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.

Label unavailable CHEBI:140325
Label unavailable CHEBI:35681
Label unavailable CHEBI:35850
Label unavailable CHEBI:36683
Label unavailable CHEBI:37143
phenicol antibiotic 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

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.

kegg.drug:D04194

Patents and articles

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

Activity roles

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

antimicrobial agent 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

16 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

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.)

UNKNOWN 5

UNKNOWN
Determinant	ARO ID	Organism	Gene families	Evidence
flo co-occurrence with florfenicol resistance in avian isolate 5334 Same-isolate co-occurrence, not isolated-gene causation or a new clinical breakpoint interpretation. Other determinants were not excluded. No exact experimental protein, allele, strain TaxID or genome is assigned. Bovine UniProtKB:Q9F0D9/AF252855 is not assigned to these avian isolates. Named compound identity is retained; the tested preparation was not independently re-identified.	—	Escherichia coli `NCBITaxon:562` strain 5334	flo	PMID:10639375 (Table 1 and adjacent native-isolate phenotype and hybridization results. Qualitative co-occurrence only.) Source-reported disk diffusion
flo co-occurrence with florfenicol resistance in avian isolate 5790 Same-isolate co-occurrence, not isolated-gene causation or a new clinical breakpoint interpretation. Other determinants were not excluded. No exact experimental protein, allele, strain TaxID or genome is assigned. Bovine UniProtKB:Q9F0D9/AF252855 is not assigned to these avian isolates. Named compound identity is retained; the tested preparation was not independently re-identified.	—	Escherichia coli `NCBITaxon:562` strain 5790	flo	PMID:10639375 (Table 1 and adjacent native-isolate phenotype and hybridization results. Qualitative co-occurrence only.) Source-reported disk diffusion
flo co-occurrence with florfenicol resistance in avian isolate 5840 Same-isolate co-occurrence, not isolated-gene causation or a new clinical breakpoint interpretation. Other determinants were not excluded. No exact experimental protein, allele, strain TaxID or genome is assigned. Bovine UniProtKB:Q9F0D9/AF252855 is not assigned to these avian isolates. Named compound identity is retained; the tested preparation was not independently re-identified.	—	Escherichia coli `NCBITaxon:562` strain 5840	flo	PMID:10639375 (Table 1 and adjacent native-isolate phenotype and hybridization results. Qualitative co-occurrence only.) Source-reported disk diffusion
flo co-occurrence with florfenicol resistance in avian isolate 6468 Same-isolate co-occurrence, not isolated-gene causation or a new clinical breakpoint interpretation. Other determinants were not excluded. No exact experimental protein, allele, strain TaxID or genome is assigned. Bovine UniProtKB:Q9F0D9/AF252855 is not assigned to these avian isolates. Named compound identity is retained; the tested preparation was not independently re-identified.	—	Escherichia coli `NCBITaxon:562` strain 6468	flo, cmlA	PMID:10639375 (Table 1 and adjacent native-isolate phenotype and hybridization results. Qualitative co-occurrence only.) Source-reported disk diffusion
flo/cmlA-positive bovine subgroup associated with florfenicol resistance Subgroup co-occurrence, not sole-gene causation or an assertion about every study isolate. Discordant source subgroups are not merged. Florfenicol categories borrow bovine-respiratory criteria; no E. coli clinical breakpoint is inferred. UniProtKB:Q9F0D9/AF252855.1 is study-linked reference context, not a subgroup-wide allele or genome assignment. EC56 belongs to a later submission and is not substituted for this subgroup. No exact experimental protein, allele, strain TaxID or genome is assigned. Named compound identity is retained; the tested preparation was not independently re-identified.	—	Escherichia coli `NCBITaxon:562`	flo, cmlA	PMID:11101601 (Table 2 flo/cmlA-positive row and adjacent cohort results; assay and accession statements. Qualitative subgroup association only.) NCCLS broth microdilution

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
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories
CURATED_RESISTANCE_EVIDENCE 2026-10-10 · codex · LLM-assisted
Added four named native flo co-occurrences and one separate flo/cmlA-positive subgroup association from primary results. Kept mechanism UNKNOWN and UniProt/archive context reference-only; did not assign exact alleles, genomes, a subgroup strain or new clinical breakpoints. Preserved all prior claims, observations, history and other fields; whole-record review remains open.

Provenance

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

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