cephapirin

CHEBI:554446 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A cephalosporin with acetoxymethyl and 2(pyridin-4-ylsulfanyl)acetamido substituents at positions 3 and 7, respectively, of the cephem skeleton. It is used (as its sodium salt) as an antibiotic, being effective against gram-negative and gram-positive organisms. — 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
ARO:0000032 ARO:0000032

Chemical structure

Computed structure properties
Molecular formula	C17H17N3O6S2
Charge	0
Average mass	423.472 Da
Monoisotopic mass	423.05588 Da
Source	ChEBI
InChIKey	UQLLWWBDSUHNEB-CZUORRHYSA-N

SMILES

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

InChI

InChI=1S/C17H17N3O6S2/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)/t13-,16-/m1/s1

Also called

cefapirin (INN)— chebi
cefapirina (INN)— chebi
cefapirine (INN)— chebi
cefapirinum (INN)— chebi
(6R,7R)-3-acetoxymethyl-7-[(pyridin-4-ylsulfanyl)acetamido]-3,4-didehydrocepham-4-carboxylic acid (EXACT_SYNONYM)— chebi
(6R,7R)-3-(acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
CEPR (EXACT_SYNONYM)— chebi
Cefaprin (EXACT_SYNONYM)— chebi
Cephapirine (EXACT_SYNONYM)— chebi
HAP (EXACT_SYNONYM)— aro
cefadyl (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3004008
beilstein:4031996
cas:21593-23-7
drugbank:DB01139
drugcentral:575
hmdb:HMDB0015270
hmdb:HMDB0030451
kegg.compound:C06896
kegg.drug:D07636
reaxys:4031966
vsdb:1845
wikipedia.en:Cephapirin
chembl:CHEMBL1599
pubchem.compound:30699

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:3004008`	cephapirin	`antibioticmech:aro-206c06dd17`	2026-08-30
CHEBI	`CHEBI:554446`	cephapirin	`antibioticmech:chebi-f8f3954945`	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:3004008 (cephapirin); 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.