cefprozil

CHEBI:3506 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A semisynthetic, second-generation cephalosporin, with prop-1-enyl and (R)-2-amino-2-(4-hydroxyphenyl)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton. It is used to treat bronchitis as well as ear, skin and other bacterial infections. — 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	C18H19N3O5S
Charge	0
Average mass	389.433 Da
Monoisotopic mass	389.10454 Da
Source	ChEBI
InChIKey	WDLWHQDACQUCJR-PBFPGSCMSA-N

SMILES

[H][C@]12SCC(C=CC)=C(C(=O)O)N1C(=O)[C@@]2([H])NC(=O)[C@H](N)c1ccc(O)cc1

InChI

InChI=1S/C18H19N3O5S/c1-2-3-10-8-27-17-13(16(24)21(17)14(10)18(25)26)20-15(23)12(19)9-4-6-11(22)7-5-9/h2-7,12-13,17,22H,8,19H2,1H3,(H,20,23)(H,25,26)/t12-,13-,17-/m1/s1

Also called

Cefzil (BRAND_NAME)— chebi
cefprozilo (INN)— chebi
cefprozilum (INN)— chebi
(6R,7R)-7-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-8-oxo-3-(prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
Cefprozil anhydrous (EXACT_SYNONYM)— chebi
Brisoral (EXACT_SYNONYM)— aro
CPR (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3004005
beilstein:8167198
cas:92665-29-7
drugbank:DB01150
hmdb:HMDB0015281
kegg.compound:C06888
kegg.drug:D07651
patent:DE3402642
patent:US4520022
wikipedia.en:Cefprozil
chembl:CHEMBL3301800
pubchem.compound:5281006

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:3004005`	cefprozil	`antibioticmech:aro-09ddcd51db`	2026-08-30
CHEBI	`CHEBI:3506`	cefprozil	`antibioticmech:chebi-796bdcb883`	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:3004005 (cefprozil); 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.