GestodeneCAS# 60282-87-3 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 60282-87-3 | SDF | Download SDF |
| PubChem ID | 43249 | Appearance | Powder |
| Formula | C21H26O2 | M.Wt | 310.43 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | SHB 331; WL 70 | ||
| Solubility | DMSO : ≥ 100 mg/mL (322.13 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | (17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14-decahydrocyclopenta[a]phenanthren-3-one | ||
| SMILES | CCC12CCC3C(C1C=CC2(C#C)O)CCC4=CC(=O)CCC34 | ||
| Standard InChIKey | SIGSPDASOTUPFS-KQMXEUTGSA-N | ||
| Standard InChI | InChI=1S/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16?,17?,18?,19?,20?,21-/m0/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. |
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| 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. |
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| 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. | ||
| Description | Gestodene(SHB 331;WL 70) is a progestogen hormonal contraceptive.
Target: Estrogen Receptor/ERR
Gestodene is androgenically neutral, meaning that contraceptive pills containing gestodene do not exhibit the androgenic side effects (e.g. acne, hirsutism, weight gain) often associated with second-generation contraceptive pills, such as those containing levonorgestrel. When 40 micrograms of gestodene was taken, six out of seven women did not ovulate, and one out of seven had a cycle with luteal insufficiency. These data indicate that 40 micrograms of gestodene is the borderline dose for inhibition of ovulation. A combination of 75 micrograms gestodene with 30 micrograms ethinyl estradiol was found to inhibit ovulation in ten subjects, and no follicular maturation was noted [1]. gestodene bound with high affinity to the progesterone receptor, as did other synthetic and natural progestogens. However, gestodene did not bind to the estradiol receptor. The relative binding affinities of all tested synthetic and natural ligands showed no organ-specific differences and no differences between neoplastically transformed and normal tissues [2].
Clinical indications: Female contraception References: | |||||
Gestodene Dilution Calculator
Gestodene Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.2213 mL | 16.1067 mL | 32.2134 mL | 64.4268 mL | 80.5335 mL |
| 5 mM | 0.6443 mL | 3.2213 mL | 6.4427 mL | 12.8854 mL | 16.1067 mL |
| 10 mM | 0.3221 mL | 1.6107 mL | 3.2213 mL | 6.4427 mL | 8.0533 mL |
| 50 mM | 0.0644 mL | 0.3221 mL | 0.6443 mL | 1.2885 mL | 1.6107 mL |
| 100 mM | 0.0322 mL | 0.1611 mL | 0.3221 mL | 0.6443 mL | 0.8053 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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Gestodene is a progestogen hormonal contraceptive.
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Preparation and in vitro/in vivo evaluation of gestodene (GEST) intravaginal ring.[Pubmed:27731811]
Pak J Pharm Sci. 2016 Sep;29(5):1545-1553.
Preparation and in vitro/in vivo evaluation of Gestodene (GEST) intravaginal ring (IVR) formulations which can release a constant dose of GEST during 3 weeks were investigated. In present study a reservoir Gestodene intravaginal ring, including a Gestodene silicone elastomer core and the non-active silicone layer, was reported, which was manufactured by reaction injection moulding at 80 degrees C for 20 min. The raw materials compatibility experiments showed that the silicone elastomer core carrier wouldn't interact with drugs. In vitro release samples were determined by HPLC and the experiment was performed under sink conditions. The equation of cumulative release verse time was Y=64.76chi+5.44 (r=0.9998), performing zero-order release at about the target dose of 60 microg/day over 21 days. Drug release increased with temperature elevating from 45 to 55 degrees C, which could be attributed to optimizing the prescription. In addition, the pharmacokinetic and safety studies of Gestodene intravaginal ring were evaluated in female New Zealand White rabbits. The GEST in plasma was analyzed by LC-MS/MS and the results proved that the correlation between in vitro and in vivo was relatively well.
Degradation of gestodene (GES)-17alpha-ethinylestradiol (EE2) mixture by electrochemical oxidation.[Pubmed:27959876]
J Water Health. 2016 Dec;14(6):980-988.
Evidence of the negative effects of several pharmaceutical molecules, such as hormones and steroids, on the environment can be observed throughout the world. This paper presents the results of the anodic oxidation of the mixture of Gestodene steroid hormones and 17 alpha-ethinylestradiol present in aqueous medium. The tests were conducted in an undivided cell containing a working volume of 50 mL, using a Na2SO4 solution as support electrolyte and boron-doped diamond electrodes. The experiments were adjusted to the structure of a 3(3) factorial design. The evaluated factors were: support electrolyte concentration (0.02, 0.05, and 0.10 M), pH of the reaction media (2, 3, and 4), and current density (16, 32, and 48 mA cm(-2)). Under the optimum conditions (0.02 M Na2SO4, pH 4, and current density of 32 mA cm(-2)), the degradation of at least 93% of the initial concentration of Gestodene and 17alpha-ethinylestradiol was reached in a reaction time of 5 and 10 min, respectively. The complete degradation of both molecules required 15 min of reaction. Under these conditions, the degradation profile of the pharmaceutical mixture as each one of the active ingredients, followed a pseudo-first order kinetic behavior (kmix = 0.0321, kGES = 0.4206, and kEE2 = 0.3209 min(-1)).
An open-label, two-period comparative study on pharmacokinetics and safety of a combined ethinylestradiol/gestodene transdermal contraceptive patch.[Pubmed:28331292]
Drug Des Devel Ther. 2017 Mar 10;11:725-731.
We investigated the pharmacokinetics and safety profiles of a newly developed combined ethinylestradiol (EE)/Gestodene (GSD) transdermal contraceptive patch after a single-dose administration and compared with the market available tablet formulation in healthy adult subjects. An open-label, two-period comparative study was conducted in 12 healthy women volunteers. A single dose of the study combined EE/GE transdermal contraceptive patch and oral tablet (Milunet((R))) were administered. Blood samples at different time points after dose were collected, and concentrations were analyzed. A reliable, highly sensitive and accurate high-performance liquid chromatography coupled with tandem mass spectrometry (HPLC/MS/MS) assay method was developed in this study to determine the plasma concentrations of EE and GSD. Compared to the tablet, the study patch had a significantly decreased maximum plasma concentration (Cmax), extended time to reach the Cmax and half-life, as well as increased clearance and apparent volume of distribution. The half-lives of EE and GSD of the patch were 3.3 and 2.2 times, respectively, than the half-life of the tablet. The areas under the plasma concentration-time curve (AUCs) of EE and GSD of the patch were 8.0 and 16.2 times, respectively, than the AUC of the tablet. No severe adverse event was observed during the whole study, and the general safety was acceptable. In conclusion, compared to the oral tablet Milunet, the study contraceptive patch was well tolerated and showed potent drug exposure, significant extended half-life and stable drug concentrations.
The synthetic progestin, gestodene, affects functional biomarkers in neonatal rat osteoblasts through an estrogen receptor-related mechanism of action.[Pubmed:28328298]
Endocr Res. 2017 Nov;42(4):269-280.
BACKGROUND: Clinical studies have shown that Gestodene (GDN), a potent third-generation synthetic progestin, affects bone resorption. However, its mode of action in bone cells is not fully understood. The aim of this study was to establish whether GDN affects bone directly or through its bioconversion to other metabolites with different biological activities. METHODS: In this study, we investigated the effects of GDN and its A-ring reduced metabolites on proliferation, differentiation, and mineralization of calvarial osteoblasts isolated from neonatal rat and their capacity to displace [(3)H]-E2 at ER binding sites. RESULTS: In contrast to progesterone, Gestodene did exert significant effects on osteoblast activities. The most striking finding was the observation that the A-ring reduced derivatives 3beta,5alpha-tetrahydro-GDN and 3alpha,5alpha-tetrahydro-GDN, though to a lesser extent, had greater stimulatory effects on the osteoblast activity than those observed with GDN. The effects on osteoblast proliferation and differentiation induced by GDN-reduced derivatives were abolished by the antiestrogen ICI 182780, consistent with their binding affinities for the estrogen receptor. In addition, the presence of a 5alpha-reductase inhibitor or inhibitors of aldo-keto hydroxysteroid dehydrogenases abolished the GDN-induced enhancement of osteoblast differentiation. These results indicated that GDN is metabolized to the A-ring reduced metabolites with estrogen-like activities and through this mechanism, GDN may affect the osteoblast activity. CONCLUSION: Together, the data suggest that synthetic progestins derived from 19-nortestosterone such as GDN, have beneficial effects on bone due to their biotransformation into metabolites with intrinsic estrogenic activity.
