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Chemical compound
Toripristone
Other names RU-40555; 17β-Hydroxy-11β-[4-[methyl(1-methylethyl)amino]phenyl]-17α-(1-propyn-1-yl)estra-4,9-dien-3-one
(8S ,11R ,13S ,14S ,17S )-17-Hydroxy-13-methyl-11-[4-[methyl(propan-2-yl)amino]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 31 H 39 N O 2
Molar mass 457.658 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)N(C)C(C)C)C)O
InChI=1S/C31H39NO2/c1-6-16-31(34)17-15-28-26-13-9-22-18-24(33)12-14-25(22)29(26)27(19-30(28,31)4)21-7-10-23(11-8-21)32(5)20(2)3/h7-8,10-11,18,20,26-28,34H,9,12-15,17,19H2,1-5H3/t26-,27+,28-,30-,31-/m0/s1
Key:LOIYXTZQBQVHSF-PABOLRIOSA-N
Toripristone (
INN ; developmental code name RU-40555 ) is a
synthetic ,
steroidal
antiglucocorticoid as well as
antiprogestogen which was never marketed.
[1]
[2] It is reported as a potent and highly selective
antagonist of the
glucocorticoid receptor (GR) (Ki = 2.4 nM),
[3]
[4] though it also acts as an antagonist of the
progesterone receptor (PR).
[5]
[6] The
pharmacological profile of toripristone is said to be very similar to that of
mifepristone , except that toripristone does not bind to
orosomucoid (α1-acid glycoprotein).
[5] The drug has been used to study the
hypothalamic-pituitary-adrenal axis and has been used as a
radiotracer for the GR.
[4]
[3] Its INN was given in 1990.
[2]
See also
References
^ Hill RA, Makin HL, Kirk DN, Murphy GM (23 May 1991).
"Toripristone" . Dictionary of Steroids . CRC Press. pp. 101–.
ISBN
978-0-412-27060-4 .
^
a
b
"International Nonproprietary Names for Pharmaceutical Substances" (PDF) . WHO Drug Information . 3 (2): 18. 1989. Archived from
the original (PDF) on 4 March 2016.
^
a
b Steiniger B, Kniess T, Bergmann R, Pietzsch J, Wuest FR (June 2008). "Radiolabeled glucocorticoids as molecular probes for imaging brain glucocorticoid receptors by means of positron emission tomography (PET)". Mini Reviews in Medicinal Chemistry . 8 (7): 728–739.
doi :
10.2174/138955708784567403 .
PMID
18537728 .
^
a
b Bachmann CG, Linthorst AC, Holsboer F, Reul JM (June 2003).
"Effect of chronic administration of selective glucocorticoid receptor antagonists on the rat hypothalamic-pituitary-adrenocortical axis" . Neuropsychopharmacology . 28 (6): 1056–1067.
doi :
10.1038/sj.npp.1300158 .
PMID
12700716 .
^
a
b Philibert D, Costerousse G, Gaillard-Moguilewsky M, Nedelec L, Nique F, Tournemine C, Teutsch G (1991). "From RU 38486 towards Dissociated Antiglucocorticoid and Antiprogesterone". Antihormones in Health and Disease . Frontiers of Hormone Research. Vol. 19. pp. 1–17.
doi :
10.1159/000419634 .
ISBN
978-3-8055-5297-4 .
ISSN
0301-3073 .
^ Fu J, Hu L, Huang W, Zhu H, Wang Q, He F, Xie L, Gan, Huang W (2012). Huang W (ed.). "Progesterone receptor antagonists and progesterone receptor modulators for endometriosis". Cochrane Database of Systematic Reviews (5): CD009881.
doi :
10.1002/14651858.CD009881 .
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 )