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.

cephalosporin CHEBI:23066
Label unavailable CHEBI:26961
Label unavailable CHEBI:33575
Label unavailable CHEBI:50896
Label unavailable CHEBI:72588
β-lactam antibiotic allergen CHEBI:88225
cephalosporin 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

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.

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

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
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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