Nafcillin

Summary

Nafcillin (CHEMBL1443) is an approved small-molecule antibacterial drug (ATC J01CF06); indicated across 5 conditions including bacterial infectious disease and osteomyelitis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J01CF06
• Indications: 5 conditions
• Clinical trials: 4
• Chemistry: 414.5 Da · C21H22N2O5S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1443
Name	Nafcillin
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	8982
ChEBI	CHEBI:7447
ATC	J01CF06
Molecular formula	C21H22N2O5S
Molecular weight	414.5
InChIKey	GPXLMGHLHQJAGZ-JTDSTZFVSA-N

SMILES: CCOC1=C(C2=CC=CC=C2C=C1)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)-6-[(2-ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

ChEBI definition: A penicillin in which the substituent at position 6 of the penam ring is a (2-ethoxy-1-naphthoyl)amino group.

Pharmacological roles (ChEBI): antibacterial drug.

Also known as: Nafcilina, Nafcillin, Nafcilline, nafcillin, NAFCILLINE, NAFCILLIN

Parent form; salt/anhydrous children: CHEMBL1568276

Patent coverage: 6,090 distinct patent families (24,035 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 23,876 (99%) of the total. 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: 2 (assay-derived). Sample: Organic anion transporter 3, Bile salt export pump.

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

1 approved indication. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
bacterial infectious disease	4	MONDO:0005113	EFO:0000771

3 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
osteomyelitis	3	MONDO:0005246	EFO:0003102
gram-positive bacterial infections	2	MONDO:0021679	MONDO:0021679
bacterial infectious disease with sepsis	2	MONDO:0005229	EFO:0003033

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

Clinical trials

Total trials: 4.

Phase distribution

Phase	Trials
PHASE2	3
PHASE3	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT02344511	PHASE3	WITHDRAWN	Dalbavancin vs Comparator in Pediatric Subjects With Acute Hematogenous Osteomyelitis
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).