cefoxitin

CHEBI:209807 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A semisynthetic cephamycin antibiotic which, in addition to the methoxy group at the 7α position, has 2-thienylacetamido and carbamoyloxymethyl side-groups. It is resistant to β-lactamase. — 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

cephalosporinARO:0000032

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:23066 CHEBI:23066
CHEBI:55429 CHEBI:55429
CHEBI:72588 CHEBI:72588
CHEBI:88225 CHEBI:88225
ARO:0000032 ARO:0000032

Chemical structure

Computed structure properties
Molecular formula	C16H17N3O7S2
Charge	0
Average mass	427.46 Da
Monoisotopic mass	427.05079 Da
Source	ChEBI
InChIKey	WZOZEZRFJCJXNZ-ZBFHGGJFSA-N

SMILES

[H][C@]12SCC(COC(N)=O)=C(C(=O)O)N1C(=O)[C@]2(NC(=O)Cc1cccs1)OC

InChI

InChI=1S/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1

Also called

cefoxitina (INN)— chebi
cefoxitine (INN)— chebi
cefoxitinum (INN)— chebi
ceftoxitin (INN)— chebi
(6R,7S)-4-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(thiophen-2-enyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
3-[(carbamoyloxy)methyl]-7α-methoxy-7β-[(thiophen-2-yl)acetamido]-3,4-didehydrocepham-4-carboxylic acid (EXACT_SYNONYM)— chebi
(6R,7S)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
CFX (EXACT_SYNONYM)— chebi
Cefoxitin (EXACT_SYNONYM)— chebi
Cephoxitin (EXACT_SYNONYM)— chebi
Rephoxitin (EXACT_SYNONYM)— chebi
FOX (EXACT_SYNONYM)— aro
Mefoxitin (EXACT_SYNONYM)— aro
mefoxin (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:0000008
beilstein:4216947
cas:35607-66-0
drugbank:DB01331
drugcentral:550
hmdb:HMDB0015426
kegg.compound:C06887
kegg.drug:D02345
lincs.smallmolecule:LSM-5786
patent:DE2129675
patent:DE2203653
patent:US4297488
pdb-ccd:CFX
reaxys:4216947
wikipedia.en:Cefoxitin
chembl:CHEMBL996
pubchem.compound:441199

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:0000008`	cefoxitin	`antibioticmech:aro-f8bb991f1c`	2026-08-30
CHEBI	`CHEBI:209807`	cefoxitin	`antibioticmech:chebi-b9a20bd574`	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:0000008 (cefoxitin); database assertion, not a primary citation.)

Resistance mechanisms

23 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_INACTIVATION 18

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
AMZ-1	ARO:3007694	not organism-specific	—	ARO:3007694 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
CAM-1	ARO:3004559	not organism-specific	—	ARO:3004559 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
CDA-1	ARO:3007650	not organism-specific	—	ARO:3007650 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
CMY-2	ARO:3002013	not organism-specific	—	ARO:3002013 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
CMY-42	ARO:3002053	not organism-specific	—	ARO:3002053 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
CTX-M-3	ARO:3001866	not organism-specific	—	ARO:3001866 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
CfxA	ARO:3003001	not organism-specific	—	ARO:3003001 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
LAQ-1	ARO:3007438	not organism-specific	—	ARO:3007438 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
NDM-5	ARO:3000467	not organism-specific	—	ARO:3000467 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
NmcA	ARO:3003589	not organism-specific	—	ARO:3003589 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
PDC-3	ARO:3002500	not organism-specific	—	ARO:3002500 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
PDC-5	ARO:3002502	not organism-specific	—	ARO:3002502 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
PJM-1	ARO:3007374	not organism-specific	—	ARO:3007374 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
PSZ-1	ARO:3007648	not organism-specific	—	ARO:3007648 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
SSA	ARO:3007442	not organism-specific	—	ARO:3007442 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
YRC-1	ARO:3005035	not organism-specific	—	ARO:3005035 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
blaC	ARO:3007182	not organism-specific	—	ARO:3007182 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
blaS1	ARO:3005111	not organism-specific	—	ARO:3005111 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)

REDUCED_PERMEABILITY 4

REDUCED_PERMEABILITY
Determinant	ARO ID	Organism	Gene families	Evidence
Burkholderia pseudomallei Omp38	ARO:3004123	not organism-specific	—	ARO:3004123 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
Klebsiella pneumoniae OmpK35	ARO:3003966	not organism-specific	—	ARO:3003966 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
Klebsiella pneumoniae OmpK37	ARO:3004122	not organism-specific	—	ARO:3004122 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)
Serratia marcescens Omp1	ARO:3004128	not organism-specific	—	ARO:3004128 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 1

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Staphylococcus aureus PBP4 mutant conferring resistance to nafcillin and cefoxitin	ARO:3009660	not organism-specific	—	ARO:3009660 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000008 (cefoxitin); 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.