| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H19N3O |
| Molecular Weight | 293.363 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCNC(=O)C1=CC=CC2=CC3=C(C=CC=C3)N=C12
InChI
InChIKey=XBGNERSKEKDZDS-UHFFFAOYSA-N
InChI=1S/C18H19N3O/c1-21(2)11-10-19-18(22)15-8-5-7-14-12-13-6-3-4-9-16(13)20-17(14)15/h3-9,12H,10-11H2,1-2H3,(H,19,22)
Acridine carboxamide (XR5000) is a tricyclic acridine-based (or carboxamide-based) drug with dual topoisomerase inhibitor and potential antineoplastic activities. Acridine carboxamide inhibits both topoisomerases I and II and intercalates into DNA, resulting in DNA damage, the disruption of DNA repair and replication, the inhibition of RNA and protein synthesis, and cell death. Acridine carboxamide has been used in trials studying the treatment of lung cancer and brain and central nervous system tumors. In clinical trials acridine carboxamide did not show efficacy when tested against various types of cancers.
Originator
Approval Year
PubMed
Patents
Sample Use Guides
Advanced ovarian cancer: Patients received Acridine carboxamide (XR5000) at the dose of 3010 mg/m(2) through a 120-h central venous infusion every 3 weeks.
Route of Administration:
Intravenous
CCRF-CEM cells were exposed to a range of concentrations of TAS-103 (0.1 to 10 uM) or Acridine carboxamide (0.1 to 100
uM) for 2 hr and then analysed using the TARDIS assay to
detect drug-stabilised topo I, topo IIa, and topo IIb cleavable complexes in individual cells. These cells were sensitive to
Acridine carboxamide and TAS-103 with IC50 values of 474 and 5 nM,
respectively. Acridine carboxamide showed a dose-dependent increase in topo IIa
FITC immunofluorescence levels, with 10 and 100
uM Acridine carboxamide giving significantly higher levels of cleavable
complexes than the untreated cells. Only
the highest concentration of 100 uM Acridine carboxamide showed any
effect on topo IIb FITC immunofluorescence. Topo IIa transformants
were found to be more sensitive (Acridine carboxamide IC50=50 uM)
than topo IIb transformants (Acridine carboxamide IC50 >137 uM).
ACTIVE MOIETY
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)
