cefazolin

CHEBI:474053 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A first-generation cephalosporin compound having [(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl and (1H-tetrazol-1-ylacetyl)amino side-groups at positions 3 and 7 respectively. — 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:35689 CHEBI:35689
CHEBI:38099 CHEBI:38099
CHEBI:88225 CHEBI:88225
ARO:0000032 ARO:0000032

Chemical structure

Computed structure properties
Molecular formula	C14H14N8O4S3
Charge	0
Average mass	454.519 Da
Monoisotopic mass	454.03001 Da
Source	ChEBI
InChIKey	MLYYVTUWGNIJIB-BXKDBHETSA-N

SMILES

[H][C@]12SCC(CSc3nnc(C)s3)=C(C(=O)O)N1C(=O)[C@H]2NC(=O)Cn1cnnn1

InChI

InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1

Also called

cefazolina (INN)— chebi
cefazoline (INN)— chebi
cefazolinum (INN)— chebi
3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-7β-[(1H-tetrazol-1-ylacetyl)amino]-3,4-didehydrocepham-4-carboxylic acid (EXACT_SYNONYM)— chebi
(6R,7R)-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
CEZ (EXACT_SYNONYM)— chebi
Cefamezin (EXACT_SYNONYM)— chebi
Cephamezine (EXACT_SYNONYM)— chebi
Cephazolidin (EXACT_SYNONYM)— chebi
Cephazolin (EXACT_SYNONYM)— chebi
Cephazoline (EXACT_SYNONYM)— chebi
CFZ (EXACT_SYNONYM)— aro
Cefazolina (EXACT_SYNONYM)— aro
Cefazoline (EXACT_SYNONYM)— aro
Cefazolinum (EXACT_SYNONYM)— aro
Elzogram (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:0000058
cas:25953-19-9
drugbank:DB01327
drugcentral:530
hmdb:HMDB0015422
kegg.compound:C06880
kegg.drug:D02299
lincs.smallmolecule:LSM-34744
patent:US3516997
reaxys:4169371
vsdb:1910
wikipedia.en:Cefazolin
chembl:CHEMBL1435
pubchem.compound:33255

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:0000058`	cefazolin	`antibioticmech:aro-91ba49115d`	2026-08-30
CHEBI	`CHEBI:474053`	cefazolin	`antibioticmech:chebi-2803cda771`	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:0000058 (cefazolin); database assertion, not a primary citation.)

Resistance mechanisms

13 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 12

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
CAE-1	ARO:3007635	not organism-specific	—	ARO:3007635 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000058 (cefazolin); database assertion, not a primary citation.)
CMY-2	ARO:3002013	not organism-specific	—	ARO:3002013 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000058 (cefazolin); database assertion, not a primary citation.)
CTX-M-15	ARO:3001878	not organism-specific	—	ARO:3001878 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000058 (cefazolin); database assertion, not a primary citation.)
CTX-M-27	ARO:3001889	not organism-specific	—	ARO:3001889 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000058 (cefazolin); database assertion, not a primary citation.)
CTX-M-3	ARO:3001866	not organism-specific	—	ARO:3001866 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000058 (cefazolin); database assertion, not a primary citation.)
LAQ-1	ARO:3007438	not organism-specific	—	ARO:3007438 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000058 (cefazolin); database assertion, not a primary citation.)
NmcA	ARO:3003589	not organism-specific	—	ARO:3003589 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000058 (cefazolin); database assertion, not a primary citation.)
PDC-3	ARO:3002500	not organism-specific	—	ARO:3002500 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000058 (cefazolin); database assertion, not a primary citation.)
PDC-5	ARO:3002502	not organism-specific	—	ARO:3002502 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000058 (cefazolin); database assertion, not a primary citation.)
PRC-1	ARO:3007085	not organism-specific	—	ARO:3007085 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000058 (cefazolin); database assertion, not a primary citation.)
PSZ-1	ARO:3007648	not organism-specific	—	ARO:3007648 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000058 (cefazolin); database assertion, not a primary citation.)
TEM-1	ARO:3000873	not organism-specific	—	ARO:3000873 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000058 (cefazolin); database assertion, not a primary citation.)

REDUCED_PERMEABILITY 1

REDUCED_PERMEABILITY
Determinant	ARO ID	Organism	Gene families	Evidence
porin OmpC	ARO:3004114	not organism-specific	—	ARO:3004114 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000058 (cefazolin); 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.