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Chemical compound
Metapristone
Other names RU-42633; Desmethylmifepristone; 17β-Hydroxy-11β-[4-(methylamino)phenyl]-17α-(prop-1-yn-1-yl)estra-4,9-dien-3-one
(8S ,11R ,13S ,14S ,17S )-17-hydroxy-13-methyl-11-[4-(methylamino)phenyl]-17-prop-1-ynyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a ]phenanthren-3-one
CAS Number
PubChem
CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (
EPA )
Formula C 28 H 33 N O 2
Molar mass 415.577 g·mol−1 3D model (
JSmol )
CC#C[C@@]1(CC[C@@H]2[C@@]1(C[C@@H](C3=C4CCC(=O)C=C4CC[C@@H]23)C5=CC=C(C=C5)NC)C)O
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.
[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 Tooltip relative binding affinity = 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
^
a
b
c Heikinheimo O (July 1997). "Clinical pharmacokinetics of mifepristone". Clin Pharmacokinet . 33 (1): 7–17.
doi :
10.2165/00003088-199733010-00002 .
PMID
9250420 .
S2CID
25101911 .
^
a
b 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 .
^
a
b 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 .
^
a
b 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 .
^ United States Pharmacopeial Convention (2006).
USP DI: United States Pharmacopeia Dispensing Information . United States Pharmacopeial Convention. p. 1992.
ISBN
978-1-56363-574-8 .
^ 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 .
GR Tooltip Glucocorticoid receptor
PR Tooltip Progesterone receptor
Agonists
Testosterone derivatives: Progestins:
6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
Desogestrel
Dienogest
Ethinylandrostenediol
Ethisterone
Ethynerone
Etonogestrel
Etynodiol
Etynodiol diacetate
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g.,
levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Metynodiol
Metynodiol diacetate
Norelgestromin
Norethisterone (norethindrone)
Norethisterone esters (e.g.,
norethisterone acetate ,
norethisterone enanthate )
Noretynodrel
Norgesterone
Norgestimate
Norgestrel
Norgestrienone
Norvinisterone
Oxendolone
Quingestanol
Quingestanol acetate
Tibolone
Tigestol
Tosagestin ; Anabolic–androgenic steroids:
11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
Bolandiol
Bolandiol dipropionate
Bolandione
Dimethisterone
Dienedione
Dienolone
Dimethandrolone
Dimethandrolone buciclate
Dimethandrolone dodecylcarbonate
Dimethandrolone undecanoate
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol (ethylnandrol)
Methyldienolone
Metribolone (R-1881)
Methoxydienone (methoxygonadiene)
Mibolerone
Nandrolone
Nandrolone esters (e.g.,
nandrolone decanoate ,
nandrolone phenylpropionate )
Norethandrolone
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
RU-2309
Tetrahydrogestrinone
Trenbolone (trienolone)
Trenbolone esters (e.g.,
trenbolone acetate ,
trenbolone enanthate )
Trendione
Trestolone
Trestolone acetate
Mixed (
SPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor (
PAQR Tooltip Progestin and adipoQ receptor )