Chemical compound
Pharmaceutical compound
Norgestrienone Clinical data Trade names Ogyline, Planor, Miniplanor Other names RU-2010; A-301; 17α-Ethynyltrienolone; 17α-Ethynyltrenbolone; Δ9,11 -Norethisterone; 17α-Ethynylestra-4,9,11-trien-17β-ol-3-one Routes of By mouth Drug class Progestogen ;Progestin ;Androgen ;Anabolic steroid ATC code Identifiers (8S ,13S ,14S ,17R )-17-ethynyl-17-hydroxy-13-methyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a ]phenanthren-3-one
CAS Number PubChem CID ChemSpider UNII KEGG CompTox Dashboard (EPA) ECHA InfoCard 100.011.544 Chemical and physical data Formula C 20 H 22 O 2 Molar mass −1 3D model (JSmol ) InChI=1S/C20H22O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,8,10,12,17-18,22H,4-7,9,11H2,2H3/t17-,18+,19+,20+/m1/s1
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Norgestrienone , sold under the brand namesOgyline ,Planor , andMiniplanor , is aprogestin medication which has been used inbirth control pills , sometimes in combination withethinylestradiol .[ 1] [ 2] [ 3] [ 4] [ 5] Roussel Uclaf and has been registered for use only inFrance .[ 4] [ 5] [ 6] Planor , it has been marketed in France as 2 mg norgestrienone and 50 μg ethinylestradiol tablets.[ 7] by mouth .[ 5]
Norgestrienone is a progestin, or asynthetic progestogen , and hence is anagonist of theprogesterone receptor , thebiological target of progestogens likeprogesterone .[ 8] androgenic activity.[ 9] [ 10] [ 11] [ 12]
Norgestrienone was first described in the literature in 1965.[ 10] [ 13] [citation needed
Norgestrienone was used inhormonal contraception to preventpregnancy .[ 2] [ 7] oral contraceptive at a dosage of 2 mg/day in combination withethinylestradiol and 350 μ/day when used alone.[ 5]
Norgestrienone has been found to possess similaraffinity for theprogesterone receptor andandrogen receptor ,[ 8] androgenic activity.[ 9] [ 10] [ 11] [ 12] 19-nortestosterone derivatives due to the presence of the C9(11)double bond , which enhances said activity.[ 12] progestogenic toandrogenic activity appears to be much lower for norgestrienone that it is for other 19-nortestosterone progestins such asnorethisterone andlevonorgestrel .[ 14] [ 15] [ 16] [ 17] Gestrinone , the 18-methylanalogue of norgestrienone, has even greater androgenic activity than norgestrienone, as this modification increases androgenic activity similarly.[ 12]
Relative affinities (%) of norgestrienone and related steroids Compound PR Tooltip Progesterone receptor AR Tooltip Androgen receptor ER Tooltip Estrogen receptor GR Tooltip Glucocorticoid receptor MR Tooltip Mineralocorticoid receptor SHBG Tooltip Sex hormone-binding globulin CBG Tooltip Corticosteroid binding globulin Norethisterone 155–156 43–45 <0.1 2.7–2.8 0.2 ? ? Norgestrienone 63–65 70 <0.1 11 1.8 ? ? Levonorgestrel 170 84–87 <0.1 14 0.6–0.9 ? ? Gestrinone 75–76 83–85 <0.1, 3–10 77 3.2 ? ? Notes: Values are percentages (%). Referenceligands (100%) wereprogesterone for thePR Tooltip progesterone receptor ,testosterone for theAR Tooltip androgen receptor ,E2 for theER Tooltip estrogen receptor ,DEXA Tooltip dexamethasone for theGR Tooltip glucocorticoid receptor ,aldosterone for theMR Tooltip mineralocorticoid receptor ,DHT Tooltip dihydrotestosterone forSHBG Tooltip sex hormone-binding globulin , andcortisol forCBG Tooltip Corticosteroid-binding globulin .Sources: [ 14] [ 15] [ 16] [ 17]
Themetabolism of norgestrienone in humans has been studied.[ 18]
Norgestrienone, also known as 17α-ethynyl-19-nor-δ9,11 -testosterone or as 17α-ethynylestra-4,9,11-trien-17β-ol-3-one, as well as δ9,11 -norethisterone or 17α-ethynyltrienolone (17α-ethynyltrenbolone), is asynthetic estrane steroid and aderivative oftestosterone and19-nortestosterone .[ 1] [ 4] [ 19] anabolic steroid trenbolone (19-nor-δ9,11 -testosterone; the non-17α-ethynylatedanalogue of norgestrienone), theprogestogenic andandrogenic steroidgestrinone (the 13β-ethyl variant or 18-methyl derivative of norgestrienone), and the anabolic steroidtetrahydrogestrinone (the 18-methyl and 17α-ethyl variant of norgestrienone).[ 1] [ 4] [ 20]
Norgestrienone was first described in the literature in 1965.[ 10] [ 13]
Society and culture [ edit ] Norgestrienone is thegeneric name of the drug and itsINN Tooltip International Nonproprietary Name .[ 1] [ 2] [ 4] RU-2010 andA-301 .[ 1] [ 2] [ 4]
Norgestrienone has been marketed under the brand names Ogyline, Planor, and Miniplanor.[ 1] [ 2] [ 4]
Norgestrienone is no longer marketed and hence is no longer available in any country.[citation needed It was previously used inFrance .[ 4] United States .[ 21]
Norgestrienone has been studied for use inmale hormonal contraception .[ 22]
^a b c d e f Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies ISBN 978-1-4757-2085-3 ^a b c d e Morton IK, Hall JM (6 December 2012).Concise Dictionary of Pharmacological Agents: Properties and Synonyms ISBN 978-94-011-4439-1 ^ Diaz S, Pavez M, Quinteros E, Diaz J, Robertson DN, Croxatto HB (October 1978). "Clinical trial with subdermal implants containing norgestrienone".Contraception .18 (4):429– 440.doi :10.1016/0010-7824(78)90027-6 .PMID 720075 . ^a b c d e f g h Index Nominum 2000: International Drug Directory ISBN 978-3-88763-075-1 ^a b c d Sweetman SC, ed. (2009)."Sex hormones and their modulators" .Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. p. 2122.ISBN 978-0-85369-840-1 Norgestrienone is a progestogen structurally related to norethisterone that has been used as an oral contraceptive. Typical doses have been 2 mg daily with an oestrogen, and 350 micrograms daily when used alone. ^ McGuire JL (2000).Pharmaceuticals, 4 Volume Set ISBN 978-3-527-29874-7 ^a b IARC Working Group on the Evaluation of Carcinogenic Risks to Humans; World Health Organization; International Agency for Research on Cancer (2007).Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy ISBN 978-92-832-1291-1 ^a b Loughney DA, Schwender CF (December 1992). "A comparison of progestin and androgen receptor binding using the CoMFA technique".Journal of Computer-Aided Molecular Design .6 (6):569– 581.Bibcode :1992JCAMD...6..569L .doi :10.1007/bf00126215 .PMID 1291626 .S2CID 22004130 . ^a b Axelrod J (1 January 1982).Biochemical Actions of Hormones ISBN 978-0-12-452809-3 ^a b c d Lauritzen C, Studd JW (22 June 2005).Current Management of the Menopause ISBN 978-0-203-48612-2 ^a b Di Giulio RT, Monosson E (6 December 2012).Interconnections Between Human and Ecosystem Health ISBN 978-94-009-1523-7 ^a b c d Rozenbaum H (March 1982). "Relationships between chemical structure and biological properties of progestogens".American Journal of Obstetrics and Gynecology .142 (6 Pt 2):719– 724.doi :10.1016/S0002-9378(16)32477-2 .PMID 7065053 . ^a b Weiss G (February 1999). "Risk of venous thromboembolism with third-generation oral contraceptives: A review".American Journal of Obstetrics and Gynecology .180 (2 Pt 2):295– 301.doi :10.1016/S0002-9378(99)70721-0 .PMID 9988833 . ^a b Delettré J, Mornon JP, Lepicard G, Ojasoo T, Raynaud JP (January 1980). "Steroid flexibility and receptor specificity".Journal of Steroid Biochemistry .13 (1):45– 59.doi :10.1016/0022-4731(80)90112-0 .PMID 7382482 . ^a b Raynaud JP, Bouton MM, Moguilewsky M, Ojasoo T, Philibert D, Beck G, et al. (January 1980). "Steroid hormone receptors and pharmacology".Journal of Steroid Biochemistry .12 :143– 157.doi :10.1016/0022-4731(80)90264-2 .PMID 7421203 . ^a b Ojasoo T, Raynaud JP, Doé JC (January 1994). "Affiliations among steroid receptors as revealed by multivariate analysis of steroid binding data".The Journal of Steroid Biochemistry and Molecular Biology .48 (1):31– 46.doi :10.1016/0960-0760(94)90248-8 .PMID 8136304 .S2CID 21336380 . ^a b Raynaud J, Ojasoo T, Bouton M, Philibert D (1979)."Receptor Binding as a Tool in the Development of New Bioactive Steroids" .Drug Design . Medicinal Chemistry: A Series of Monographs. Vol. 11. Academic Press. pp. 169– 214.doi :10.1016/B978-0-12-060308-4.50010-X .ISBN 9781483216102 ^ Raynaud JP (1970)."Metabolism of contraceptive steroids in man" .Excerpta Medica International Congress Series .219 :915– 922. Archived fromthe original on 29 March 2018. ^ Lavery JP, Sanfilippo JS (6 December 2012).Pediatric and Adolescent Obstetrics and Gynecology ISBN 978-1-4612-5064-7 ^ Gomel V, Brill A (27 September 2010).Reconstructive and Reproductive Surgery in Gynecology ISBN 978-1-84184-757-3 ^ Lednicer D (4 March 2009).Strategies for Organic Drug Synthesis and Design ISBN 978-0-470-39959-0 ^ Schearer SD (1978).The use of progestins and androgens as a male contraceptive. Hormonal control of male fertility .DHEW Publication No.(NIH). (Report). pp. 78– 1097. Archived fromthe original on 29 March 2018.
Androgens AAS Tooltip anabolic–androgenic steroid )
Antiandrogens
AR Tooltip Androgen receptor antagonists Steroidogenesis
Antigonadotropins D2 receptor antagonists (prolactin releasers ) (e.g.,domperidone ,metoclopramide ,risperidone ,haloperidol ,chlorpromazine ,sulpiride )Estrogens (e.g.,bifluranol ,diethylstilbestrol ,estradiol ,estradiol esters ,ethinylestradiol ,ethinylestradiol sulfonate ,paroxypropione )GnRH agonists (e.g.,leuprorelin )GnRH antagonists (e.g.,cetrorelix )Progestogens (incl.,chlormadinone acetate ,cyproterone acetate ,hydroxyprogesterone caproate ,gestonorone caproate ,medroxyprogesterone acetate ,megestrol acetate )Others
PR Tooltip Progesterone receptor
Agonists Testosterone derivatives: Progestins:6,6-Difluoronorethisterone 6,6-Difluoronorethisterone acetate 17α-Allyl-19-nortestosterone Allylestrenol Altrenogest Chloroethynylnorgestrel Cingestol Danazol Desogestrel Dienogest Ethinylandrostenediol Ethisterone Ethynerone Etonogestrel Etynodiol Etynodiol diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel esters (e.g.,levonorgestrel butanoate )Lynestrenol Lynestrenol phenylpropionate Metynodiol Metynodiol diacetate Norelgestromin Norethisterone (norethindrone) Norethisterone esters (e.g.,norethisterone acetate ,norethisterone enanthate )Noretynodrel Norgesterone Norgestimate Norgestrel Norgestrienone Norvinisterone Oxendolone Quingestanol Quingestanol acetate Tibolone Tigestol Tosagestin ; Anabolic–androgenic steroids:11β-Methyl-19-nortestosterone 11β-Methyl-19-nortestosterone dodecylcarbonate 19-Nor-5-androstenediol 19-Nor-5-androstenedione 19-Nordehydroepiandrosterone Bolandiol Bolandiol dipropionate Bolandione Dimethisterone Dienedione Dienolone Dimethandrolone Dimethandrolone buciclate Dimethandrolone dodecylcarbonate Dimethandrolone undecanoate Dimethyldienolone Dimethyltrienolone Ethyldienolone Ethylestrenol (ethylnandrol) Methyldienolone Metribolone (R-1881) Methoxydienone (methoxygonadiene) Mibolerone Nandrolone Nandrolone esters (e.g.,nandrolone decanoate ,nandrolone phenylpropionate )Norethandrolone Normethandrone (methylestrenolone, normethandrolone, normethisterone) RU-2309 Tetrahydrogestrinone Trenbolone (trienolone) Trenbolone esters (e.g.,trenbolone acetate ,trenbolone enanthate )Trendione Trestolone Trestolone acetate MixedSPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor PAQR Tooltip Progestin and adipoQ receptor )
