cefmetazole

CHEBI:3489 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A second-generation cephalosporin antibiotic having N1-methyltetrazol-5-ylthiomethyl, {[(cyanomethyl)sulfanyl]acetyl}amino and methoxy side-groups at positions 3, 7β and 7α respectively of the parent cephem bicyclic structure. — 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	C15H17N7O5S3
Charge	0
Average mass	471.546 Da
Monoisotopic mass	471.04533 Da
Source	ChEBI
InChIKey	SNBUBQHDYVFSQF-HIFRSBDPSA-N

SMILES

[H][C@]12SCC(CSc3nnnn3C)=C(C(=O)O)N1C(=O)[C@]2(NC(=O)CSCC#N)OC

InChI

InChI=1S/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1

Also called

cefmetazolo (INN)— chebi
cefmetazolum (INN)— chebi
7β-{[(cyanomethyl)sulfanyl]acetamido}-7α-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}ceph-3-em-4-carboxylic acid (EXACT_SYNONYM)— chebi
(6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
CMZ (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3004001
beilstein:5406306
cas:56796-20-4
drugbank:DB00274
drugcentral:539
kegg.compound:C08103
kegg.drug:D00910
lincs.smallmolecule:LSM-5594
wikipedia.en:Cefmetazole
chembl:CHEMBL1201195
pubchem.compound:42008

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:3004001`	cefmetazole	`antibioticmech:aro-efdfdb5f47`	2026-08-30
CHEBI	`CHEBI:3489`	cefmetazole	`antibioticmech:chebi-0a09ad31af`	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:3004001 (cefmetazole); database assertion, not a primary citation.)

Resistance mechanisms

1 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
CfxA	ARO:3003001	not organism-specific	—	ARO:3003001 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3004001 (cefmetazole); 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.