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.

Label unavailable CHEBI:140325
Label unavailable CHEBI:37143
Label unavailable CHEBI:38164
Label unavailable CHEBI:38314
Label unavailable 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

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

patent:US20060029950

Activity roles

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

antimalarial 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
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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