Dienogest

CAS# 65928-58-7

Dienogest

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Chemical structure

Dienogest

3D structure

Chemical Properties of Dienogest

Cas No. 65928-58-7 SDF Download SDF
PubChem ID 68861 Appearance Powder
Formula C20H25NO2 M.Wt 311.42
Type of Compound N/A Storage Desiccate at -20°C
Synonyms STS 557
Solubility DMSO : 25 mg/mL (80.28 mM; Need ultrasonic)
Chemical Name 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
SMILES CC12CCC3=C4CCC(=O)C=C4CCC3C1CCC2(CC#N)O
Standard InChIKey AZFLJNIPTRTECV-FUMNGEBKSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Dienogest

DescriptionDienogest(STS-557) is a specific progesterone receptor agonist with potent oral endometrial activity and is used in the treatment of endometriosis. Target: progesterone receptor agonist 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. It is a non-ethinylated progestin which is structurally related to testosterone [1]. Complete sperm suppression was observed in rats sacrificed either 60 or 90 days after dienogest (DNG)+ testosterone undecanoate (TU) administration, for two injections at 45-day interval. The neutral α-glucosidase activity in these treated rats remained in the normal range. Germ cell loss due to apoptosis was frequently observed both after 60 or 90 days of combination treatment. Significant decline in serum gonadotropin and testosterone, both serum and intratesticular levels, were observed in the treated rats. Following stoppage of treatment (given at 45-day interval) after two (0 and 45 days) or three injections (0, 45 and 90 days), complete restoration of spermatogenesis was observed by 120 and 165 days, respectively [2]. Clinical indications: Adenomyosis; Endometriosis FDA Approved Date: 1995 Toxicity: weight gain; increased blood pressure; breast tenderness and nausea

References:
[1]. Oettel M, et al. Effect of ethinyl estradiol-dienogest combination on serum androgen concentrations. Zentralbl Gynakol. 1997;119(12):597-606. [2]. Meena R, et al. Extended intervention time and evaluation of sperm suppression by dienogest plus testosterone undecanoate in male rat. Contraception. 2012 Jan;85(1):113-21.

Dienogest Dilution Calculator

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Dienogest Molarity Calculator

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Preparing Stock Solutions of Dienogest

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.2111 mL 16.0555 mL 32.111 mL 64.222 mL 80.2774 mL
5 mM 0.6422 mL 3.2111 mL 6.4222 mL 12.8444 mL 16.0555 mL
10 mM 0.3211 mL 1.6055 mL 3.2111 mL 6.4222 mL 8.0277 mL
50 mM 0.0642 mL 0.3211 mL 0.6422 mL 1.2844 mL 1.6055 mL
100 mM 0.0321 mL 0.1606 mL 0.3211 mL 0.6422 mL 0.8028 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Dienogest

Dienogest is a specific progesterone receptor agonist with potent oral endometrial activity and is used in the treatment of endometriosis.

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References on Dienogest

Dienogest and deep infiltrating endometriosis: The remission of symptoms is not related to endometriosis nodule remission.[Pubmed:28231497]

Eur J Obstet Gynecol Reprod Biol. 2017 Apr;211:108-111.

OBJECTIVE: To evaluate the effectiveness of Dienogest in controlling pain caused by deep infiltrating endometriosis (DIE), its influence on the quality of live (QoL) of women affected by the disease, and the effect of the drug on the volume of endometriotic lesions. STUDY DESIGN: A prospective cohort study including 30 women with a sonographic diagnosis of DIE (intestinal and posterior fornix) treated with Dienogest 2mg per day for 12 months. We evaluated the pain symptoms and the volume of the intestinal and posterior fornix lesions before and after 12 months of use of Dienogest. To perform the statistical analysis, we used the Wilcoxon signed-rank test, and the relationship between the data was tested using the Spearman correlation coefficient. RESULTS: Women were on average 36.13+/-6.24years old. Pain symptoms most commonly reported were dyspareunia (83.3%), dysmenorrhea (73.3%), and pelvic pain (66.7%). After 12 months of treatment with Dienogest, there was significant improvement of various symptoms (dyspareunia p=0.0093, dysmenorrhea p<0.0001; pelvic pain p=0.0007; and bowel pain p<0.0001), without a reduction in the volume of endometriotic nodules. There were significant improvements in the parameters that comprise the QoL (physical p<0.0001; p=0.0007 psychological) and the self-assessment of QoL (p=0.0069) and health (p=0.0001). CONCLUSION: Dienogest is an effective medication to control symptoms of pain related to DIE, even without reducing the volume of DIE nodules.

Effects of long-term postoperative dienogest use for treatment of endometriosis on bone mineral density.[Pubmed:28314166]

Eur J Obstet Gynecol Reprod Biol. 2017 May;212:9-12.

OBJECTIVE: This study was conducted to evaluate the effects of long-term postoperative Dienogest (DNG) use for the treatment of endometriosis on bone mineral density (BMD). STUDY DESIGN: Sixty reproductive-aged women who underwent conservative surgery for endometriomas and received postoperative DNG (2mg/day) for at least 12 months to prevent recurrence were analyzed. BMD was measured before and after DNG treatment by using dual energy X-ray absorptiometry, and changes in BMD were evaluated. RESULTS: Mean patient age was 30.5 years, and mean duration of DNG treatment was 18.6 months. BMD at the lumbar spine significantly decreased after the first 6 months (-2.2%), and 1year (-2.7%) of DNG treatment, compared to baseline. The proportion of women who had significantly decreased BMD at the lumbar spine after 1year was 75% (45/60). In addition, BMD at the femur neck also decreased significantly after 1year (-2.8%). BMDs after 2 years were not different from those after 1year at both sites in 24 women who received DNG for >/=2years. In addition, there were no differences in baseline characteristics between women who had significantly reduced BMD at the lumbar spine after 1year (N=45) and women who did not (N=15). CONCLUSION: This study suggests that long-term postoperative DNG treatment might have an adverse effect on BMD in reproductive-aged women. Bone loss mostly occurs during the first 6 months of treatment with DNG. A clinical trial is warranted to establish the effects of long-term DNG treatment on bone mass.

Long-term medical management of endometriosis with dienogest and with a gonadotropin-releasing hormone agonist and add-back hormone therapy.[Pubmed:28139239]

Fertil Steril. 2017 Mar;107(3):537-548.

Endometriosis can recur after either surgical or medical therapy. Long-term medical therapy is implemented to treat symptoms or prevent recurrence. Dienogest and gonadotropin-releasing hormone (GnRH) analogues with hormone add-back therapy seem to be equally effective for long-term treatment of pain symptoms associated with endometriosis. There is insufficient evidence to support the superiority of one therapy over the other. However, add-back hormone therapy (HT) is recommended for patients using GnRH agonists. The treatment selection depends on therapeutic effectiveness, tolerability, drug cost, the physician's experience, and expected patient compliance.

Dienogest 2 mg Daily in the Treatment of Adolescents with Clinically Suspected Endometriosis: The VISanne Study to Assess Safety in ADOlescents.[Pubmed:28189702]

J Pediatr Adolesc Gynecol. 2017 Oct;30(5):560-567.

STUDY OBJECTIVE: To study the safety and efficacy of Dienogest 2 mg in adolescents with suspected endometriosis. DESIGN: A 52-week, open-label, single-arm study. SETTING: In 21 study centers, in 6 European countries. PARTICIPANTS: Adolescents aged 12 to younger than 18 years with clinically suspected or laparoscopically confirmed endometriosis. INTERVENTIONS: Dienogest 2 mg once daily. MAIN OUTCOME MEASURES: The primary end point was relative change in lumbar spine (L2-L4) bone mineral density (BMD) measured using dual-energy x-ray absorptiometry. A key secondary end point was change in endometriosis-associated pain assessed using a visual analogue scale. RESULTS: Of 120 patients screened, 111 comprised the full-analysis set (ie, patients who took >/=1 dose of study drug and had >/=1 post-treatment observation) and 97 (87.4%) completed the study. Mean lumbar BMD at baseline was 1.1046 (SD, 0.1550) g/cm(2). At the end of Dienogest treatment (EOT; defined as at 52 weeks or premature study discontinuation), mean relative change in BMD from baseline was -1.2% (SD, 2.3%; n = 103). Follow-up measurement 6 months after EOT in the subgroup with decreased BMD at EOT (n = 60) showed partial recovery in lumbar BMD (mean change from baseline: -2.3% at EOT, -0.6% 6 months after EOT). Mean endometriosis-associated pain score was 64.3 (SD, 19.1) mm at baseline and decreased to 9.0 (SD, 13.9) mm by week 48. CONCLUSION: In adolescents with suspected endometriosis, Dienogest 2 mg for 52 weeks was associated with a decrease in lumbar BMD, followed by partial recovery after treatment discontinuation. Endometriosis-associated pain was substantially reduced during treatment. Because bone accretion is critical during adolescence, results of the VISanne study to assess safety in ADOlescents (VISADO) study highlights the need for tailored treatment in this population, taking into account the expected efficacy on endometriosis-associated pain and an individual's risk factors for osteoporosis.

Description

Dienogest(STS-557) is a specific progesterone receptor agonist with potent oral endometrial activity and is used in the treatment of endometriosis.

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