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Details

Stereochemistry EPIMERIC
Molecular Formula C35H33FN6O3
Molecular Weight 604.6733
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUARFLOXIN

SMILES

CN1CCC[C@H]1CCNC(=O)C2=CN3C4=C(OC5=C3C(=CC(F)=C5N6CCC(C6)C7=CN=CC=N7)C2=O)C=C8C=CC=CC8=C4

InChI

InChIKey=WOQIDNWTQOYDLF-CGAIIQECSA-N
InChI=1S/C35H33FN6O3/c1-40-13-4-7-24(40)8-10-39-35(44)26-20-42-29-15-21-5-2-3-6-22(21)16-30(29)45-34-31(42)25(33(26)43)17-27(36)32(34)41-14-9-23(19-41)28-18-37-11-12-38-28/h2-3,5-6,11-12,15-18,20,23-24H,4,7-10,13-14,19H2,1H3,(H,39,44)/t23?,24-/m0/s1

HIDE SMILES / InChI

Molecular Formula C35H33FN6O3
Molecular Weight 604.6733
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 1 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Quarfloxin (also known as CX-3543) is a fluoroquinolone derivative patented by Cyclene Pharmaceuticals, Inc. as an antitumor agent. Quarfloxin selectively disrupts nucleolin/rDNA G-quadruplex complexes in the nucleolus, thereby inhibiting DNA polymerase I transcription and inducing apoptosis in cancer cells. CX-3543 was evaluated in phase II clinical studies for the treatment of low or intermediate grade neuroendocrine carcinoma, including carcinoid and islet cell cancer. In 2008, a trial for the treatment of chronic lymphocytic leukemia (CLL) was withdrawn prior to patient enrollment. In 2010, phase I clinical studies for the treatment of solid tumors and for the treatment of lymphoma were terminated upon the observation that the modified dose schedule presented no advantage over previously studies schedule solid tumors/ Cylene discontinued development of quarfloxin in 2010.

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
IV Quarfloxin 240 mg/m2 daily x5 days every 21 days
Route of Administration: Intravenous
Substance Class Chemical
Record UNII
8M31J5031Q
Record Status Validated (UNII)
Record Version