azlocillin

CHEBI:2956 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A semisynthetic penicillin having a 6β-{(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl}amino side-group. It is an antibiotic used in treating infections caused by Pseudomonas aeruginosa, Escherichia coli and Haemophilus influenzae. — 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

penicillin beta-lactamARO:3000008

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:17334 CHEBI:17334
CHEBI:72588 CHEBI:72588
CHEBI:88187 CHEBI:88187
ARO:3000008 ARO:3000008

Chemical structure

Computed structure properties
Molecular formula	C20H23N5O6S
Charge	0
Average mass	461.5 Da
Monoisotopic mass	461.1369 Da
Source	ChEBI
InChIKey	JTWOMNBEOCYFNV-NFFDBFGFSA-N

SMILES

[H][C@](NC(=O)N1CCNC1=O)(C(=O)N[C@@H]1C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@]12[H])c1ccccc1

InChI

InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1

Also called

azlocilina (INN)— chebi
azlocilline (INN)— chebi
azlocillinum (INN)— chebi
2,2-dimethyl-6β-[(2R)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetamido]penam-3α-carboxylic acid (EXACT_SYNONYM)— chebi
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-{[(2R)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
AZL (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000638
cas:37091-66-0
drugbank:DB01061
drugcentral:277
kegg.compound:C06839
kegg.drug:D02339
lincs.smallmolecule:LSM-15179
patent:CN101585844
patent:FR2100682
patent:US3933795
reaxys:5785146
wikipedia.en:Azlocillin
chembl:CHEMBL1537
pubchem.compound:6479523

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:3000638`	azlocillin	`antibioticmech:aro-b556f68684`	2026-08-30
CHEBI	`CHEBI:2956`	azlocillin	`antibioticmech:chebi-190d64eeee`	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:3000638 (azlocillin); 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.