nafcillin

CHEBI:7447 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A penicillin in which the substituent at position 6 of the penam ring is a (2-ethoxy-1-naphthoyl)amino group. — 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:88187 CHEBI:88187
ARO:3000008 ARO:3000008

Chemical structure

Computed structure properties
Molecular formula	C21H22N2O5S
Charge	0
Average mass	414.483 Da
Monoisotopic mass	414.12494 Da
Source	ChEBI
InChIKey	GPXLMGHLHQJAGZ-JTDSTZFVSA-N

SMILES

[H][C@]12SC(C)(C)[C@H](C(=O)O)N1C(=O)[C@H]2NC(=O)c1c(OCC)ccc2ccccc12

InChI

InChI=1S/C21H22N2O5S/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27)/t15-,16+,19-/m1/s1

Also called

nafcilina (INN)— chebi
nafcilline (INN)— chebi
nafcillinum (INN)— chebi
6β-(2-ethoxynaphthalene-1-carboxamido)-2,2-dimethylpenam-3α-carboxylic acid (EXACT_SYNONYM)— chebi
(2-ethoxy-1-naphthalenyl)penicillin (EXACT_SYNONYM)— chebi
(2-ethoxy-1-naphthyl)penicillin (EXACT_SYNONYM)— chebi
(2S,5R,6R)-6-[(2-ethoxy-1-naphthoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
(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 (EXACT_SYNONYM)— chebi
(2S,5R,6R)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
6-(2-ethoxy-1-naphthamido)penicillanic acid (EXACT_SYNONYM)— chebi
naphcillin (EXACT_SYNONYM)— chebi
Nafcil (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3004018
cas:147-52-4
drugbank:DB00607
drugcentral:1869
kegg.compound:C07250
kegg.drug:D08242
lincs.smallmolecule:LSM-2402
patent:GB880400
patent:US3157639
patent:US3506645
reaxys:5405727
wikipedia.en:Nafcillin
chembl:CHEMBL1443
pubchem.compound:8982

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:3004018`	nafcillin	`antibioticmech:aro-5a153f848b`	2026-08-30
CHEBI	`CHEBI:7447`	nafcillin	`antibioticmech:chebi-d2be08e716`	2026-08-30

Resistance mechanisms

2 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

ANTIBIOTIC_TARGET_ALTERATION 2

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Staphylococcus aureus PBP4 mutant conferring resistance to nafcillin	ARO:3009661	not organism-specific	—	ARO:3009661 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3004018 (nafcillin); database assertion, not a primary citation.)
Staphylococcus aureus PBP4 mutant conferring resistance to nafcillin and cefoxitin	ARO:3009660	not organism-specific	—	ARO:3009660 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3004018 (nafcillin); 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

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.