Etonogestrel
| Physical Appearance | A solid |
| Storage | Store at -20°C |
| M.Wt | 324.46 |
| Cas No. | 54048-10-1 |
| Formula | C22H28O2 |
| Solubility | insoluble in H2O; ≥15.05 mg/mL in DMSO; ≥2.78 mg/mL in EtOH with gentle warming and ultrasonic |
| Chemical Name | (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-11-methylene-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one |
| SDF | Download SDF |
| Canonical SMILES | CC[C@@]1([C@@]([C@]2([H])CCC3=CC(CC[C@]3([H])[C@@]42[H])=O)([H])CC[C@@]1(O)C#C)CC4=C |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Cell experiment[1]: | |
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Cell lines |
human endometrial stromal cells |
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Preparation method |
The solubility of this compound in DMSO is > 10 mM. General tips for obtaining a higher concentration: Please warm the tube at 37 ℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months. |
|
Reacting condition |
7 days, 100 nM |
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Applications |
Etonogestrel is the active metabolite of prodrug desogestrel. Etonogestrel activates GR signaling and induces FKBP51 mRNA and protein expression in HESCs. |
| Animal experiment [2]: | |
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Animal models |
Female C57BL/6 mice aged 8–12 weeks |
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Dosage form |
Ovariectomized mice received three daily s.c. injections of 100 ng 17β-estradiol. Then mice were rested for 3 days before insertion of one-fourth of a standard Implanon rod containing etonogestrel subcutaneously into the back of the animals. Examine the effect of long-term exposure (up to 45 days) to etonogestrel on endometrium. |
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Application |
Large blood vessels developed in decidualized horns. Disturbance of tissue integrity occurred at 5d with substantial stromal breakdown at 10d. This progress proceeded until 25d when re-epithelialization was initiated. At 45d, the tissue was recovered to its pre-decidualized state but with plentiful tortuosity of the luminal epithelium. |
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Other notes |
Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
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References: [1]. Kayisli O G, Kayisli U A, Basar M, et al. Progestins Upregulate FKBP51 Expression in Human Endometrial Stromal Cells to Induce Functional Progesterone and Glucocorticoid Withdrawal: Implications for Contraceptive-Associated Abnormal Uterine Bleeding[J]. PloS one, 2015, 10(10): e0137855. [2]. Morison N B, Zhang J, Tu’uhevaha J, et al. The long-term actions of etonogestrel and levonorgestrel on decidualized and non-decidualized endometrium in a mouse model mimic some effects of progestogen-only contraceptives in women[J]. Reproduction, 2007, 133(1): 309-321. | |
Quality Control & MSDS
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Chemical structure
