Abiraterone
Abiraterone
CAS: 154229-19-3
Molecular Formula: C24H31NO
Abiraterone - Names and Identifiers
| Name | Abiraterone |
| Synonyms | CB7598 Cb-7598 CB-7598 CB 7598 Cb 7598 Abiraterone abiraterone Unii-G819A456D0 Abiraterone(CB-7598) 17-(3-Pyridyl)androsta-5,16-dien-3beta-ol (3b)-17-(3-pyridinyl)-Androsta-5,16-dien-3-ol (3beta)-17-(pyridin-3-yl)androsta-5,16-dien-3-ol Androsta-5,16-dien-3-ol, 17-(3-pyridinyl)-, (3beta)- |
| CAS | 154229-19-3 |
| EINECS | 810-941-6 |
| InChI | InChI=1/C24H31NO/c1-23-11-9-18(26)14-17(23)5-6-19-21-8-7-20(16-4-3-13-25-15-16)24(21,2)12-10-22(19)23/h3-5,7,13,15,18-19,21-22,26H,6,8-12,14H2,1-2H3/t18-,19-,21-,22-,23-,24+/m0/s1 |
Abiraterone - Physico-chemical Properties
| Molecular Formula | C24H31NO |
| Molar Mass | 349.52 |
| Density | 1.14±0.1 g/cm3(Predicted) |
| Melting Point | 227-228 °C(Solv: toluene (108-88-3)) |
| Boling Point | 500.2±50.0 °C(Predicted) |
| Flash Point | 256.3°C |
| Solubility | DMSO 0.1 mg/mL Water 0.02 mg/mL Ethanol 0.2 mg/mL |
| Vapor Presure | 7.99E-11mmHg at 25°C |
| Appearance | Solid |
| Color | White to Pale Yellow |
| pKa | 14.71±0.70(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.605 |
| Physical and Chemical Properties |
|
| Use | Androgen antagonists |
| In vitro study | Abiraterone binds to wild-type and mutant androgen receptors (AR). In Vitro, Abiraterone inhibits proliferation and androgen receptor-regulated gene expression in androgen receptor-positive prostate cancer cells, explaining the mechanism by inhibition of steroid and antiandrogen receptors. In fact, the mutant androgen receptor activated by Eplerenone can be inhibited by higher concentrations of Abiraterone. The Abiraterone replaces the ligand in WT-AR and T877A with an EC50 of 13.4 μm and 7.9 μm, respectively. Abiraterone acts on rat testis microparticles and inhibits lyase activity with an IC50 of 5.8 nM. Abiraterone acetate significantly inhibited T secretion (− 48%) and in turn increased LH concentrations. (192 percent). |
| In vivo study | In human testis microsomes, Abiraterone inhibits CYP17 with an IC50 of 72 nM. Abiraterone did not significantly reduce any organ size. Abiraterone strongly reduces the level of testosterone, almost to the level of removal of the testicles. Compared with the control group, Abiraterone reduced testosterone levels by more than 95%. |
Abiraterone - Reference Information
| Overview | Abiraterone is a targeted cytochrome CYP17 (17 α-hydroxylase/C17, 20-lyase) inhibitor. After hydrolysis, Abiraterone is produced. Abiraterone acetate reduces the production of testosterone by inhibiting cytochrome CYP17, it is suitable for the treatment of castration-refractory prostate cancer (CRPC) patients who have received previous chemotherapy containing docetaxel. Clinical trials have proved that abiraterone combined with prednisone can significantly prolong the overall survival of metastatic prostate cancer patients who have received docetaxel chemotherapy before. Follow-up studies have found that abiraterone also has a significant effect on patients who have not received docetaxel chemotherapy, according to which abiraterone is listed as the first-line treatment of human metastatic CRPC. Recent studies have shown that abiraterone can benefit patients with locally advanced or metastatic prostate cancer. These results will promote the early entry of abiraterone into the first-line treatment of advanced prostate cancer. |
| application | abiraterone is only approved for the treatment of CPRC refractory to multi-thin paclitaxel chemotherapy. However, a better understanding of its activity mechanism and tolerability adverse reactions is essential for abiraterone to be more widely used in clinic. Ryan et al. conducted a mid-term analysis of data in a cOuAA -302 study showing that this study used abiraterone acetate combined with prednisone to treat 1088 metastatic CPRC patients who had not received chemotherapy. The main observation indicators were the overall survival rate. And imaging indicators, the experiment confirmed that in an average of 8 months, compared with the contrast group abiraterone combined with prednisone slowed down the spread of cancer, delaying the chemotherapy time from 16.8 months to 25. |
| prostate cancer treatment | currently, castration treatment including drugs and surgery is generally the first choice for patients with advanced prostate cancer to reduce androgen synthesis in testis, but this treatment cannot inhibit androgen production in other parts of body body. Abiraterone is a prostate cancer treatment drug, whose English name is Abiraterone. It has not been sold in China. It was developed by researchers at the Royal Marsden Hospital (the world-renowned cancer research and treatment center) in southwest London. Invented. It can inhibit the production of androgens in any part of the body. It can not only reduce the level of prostate specific antigen (PSA) that represents tumor activity, but also help to shrink tumors. At the same time, it is suitable for tumor patients who have had chemotherapy in the past, showing treatment Hope. The previous patent of abiraterone was owned by the British Cougar Biopharmaceutical Company, but Johnson & Johnson acquired Cougar Biologics Company for US $0.97 billion in 2009, and thus obtained the license right of this drug. The results of phase III clinical trials show that this product can significantly prolong the lives of patients with advanced prostate cancer, including patients who use one or two chemotherapeutic drugs containing polyene violet alcohol but whose condition is still deteriorating, and the side effects of the drug are small and the safety is good. Abiraterone is an oral cytochrome oxidase P450(CYP450)c17 inhibitor, which reduces androgen levels by inhibiting CYP450c17, a key enzyme in androgen synthesis, and has inhibitory effects on androgens in testis and other parts of the body. |
| biological activity | Abiraterone (CB-7598) is an effective CYP17 inhibitor with IC50 of 2 nM in cell-free test. Abiraterone (CB-7598) is an inhibitor of male hormone androgen biosynthesis. |
| Target | Value |
| CYP17 (Cell-free assay) | 2 nM |
| use | androgen antagonist |
Last Update：2024-04-09 15:16:48
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View History
Abiraterone
Cyclopropaneacetic acid, α-amino-2-carboxy-, (αS,2S)-
110199-16-1
Benzenecarbodithioic acid phenylmethyl ester
2-amino-3-(thiazol-5-yl)propanoic acid hydrochloride
1,5-dioxo-4-propyl-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinazoline-3a-carboxylic acid
2-[(3,5-Dimethyl-1H-pyrazol-1-yl)carbonyl]-N-(4-ethylphenyl)-N-methylthiophene-3-sulfonamide
6-[(4-nitrophenyl)hydrazinylidene]hexane-1,2,3,4,5-pentol
1895922-78-7
1463527-59-4
Cyclopropaneacetic acid, α-amino-2-carboxy-, (αS,2S)-
110199-16-1
Benzenecarbodithioic acid phenylmethyl ester
2-amino-3-(thiazol-5-yl)propanoic acid hydrochloride
1,5-dioxo-4-propyl-1,2,3,3a,4,5-hexahydropyrrolo[1,2-a]quinazoline-3a-carboxylic acid
2-[(3,5-Dimethyl-1H-pyrazol-1-yl)carbonyl]-N-(4-ethylphenyl)-N-methylthiophene-3-sulfonamide
6-[(4-nitrophenyl)hydrazinylidene]hexane-1,2,3,4,5-pentol
1895922-78-7
1463527-59-4