Pentagestrone acetate

Pentagestrone acetate
Clinical data
Trade names	Gestovis, Gestovister
Other names	PGA; Gestovis; 17α-Acetoxyprogesterone 3-cyclopentyl enol ether
Routes of; administration	By mouth
Drug class	Progestogen; Progestin; Progestogen ether; Progestogen ester
Identifiers
	IUPAC name [(8R,9S,10R,13S,14S,17R)-17-acetyl-3-cyclopentyloxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl] acetate;
CAS Number	1178-60-5;
PubChem CID	10321047;
ChemSpider	8496511;
UNII	3Y30374T6H;
CompTox Dashboard (EPA)	DTXSID701017067 ;
Chemical and physical data
Formula	C28H40O4
Molar mass	440.624 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=O)C1(CCC2C1(CCC3C2CC=C4C3(CCC(=C4)OC5CCCC5)C)C)OC(=O)C;
	InChI InChI=1S/C28H40O4/c1-18(29)28(32-19(2)30)16-13-25-23-10-9-20-17-22(31-21-7-5-6-8-21)11-14-26(20,3)24(23)12-15-27(25,28)4/h9,17,21,23-25H,5-8,10-16H2,1-4H3/t23-,24+,25+,26+,27+,28+/m1/s1; Key:NSRLWNNZHGRGJS-JVACCQEYSA-N;

Pentagestrone acetate (PGA), sold under the brand names Gestovis and Gestovister, is a progestin which was described in the literature in 1960 and was introduced by Vister in Italy in 1961.^[1]^[2]^[3] It is the 3-cyclopentyl enol ether of 17α-hydroxyprogesterone acetate.^[4] PGA, along with quingestrone (the 3-cyclopentyl enol ether of progesterone), is said to have very similar properties to those of dydrogesterone, a pure progestogen and close analogue of progesterone.^[5]

PGA is orally active, was provided in 10 and 20 mg capsules, and has been used to treat habitual abortion and menstrual disorders at a dosage of 10 to 20 mg/day.^[6] It has been said to have equivalent potency to intramuscular progesterone.^[6] The combination of 20 mg/day PGA and 100 μg/day mestranol is an effective ovulation inhibitor in women.^[7]^[8] The effective dosage of PGA in the menstrual delay test has been studied.^[9]

Chemistry

PGA, also known as 17α-acetoxyprogesterone 3-cyclopentyl enol ether, is a synthetic pregnane steroid and a derivative of progesterone and 17α-hydroxyprogesterone.^[1]

References

^ ^a ^b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 943–. ISBN 978-1-4757-2085-3.
^ Drugs Available Abroad. Gale Research. 1991. ISBN 978-0-8103-7177-4.
^ List PH, Hörhammer L (12 March 2013). "Pentagestrone". Chemikalien und Drogen Teil A: N-Q. Springer-Verlag. pp. 508–. ISBN 978-3-642-65035-2.
^ Wermuth DG (2 May 2011). "Designing Prodrugs and Bioprecursors". In Wermuth CG (ed.). The Practice of Medicinal Chemistry. Academic Press. pp. 731–. ISBN 978-0-08-056877-5.
^ Revue générale des sciences pures et appliquées et bulletin de l'Association française pour l'avancement des sciences. Société d'édition d'enseignement supérieur. 1964. [[...] Ercoli (1960) developed cyclopentyl enol ethers of progesterone (Luteovis) and acetoxy progesterone (Gestovis), which have almost exactly the same properties as dydrogesterone.]
^ ^a ^b "Gestovis". South African Medical Journal. 40 (5): 99. January 1966. ISSN 0256-9574. Comopharm (Pty) Limited. on behalf of Vister Laboratories, announce the introduction of Gestovis, and supply the following information: Gestovis is a new highly effective oral progesterone derivative (cyclopentyl enol-ether of 17-alpha-acetoxy progesterone) for the treatment of threatened and habitual abortion and menstrual disturbances. Gestovis is efficacious orally at the same dose as parenterally administered progesterone. Dosage. 10 - 20 mg. daily or as necessary. Presentation. Available in capsules of 10 and 20 mg.
^ Pincus G (3 September 2013). "The Inhibition of Ovulation". The Control of Fertility. Elsevier. pp. 221–. ISBN 978-1-4832-7088-3.
^ Current Medicine and Drugs. 1962. p. 32. Gestovis (3-cyclo-pentyl-enol ether of 17a acetoxyprogesterone) is a potent non-oestrogenic preparation but does not give very good cycle control. In doses of 20 mg daily from the fifth to the twenty-fifth day of the cycle it will inhibit ovulation.
^ Edgren RA, Sturtevant FM (August 1976). "Potencies of oral contraceptives". American Journal of Obstetrics and Gynecology. 125 (8): 1029–1038. doi:10.1016/0002-9378(76)90804-8. PMID 952300.

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[Elks2014-1] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 943–. ISBN 978-1-4757-2085-3.

[GaleResearch1991-2] Drugs Available Abroad. Gale Research. 1991. ISBN 978-0-8103-7177-4.

[ListHörhammer2013-3] List PH, Hörhammer L (12 March 2013). "Pentagestrone". Chemikalien und Drogen Teil A: N-Q. Springer-Verlag. pp. 508–. ISBN 978-3-642-65035-2.

[Wermuth2011-4] Wermuth DG (2 May 2011). "Designing Prodrugs and Bioprecursors". In Wermuth CG (ed.). The Practice of Medicinal Chemistry. Academic Press. pp. 731–. ISBN 978-0-08-056877-5.

[5] Revue générale des sciences pures et appliquées et bulletin de l'Association française pour l'avancement des sciences. Société d'édition d'enseignement supérieur. 1964. [[...] Ercoli (1960) developed cyclopentyl enol ethers of progesterone (Luteovis) and acetoxy progesterone (Gestovis), which have almost exactly the same properties as dydrogesterone.]

[SAMJ1966-6] "Gestovis". South African Medical Journal. 40 (5): 99. January 1966. ISSN 0256-9574. Comopharm (Pty) Limited. on behalf of Vister Laboratories, announce the introduction of Gestovis, and supply the following information: Gestovis is a new highly effective oral progesterone derivative (cyclopentyl enol-ether of 17-alpha-acetoxy progesterone) for the treatment of threatened and habitual abortion and menstrual disturbances. Gestovis is efficacious orally at the same dose as parenterally administered progesterone. Dosage. 10 - 20 mg. daily or as necessary. Presentation. Available in capsules of 10 and 20 mg.

[Pincus2013-7] Pincus G (3 September 2013). "The Inhibition of Ovulation". The Control of Fertility. Elsevier. pp. 221–. ISBN 978-1-4832-7088-3.

[CMD1962-8] Current Medicine and Drugs. 1962. p. 32. Gestovis (3-cyclo-pentyl-enol ether of 17a acetoxyprogesterone) is a potent non-oestrogenic preparation but does not give very good cycle control. In doses of 20 mg daily from the fifth to the twenty-fifth day of the cycle it will inhibit ovulation.

[pmid952300-9] Edgren RA, Sturtevant FM (August 1976). "Potencies of oral contraceptives". American Journal of Obstetrics and Gynecology. 125 (8): 1029–1038. doi:10.1016/0002-9378(76)90804-8. PMID 952300.

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Pentagestrone acetate

Chemistry

See also

References

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