raloxifene   Click here for help

GtoPdb Ligand ID: 2820

Synonyms: Evista® | LY-156758 | Optruma® | raloxifene hydrochloride
Approved drug PDB Ligand
raloxifene is an approved drug (FDA (1997), EMA (1998))
Compound class: Synthetic organic
Comment: Raloxifene is a selective estrogen receptor modulator (SERM).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 98.24
Molecular weight 473.17
XLogP 5.65
No. Lipinski's rules broken 1
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Canonical SMILES Oc1ccc2c(c1)sc(c2C(=O)c1ccc(cc1)OCCN1CCCCC1)c1ccc(cc1)O
Isomeric SMILES Oc1ccc2c(c1)sc(c2C(=O)c1ccc(cc1)OCCN1CCCCC1)c1ccc(cc1)O
InChI InChI=1S/C28H27NO4S/c30-21-8-4-20(5-9-21)28-26(24-13-10-22(31)18-25(24)34-28)27(32)19-6-11-23(12-7-19)33-17-16-29-14-2-1-3-15-29/h4-13,18,30-31H,1-3,14-17H2
1. Henke BR, Drewry DH, Jones SA, Stewart EL, Weaver SL, Wiethe RW. (2001)
2-Amino-4,6-diarylpyridines as novel ligands for the estrogen receptor.
Bioorg Med Chem Lett, 11 (14): 1939-42. [PMID:11459665]
2. Ishii Y, Takeuchi K. (2018)
Therapeutic agent for nonalcoholic fatty liver disease.
Patent number: WO2018198842A1. Assignee: National University Corporation Kyushu University. Priority date: 14/04/2018. Publication date: 01/11/2018.
3. Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA. (1997)
Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta.
Endocrinology, 138 (3): 863-70. [PMID:9048584]
4. Petrie WK, Dennis MK, Hu C, Dai D, Arterburn JB, Smith HO, Hathaway HJ, Prossnitz ER. (2013)
G protein-coupled estrogen receptor-selective ligands modulate endometrial tumor growth.
Obstet Gynecol Int, 2013: 472720. [PMID:24379833]
5. Stauffer SR, Coletta CJ, Tedesco R, Nishiguchi G, Carlson K, Sun J, Katzenellenbogen BS, Katzenellenbogen JA. (2000)
Pyrazole ligands: structure-affinity/activity relationships and estrogen receptor-alpha-selective agonists.
J Med Chem, 43 (26): 4934-47. [PMID:11150164]