Oxacillin

Summary

Oxacillin (CHEMBL819) is an approved small-molecule antibacterial agent (ATC J01CF04); indicated across 5 conditions including bacterial infectious disease and osteomyelitis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J01CF04
• Indications: 5 conditions
• Clinical trials: 8
• Chemistry: 401.4 Da · C19H19N3O5S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL819
Name	Oxacillin
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	6196
ChEBI	CHEBI:7809
ATC	J01CF04
Molecular formula	C19H19N3O5S
Molecular weight	401.4
InChIKey	UWYHMGVUTGAWSP-JKIFEVAISA-N

SMILES: CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O

IUPAC name: (2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

ChEBI definition: A penicillin antibiotic carrying a 5-methyl-3-phenylisoxazole-4-carboxamide group at position 6β.

Pharmacological roles (ChEBI): antibacterial agent, antibacterial drug.

Also known as: Oxacilina, Oxacillin, Oxacilline, Oxazocilline, oxacillin, Oxa, OXacillin, OXACILLINE, OXACILLIN

Parent form; salt/anhydrous children: CHEMBL693, CHEMBL3989567

Patent coverage: 8,550 distinct patent families (30,964 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 1 (assay-derived). Sample: Organic anion transporter 3.

Bioactivity

No ChEMBL bioactivity rows at pChembl ≥ 5 (expected for biologics / antibodies).

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

5 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
bacterial infectious disease	4	MONDO:0005113	EFO:0000771
bacterial infectious disease with sepsis	3	MONDO:0005229	EFO:0003033
osteomyelitis	3	MONDO:0005246	EFO:0003102
gram-positive bacterial infections	3	MONDO:0021679	MONDO:0021679

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 8.

Phase distribution

Phase	Trials
PHASE3	3
PHASE2	3
PHASE4	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT01166932	PHASE4	COMPLETED	Comparison Between Amoxycillin/Clavulanic Acid and Oxacillin/Ceftriaxone for Community Acquired-pneumonia
NCT05156437	PHASE4	TERMINATED	Postoperative Antibiotic Management Duration Following Surgery for Intravenous Drug Abuse (IVDA) Endocarditis (OPTIMAL)
NCT00037050	PHASE3	COMPLETED	Antibiotic Treatment for Infections of Short Term In-dwelling Vascular Catheters Due to Gram Positive Bacteria
NCT02701608	PHASE3	COMPLETED	Oral Switch During Treatment of Left-sided Endocarditis Due to Multi-susceptible Staphylococcus
NCT02814916	PHASE3	COMPLETED	Dalbavancin for the Treatment of Acute Bacterial Skin and Skin Structure Infections in Children, Known or Suspected to be Caused by Susceptible Gram-positive Organisms, Including MRSA
NCT00062647	PHASE2	COMPLETED	Telavancin for Treatment of Uncomplicated Staphylococcus Aureus Bacteremia
NCT00428844	PHASE2	COMPLETED	Study of Daptomycin in Subjects Undergoing Surgery for Osteomyelitis Associated With an Infected Prosthetic Caused by Staphylococci
NCT04775953	PHASE2	COMPLETED	DOTS: Dalbavancin as an Option for Treatment of Staphylococcus Aureus Bacteremia

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).