Quarfloxin
Basic information
- CAS
865311-47-3- Standard SMILES
CN1CCC[C@H]1CCNC(=O)c1cn2c3c(c(N4CCC(c5cnccn5)C4)c(F)cc3c1=O)Oc1cc3ccccc3cc1-2- InChIKey
WOQIDNWTQOYDLF-CGAIIQECSA-N- Molecular formula
- C35H33FN6O3
- Average molar mass
- 604.7 g/mol
- Monoisotopic mass
- 604.2598171
Overview
Itarnafloxin is an organic heteropentacyclic compound that is 3H-benzo[b]pyrido[3,2,1-kl]phenoxazin-3-one substituted by 2-[(2S)-1-methylpyrrolidin-2-yl]ethanaminoacyl, fluoro, and 3-(pyrazin-2-yl)pyrrolidin-1-yl groups at positions 2, 5 and 6, respectively. It is a G-quadruplex interactive agent, previously in clinical trials for the treatment of carcinoid/neuroendocrine tumours (now discontinued). It has a role as a topoisomerase II inhibitor, an antineoplastic agent, an antimalarial and an apoptosis inducer. It is a secondary carboxamide, a phenoxazine, an organofluorine compound, an organic heteropentacyclic compound, a member of pyrazines and a N-alkylpyrrolidine.
Names & identifiers
- Preferred name
- Quarfloxin
- IUPAC
- 15-fluoro-N-[2-[(2S)-1-methylpyrrolidin-2-yl]ethyl]-18-oxo-14-(3-pyrazin-2-ylpyrrolidin-1-yl)-12-oxa-1-azapentacyclo[11.7.1.02,11.04,9.017,21]henicosa-2,4,6,8,10,13(21),14,16,19-nonaene-19-carboxamide
- English name
- CX-3543
- Molecular formula
- C35H33FN6O3
- Molecular weight
- 604.67
Names & synonyms
Quarfloxin865311-47-3ItarnafloxinCX-3543QuarfloxacinQuarfloxin [USAN]Itarnafloxin [INN]itarnafloxinaitarnafloxine15-fluoro-N-[2-[(2s)-1-methylpyrrolidin-2-yl]ethyl]-18-oxo-14-(3-pyrazin-2-ylpyrrolidin-1-yl)-12-oxa-1-azapentacyclo[11.7.1.02,11.04,9.017,21]henicosa-2,4,6,8,10,13(21),14,16,19-nonaene-19-carboxamideITARNAFLOXIN [WHO-DD]8M31J5031Q
Show more names
CX-3543/QuarfloxinQuarfloxin (CX-3543)Quarfloxin, 10 mM in DMSOCX 3543CX3543inhibit,CX3543,Inhibitor,Quarfloxin,CX 3543,DNA/RNA Synthesis2-(4-((R)-1-Methylpyrrolidin-2-yl)butanoyl)-6-(3-(pyrazin-2-yl)pyrrolidin-1-yl)-3H-benzo[b]pyrido[3,2,1-kl]phenoxazin-3-one
Quarfloxin (USAN)UNII-8M31J5031Q3H-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)-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-CARBOXAMIDEitarnafloxinum15-fluoro-N-(2-((2S)-1-methylpyrrolidin-2-yl)ethyl)-18-oxo-14-(3-pyrazin-2-ylpyrrolidin-1-yl)-12-oxa-1-azapentacyclo(11.7.1.02,11.04,9.017,21)henicosa-2,4,6,8,10,13(21),14,16,19-nonaene-19-carboxamideRefChem:1780415-Fluoro-N-(2-((2S)-1-methylpyrrolidin-2-yl)ethyl)-3-oxo-6-(3-(pyrazin-2-yl)pyrrolidin-1-yl)-3H-benzo(b)pyrido(3,2,1-kl)phenoxazine-2-carboxamide
Properties
Computed structural properties
- XLogP
- 5.1
- Topological polar surface area
- 90.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 6
- Heavy atoms
- 45
- Formal charge
- 0
- Complexity
- 1,150
Physicochemical properties
- Boiling point
- 845.3 · 845.3±65.0 °C(Predicted)
- Density
- 1.44 · 1.44
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Soluble in DMSO
- pka
- 11.46 · 11.46±0.20(Predicted)
- form
- Solid
- color
- Light yellow to yellow
- FDA UNII
- 8 M31J5031Q · 8M31J5031Q
- NCI Drug Dictionary
- quarfloxacin
Chemistry & industry
Applications
UsesQuarfloxin (CX-3543), a fluoroquinolone derivative with antineoplastic activity, targets and inhibits RNA pol I activity, with IC50 values in the nanomolar range in neuroblastoma cells. Quarfloxin disrupts the interaction between the nucleolin protein and a G-quadruplex DNA structure in the ribosomal DNA (rDNA) template[1].
Additional notes
DefinitionChEBI: Itarnafloxin is a phenoxazine.
Suppliers
Loading…
Open inquiries
Loading…
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…