itarnafloxin (CHEBI:177533)

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CHEBI:177533 - itarnafloxin

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ChEBI ID	CHEBI:177533
ChEBI Name	itarnafloxin
Stars
Definition	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).
Last Modified	17 April 2025
Submitter	MetaboLights
Downloads	Molfile

Formula	C35H33FN6O3
Net Charge	0
Average Mass	604.686
Monoisotopic Mass	604.25982
SMILES	CN1CCC[C@H]1CCNC(=O)c1cn2c3c(c(N4CCC(c5cnccn5)C4)c(F)cc3c1=O)Oc1cc3ccccc3cc1-2
InChI	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
InChIKey	WOQIDNWTQOYDLF-CGAIIQECSA-N

Species of Metabolite	Component	Source	Comments
Sus scrofa (ncbitaxon:9823)	sausage (ENVO:00002166)	MetaboLights (MTBLS2871)

Roles Classification

Chemical Role:	Bronsted base A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:	antimalarial A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human. apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. topoisomerase II inhibitor A topoisomerase inhibitor that inhibits DNA topoisomerase II.
Applications:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. antimalarial A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.

ChEBI Ontology

Outgoing Relation(s)
	itarnafloxin (CHEBI:177533) has role antimalarial (CHEBI:38068)
	itarnafloxin (CHEBI:177533) has role antineoplastic agent (CHEBI:35610)
	itarnafloxin (CHEBI:177533) has role apoptosis inducer (CHEBI:68495)
	itarnafloxin (CHEBI:177533) has role topoisomerase II inhibitor (CHEBI:156203)
	itarnafloxin (CHEBI:177533) is a N-alkylpyrrolidine (CHEBI:46775)
	itarnafloxin (CHEBI:177533) is a organic heteropentacyclic compound (CHEBI:38164)
	itarnafloxin (CHEBI:177533) is a organofluorine compound (CHEBI:37143)
	itarnafloxin (CHEBI:177533) is a phenoxazine (CHEBI:25970)
	itarnafloxin (CHEBI:177533) is a pyrazines (CHEBI:38314)
	itarnafloxin (CHEBI:177533) is a secondary carboxamide (CHEBI:140325)

IUPAC Name
5-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

INNs	Source
itarnafloxin	WHO MedNet
itarnafloxinum	WHO MedNet
itarnafloxine	WHO MedNet
itarnafloxina	WHO MedNet

Synonyms	Source
CX 3543	DrugBank
CX-3543	DrugBank
CX3543	ChEBI
quarfloxin	DrugBank
quarfloxacin	ChEBI
5-fluoro-N-(2-((S)-1-methylpyrrolidin-2-yl)ethyl)-3-oxo-6-((R)-3-(pyrazin-2-yl)pyrrolidin-1-yl)-3H-benzo[b]pyrido[3,2,1-kl]phenoxazine-2-carboxamide	ChEBI

Manual Xrefs	Databases
DB06638	DrugBank
9810507	ChemSpider
D08981	KEGG DRUG
US20060029950	Patent

Registry Numbers	Sources
CAS:865311-47-3	DrugBank

Citations