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.

cephalosporin CHEBI:23066
Label unavailable CHEBI:72588
cephalosporin 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

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

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

antimicrobial agent CHEBI:33281
antibacterial drug 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 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

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
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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