Dienogestrel
Description Pharmacodynamics Features Side effects- Product Name
- Dienogestrel
- CAS No.
- 65928-58-7
- Chemical Name
- Dienogestrel
- Synonyms
- MJR-35;STS 557;ienoges;M 18575;Visanne;Dinagest;Dinogest;ZK 37659;Dienogest;Ene, with
- CBNumber
- CB4947237
- Molecular Formula
- C20H25NO2
- Formula Weight
- 311.43
- MOL File
- 65928-58-7.mol
Dienogestrel Property
- 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)
- pka
- 13?+-.0.40(Predicted)
- form
- powder
- color
- white to beige
- optical activity
- [α]/D -305 to -325°, c = 1 in dichloromethane
- Merck
- 14,3106
- 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-/s3
- InChIKey
- AZFLJNIPTRTECV-XAYGXGNENA-N
- SMILES
- C[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 Reference
- 65928-58-7(CAS DataBase Reference)
Safety
- RTECS
- RC8899500
- HS Code
- 2937.23.5050
- Toxicity
- LD50 oral in mouse: 4gm/kg
N-Bromosuccinimide Price
- Product number
- SML1468
- Product name
- Dienogest
- Purity
- ≥98% (HPLC)
- Packaging
- 10MG
- Price
- $105.45
- Updated
- 2025/07/31
- Product number
- Y0001782
- Product name
- Dienogest for system suitability
- Purity
- European Pharmacopoeia (EP) Reference Standard
- Packaging
- 10 mg
- Price
- $164
- Updated
- 2025/07/31
- Product number
- SML1468
- Product name
- Dienogest
- Purity
- ≥98% (HPLC)
- Packaging
- 50MG
- Price
- $340
- Updated
- 2025/07/31
- Product number
- D5230
- Product name
- Dienogest
- Purity
- >98.0%(HPLC)
- Packaging
- 50mg
- Price
- $171
- Updated
- 2025/07/31
- Product number
- D5230
- Product name
- Dienogest
- Purity
- >98.0%(HPLC)
- Packaging
- 250mg
- Price
- $597
- Updated
- 2025/07/31
Dienogestrel Chemical Properties,Usage,Production
Description
Dienoest 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.
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.
Physical properties
Dienogestrel is a pale yellow solid.
Uses
Derivative of 19-Nortestosterone. In combination with estrogen as oral contraceptive. Progestogen.
Uses
Dienogest 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.
Definition
ChEBI: 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 name
Endometrion (Schering A.G., Germany).
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.
Synthesis
65928-65-6
65928-58-7
Using 17α-cyanomethyl-17β-hydroxy-estra-5(10)-en-3-one (142 g, 0.45 mol) as raw material, it was dissolved in 850 ml of pyridine, stirred and cooled to 20-25 °C to form a homogeneous solution. Subsequently, a solution of tribrominated pyridine (150 g, 0.47 mol) in 640 ml of pyridine was slowly added and the reaction temperature was controlled to gradually increase to 50 °C. The reaction mixture was stirred continuously at this temperature for 1 hour. After completion of the reaction, the mixture was slowly poured into a stirred mixture consisting of 320 ml of concentrated sulfuric acid and 5600 ml of water to quench the reaction. The precipitated crystals were separated by filtration and dried under vacuum at below 60°C. The crude product was purified by recrystallization from acetone to give 116 g (83% yield) of the final target compound 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. The product was analyzed by HPLC showing no less than 97% active ingredient content and no more than 1% impurity of 4-bromo-dienoglucose. The compound has a melting point of 210-213°C and a specific optical rotation [α]20D of -318° (c=1%, dichloromethane).
References
[1] Zeitschrift fur Chemie, 1986, vol. 26, # 10, p. 371 - 371
[2] Patent: WO2007/66158, 2007, A2. Location in patent: Page/Page column 9
[3] Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 3, p. 401 - 406
[4] Patent: US2010/298585, 2010, A1. Location in patent: Page/Page column 3, 4
Dienogestrel Preparation Products And Raw materials
Raw materials
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View Lastest Price from Dienogestrel manufacturers
- Product
- Dienogestrel 65928-58-7
- Price
- US $5.00-0.50/KG
- Min. Order
- 1KG
- Purity
- 99% hplc
- Supply Ability
- 500TONS
- Release date
- 2025-05-30
- Product
- Dienogestrel 65928-58-7
- Price
- US $0.00/g
- Min. Order
- 10g
- Purity
- 99%min
- Supply Ability
- 10kg/month
- Release date
- 2021-06-19
- Product
- Dienogestrel 65928-58-9
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 2000kg
- Release date
- 2025-02-27