65928-58-7

Basic information

• Product Name: Dienogestrel
• Synonyms: Dienogestrel;Dienogest;(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;(17R)-17-Hydroxy-3-oxo-19-norpregna-4,9-diene-21-nitrile
• CAS NO: 65928-58-7
• Molecular Formula: C20H25NO2
• Molecular Weight: 311.422
• EINECS: 1312995-182-4
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Final material;Natazia;Inhibitors
• Mol File: 65928-58-7.mol

Chemical Properties

• Melting Point: 210-2140C
• Boiling Point: 451.46°C (rough estimate)
• Flash Point: 285.8 °C
• Appearance: Pale yellow solid
• Density: 1.0899 (rough estimate)
• Vapor Pressure: 2.42E-14mmHg at 25°C
• Refractive Index: 1.5614 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Pyridine (Slightly)
• PKA: 13?+-.0.40(Predicted)
• Merck: 14,3106
• CAS DataBase Reference: Dienogestrel(CAS DataBase Reference)
• NIST Chemistry Reference: Dienogestrel(65928-58-7)
• EPA Substance Registry System: Dienogestrel(65928-58-7)

Safety Data

• RTECS: RC8899500
• Hazardous Substances Data: 65928-58-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Dienogestrel is used as an oral contraceptive in combination with ethinylestradiol. It serves as a progestogen, which is a synthetic form of the naturally occurring hormone progesterone. The combination of Dienogestrel and ethinylestradiol helps prevent ovulation, thickening of the uterine lining, and the ability of sperm to reach an egg, thus providing effective birth control.
Used in Endometriosis Treatment:
Dienogestrel is used as a treatment for endometriosis, a condition where the tissue that lines the uterus grows outside the uterus, causing pain and heavy bleeding. As a selective progesterone drug, Dienogestrel helps stabilize endometrial tissue and may contribute to the regulation of TNF and IL-8 levels, which are known to increase in patients with endometriosis.
Used in Antiandrogenic Therapy:
Dienogestrel is also used in antiandrogenic therapy due to its antiandrogenic activity. This property allows it to improve androgenic symptoms, which are related to an excess of male sex hormones or androgens in the body.
Brand Name:
Endometrion (Schering A.G., Germany) is a brand name under which Dienogestrel is marketed, particularly for the treatment of endometriosis.

Pharmacodynamics

Dienogest 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.

Features

Dienogest 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 effects

Side 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.

Biochem/physiol Actions

Dienogest 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.

InChI:InChI=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-/m1/s1

Upstream product

• 65928-65-6 17β-Cyanmethyl-17β-hydroxy-oestr-5(10)-en-3-on 
• 65928-65-6 17α-Cyanomethyl-13β-methyl-17β-hydroxy-gon-5(10)-en-3-on 
• 190662-30-7 17α-cyanomethyl-17β-hydroxy-5,9-androstadiene-3,17-dione-3,3-ethylene ketal 
• 10109-76-9 3,3-dimethoxy-estra-5⁽¹⁰⁾,9⁽¹¹⁾-diene-17-one 
• 102193-41-9 3,3-dimethoxy-17α-cyanomethyl-17β-hydroxy-estra-5(10),9(11)-diene 
• 6218-29-7 17β-hydroxyestra-4,9-dien-3-one 
• 75-05-8 acetonitrile 
• 5190-40-9 3-ethoxy-estra-3,5⁽¹⁰⁾,9⁽¹¹⁾-trien-17-one 
• 138123-05-4 C₂H₂CeCl₂N 
• 65928-64-5 17α-Cyanomethyl-13β-methyl-3-methoxy-gona-2,5(10)-dien-17β-ol 
• 30925-89-4 3-methoxy-2,5⁽¹⁰⁾-estradiene-17S-spiro-oxirane 

Downstream Products

• 16669-06-0 2-((8R,9S,13S,14S,17R)-3,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)acetonitrile 
• 86153-38-0 17α-Cyanomethylestra-1,3,5(10),9(11)-tetraen-3,17β-diol 
• 106111-43-7 ((8S,11S,13S,14S,17R)-11-Hydroperoxy-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 
• 106111-42-6 17α-Cyanomethyl-17β-hydroxy-estra-5(10),9(11)-dien-3-on 
• 86153-39-1 17α-Cyanomethyl-11β,17β-dihydroxy-estra-4,9-dien-3-on 
• 24284-84-2 17α-cyanomethyl-1,3,5(10)-estratriene-3,17-diol 3-methyl ether 

Relevant articles and documents

Preparation method of dienogest

The invention relates to a preparation method of dienogest. The preparation method comprises the following steps: providing a compound with a structure shown as a formula (II); and carrying out an acidolysis deprotection reaction on the compound shown in the formula (II) in an aqueous fluoboric acid solution to prepare a compound with a structure shown in a formula (I). According to the preparation method of the dienogest, the problems of low purity and dark color of a crude product of an acidolysis deprotection process are fundamentally solved, a production process is greatly simplified, andthe production cost of an enterprise is reduced.

Preparation method of dienogest and method for recovering dienogest from dienogest mother liquor

The invention belongs to the technical field of steroid hormone drug preparation, and particularly relates to a preparation method of dienogest and a method for recovering the dienogest from dienogestmother liquor. The preparation method of the dienogest comprises the following steps: dissolving 17 alpha-cyanomethyl-17 beta-hydroxyl-5, 9-androstane diene-3, 17-diketone-3,3-ethyleneketal, adding fluoboric acid, carrying out acidolysis to remove protection, and after the reaction is completed, carrying out treatment to obtain the dinogestrol. The method for recovering the dienogestrol from thedienogestrol mother liquor comprises the following steps: dissolving the dienogestrol with a solvent to obtain the dienogestrol mother liquor, adding perchloric acid or concentrated hydrochloric acid,reacting for a period of time, heating to 45-55 DEG C, concentrating under reduced pressure, removing part of the solvent by concentrating until a solid is separated out, stopping concentrating, cooling, continuing the reaction, and treating to obtain the dienogestrol. The product provided by the invention has high purity and high yield.

Dienogest compound

The invention provides a dienogest compound. The dienogest compound is characterized in that X-ray diffraction peaks exist when 2*theta is about 12.1+/-0.2, 15.2+/-0.2, 16.6+/-0.2, 18.4+/-0.2, 18.8+/-0.2, 21.9+/-0.2, 23.1+/-0.2 and 24.5+/-0.2.

PROCESS FOR THE PREPARATION OF DIENOGEST SUBSTANTIALLY FREE OF IMPURITIES

The present invention provides novel process for preparation and purification of dienogest (I). The present invention provides dienogest (I) substantially free of impurities.

PROCESS FOR THE PREPARATION OF DIENOGEST SUBSTANTIALLY FREE OF IMPURITIES

The present invention provides novel process for preparation and purification of dienogest (I). The present invention provides dienogest (I) substantially free of impurities.

METHOD FOR SYNTHESIS OF DIENOGEST FROM ESTRONE-3-METHYLETHER

A method for the synthesis of dienogest from 3-methoxy-estra-1,3,5-trien-17-one includes the steps of a) reacting 3-methoxy-estra-1,3,5-trien-17-one with alcohol in the presence of an acid in an organic solvent to form 3-methoxy-17,17-dialkoxy-estra-1,3,5

Process for the preparation of 17alpha-cyanomethyl-17beta-hydroxy steriods

The invention relates to a process for the preparation of 17α-cyanomethyl-17β hydroxy steroids comprising the reaction of 17-keto steroids with cyanomethyl cerium derivatives. The process is advantageous for the industrial production, since it avoids the use of cyanides and allows to obtain higher yields compared to the use of lithium acetonitrile.

HIGH PURITY 17α-CYANOMETHYL-17β-HYDROXY-ESTRA-4,9-DIENE-3-ONE AND PROCESS FOR THE SYNTHESIS THEREOF

The invention relates to a new process for the synthesis of high purity 17α- cyanomethyl-17β-hydroxy-estra-4,9-diene-3-one (further on dienogest) of formula (I) from 3-methoxy-17-hydroxy-estra-2,5(10)-diene of formula (V). The invention relates also to th

Pharmaceutical combined preparation, kit and method for hormonal contraception

PCT No. PCT/DE96/01192 Sec. 371 Date Jun. 3, 1998 Sec. 102(e) Date Jun. 3, 1998 PCT Filed Jun. 27, 1996 PCT Pub. No. WO97/01342 PCT Pub. Date Jan. 16, 1997The present invention describes a two-stage pharmaceutical combined preparation for hormonal contraception containing at least 30 daily unit doses, which preparation, in its first stage, comprises as hormonal active ingredient a combination of an oestrogen preparation and, in a dose that is at least sufficient to inhibit ovulation, a gestagen preparation, in single stage form and, in the second stage comprises as hormonal active ingredient an oestrogen preparation only, wherein the first stage comprises a minimum of 25 and a maximum of 77 daily discrete or continuous unit doses and the second stage comprises 5, 6 or 7 daily discrete or continuous unit doses, and wherein the total number of daily units is equal to the total number of days of the desired cycle of a minimum of 30 and a maximum of 84 days. This combined preparation, in the form of a monthly pack, which is used for female fertility control, permits as low as possible an oestrogen content in each individual unit dose and also has a low total hormone content per cycle of administration, with high contraceptive reliability, low incidence of follicle development, and satisfactory cycle control with reliable avoidance of intermediate bleeding as well as undesired side effects.