cefalotin

CHEBI:124991 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A semisynthetic, first-generation cephalosporin antibiotic with acetoxymethyl and (2-thienylacetyl)nitrilo moieties at positions 3 and 7, respectively, of the core structure. Administered parenterally during surgery and to treat a wide spectrum of blood infections. — 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:26961 CHEBI:26961
CHEBI:33575 CHEBI:33575
CHEBI:50896 CHEBI:50896
CHEBI:72588 CHEBI:72588
CHEBI:88225 CHEBI:88225
ARO:0000032 ARO:0000032

Chemical structure

Computed structure properties
Molecular formula	C16H16N2O6S2
Charge	0
Average mass	396.446 Da
Monoisotopic mass	396.04498 Da
Source	ChEBI
InChIKey	XIURVHNZVLADCM-IUODEOHRSA-N

SMILES

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

InChI

InChI=1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1

Also called

cefalotina (INN)— chebi
cefalotinum (INN)— chebi
céfalotine (INN)— chebi
(6R,7R)-3-(acetoxymethyl)-8-oxo-7-(thiophen-2-ylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
7β-(thiophen-2-ylacetamido)-3-acetoxymethyl-3,4-didehydrocepham-4-carboxylic acid (EXACT_SYNONYM)— chebi
3-Acetoxymethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid (EXACT_SYNONYM)— chebi
7-(2'-thienylacetamido)cephalosporanic acid (EXACT_SYNONYM)— chebi
7-(2-Thienylacetamido)cephalosporanic acid (EXACT_SYNONYM)— chebi
7-(Thiophene-2-acetamido)cephalosporin (EXACT_SYNONYM)— chebi
CEPHALOTHIN (EXACT_SYNONYM)— chebi
CET (EXACT_SYNONYM)— chebi
Cefalothin (EXACT_SYNONYM)— chebi
Cefalotin (EXACT_SYNONYM)— chebi
Cephalothin (EXACT_SYNONYM)— chebi
Cephalotin (EXACT_SYNONYM)— chebi
CEF (EXACT_SYNONYM)— aro
cephalothin (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000704
beilstein:945586
cas:153-61-7
drugbank:DB00456
drugcentral:574
hmdb:HMDB0014599
kegg.compound:C07761
kegg.drug:D07635
lincs.smallmolecule:LSM-15184
patent:FR1384197
patent:US3218318
pdb-ccd:CLS
reaxys:945586
wikipedia.en:Cephalothin
chembl:CHEMBL617
pubchem.compound:6024

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:3000704`	cefalotin	`antibioticmech:aro-dfb1f7b1a1`	2026-08-30
CHEBI	`CHEBI:124991`	cefalotin	`antibioticmech:chebi-326999c3c7`	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:3000704 (cefalotin); database assertion, not a primary citation.)

Resistance mechanisms

27 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 24

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:3000704 (cefalotin); database assertion, not a primary citation.)
CDA-1	ARO:3007650	not organism-specific	—	ARO:3007650 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
CMY-2	ARO:3002013	not organism-specific	—	ARO:3002013 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
CTX-M-15	ARO:3001878	not organism-specific	—	ARO:3001878 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
CTX-M-27	ARO:3001889	not organism-specific	—	ARO:3001889 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
CTX-M-3	ARO:3001866	not organism-specific	—	ARO:3001866 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
EBR-5	ARO:3007437	not organism-specific	—	ARO:3007437 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
LAP-1	ARO:3004825	not organism-specific	—	ARO:3004825 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
LAP-2	ARO:3004826	not organism-specific	—	ARO:3004826 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
MAB	ARO:3007180	not organism-specific	—	ARO:3007180 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
OXA-1	ARO:3001396	not organism-specific	—	ARO:3001396 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
OXA-50	ARO:3001796	not organism-specific	—	ARO:3001796 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
PDC-3	ARO:3002500	not organism-specific	—	ARO:3002500 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
PDC-5	ARO:3002502	not organism-specific	—	ARO:3002502 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
PJM-1	ARO:3007374	not organism-specific	—	ARO:3007374 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
PSZ-1	ARO:3007648	not organism-specific	—	ARO:3007648 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
SCO-1	ARO:3004856	not organism-specific	—	ARO:3004856 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
SED-1	ARO:3003561	not organism-specific	—	ARO:3003561 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
SHV-12	ARO:3001071	not organism-specific	—	ARO:3001071 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
TEM-1	ARO:3000873	not organism-specific	—	ARO:3000873 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
TEM-30	ARO:3000900	not organism-specific	—	ARO:3000900 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
TRU-1	ARO:3004450	not organism-specific	—	ARO:3004450 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
YRC-1	ARO:3005035	not organism-specific	—	ARO:3005035 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
blaC	ARO:3007182	not organism-specific	—	ARO:3007182 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)

REDUCED_PERMEABILITY 2

REDUCED_PERMEABILITY
Determinant	ARO ID	Organism	Gene families	Evidence
Klebsiella pneumoniae OmpK35	ARO:3003966	not organism-specific	—	ARO:3003966 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)
Klebsiella pneumoniae OmpK36	ARO:3003968	not organism-specific	—	ARO:3003968 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 1

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
AcrAB-TolC	ARO:3000384	not organism-specific	—	ARO:3000384 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000704 (cefalotin); 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.