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Metapristone

Clinical data
Other names	RU-42633; Desmethylmifepristone; 17β-Hydroxy-11β--17α-(prop-1-yn-1-yl)estra-4,9-dien-3-one
Identifiers
IUPAC name (8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-11--17-prop-1-ynyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopentaphenanthren-3-one
CAS Number	104004-96-8
PubChem CID	10070462
ChemSpider	8246002
UNII	K1P8OGJ86J
ChEMBL	ChEMBL1608
CompTox Dashboard (EPA)	DTXSID60146216
Chemical and physical data
Formula	C28H33NO2
Molar mass	415.577 g·mol
3D model (JSmol)	Interactive image
SMILES CC#C1(CC21(C(C3=C4CCC(=O)C=C4CC23)C5=CC=C(C=C5)NC)C)O
InChI InChI=1S/C28H33NO2/c1-4-14-28(31)15-13-25-23-11-7-19-16-21(30)10-12-22(19)26(23)24(17-27(25,28)2)18-5-8-20(29-3)9-6-18/h5-6,8-9,16,23-25,29,31H,7,10-13,15,17H2,1-3H3/t23-,24+,25-,27-,28-/m0/s1 Key:IBLXOBHABOVXDY-WKWWZUSTSA-N

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. It is formed from mifepristone in the liver by the enzyme CYP3A4 via monodemethylation, and circulates at concentrations higher than those of mifepristone. The metabolite retains partial but considerable affinity for the progesterone receptor (PR) and the glucocorticoid receptor (GR) (RBATooltip relative binding affinity = 21% and 61% of that of mifepristone for the human forms of these receptors, respectively). On the basis of actions that are apparently independent of its hormonal activity, metapristone is being researched as a potential cancer metastatic chemopreventive agent.

References

1. ^ Heikinheimo O (July 1997). "Clinical pharmacokinetics of mifepristone". Clin Pharmacokinet. 33 (1): 7–17. doi:10.2165/00003088-199733010-00002. PMID 9250420. S2CID 25101911.
2. ^ Wang J, Chen J, Wan L, Shao J, Lu Y, Zhu Y, Ou M, Yu S, Chen H, Jia L (March 2014). "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. doi:10.1208/s12248-013-9559-2. PMC 3933578. PMID 24442753.
3. ^ Wang J, Chen J, Zhu Y, Zheng N, Liu J, Xiao Y, Lu Y, Dong H, Xie J, Yu S, Shao J, Jia L (March 2016). "In vitro and in vivo efficacy and safety evaluation of metapristone and mifepristone as cancer metastatic chemopreventive agents". Biomed. Pharmacother. 78: 291–300. doi:10.1016/j.biopha.2016.01.017. PMID 26898454.
4. ^ Chen W, Xiao Y, Chen J, Liu J, Shao J, Li T, Zhu Y, Ma J, Gao Y, Wang J, Xu J, Lu Y, Jia L (December 2017). "Sex-related pharmacokinetic differences and mechanisms of metapristone (RU486 metabolite)". Sci Rep. 7 (1): 17190. Bibcode:2017NatSR...717190C. doi:10.1038/s41598-017-17225-0. PMC 5719405. PMID 29215040.
5. United States Pharmacopeial Convention (2006). USP DI: United States Pharmacopeia Dispensing Information. United States Pharmacopeial Convention. p. 1992. ISBN 978-1-56363-574-8.
6. Heikinheimo O, Kekkonen R, Lähteenmäki P (December 2003). "The pharmacokinetics of mifepristone in humans reveal insights into differential mechanisms of antiprogestin action". Contraception. 68 (6): 421–6. doi:10.1016/S0010-7824(03)00077-5. PMID 14698071.

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