cephalexin

CHEBI:3534 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A semisynthetic first-generation cephalosporin antibiotic having methyl and β-(2R)-2-amino-2-phenylacetamido groups at the 3- and 7- of the cephem skeleton, respectively. It is effective against both Gram-negative and Gram-positive organisms, and is used for treatment of infections of the skin, respiratory tract and urinary tract. — 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
β-lactam antibiotic allergen CHEBI:88225
cephalosporin ARO:0000032

Chemical structure

Computed structure properties
Molecular formula	C16H17N3O4S
Charge	0
Average mass	347.396 Da
Monoisotopic mass	347.09398 Da
Source	ChEBI
InChIKey	ZAIPMKNFIOOWCQ-UEKVPHQBSA-N

SMILES

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

InChI

InChI=1S/C16H17N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1

Also called

cefalexina (INN)— chebi
cefalexine (INN)— chebi
cefalexinum (INN)— chebi
7β-[(2R)-2-amino-2-phenylacetamido]-3-methyl-3,4-didehydrocepham-4-carboxylic acid (EXACT_SYNONYM)— chebi
(6R,7R)-7-{[(2R)-2-amino-2-phenylacetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
7-(D-α-Aminophenylacetamido)desacetoxycephalosporanic acid (EXACT_SYNONYM)— chebi
7-β-(D-alpha-Amino-alpha-phenylacetylamino)-3-methyl-3-cephem-4-carboxylic acid (EXACT_SYNONYM)— chebi
CEX (EXACT_SYNONYM)— chebi
Cefalexin (EXACT_SYNONYM)— chebi
Celexin (EXACT_SYNONYM)— chebi
Cepastar (EXACT_SYNONYM)— chebi
Cepexin (EXACT_SYNONYM)— chebi
Cephacillin (EXACT_SYNONYM)— chebi
Ceporexin (EXACT_SYNONYM)— chebi
LEX (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:3000641`	cefalexin	`antibioticmech:aro-90e5cc8a68`	2026-08-30
CHEBI	`CHEBI:3534`	cephalexin	`antibioticmech:chebi-f5d0d76424`	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:3000641 (cefalexin); 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
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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