flucloxacillin

CHEBI:5098 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A penicillin compound having a 6β-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxamido] side-chain. — 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

penicillin beta-lactamARO:3000008

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:17334 CHEBI:17334
CHEBI:88187 CHEBI:88187
ARO:3000008 ARO:3000008

Chemical structure

Computed structure properties
Molecular formula	C19H17ClFN3O5S
Charge	0
Average mass	453.879 Da
Monoisotopic mass	453.05615 Da
Source	ChEBI
InChIKey	UIOFUWFRIANQPC-JKIFEVAISA-N

SMILES

[H][C@]12SC(C)(C)[C@H](C(=O)O)N1C(=O)[C@H]2NC(=O)c1c(-c2c(F)cccc2Cl)noc1C

InChI

InChI=1S/C19H17ClFN3O5S/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28)/t13-,14+,17-/m1/s1

Also called

Floxapen (BRAND_NAME)— chebi
flucloxacilline (INN)— chebi
flucloxacillinum (INN)— chebi
6β-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxamido]-2,2-dimethylpenam-3α-carboxylic acid (EXACT_SYNONYM)— chebi
(2S,5R,6R)-6-({[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolylpenicillin (EXACT_SYNONYM)— chebi
Floxacillin (EXACT_SYNONYM)— chebi
Flucloxacillin (EXACT_SYNONYM)— chebi
flucloxacilina (EXACT_SYNONYM)— chebi
floxacillin (EXACT_SYNONYM)— aro
floxapen (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000636
cas:5250-39-5
drugbank:DB00301
drugcentral:1183
kegg.compound:C11748
kegg.drug:D04196
reaxys:4771988
wikipedia.en:Flucloxacillin
pubchem.compound:21319

Activity roles

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

CHEBI:33281 CHEBI:33281
CHEBI:36047 CHEBI:36047

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
ARO	`ARO:3000636`	flucloxacillin	`antibioticmech:aro-6c336b8be9`	2026-08-30
CHEBI	`CHEBI:5098`	flucloxacillin	`antibioticmech:chebi-cfd57d7650`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

beta-lactam sensitive penicillin-binding protein PROTEIN DIRECT_BINDING_TARGET

ARO:3000749

CARD/ARO database assertion; target organism, strain, and assay are not specified. Penicillin-binding proteins are asserted as inhibited transpeptidases. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000749 (CARD/ARO asserts targeted_by_antibiotic ARO:3000636 (flucloxacillin); database assertion, not a primary citation.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, 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 2026-08-31 · 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.