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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
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 1 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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 In 2008, a trial for the treatment of chronic lymphocytic leukemia (CLL) was withdrawn prior to patient enrollment.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.

Approval Year

PubMed

PubMed

TitleDatePubMed
CX-3543 Promotes Cell Apoptosis through Downregulation of CCAT1 in Colon Cancer Cells.
2018
Patents

Sample Use Guides

IV Quarfloxin 240 mg/m2 daily x5 days every 21 days
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:17:58 GMT 2023
Edited
by admin
on Fri Dec 15 17:17:58 GMT 2023
Record UNII
8M31J5031Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUARFLOXIN
USAN  
USAN  
Official Name English
itarnafloxin [INN]
Common Name English
QUARFLOXIN [USAN]
Common Name English
3H-BENZO(B)PYRIDO(3,2,1-KL)PHENOXAZINE-2-CARBOXAMIDE, 5-FLUORO-N-(2-((2S)-1-METHYL-2-PYRROLIDINYL)ETHYL)-3-OXO-6-(3-PYRAZINYL-1-PYRROLIDINYL)-
Systematic Name English
CX-3543
Code English
ITARNAFLOXIN
INN   WHO-DD  
INN  
Official Name English
Itarnafloxin [WHO-DD]
Common Name English
5-FLUORO-N-(2-((2S)-1-METHYLPYRROLIDIN-2-YL)ETHYL)-3-OXO-6-(3-PYRAZIN-2-YLPYRROLIDIN-1-YL)-3H-BENZO(B)PYRIDO(3,2,1-KL)PHENOXAZINE-2-CARBOXAMIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C274
Created by admin on Fri Dec 15 17:17:58 GMT 2023 , Edited by admin on Fri Dec 15 17:17:58 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C71726
Created by admin on Fri Dec 15 17:17:58 GMT 2023 , Edited by admin on Fri Dec 15 17:17:58 GMT 2023
PRIMARY
CAS
865311-47-3
Created by admin on Fri Dec 15 17:17:58 GMT 2023 , Edited by admin on Fri Dec 15 17:17:58 GMT 2023
PRIMARY
FDA UNII
8M31J5031Q
Created by admin on Fri Dec 15 17:17:58 GMT 2023 , Edited by admin on Fri Dec 15 17:17:58 GMT 2023
PRIMARY
USAN
SS-130
Created by admin on Fri Dec 15 17:17:58 GMT 2023 , Edited by admin on Fri Dec 15 17:17:58 GMT 2023
PRIMARY
SMS_ID
300000036883
Created by admin on Fri Dec 15 17:17:58 GMT 2023 , Edited by admin on Fri Dec 15 17:17:58 GMT 2023
PRIMARY
INN
8933
Created by admin on Fri Dec 15 17:17:58 GMT 2023 , Edited by admin on Fri Dec 15 17:17:58 GMT 2023
PRIMARY
EPA CompTox
DTXSID001006893
Created by admin on Fri Dec 15 17:17:58 GMT 2023 , Edited by admin on Fri Dec 15 17:17:58 GMT 2023
PRIMARY
PUBCHEM
11635763
Created by admin on Fri Dec 15 17:17:58 GMT 2023 , Edited by admin on Fri Dec 15 17:17:58 GMT 2023
PRIMARY
DRUG BANK
DB06638
Created by admin on Fri Dec 15 17:17:58 GMT 2023 , Edited by admin on Fri Dec 15 17:17:58 GMT 2023
PRIMARY
ChEMBL
CHEMBL2103818
Created by admin on Fri Dec 15 17:17:58 GMT 2023 , Edited by admin on Fri Dec 15 17:17:58 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Quarfloxin disrupts the interaction between the nucleolin protein and a G-quadruplex DNA structure in the ribosomal DNA (rDNA) template, a critical interaction for rRNA biogenesis that is overexpressed in cancer cells.
Related Record Type Details
ACTIVE MOIETY