2-(4-hydroxyphenyl)-3-{4-[2-(piperidin-1-yl)ethoxy]benzoyl}-2,3-dihydro-1-benzothiophen-6-ol hydrochloride

• ChemBase ID: 179709
• Molecular Formular: C28H30ClNO4S
• Molecular Mass: 512.0601
• Monoisotopic Mass: 511.15840713
• SMILES: C1(C(Sc2c1ccc(c2)O)c1ccc(cc1)O)C(=O)c1ccc(cc1)OCCN1CCCCC1.Cl
• Canonical SMILES: Oc1ccc2c(c1)SC(C2C(=O)c1ccc(cc1)OCCN1CCCCC1)c1ccc(cc1)O.Cl
• InChI: InChI=1S/C28H29NO4S.ClH/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;/h4-13,18,26,28,30-31H,1-3,14-17H2;1H
• InChIKey: IDYFBWFWDHZMOX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-hydroxyphenyl)-3-{4-[2-(piperidin-1-yl)ethoxy]benzoyl}-2,3-dihydro-1-benzothiophen-6-ol hydrochloride
• IUPAC Traditional name: 2-(4-hydroxyphenyl)-3-{4-[2-(piperidin-1-yl)ethoxy]benzoyl}-2,3-dihydro-1-benzothiophen-6-ol hydrochloride
• Synonyms: Evista; Raloxifene Hydrochloride

Database IDs

• CAS Number: 82640-04-8
• PubChem SID: 164235619
• PubChem CID: 45370996

CALCULATED PROPERTIES

• Acid pKa: 9.218011
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.9834578
• LogD (pH = 7.4): 4.7415514
• Log P: 5.1758304
• Molar Refractivity: 136.9968 cm^3
• Polarizability: 52.979584 Å^3
• Polar Surface Area: 70.0 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Selective estrogen receptor modulator (SERM)

Product Information

• Salt Data: HCl
• Application(s): Antiestrogen; Prevents bone loss and reduces serum cholesterol in ovariectomized rats; Used in the treatment of postmenopausal osteoporosis

REFERENCES

• Wakeling, A.E. et al., J. Endocrinol., 1983, 99, 455, (pharmacol)
• Jones, C.D. et al., J. Med. Chem., 1984, 27, 1057, (synth, pharmacol)
• Wakeling, A.E. et al., J. Steroid Biochem., 1984, 20, 111, (pharmacol)
• Lindstrom, T.D. et al., Xenobiotica, 1984, 14, 841, (metab)
• Sato, M. et al., J. Bone Min. Res., 1994, 9, 715, (pharmacol)
• Black, L.J. et al., J. Clin. Invest., 1994, 93, 63, (pharmacol)
• Schmid, C.R. et al., Bioorg. Med. Chem. Lett., 1999, 9, 1137-1140, (dihydroraloxifene)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1461
• Clemett, D. et al., Drugs, 2000, 60, 379-411, (rev)