Chemistry:Metapristone
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| Other names | RU-42633; Desmethylmifepristone; 17β-Hydroxy-11β-[4-(methylamino)phenyl]-17α-(prop-1-yn-1-yl)estra-4,9-dien-3-one |
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| Formula | C28H33NO2 |
| Molar mass | 415.577 g·mol−1 |
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Metapristone (developmental code name RU-42633; also known as desmethylmifepristone) is the major metabolite of mifepristone (RU-486, RU-38486) and a selective progesterone receptor modulator (SPRM) which itself was never marketed.[1][2][3][4] It is formed from mifepristone in the liver by the enzyme CYP3A4 via monodemethylation, and circulates at concentrations higher than those of mifepristone.[1][5] The metabolite retains partial but considerable affinity for the progesterone receptor (PR) and the glucocorticoid receptor (GR) (RBA = 21% and 61% of that of mifepristone for the human forms of these receptors, respectively).[6][1] On the basis of actions that are apparently independent of its hormonal activity, metapristone is being researched as a potential cancer metastatic chemopreventive agent.[2][3][4]
References
- ↑ 1.0 1.1 1.2 "Clinical pharmacokinetics of mifepristone". Clin Pharmacokinet 33 (1): 7–17. July 1997. doi:10.2165/00003088-199733010-00002. PMID 9250420.
- ↑ 2.0 2.1 "Synthesis, spectral characterization, and in vitro cellular activities of metapristone, a potential cancer metastatic chemopreventive agent derived from mifepristone (RU486)". AAPS J 16 (2): 289–98. March 2014. doi:10.1208/s12248-013-9559-2. PMID 24442753.
- ↑ 3.0 3.1 "In vitro and in vivo efficacy and safety evaluation of metapristone and mifepristone as cancer metastatic chemopreventive agents". Biomed. Pharmacother. 78: 291–300. March 2016. doi:10.1016/j.biopha.2016.01.017. PMID 26898454.
- ↑ 4.0 4.1 "Sex-related pharmacokinetic differences and mechanisms of metapristone (RU486 metabolite)". Sci Rep 7 (1): 17190. December 2017. doi:10.1038/s41598-017-17225-0. PMID 29215040. Bibcode: 2017NatSR...717190C.
- ↑ United States Pharmacopeial Convention (2006). USP DI: United States Pharmacopeia Dispensing Information. United States Pharmacopeial Convention. p. 1992. ISBN 978-1-56363-574-8. https://books.google.com/books?id=QWNPAQAAIAAJ.
- ↑ "The pharmacokinetics of mifepristone in humans reveal insights into differential mechanisms of antiprogestin action". Contraception 68 (6): 421–6. December 2003. doi:10.1016/S0010-7824(03)00077-5. PMID 14698071.
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