itarnafloxin

CHEBI:177533 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

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). — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:140325 CHEBI:140325
CHEBI:37143 CHEBI:37143
CHEBI:38164 CHEBI:38164
CHEBI:38314 CHEBI:38314
CHEBI:46775 CHEBI:46775

Chemical structure

Computed structure properties
Molecular formula	C35H33FN6O3
Charge	0
Average mass	604.686 Da
Monoisotopic mass	604.25982 Da
Source	ChEBI
InChIKey	WOQIDNWTQOYDLF-CGAIIQECSA-N

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

Also called

itarnafloxina (INN)— chebi
itarnafloxine (INN)— chebi
itarnafloxinum (INN)— chebi
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 (EXACT_SYNONYM)— 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 (EXACT_SYNONYM)— chebi
CX 3543 (EXACT_SYNONYM)— chebi
CX-3543 (EXACT_SYNONYM)— chebi
CX3543 (EXACT_SYNONYM)— chebi
quarfloxacin (EXACT_SYNONYM)— chebi
quarfloxin (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:865311-47-3
chemspider:9810507
drugbank:DB06638
kegg.drug:D08981
patent:US20060029950

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:38068 CHEBI:38068

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:177533`	itarnafloxin	`antibioticmech:chebi-7b72754817`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.