florfenicol

CHEBI:87185 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A carboxamide that is the N-dichloroacetyl derivative of (1R,2S)-2-amino-3-fluoro-1-[4-(methanesulfonyl)phenyl]propan-1-ol. A synthetic veterinary antibiotic that is used for treatment of bovine respiratory disease and foot rot; also used in aquaculture. — 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

phenicol antibioticARO:3000387

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:140325 CHEBI:140325
CHEBI:35681 CHEBI:35681
CHEBI:35850 CHEBI:35850
CHEBI:36683 CHEBI:36683
CHEBI:37143 CHEBI:37143
ARO:3000387 ARO:3000387

Chemical structure

Computed structure properties
Molecular formula	C12H14Cl2FNO4S
Charge	0
Average mass	358.218 Da
Monoisotopic mass	357.00046 Da
Source	ChEBI
InChIKey	AYIRNRDRBQJXIF-NXEZZACHSA-N

SMILES

CS(=O)(=O)c1ccc([C@@H](O)[C@@H](CF)NC(=O)C(Cl)Cl)cc1

InChI

InChI=1S/C12H14Cl2FNO4S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-15)16-12(18)11(13)14/h2-5,9-11,17H,6H2,1H3,(H,16,18)/t9-,10-/m1/s1

Also called

Nuflor (BRAND_NAME)— chebi
Nuflor gold (BRAND_NAME)— chebi
2,2-dichloro-N-{(1R,2S)-3-fluoro-1-hydroxy-1-[4-(methanesulfonyl)phenyl]propan-2-yl}acetamide (EXACT_SYNONYM)— chebi
(-)-Florfenicol (EXACT_SYNONYM)— chebi
D-threo-2,2-Dichloro-N-(alpha-(fluoromethyl)-beta-hydroxy-p-(methylsulfonyl)phenethyl)acetamide (EXACT_SYNONYM)— chebi
Sch 25298 (EXACT_SYNONYM)— chebi
Sch-25298 (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000461
cas:73231-34-2
kegg.drug:D04194
lincs.smallmolecule:LSM-5287
patent:EP14437
patent:US4235892
reaxys:4202553
vsdb:1777
wikipedia.en:Florfenicol
chembl:CHEMBL1241590
pubchem.compound:114811

Activity roles

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

CHEBI:33281 CHEBI:33281

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:3000461`	florfenicol	`antibioticmech:aro-5edaafadec`	2026-08-30
CHEBI	`CHEBI:87185`	florfenicol	`antibioticmech:chebi-5c111856af`	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.

antibiotic sensitive peptidyl transferase (23S rRNA) NUCLEIC_ACID DIRECT_BINDING_TARGET

ARO:3000754

CARD/ARO database assertion; target organism, strain, and assay are not specified. 23S rRNA peptidyl-transferase center is asserted as the target. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000754 (CARD/ARO asserts targeted_by_antibiotic ARO:3000461 (florfenicol); database assertion, not a primary citation.)

Resistance mechanisms

11 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_EFFLUX 7

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
Staphylococcus aureus LmrS	ARO:3004572	not organism-specific	—	ARO:3004572 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000461 (florfenicol); database assertion, not a primary citation.)
fexA	ARO:3002704	not organism-specific	—	ARO:3002704 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000461 (florfenicol); database assertion, not a primary citation.)
fexB	ARO:3007019	not organism-specific	—	ARO:3007019 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000461 (florfenicol); database assertion, not a primary citation.)
flo	ARO:3003963	not organism-specific	—	ARO:3003963 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000461 (florfenicol); database assertion, not a primary citation.)
floR	ARO:3002705	not organism-specific	—	ARO:3002705 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000461 (florfenicol); database assertion, not a primary citation.)
pexA	ARO:3004666	not organism-specific	—	ARO:3004666 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000461 (florfenicol); database assertion, not a primary citation.)
pp-flo	ARO:3002812	not organism-specific	—	ARO:3002812 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000461 (florfenicol); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 2

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
cfrC	ARO:3004146	not organism-specific	—	ARO:3004146 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000461 (florfenicol); database assertion, not a primary citation.)
clcD	ARO:3004599	not organism-specific	—	ARO:3004599 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000461 (florfenicol); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_PROTECTION 2

ANTIBIOTIC_TARGET_PROTECTION
Determinant	ARO ID	Organism	Gene families	Evidence
optrA	ARO:3003746	not organism-specific	—	ARO:3003746 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000461 (florfenicol); database assertion, not a primary citation.)
poxtA	ARO:3004470	not organism-specific	—	ARO:3004470 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000461 (florfenicol); 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.