{"ATC Code":["G - Genito urinary system and sex hormones","G03 - Sex hormones and modulators of the genital system","G03D - Progestogens","G03DB - Pregnadien derivatives","G03DB08","G03DB08 - Dienogest","QG - Genito urinary system and sex hormones","QG03 - Sex hormones and modulators of the genital system","QG03D - Progestogens","QG03DB - Pregnadien derivatives","QG03DB08 - Dienogest"],"Abbreviation":["DNG"],"Absorption, Distribution and Excretion":"Dienogest is rapidly absorbed following oral administration, with 91% bioavailability. The peak plasma concentration of 47 ng/mL is reached at about 1.5 hours after single ingestion of 2 mg. The stable concentrations of the drug are reached after two days of initial treatment.","Aliases":["Dienogestril","Dienogestum","Endometrion","STS 557","STS-557","MJR-35","17α-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile","ZK 37659","M 18575","M-18575","17-α-Cyanomethyl-17-β-hydroxy-estra-4,9(10)-dien-3-one","19-Norpregna-4,9-diene-21-nitrile, 17-hydroxy-3-oxo-, (17α)-","ZK-37659","Chebi:70708","17-Hydroxy-3-oxo-19-nor-17α-pregna-4,9-diene-21-nitrile","19-Norpregna-4,9-diene-21-nitrile, 17-hydroxy-3-oxo-, (17-α)-","[(17β)-17-hydroxy-3-oxoestra-4,9-dien-17-yl]acetonitrile","((17β)-17-hydroxy-3-oxoestra-4,9-dien-17-yl)acetonitrile","17 α-cyanomethyl-17 β-hydroxyestra-4,9(10)-diene-3-one","17 α-cyanomethyl-17 β-hydroxy-13 β-methylgona-4,9-dien-3-one","G03DB08","Dtxcid101030584","Dienogestrel","Dinagest","Visanne","Mfcd00868356","2-((8S,13S,14S,17R)-17-hydroxy-13-methyl-3-oxo-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)acetonitrile","(17-hydroxy-3-oxoestra-4,9-dien-17β-yl)acetonitrile","17α-Cyanomethyl-17β-hydroxyestra-4,9(10)-dien-3-one","BAY86-5258","Dienogest CRS","Dienogest; Dienogestril; Dinagest; STS 557; (17α)-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile; 17α-Cyanomethyl-17β-hydroxyestra-4,9-dien-3-one","Bay 86-5258","17-α-Cyanomethyl-17-β-hydroxyestra-4,9(10)-diene-3-one","17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile","Schembl37293","(17a)-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile","GTPL7654","STS557","Chembl1201864","Dienogest, \u003e=98%","HY-B0084R","Sh-t00660aa","GLXC-05824","HY-B0084","MSK10876","Dienogest for system suitability CRS","EBC-07864","s1251","Akos015840152","Akos015896680","AC-2166","CCG-267594","CS-1782","DB09123","FH21758","Ncgc00346502-04","Ncgc00346502-07","2-[(1R,3aS,3bS,11aS)-1-hydroxy-11a-methyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]acetonitrile","DA-72748","D5230","NS00000598","A10563","D03799","Ab01566807_01","En300-6477654","17-Cyanomethyl-17-hydroxyestra-4, 9-dien-3-one","F794972","Sr-01000942230","Sr-01000942230-1","Brd-k50853363-001-02-3","Dienogest, EuropePharmacopoeia (EP) Reference Standard","Z2235801839","17-Hydroxy-3-oxo-17α-19-norpregna-4,9-diene-21-nitrile","Dienogest for system suitability, EuropePharmacopoeia (EP) Reference Standard"],"Biological Half-Life":"Elimination half-life of dienogest is around 9-10 hours. The half-life of urinary metabolites excretion is 14 hours.","CAS":"65928-58-7","ChemicalClasses":[],"Chirality":"achiral","DTXSID":"80891478","Drug Classes":["Breast Feeding","Lactation","Milk, Human","Contraceptive Agents, Female","Contraceptives, Oral, Synthetic"],"Drug Indication":"Indicated for use as the treatment of endometriosis alone and as a contraceptive in combination with ethinylestradiol.","Druglikeness":{"Lipinski":{"Passes":true,"Violations":0}},"DurationOfAction":"","Erowid Experience Reports":[],"Esters":[],"European Community (EC) Number":"639-448-2","FDA Pharmacological Classification":[{"Name":"FDA UNII","ReferenceNumber":23,"Value":{"StringWithMarkup":[{"String":"46M3EV8HHE"}]}},{"Name":"Active Moiety","ReferenceNumber":23,"Value":{"StringWithMarkup":[{"String":"DIENOGEST"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":23,"Value":{"StringWithMarkup":[{"String":"Established Pharmacologic Class [EPC] - Progestin"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":23,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-5994","Length":12,"Start":26,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Progesterone"}],"String":"Chemical Structure [CS] - Progesterone Congeners"}]}},{"Name":"FDA Pharmacology Summary","ReferenceNumber":23,"Value":{"StringWithMarkup":[{"String":"Dienogest is a Progestin."}]}}],"Formating":[],"HeavyAtomCount":23,"Human Drugs":"Breast Feeding; Lactation; Milk, Human; Contraceptive Agents, Female; Contraceptives, Oral, Synthetic","IUPACName":"2-[(8S,13S,14S,17R)-17-hydroxy-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]acetonitrile","InChI":"InChI=1S/C20H25NO2/c1-19-8-6-16-15-5-3-14(22)12-13(15)2-4-17(16)18(19)7-9-20(19,23)10-11-21/h12,17-18,23H,2-10H2,1H3/t17-,18+,19+,20-/m1/s1","InChIKey":"AZFLJNIPTRTECV-FUMNGEBKSA-N","MeSH Headers":[{"Id":"M0081095","Link":"https://id.nlm.nih.gov/mesh/M0081095.html","Name":"dienogest","Ref":61},{"Id":"M000645442","Link":"https://id.nlm.nih.gov/mesh/M000645442.html","Name":"19-norpregna-4,9-diene-21-nitrile, 17-hydroxy-3-oxo-, (17alpha)-","Ref":63},{"Id":"M0081093","Link":"https://id.nlm.nih.gov/mesh/M0081093.html","Name":"STS 557","Ref":64},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":65},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":85},{"Id":"M0005104","Link":"https://id.nlm.nih.gov/mesh/M0005104.html","Name":"Contraceptive Agents, Male","Ref":86},{"Id":"M0005118","Link":"https://id.nlm.nih.gov/mesh/M0005118.html","Name":"Contraceptives, Oral, Hormonal","Ref":87},{"Id":"M0010537","Link":"https://id.nlm.nih.gov/mesh/M0010537.html","Name":"Hormone Antagonists","Ref":88},{"Id":"M0028300","Link":"https://id.nlm.nih.gov/mesh/M0028300.html","Name":"Antineoplastic Agents, Hormonal","Ref":89}],"MeSH Pharmacological Classification":[{"Id":"M0005104","Link":"https://id.nlm.nih.gov/mesh/M0005104.html","Name":"Contraceptive Agents, Male","Ref":86},{"Id":"M0005118","Link":"https://id.nlm.nih.gov/mesh/M0005118.html","Name":"Contraceptives, Oral, Hormonal","Ref":87},{"Id":"M0010537","Link":"https://id.nlm.nih.gov/mesh/M0010537.html","Name":"Hormone Antagonist","Ref":88},{"Id":"M0028300","Link":"https://id.nlm.nih.gov/mesh/M0028300.html","Name":"Antineoplastic Agents, Hormonal","Ref":89}],"Mechanism of Action":"Dienogest acts as an agonist at the progesterone receptor (PR) with weak affinity that is comparable to that of progesterone but has a very potent progestagenic effect in the endometrium, causing endometrial atrophy after prolonged use. It promotes antiproliferative, immunologic and antiangiogenic effects on endometrial tissue. Dienogest reduces the level of endogenous production of oestradiol and thereby suppressing the trophic effects of oestradiol on both the eutopic and ectopic endometrium. Continous administration of dienogest results in hyperprogestogenic and moderately hypoestrogenic endocrine environment, which causes initial decidualization of endometrial tissue.  It is an antagonist at androgen receptors, improve androgenic symptoms such as acne and hirsutism.","Melting Point":"210-218","Metabolism/Metabolites":"Dienogest undergoes complete metabolism that is mainly mediated by CYP3A4. The metabolites are pharmacologically inactive and rapidly eliminated from the plasma.","MolecularFormula":"C\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e25\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"311.4 g/mol","Passes":true,"Pharmacodynamics":"Dienogest exhibits a very potent progestagenic effect in the endometrium, and causes endometrial atrophy after prolonged use . It also mediates an antiandrogenic effect that is equivalent to approximately one third that of cyproterone acetate. A dose of 2 mg inhibits the growth of ovarian follicles at 10 mm and maintains the concentration of progesterone at a low level, but has a weak inhibitory effect on FSH and LH. 1mg/kg of dienogest also directly inhibits ovulation. In clinical trials composing of patients with endometriosis, dienogest therapy effectively reduced painful symptoms and endometriotic lesions associated with the disorder. Dienogest displays no antiestrogenic activity as it activate neither estrogen receptor (ER) α nor ERβ, and causes hypoestrogenic effects instead as it is shown to decrease the relative expressions of ERβ and ERα. It has no glucocorticoid or mineralocorticoid effects. In combined oral contraceptive pills (COCP) with ethinyloestradiol, dienogest conjuction therapy effectively reduces the symptoms of acne and hirsutism, as well as improving excessively heavy or prolonged menstrual bleeding.","PubChemId":68861,"PubChemTitle":"Dienogest","RefChem":"586937","RefCount":2,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Dienogest","Name":"Dienogest","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q139160","Name":"Dienogest","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB09123","Name":"Dienogest","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/68861","Name":"Dienogest","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=65928-58-7","Name":"Dienogest","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/D03799","Name":"Dienogest","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/46M3EV8HHE","Name":"Dienogest","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID80891478","Name":"Dienogest","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 68861, Dienogest. 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