1-{4-[(2R,4S,11R)-3,3-difluorotetracyclo[10.4.0.02,4.05,10]hexadeca-1(12),5(10),6,8,13,15-hexaen-11-yl]piperazin-1-yl}-3-(quinolin-5-yloxy)(2H5)propan-2-ol

• ChemBase ID: 179682
• Molecular Formular: C32H31F2N3O2
• Molecular Mass: 527.6042464
• Monoisotopic Mass: 527.23843369
• SMILES: [C@@H]12[C@@H](c3c([C@H](c4c1cccc4)N1CCN(CC1)CC(COc1c4c(ccc1)nccc4)O)cccc3)C2(F)F
• Canonical SMILES: OC(CN1CCN(CC1)[C@@H]1c2ccccc2[C@@H]2[C@H](c3c1cccc3)C2(F)F)COc1cccc2c1cccn2
• InChI: InChI=1S/C32H31F2N3O2/c33-32(34)29-22-7-1-3-9-24(22)31(25-10-4-2-8-23(25)30(29)32)37-17-15-36(16-18-37)19-21(38)20-39-28-13-5-12-27-26(28)11-6-14-35-27/h1-14,21,29-31,38H,15-20H2/t21?,29-,30+,31-
• InChIKey: IHOVFYSQUDPMCN-FEVGKOQGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{4-[(2R,4S,11R)-3,3-difluorotetracyclo[10.4.0.0^2,^4.0^5,^1^0]hexadeca-1(12),5(10),6,8,13,15-hexaen-11-yl]piperazin-1-yl}-3-(quinolin-5-yloxy)(^2H₅)propan-2-ol
• IUPAC Traditional name: 1-{4-[(2R,4S,11R)-3,3-difluorotetracyclo[10.4.0.0^2,^4.0^5,^1^0]hexadeca-1(12),5(10),6,8,13,15-hexaen-11-yl]piperazin-1-yl}-3-(quinolin-5-yloxy)(^2H₅)propan-2-ol
• Synonyms: rac-4-[(1aα,6α,10bα)-1,1-Difluoro-1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-yl]-α-[(5-quinolinyloxy)methyl]-1-piperazineethanol-d5 Hydrochloride; Zosuquidar-d5 Hydrochloride; LY 335979-d5; RS 33295-198-d5; rac Zosuquidar-d5 Trihydrochloride

Database IDs

• PubChem SID: 164235592
• PubChem CID: 71753037

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.281876
• LogD (pH = 7.4): 4.1407084
• Log P: 4.8176975
• Molar Refractivity: 146.6752 cm^3
• Polarizability: 57.741096 Å^3
• Polar Surface Area: 48.83 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false
• Acid pKa: 14.07888

DETAILS

Toronto Research Chemicals - Z700872

Labelled Zosuquidar (Z700870). Multi-drug resistance (MDR) modulator; selective inhibitor of P-glycoprotein (P-gp). Antineoplastic adjunct (chemosensitizer).

REFERENCES

• Green, L.J., et al.: Biochem. Pharmacol., 61, 1393 (2001)
• Shepard, R.L., et al.: Int. J. Cancer, 103, 121 (2001)