moxalactam

CHEBI:599928 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A broad-spectrum oxacephem antibiotic in which the oxazine ring is substituted with a tetrazolylthiomethyl group and the azetidinone ring carries methoxy and 2-carboxy-2-(4-hydroxyphenyl)acetamido substituents. — 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:55506 CHEBI:55506
ARO:0000032 ARO:0000032

Chemical structure

Computed structure properties
Molecular formula	C20H20N6O9S
Charge	0
Average mass	520.48 Da
Monoisotopic mass	520.10125 Da
Source	ChEBI
InChIKey	JWCSIUVGFCSJCK-CAVRMKNVSA-N

SMILES

[H][C@]12OCC(CSc3nnnn3C)=C(C(=O)O)N1C(=O)[C@]2(NC(=O)C(C(=O)O)c1ccc(O)cc1)OC

InChI

InChI=1S/C20H20N6O9S/c1-25-19(22-23-24-25)36-8-10-7-35-18-20(34-2,17(33)26(18)13(10)16(31)32)21-14(28)12(15(29)30)9-3-5-11(27)6-4-9/h3-6,12,18,27H,7-8H2,1-2H3,(H,21,28)(H,29,30)(H,31,32)/t12?,18-,20+/m1/s1

Also called

latamoxef (INN)— chebi
latamoxefum (INN)— chebi
(6R,7R)-7-{[carboxy(4-hydroxyphenyl)acetyl]amino}-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
LMOX (EXACT_SYNONYM)— chebi
Lamoxactam (EXACT_SYNONYM)— chebi
Latamoxef (EXACT_SYNONYM)— chebi
Moxalactam (EXACT_SYNONYM)— chebi
Oxa-cephem (EXACT_SYNONYM)— chebi
festamoxin (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3004017
cas:64952-97-2
drugbank:DB04570
drugcentral:1851
hmdb:HMDB0015574
kegg.compound:C07231
kegg.drug:D08109
patent:DE2713370
patent:US413486
pdb-ccd:MXL
reaxys:4222777
chembl:CHEMBL74632
pubchem.compound:47499

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:3004017`	moxalactam	`antibioticmech:aro-5a7184ea7e`	2026-08-30
CHEBI	`CHEBI:599928`	moxalactam	`antibioticmech:chebi-516843da45`	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:3004017 (moxalactam); database assertion, not a primary citation.)

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:3004017 (moxalactam); database assertion, not a primary citation.)

REDUCED_PERMEABILITY 1

REDUCED_PERMEABILITY
Determinant	ARO ID	Organism	Gene families	Evidence
Serratia marcescens Omp1	ARO:3004128	not organism-specific	—	ARO:3004128 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3004017 (moxalactam); 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.