(11beta,17alpha)-17-acetyl-11-[4-(dimethylamino)phenyl]-3-oxoestra-4,9-dien-17-yl acetate
17alpha-Acetoxy-11beta-[4-(dimethylamino)phenyl]-19-norpregna-4,9-diene-3,20-dione
CAS: 126784-99-4
Molecular Formula: C30H37NO4
(11beta,17alpha)-17-acetyl-11-[4-(dimethylamino)phenyl]-3-oxoestra-4,9-dien-17-yl acetate - Names and Identifiers
| Name | 17alpha-Acetoxy-11beta-[4-(dimethylamino)phenyl]-19-norpregna-4,9-diene-3,20-dione |
| Synonyms | VA 2914 CDB-2914 CBD 2914 HRP 2000 Ulipristal RTI-3021-012 Ulipristal,Ella ulipristal acetate Ulipristal acetate Ulipristal Acetate 17α-Acetoxy-11β-(4-dimethylaminophenyl)-19-norpregna-4,9-dien-3,20-dione 17alpha-Acetoxy-11beta-[4-(dimethylamino)phenyl]-19-norpregna-4,9-diene-3,20-dione (11b)-17-(Acetyloxy)-11-[4-(dimethylamino)phenyl]-19-norpregna-4,9-diene-3,20-dione (11beta,17alpha)-17-acetyl-11-[4-(dimethylamino)phenyl]-3-oxoestra-4,9-dien-17-yl acetate |
| CAS | 126784-99-4 |
| EINECS | 682-170-1 |
| InChI | InChI=1/C30H37NO4/c1-18(32)30(35-19(2)33)15-14-27-25-12-8-21-16-23(34)11-13-24(21)28(25)26(17-29(27,30)3)20-6-9-22(10-7-20)31(4)5/h6-7,9-10,16,25-27H,8,11-15,17H2,1-5H3/t25-,26+,27-,29-,30-/m0/s1 |
(11beta,17alpha)-17-acetyl-11-[4-(dimethylamino)phenyl]-3-oxoestra-4,9-dien-17-yl acetate - Physico-chemical Properties
| Molecular Formula | C30H37NO4 |
| Molar Mass | 475.62 |
| Density | 1.19 |
| Melting Point | 183-185 ºC |
| Boling Point | 640.1±55.0 °C(Predicted) |
| Flash Point | 340.9°C |
| Solubility | Chloroform, Ethyl Acetate, Methanol |
| Vapor Presure | 2.77E-16mmHg at 25°C |
| Appearance | White to beige powder |
| Color | white to beige |
| pKa | 5.49±0.24(Predicted) |
| Storage Condition | -20°C |
| Refractive Index | 1.593 |
| MDL | MFCD00899035 |
(11beta,17alpha)-17-acetyl-11-[4-(dimethylamino)phenyl]-3-oxoestra-4,9-dien-17-yl acetate - Reference Information
| oral emergency contraceptives | uriestat acetate is a new type of oral emergency contraceptives, which is the active chemical ingredient of Ella, a new generation of emergency contraceptives currently on the market in the United States. Not only can it be administered within 120 hours after unprotected sexual intercourse, but the efficacy of emergency contraception will not decrease with the delay of medication, and the safety and tolerance are very good. Compared with levonorgestrel, which is currently the most commonly used emergency contraceptive, uprostat acetate has a wider clinical applicability and has the potential to prevent more unintended pregnancies. Ulistat acetate was developed by HRA Pharmaceutical Company and approved by the FDA of the US Food and Drug Administration in August 2010. Its trade name is Ella. It is used for the prevention of pregnancy within 120h after unprotected sex or known or suspected contraceptive failure. Uristat acetate is a selective progesterone receptor modulator, which mainly exerts emergency contraceptive effect by inhibiting ovulation. Relevant studies have found that when administered close to the day of puffing (the highest chance of conception), ulinostat acetate can inhibit puffing more effectively than levonorgestrel, suggesting that ulinostat acetate may have a stronger emergency Contraceptive efficacy. Figure 1 is the structural formula of Uristat acetate. |
| Pharmacological action | Ulinistar acetate (ulipristal acetate) is a progesterone agonist/antagonist, Its mechanism of action is to inhibit or delay ovulation; however, changes in the endometrium may also be one of the reasons for the efficacy. Uristat acetate is a selective progesterone receptor modulator, which has antagonistic and partial agonistic effects on progesterone receptors. It binds to the progesterone receptor in the human body to prevent the binding of progesterone to the progesterone receptor. The efficacy of ulisostat acetate depends on the time of administration during the menstrual cycle. Administration in the middle stage of follicular hyperplasia inhibits follicle production and reduces estradiol concentration. The administration of luteinizing hormone during the peak period can delay the rupture of follicles for 5~9 days. Early administration of corpus luteum did not significantly delay endometrial maturation, but could reduce endometrial thickness by 0.6±2.2mm (mean ± SD). |
| pharmacokinetics | absorption: under fasting conditions, 20 women were given Ulistat acetate (ulipristal acetate) in a single dose, the highest plasma concentrations of ulipristal acetate and active metabolite (monodesmethyl-ulipristal acetate) reached 176 and 69ng/mL at 0.9h and 1h, respectively. The average Cmax of ulipristal acetat and mono-desmethyl-ulipristal acetate was lower by 40% ~ 45%, the delay tmax (delayed from median 0.75h to 3h) and the average AUC0-∞ were higher by 20% ~ 25% when taken together with high-fat breakfast. These differences are not expected to impair the efficacy or safety of ulipril acetate, so ulipril acetate can be taken with or without food. Distribution: This product has a high binding rate (>94%) with plasma proteins, including high density lipoprotein, α-1-acid glycoprotein and albumin. Metabolism: Ulipristal acetate are metabolized as mono-demethylated and bis-demethylated metabolites. In vitro data show that mono-demethylated metabolites have pharmacological activity mainly due to the mediation of CYP3A4. Excretion: The estimated terminal half-life of ulipristal acetate in plasma after a single dose of 30mg of ulinastat acetate is (32.4±6.3)h. |
| market prospect | emergency contraceptives, also known as post-event contraceptives, are emergency contraceptives for women of childbearing age to prevent unintended pregnancy after unprotected sexual intercourse or contraceptive failure. at present, levonorgestrel (1 evonorgestre1) is the most widely used emergency contraceptive. one tablet (0.75 mg) is taken at intervals of 12 hours or two tablets (1.5mg) is taken at a single dose. However, levonorgestrel is only approved for use as an emergency contraceptive within 72 hours (3 days) after unprotected sexual intercourse or contraceptive failure. Even so, the emergency contraceptive efficacy of levonorgestrel will decrease significantly with the delay of medication time, so it is recommended to start medication within 12 hours after unprotected sexual intercourse or contraceptive failure. In May 2009, the European Union approved a new type of emergency contraception, Ulipristine acetate (ulipristal acetate/EllaOne). The drug is not only allowed to be taken within 120 hours (5d) after unprotected sexual intercourse or contraceptive failure, but also the effectiveness of emergency contraception will not decrease with the delay of medication. Uristat acetate is the first oral emergency contraceptive approved worldwide to be used within 120 hours after unprotected sexual intercourse or contraceptive failure. It has the potential benefit of preventing more unwanted pregnancies than levonorgestrel. As a new type of oral emergency contraceptive, Ulipristine acetate can not only be administered within 120 h after unprotected sexual intercourse in women, but also the effectiveness of emergency contraception will not decrease with the delay of medication. At the same time, the safety and tolerance are very good. Compared with levonorgestrel, which is currently the most commonly used emergency contraceptive, uproxil acetate has a wider clinical applicability and has the potential to prevent more unintended pregnancies. |
| intellectual property situation | the original research manufacturer has applied for the patent of ulisstat acetate tablets, indications and usage in China, which has not been authorized at present and there is no intellectual property obstacle. |
| other clinical studies | two clinical trial studies published in the new england journal of medicine on February 2, 2012 found that ulipat acetate has excellent therapeutic effect on uterine fibroids. The results of the study show that ulutake acetate is better than placebo in controlling uterine fibroids bleeding, reducing fibroids volume, and improving pain effects, and is comparable to leuprolide. According to statistics, about 1/4 women suffer from uterine fibroids. Leuprolide acetate, as a gonadotropin-releasing hormone (GnRH) agonist, has been used for preoperative treatment of uterine fibroids since it was approved in 1995. Whether ulipristine acetate can successfully challenge leuprolide and become a new choice for preoperative drug treatment of uterine fibroids, let the later trials reveal the answer. |
Last Update：2024-04-09 20:02:46
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QQ: 2853786052
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