AntibioticMech

cefpirome

CHEBI:3503 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A fourth-generation cephalosporin antibiotic having 6,7-dihydro-5H-cyclopenta[b]pyridinium-1-ylmethyl and [(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side groups located at positions 3 and 7 respectively. — ChEBI

Classification

cephalosporinARO:0000032

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:23066 CHEBI:23066
• CHEBI:37940 CHEBI:37940
• ARO:0000032 ARO:0000032

Chemical structure

Computed structure properties

Molecular formula	C22H22N6O5S2
Charge	0
Average mass	514.589 Da
Monoisotopic mass	514.10931 Da
Source	ChEBI
InChIKey	DKOQGJHPHLTOJR-WHRDSVKCSA-N

SMILES

[H][C@]12SCC(C[n+]3cccc4c3CCC4)=C(C(=O)[O-])N1C(=O)[C@H]2NC(=O)/C(=N\OC)c1csc(N)n1

InChI

InChI=1S/C22H22N6O5S2/c1-33-26-15(13-10-35-22(23)24-13)18(29)25-16-19(30)28-17(21(31)32)12(9-34-20(16)28)8-27-7-3-5-11-4-2-6-14(11)27/h3,5,7,10,16,20H,2,4,6,8-9H2,1H3,(H3-,23,24,25,29,31,32)/b26-15-/t16-,20-/m1/s1

Also called

• cefpiroma (INN)— chebi
• cefpiromum (INN)— chebi
• 7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(6,7-dihydro-5H-cyclopenta[b]pyridinium-1-ylmethyl)-3,4-didehydrocepham-4-carboxylic acid (EXACT_SYNONYM)— chebi
• (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(6,7-dihydro-5H-cyclopenta[b]pyridinium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (EXACT_SYNONYM)— chebi
• Cefpirome (EXACT_SYNONYM)— chebi
• HR 810 (EXACT_SYNONYM)— chebi
• cefrom (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• ARO:3004726
• cas:84957-29-9
• drugcentral:553
• kegg.compound:C11199
• kegg.drug:D07649
• reaxys:4241500
• wikipedia.en:Cefpirome
• chembl:CHEMBL65794
• pubchem.compound:5479539

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

• CHEBI:33281 CHEBI:33281

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:3004726	cefpirome	antibioticmech:aro-ab2c9a8de3	2026-08-30
CHEBI	CHEBI:3503	cefpirome	antibioticmech:chebi-ef53a97480	2026-08-30

Resistance mechanisms

2 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 1

ANTIBIOTIC_INACTIVATION

Determinant	ARO ID	Organism	Gene families	Evidence
ACC-1	ARO:3001815	not organism-specific	—	ARO:3001815 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3004726 (cefpirome); database assertion, not a primary citation.)

REDUCED_PERMEABILITY 1

REDUCED_PERMEABILITY

Determinant	ARO ID	Organism	Gene families	Evidence
Klebsiella aerogenes Omp36	ARO:3003385	not organism-specific	—	ARO:3003385 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3004726 (cefpirome); database assertion, not a primary citation.)

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

Provenance

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