Gestonorone acetate

Gestonorone acetate
Clinical data
Other names	Gestronol 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 class	Progestin; Progestogen
Identifiers
	IUPAC name [(8R,9S,10R,13S,14S,17R)-17-Acetyl-13-methyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate;
CAS Number	31981-44-9;
PubChem CID	134963;
ChemSpider	118930;
CompTox Dashboard (EPA)	DTXSID90953874 ;
ECHA InfoCard	100.046.242
Chemical and physical data
Formula	C22H30O4
Molar mass	358.478 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)C)OC(=O)C;
	InChI InChI=1S/C22H30O4/c1-13(23)22(26-14(2)24)11-9-20-19-6-4-15-12-16(25)5-7-17(15)18(19)8-10-21(20,22)3/h12,17-20H,4-11H2,1-3H3/t17-,18+,19+,20-,21-,22-/m0/s1; Key:MTSLFKWJINJVBO-ZCPXKWAGSA-N;

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]

References

Noguchi, Shunsaku (1961). "Steroids. XX. Hydrolysis of steroidal esters by malt enzyme. 1. Selective hydrolysis of steroidal acetates". Yakugaku Zasshi. 81 (3): 369–373. doi:10.1248/yakushi1947.81.3_369. ISSN 0031-6903.
Noguchi, Shunsaku (1961). "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. doi:10.1248/yakushi1947.81.3_381. ISSN 0031-6903.
Dorfman, R; Kincl, F (1963). "Steroid anti-estrogens". Steroids. 1 (2): 185–209. doi:10.1016/S0039-128X(63)80136-1. ISSN 0039-128X.
Suchowsky GK (April 1963). "Pregnancy-maintaining effect of synthetic progestogens in the rat". Acta Endocrinol. 42 (4): 533–6. doi:10.1530/acta.0.0420533. ISSN 0001-5598. PMID 13979052.
Kalvoda, J; Heusler, K; Anner, G; Wettstein, A (1963). "Steroids. CXCVI. 19-Norsteroids. III. Synthesis of 19-norprogesterones". Helvetica Chimica Acta. 46: 1017–1029. doi:10.1002/hlca.19630460332. ISSN 0018-019X.
Junkmann, K (1963). "Evaluation of synthetic gestagenic substances". Deutsche Medizinische Wochenschrift. 88 (13): 629–638. doi:10.1055/s-0028-1111990. ISSN 0012-0472. PMID 13958089.
Kincl, Fred A.; Dorfman, Ralph I. (1963). "Orally active steroidal ovulation inhibitors in the adult estrus rabbit". Steroids. 2 (5): 521–525. doi:10.1016/0039-128X(63)90029-1. ISSN 0039-128X.
Suchowsky, GK (1963). "Inhibition of ovulation by steroids". Journal of the Egyptian Medical Association. 1962–1963: 67–73. ISSN 0013-2411.
Junkmann, K (1962). "The pharmacology of new gestational and anabolic steroids". Deutsch-Englische Medizinische Rundschau. 1 (4): 385–399. ISSN 0003-3332.
Suchowsky GK, Baldratti G (September 1964). "Relationship Between Progestational Activity and Chemical Structure of Synthetic Steroids". J. Endocrinol. 30 (2): 159–70. doi:10.1677/joe.0.0300159. PMID 14207040.
Nevinny-Stickel J (1964). "Inhibition of ovulation determined by estimation of pregnanediol excretion". Int. J. Fertil. 9: 57–67. PMID 14106269.
Jung, H; Peters, A (1967). "Effect of various gestagens on the fetal development and death rate in animals". Archiv für Gynäkologie. 204 (1): 68–77. doi:10.1007/BF00668265. ISSN 0003-9128. PMID 5630697. S2CID 22416963.
Gilbert, H.G.; Phillipps, G.H.; English, A.F.; Stephenson, L.; Voollett, E.A.; Newall, C.E.; Child, K.J. (1974). "The progestational and anti-estrogenic activities of some novel 11β-substituted steroids". Steroids. 23 (4): 585–602. doi:10.1016/0039-128X(74)90010-5. ISSN 0039-128X. PMID 4829347.
Tang, Rui-ren; Guo, Can-cheng; Fan, Bo-lin (2004). "Stereoselective asymmetric synthesis and characterization of 17α-acetyoxy-19-nor-progesterone". Journal of Central South University of Technology. 11 (3): 300–303. doi:10.1007/s11771-004-0061-y. ISSN 1005-9784. S2CID 195244927.
Gregory Pincus (3 September 2013). The Control of Fertility. Elsevier. pp. 222–. ISBN 978-1-4832-7088-3.
Nevinny-Stickel, J. (1962). "Die gestagene Wirkung von Hydroxy-nor-Progesteronestern bei der Frau". Gewebs- und Neurohormone [The progestational effects of hydroxy-nor-progesterone esters in women]. 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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[Noguchi1961a-1] Noguchi, Shunsaku (1961). "Steroids. XX. Hydrolysis of steroidal esters by malt enzyme. 1. Selective hydrolysis of steroidal acetates". Yakugaku Zasshi. 81 (3): 369–373. doi:10.1248/yakushi1947.81.3_369. ISSN 0031-6903.

[Noguchi1961b-2] Noguchi, Shunsaku (1961). "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. doi:10.1248/yakushi1947.81.3_381. ISSN 0031-6903.

[DorfmanKincl1963-3] Dorfman, R; Kincl, F (1963). "Steroid anti-estrogens". Steroids. 1 (2): 185–209. doi:10.1016/S0039-128X(63)80136-1. ISSN 0039-128X.

[pmid13979052-4] Suchowsky GK (April 1963). "Pregnancy-maintaining effect of synthetic progestogens in the rat". Acta Endocrinol. 42 (4): 533–6. doi:10.1530/acta.0.0420533. ISSN 0001-5598. PMID 13979052.

[KalvodaHeusler1963-5] Kalvoda, J; Heusler, K; Anner, G; Wettstein, A (1963). "Steroids. CXCVI. 19-Norsteroids. III. Synthesis of 19-norprogesterones". Helvetica Chimica Acta. 46: 1017–1029. doi:10.1002/hlca.19630460332. ISSN 0018-019X.

[Junkmann1963-6] Junkmann, K (1963). "Evaluation of synthetic gestagenic substances". Deutsche Medizinische Wochenschrift. 88 (13): 629–638. doi:10.1055/s-0028-1111990. ISSN 0012-0472. PMID 13958089.

[KinclDorfman1963-7] Kincl, Fred A.; Dorfman, Ralph I. (1963). "Orally active steroidal ovulation inhibitors in the adult estrus rabbit". Steroids. 2 (5): 521–525. doi:10.1016/0039-128X(63)90029-1. ISSN 0039-128X.

[Suchowsky1963-8] Suchowsky, GK (1963). "Inhibition of ovulation by steroids". Journal of the Egyptian Medical Association. 1962–1963: 67–73. ISSN 0013-2411.

[Junkmann1962-9] Junkmann, K (1962). "The pharmacology of new gestational and anabolic steroids". Deutsch-Englische Medizinische Rundschau. 1 (4): 385–399. ISSN 0003-3332.

[pmid14207040-10] Suchowsky GK, Baldratti G (September 1964). "Relationship Between Progestational Activity and Chemical Structure of Synthetic Steroids". J. Endocrinol. 30 (2): 159–70. doi:10.1677/joe.0.0300159. PMID 14207040.

[pmid14106269-11] Nevinny-Stickel J (1964). "Inhibition of ovulation determined by estimation of pregnanediol excretion". Int. J. Fertil. 9: 57–67. PMID 14106269.

[JungPeters1967-12] Jung, H; Peters, A (1967). "Effect of various gestagens on the fetal development and death rate in animals". Archiv für Gynäkologie. 204 (1): 68–77. doi:10.1007/BF00668265. ISSN 0003-9128. PMID 5630697. S2CID 22416963.

[GilbertPhillipps1974-13] Gilbert, H.G.; Phillipps, G.H.; English, A.F.; Stephenson, L.; Voollett, E.A.; Newall, C.E.; Child, K.J. (1974). "The progestational and anti-estrogenic activities of some novel 11β-substituted steroids". Steroids. 23 (4): 585–602. doi:10.1016/0039-128X(74)90010-5. ISSN 0039-128X. PMID 4829347.

[TangGuo2004-14] Tang, Rui-ren; Guo, Can-cheng; Fan, Bo-lin (2004). "Stereoselective asymmetric synthesis and characterization of 17α-acetyoxy-19-nor-progesterone". Journal of Central South University of Technology. 11 (3): 300–303. doi:10.1007/s11771-004-0061-y. ISSN 1005-9784. S2CID 195244927.

[Pincus2013-15] Gregory Pincus (3 September 2013). The Control of Fertility. Elsevier. pp. 222–. ISBN 978-1-4832-7088-3.

[Nevinny-Stickel1962-16] Nevinny-Stickel, J. (1962). "Die gestagene Wirkung von Hydroxy-nor-Progesteronestern bei der Frau". Gewebs- und Neurohormone [The progestational effects of hydroxy-nor-progesterone esters in women]. 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: [...]

Gestonorone acetate

See also

References