): 585–602. April 1974. doi:10.1016/0039-128X(74)90010-5. PMID 4829347. 
  14. ↑ "Stereoselective asymmetric synthesis and characterization of 17α-acetyoxy-19-nor-progesterone". Journal of Central South University of Technology 11 (3): 300–303. 2004. doi:10.1007/s11771-004-0061-y. ISSN 1005-9784. 
  15. ↑ The Control of Fertility. Elsevier. 3 September 2013. pp. 222–. ISBN 978-1-4832-7088-3. https://books.google.com/books?id=ehQlBQAAQBAJ&pg=PA222. 
  16. ↑ "Die gestagene Wirkung von Hydroxy-nor-Progesteronestern bei der Frau". Gewebs- und Neurohormone. Symposion der Deutschen Gesellschaft für Endokrinologie. Springer. 1962. pp. 248–255. doi:10.1007/978-3-642-86860-3_27. ISBN 978-3-540-02909-0. "Nach oraler Verabreichung von 100 mg des Hydroxy-nor-ProgesteronAcetats sah man nur schwache oder noch keine gestagene Wirkung am Endometrium (Abb. 3). Nach der oralen Dosis von 130- 140 mg traten basale Vacuolen auf, nach 220 mg war - außer bei einer Patientin mit individuell geringerer Ansprechbarkeit des Endometriums (2) - eine volle sekretorische Umwandlung erreicht: [...]" 



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