N-{4-[2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)(2H4)ethyl]phenyl}-5-methoxy-9-oxo-9,10-dihydroacridine-4-carboxamide

• ChemBase ID: 167962
• Molecular Formular: C34H33N3O5
• Molecular Mass: 563.64292
• Monoisotopic Mass: 563.24202117
• SMILES: c1(cc2c(cc1OC)CCN(C2)CCc1ccc(cc1)NC(=O)c1cccc2c1[nH]c1c(c2=O)cccc1OC)OC
• Canonical SMILES: COc1cc2CN(CCc3ccc(cc3)NC(=O)c3cccc4c3[nH]c3c(OC)cccc3c4=O)CCc2cc1OC
• InChI: InChI=1S/C34H33N3O5/c1-40-28-9-5-7-26-32(28)36-31-25(33(26)38)6-4-8-27(31)34(39)35-24-12-10-21(11-13-24)14-16-37-17-15-22-18-29(41-2)30(42-3)19-23(22)20-37/h4-13,18-19H,14-17,20H2,1-3H3,(H,35,39)(H,36,38)
• InChIKey: OSFCMRGOZNQUSW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{4-[2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)(^2H₄)ethyl]phenyl}-5-methoxy-9-oxo-9,10-dihydroacridine-4-carboxamide
• IUPAC Traditional name: N-{4-[2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)(^2H₄)ethyl]phenyl}-5-methoxy-9-oxo-10H-acridine-4-carboxamide
• Synonyms: N-[4-[2-(3,4-Dihydro-6,7-dimethoxy-2(1H)-isoquinolinyl)ethyl-d4]phenyl]-9,10-dihydro-5-methoxy-9-oxo-4-acridinecarboxamide; GF 120918-d4; GG 918-d4; GW 0918-d4; Elacridar-d4 (Major)

Database IDs

• CAS Number: 1189481-51-3
• PubChem SID: 162262095
• PubChem CID: 46781443

CALCULATED PROPERTIES

• Acid pKa: 12.058339
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 4.048012
• LogD (pH = 7.4): 5.8160267
• Log P: 6.8125696
• Molar Refractivity: 165.2047 cm^3
• Polarizability: 62.066082 Å^3
• Polar Surface Area: 89.13 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: 198-200°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E489002

A prototypical BCRP inhibitor. Inhibits the Bcrp1-mediated transport.

REFERENCES

• Neville, K., et al.: Clin. Cancer Res., 10, 2525 (2004)
• Reardon, D., et al.: J. Clin. Oncol. 23, 9359 (2004)
• Pan, G., et al.: Drug Metab. Dispos., 35, 1165 (2007).