pentagestrone acetate

{{Short description|Chemical compound}}

{{Drugbox

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| 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

| image = Pentagestrone acetate.svg

| width = 250px

| tradename = Gestovis, Gestovister

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| routes_of_administration = By mouth

| class = Progestogen; Progestin; Progestogen ether; Progestogen ester

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| CAS_number_Ref =

| CAS_number = 1178-60-5

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| PubChem = 10321047

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| ChemSpiderID_Ref =

| ChemSpiderID = 8496511

| UNII = 3Y30374T6H

| synonyms = PGA; Gestovis; 17α-Acetoxyprogesterone 3-cyclopentyl enol ether

| C=28 | H=40 | O=4

| SMILES = CC(=O)C1(CCC2C1(CCC3C2CC=C4C3(CCC(=C4)OC5CCCC5)C)C)OC(=O)C

| StdInChI_Ref =

| StdInChI = 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

| StdInChIKey_Ref =

| StdInChIKey = 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.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA943|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=943–}}{{cite book|title=Drugs Available Abroad|url=https://books.google.com/books?id=2x1tAAAAMAAJ|year=1991|publisher=Gale Research|isbn=978-0-8103-7177-4}}{{cite book| vauthors = List PH, Hörhammer L | chapter = Pentagestrone |title=Chemikalien und Drogen Teil A: N-Q| chapter-url = https://books.google.com/books?id=4TWnBgAAQBAJ&pg=PA508|date=12 March 2013|publisher=Springer-Verlag|isbn=978-3-642-65035-2|pages=508–}} It is the 3-cyclopentyl enol ether of 17α-hydroxyprogesterone acetate.{{cite book| vauthors = Wermuth DG | chapter = Designing Prodrugs and Bioprecursors | veditors = Wermuth CG |title=The Practice of Medicinal Chemistry| chapter-url = https://books.google.com/books?id=Qmt1_DQkCpEC&pg=PA731|date=2 May 2011|publisher=Academic Press|isbn=978-0-08-056877-5|pages=731–|author-link=Camille Georges Wermuth}} 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.{{cite book|title=Revue générale des sciences pures et appliquées et bulletin de l'Association française pour l'avancement des sciences|url=https://books.google.com/books?id=UuEkAQAAIAAJ|year=1964|publisher=Société d'édition d'enseignement supérieur|quote=[[...] Ercoli (1960) developed cyclopentyl enol ethers of progesterone (Luteovis) and acetoxy progesterone (Gestovis), which have almost exactly the same properties as dydrogesterone.]}}

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.{{cite journal | title = Gestovis | journal = South African Medical Journal | volume = 40 | issue = 5 | date = January 1966 | page = 99 | issn = 0256-9574 | url = https://journals.co.za/content/m_samj/40/5/AJA20785135_36784 | quote = 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.}} It has been said to have equivalent potency to intramuscular progesterone. The combination of 20 mg/day PGA and 100 μg/day mestranol is an effective ovulation inhibitor in women.{{cite book| vauthors = Pincus G | chapter = The Inhibition of Ovulation |title=The Control of Fertility| chapter-url = https://books.google.com/books?id=ehQlBQAAQBAJ&pg=PA221 |date=3 September 2013|publisher=Elsevier|isbn=978-1-4832-7088-3|pages=221–}}{{cite book|title=Current Medicine and Drugs|url=https://books.google.com/books?id=auc1AQAAIAAJ|year=1962|page=32|quote=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.}} The effective dosage of PGA in the menstrual delay test has been studied.{{cite journal | vauthors = Edgren RA, Sturtevant FM | title = Potencies of oral contraceptives | journal = American Journal of Obstetrics and Gynecology | volume = 125 | issue = 8 | pages = 1029–1038 | date = August 1976 | pmid = 952300 | doi = 10.1016/0002-9378(76)90804-8 }}