Toripristone

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]

Toripristone
Clinical data
Other namesRU-40555; 17β-Hydroxy-11β-[4-[methyl(1-methylethyl)amino]phenyl]-17α-(1-propyn-1-yl)estra-4,9-dien-3-one
Identifiers
IUPAC name
  • (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)
Chemical and physical data
FormulaC31H39NO2
Molar mass457.658 g·mol−1
3D model (JSmol)
SMILES
  • 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
  • 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

See also

References
  1. R.A. Hill; H.L.J. Makin; D.N. Kirk; G.M. Murphy (23 May 1991). Dictionary of Steroids. CRC Press. pp. 101–. ISBN 978-0-412-27060-4.
  2. https://mednet-communities.net/inn/db/media/docs/p-innlist61.pdf
  3. Steiniger, Bjorn; Kniess, Torsten; Bergmann, Ralf; Pietzsch, Jens; Wuest, Frank (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. ISSN 1389-5575. PMID 18537728.
  4. Bachmann CG, Linthorst AC, Holsboer F, Reul JM (2003). "Effect of chronic administration of selective glucocorticoid receptor antagonists on the rat hypothalamic-pituitary-adrenocortical axis". Neuropsychopharmacology. 28 (6): 1056–67. doi:10.1038/sj.npp.1300158. PMID 12700716.
  5. 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.
  6. Fu, Jing; Hu, Lina; Huang, Wei; Zhu, Huili; Wang, Qiushi; He, Fan; Xie, Lingxia; Gan, Xiaoling; Huang, Wei (2012). "Progesterone receptor antagonists and progesterone receptor modulators for endometriosis". In Huang, Wei (ed.). Cochrane Database of Systematic Reviews. doi:10.1002/14651858.CD009881.


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