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

Classification

cephalosporinARO:0000032

Strictly broader compounds or drug classes this molecule belongs to.

• cephalosporin CHEBI:23066
• Label unavailable CHEBI:35689
• Label unavailable CHEBI:38099
• β-lactam antibiotic allergen CHEBI:88225
• cephalosporin ARO:0000032

Chemical structure

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

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.

• cefazolinARO:0000058
• cas:25953-19-9
• hmdb:HMDB0015422
• kegg.compound:C06880
• lincs.smallmolecule:LSM-34744
• reaxys:4169371
• vsdb:1910
• chembl:CHEMBL1435
• pubchem.compound:33255

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.

• drugbank:DB01327
• drugcentral:530
• kegg.drug:D02299

Patents and articles

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

• patent:US3516997
• wikipedia.en:Cefazolin

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.

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.)

Activity spectrum

Measured or curated activity against specific taxa. A number without a method is not an observation — every row here carries an assay.

7 observations · Browse all observations · Complete record (JSON.gz)

Resistance mechanisms

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

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

5. RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

6. CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted

   Added one stable-URL CDC/FDA AR Isolate Bank cefazolin-resistant Escherichia coli isolate MIC observation.

7. CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted

   Added one stable-URL CDC/FDA AR Isolate Bank cefazolin-resistant Klebsiella pneumoniae isolate MIC observation.

8. CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted

   Added one stable-URL CDC/FDA AR Isolate Bank cefazolin-resistant Klebsiella aerogenes isolate MIC observation.

9. CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted

   Corrected the CDC/FDA AR Isolate Bank 0349 breakpoint context from CLSI 2024 M100 S34 to CLSI 2025 M100 S35.

10. CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted

    Fixes #286. Corrected the CDC/FDA AR Isolate Bank 0074 breakpoint context from CLSI 2024 M100 S34 to CLSI 2025 M100 S35.

11. CURATED_RESISTANT_TAXA 2026-09-12 · codex · LLM-assisted

    Added one stable-URL CDC/FDA AR Isolate Bank cefazolin-resistant Escherichia coli MIC observation from isolate 0346.

12. CURATED_RESISTANT_TAXA 2026-09-13 · codex · LLM-assisted

    Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 cefazolin-resistant Citrobacter freundii MIC observation for AR-0637.

13. CURATED_RESISTANT_TAXA 2026-09-17 · codex · LLM-assisted

    Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 cefazolin-resistant Escherichia coli MIC observation for AR-0495.

14. CURATED_RESISTANT_TAXA 2026-09-19 · codex · LLM-assisted

    Added one stable-URL CDC/FDA AR Isolate Bank Panel 10 cefazolin-resistant Escherichia coli MIC observation for AR-0538; preserved BioSample SAMN11953785 and Study ID NEW-22 in evidence notes.

15. STRUCTURED_ACTIVITY_BIOSAMPLE_ACCESSIONS 2026-09-26 · codex · LLM-assisted

    Structured BioSample accessions on 7 activity_spectrum observation(s) where evidence notes already named exactly one accession.

Provenance

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

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