AntibioticMech

cephapirin sodium

CHEBI:3545 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

The sodium salt of cephapirin. A first-generation cephalosporin antibiotic, it is effective against gram-negative and gram-positive organisms. Being more resistant to β-lactamases than penicillins, it is effective agains most staphylococci, though not methicillin-resistant staphylococci. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:23066 CHEBI:23066
• CHEBI:38700 CHEBI:38700

Chemical structure

Computed structure properties

Molecular formula	C17H16N3O6S2.Na
Charge	0
Average mass	445.454 Da
Monoisotopic mass	445.03782 Da
Source	ChEBI
InChIKey	VGEOUKPOQQEQSX-OALZAMAHSA-M

SMILES

[H][C@]12SCC(COC(C)=O)=C(C(=O)[O-])N1C(=O)[C@H]2NC(=O)CSc1ccncc1.[Na+]

InChI

InChI=1S/C17H17N3O6S2.Na/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11;/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25);/q;+1/p-1/t13-,16-;/m1./s1

Also called

• sodium (6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (EXACT_SYNONYM)— chebi
• Cefapirin sodium (EXACT_SYNONYM)— chebi
• Cephapirin sodium (EXACT_SYNONYM)— chebi
• Sodium cefapirin (EXACT_SYNONYM)— chebi
• monosodium (6R,7R)-3-(hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate acetate (EXACT_SYNONYM)— chebi
• sodium 7-(pyrid-4-ylthioacetamido)cephalosporanate (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• beilstein:4900637
• cas:24356-60-3
• drugbank:DB01139
• kegg.compound:C08101
• kegg.drug:D00908
• patent:US3422100
• patent:US3503967
• patent:US3578661

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
CHEBI	CHEBI:3545	cephapirin sodium	antibioticmech:chebi-de1b30d07e	2026-08-30

Mechanism summary

Clinical status

APPROVED

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (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 2026-08-31 · 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.