cefamandole

CHEBI:3480 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A cephalosporin compound having (R)-mandelamido and N-methylthiotetrazole side-groups. — 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
CHEBI:72588 CHEBI:72588
ARO:0000032 ARO:0000032

Chemical structure

Computed structure properties
Molecular formula	C18H18N6O5S2
Charge	0
Average mass	462.513 Da
Monoisotopic mass	462.07801 Da
Source	ChEBI
InChIKey	OLVCFLKTBJRLHI-AXAPSJFSSA-N

SMILES

[H][C@]12SCC(CSc3nnnn3C)=C(C(=O)O)N1C(=O)[C@H]2NC(=O)[C@H](O)c1ccccc1

InChI

InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1

Also called

cefamandol (INN)— chebi
cefamandolum (INN)— chebi
céfamandole (INN)— chebi
7β-[(2R)-2-hydroxy-2-phenylacetamido]-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}ceph-3-em-4-carboxylic acid (EXACT_SYNONYM)— chebi
(6R,7R)-7-(R)-Mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylic acid (EXACT_SYNONYM)— chebi
(6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-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
Cefadole (EXACT_SYNONYM)— chebi
Cephadole (EXACT_SYNONYM)— chebi
Cephamandole (EXACT_SYNONYM)— chebi
L-Cefamandole (EXACT_SYNONYM)— chebi
FAM (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3003999
beilstein:5406309
cas:34444-01-4
drugbank:DB01326
drugcentral:527
kegg.compound:C06879
kegg.drug:D02344
patent:DE2018600
patent:DE2312997
patent:US3641021
patent:US3840531
wikipedia.en:Cefamandole
chembl:CHEMBL1146
pubchem.compound:456255

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:3003999`	cefamandole	`antibioticmech:aro-19fea9c31e`	2026-08-30
CHEBI	`CHEBI:3480`	cefamandole	`antibioticmech:chebi-f13162af9a`	2026-08-30

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.

REDUCED_PERMEABILITY 1

REDUCED_PERMEABILITY
Determinant	ARO ID	Organism	Gene families	Evidence
Klebsiella pneumoniae OmpK35	ARO:3003966	not organism-specific	—	ARO:3003966 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003999 (cefamandole); 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

Provenance

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