loracarbef

CHEBI:47544 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A synthetic "carba" analogue of cefaclor, with carbon replacing sulfur at position 1. Used to treat a wide range of infections caused by both gram-positive and gram-negative bacteria. — 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:55504 CHEBI:55504
ARO:0000032 ARO:0000032

Chemical structure

Computed structure properties
Molecular formula	C16H16ClN3O4
Charge	0
Average mass	349.774 Da
Monoisotopic mass	349.08293 Da
Source	ChEBI
InChIKey	JAPHQRWPEGVNBT-UTUOFQBUSA-N

SMILES

N[C@@H](C(=O)N[C@@H]1C(=O)N2C(C(=O)O)=C(Cl)CC[C@H]12)c1ccccc1

InChI

InChI=1S/C16H16ClN3O4/c17-9-6-7-10-12(15(22)20(10)13(9)16(23)24)19-14(21)11(18)8-4-2-1-3-5-8/h1-5,10-12H,6-7,18H2,(H,19,21)(H,23,24)/t10-,11-,12+/m1/s1

Also called

loracarbefum (INN)— chebi
(6R,7S)-7-{[(2R)-2-amino-2-phenylacetyl]amino}-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
7β-[(2R)-2-amino-2-phenylacetyl]nitrilo-3-chloro-3,4-didehydrocepham-4-carboxylic acid (EXACT_SYNONYM)— chebi
LORACABEF (EXACT_SYNONYM)— chebi
Lorabid (EXACT_SYNONYM)— aro
Loracarbefum (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3004016
cas:76470-66-1
drugbank:DB00447
drugcentral:1603
hmdb:HMDB0014590
kegg.drug:D08143
lincs.smallmolecule:LSM-5429
patent:EP14476
patent:US4708956
pdb-ccd:LOR
reaxys:3631282
chembl:CHEMBL1200610
pubchem.compound:5284585

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:3004016`	loracarbef	`antibioticmech:aro-fdbaf42415`	2026-08-30
CHEBI	`CHEBI:47544`	loracarbef	`antibioticmech:chebi-21d4c566e7`	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:3004016 (loracarbef); 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.