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Dienogestrel

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CAS:65928-58-7
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Dienogestrel Basic information
Description Pharmacodynamics Features Side effects
Product Name:Dienogestrel
Synonyms:(17a)-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile;17a-Cyanomethyl-17-hydroxyestra-4, 9-dien-3-one;Dienogestril;Endometrion;STS 557;Dienogestrel;Dienogest;(17R)-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile
CAS:65928-58-7
MF:C20H25NO2
MW:311.43
EINECS:639-448-2
Product Categories:Inhibitors;Natazia;Final material;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;65928-58-7
Mol File:65928-58-7.mol
Dienogestrel Structure
Dienogestrel Chemical Properties
Melting point 210-2140C
alpha D25 -290° (c = 0.5 in pyridine)
Boiling point 451.46°C (rough estimate)
density 1.0899 (rough estimate)
refractive index 1.5614 (estimate)
storage temp. 2-8°C
solubility Chloroform (Slightly), Pyridine (Slightly)
pka13?+-.0.40(Predicted)
form powder
color white to beige
optical activity[α]/D -305 to -325°, c = 1 in dichloromethane
Merck 14,3106
InChIInChI=1/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-/s3
InChIKeyAZFLJNIPTRTECV-XAYGXGNENA-N
SMILESC[C@]12CCC3=C4CCC(=O)C=C4CC[C@@]3([H])[C@]1([H])CC[C@@]2(O)CC#N |&1:1,14,16,20,r|
CAS DataBase Reference65928-58-7(CAS DataBase Reference)
Safety Information
RTECS RC8899500
HS Code 2937.23.5050
ToxicityLD50 oral in mouse: 4gm/kg
MSDS Information
Dienogestrel Usage And Synthesis
DescriptionDienoest is a selective progesterone drug that has been launched in recent years. It can stabilize endometrial tissue by specifically binding to ethylene nortestosterone and progesterone derivatives. Studies have found that tumor necrosis factor (TNF) and interleukin (IL-8) tend to increase in patients with endometriosis.
PharmacodynamicsDienogest has progestogenic activity, possibly some antiprogestogenic activity, and has antiandrogenic activity.The medication does not interact with the estrogen receptor, the glucocorticoid receptor, or the mineralocorticoid receptor, and hence has no estrogenic, glucocorticoid, or antimineralocorticoid activity.Because of its relatively high selectivity as a progestogen, dienogest may have favorable safety and tolerability compared to various other progestins.
FeaturesDienogest is a mixed progestogen with dual properties of 19-nortestosterone derivatives and progesterone derivatives; therefore, it combines the pharmacological advantages of natural and synthetic progestins with high progestogenic activity .
Side effectsSide effects associated with dienogestrel are the same as those expected of a progestogen.They include menstrual irregularities, headaches, nausea, breast tenderness, depression, acne, weight gain, flatulence, and others.Dienogest produces no androgenic side effects and has little effect on metabolic and lipid hemostatic parameters.
Physical propertiesDienogestrel is a pale yellow solid.
UsesDienogest is an orally active synthetic progesterone (or progestin). It is available for use as an oral contraceptive in combination with ethinylestradiol. It has antiandrogenic activity and as a result can improve androgenic symptoms.
UsesDerivative of 19-Nortestosterone. In combination with estrogen as oral contraceptive. Progestogen.
DefinitionChEBI: A steroid hormone that is 17beta-hydroxy-3-oxoestra-4,9-diene substituted at position 17 by a cyanomethyl group. Used as an oral contraceptive.
Brand nameEndometrion (Schering A.G., Germany).
Biochem/physiol ActionsDienogest is used to treat endometriosis. It might also help to decrease the levels of plasma estradiol by stimulating cell death of granulosa cells in the ovary.
Dienogestrel Preparation Products And Raw materials
Tag:Dienogestrel(65928-58-7) Related Product Information
Dienogest Impurity I (17α)-3,3-[1,2-Ethanediylbis(oxy)]-17-hydroxy-19-norpregna-5(10),9(11)-diene-21-nitrile DiMethoxy Dienogest 9,11-Dehydro-17α-cyanoMethyl Estradiol Sts 64 (17α)-17-Hydroxy-3-oxo-19-norpregna-5(10),9(11)-diene-21-nitrile 3,3-DiMethoxyestra-5(10),9(11)-dien-17-one 17 alpha-cyanomethyl-19-nortestosterone (17α)-4-Bromo-17-hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile Estra-4,9-diene-3,17-dione 19-HYDROXY-4-ANDROSTENE-3,17-DIONE Estradiene dione-3-keta 17β-Cyanmethyl-oestra-1,3,5(10)-trien-3,17β-diol 11β-Hydroperoxy Dienogest Dodecanenitrile N-HEPTADECANONITRILE 3-HYDROXY-3-METHYLBUTYRONITRILE ORANILE