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.

penicillin CHEBI:17334
penicillin allergen CHEBI:88187
penicillin beta-lactam 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

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

antimicrobial agent CHEBI:33281
antibacterial drug 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 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

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
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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