Structure via PubChem · Public domain (PubChem)
nafcillin
Sign in to saveAlso known as (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, naphcillin, (2-ethoxy-1-naphthalenyl)penicillin, 6-(2-ethoxy-1-naphthamido)penicillanic acid, (2-ethoxy-1-naphthyl)penicillin
Nafcillin sodium is a narrow-spectrum, second-generation beta-lactam antibiotic of the penicillin class. As a beta-lactamase-resistant penicillin, it is used to treat infections caused by Gram-positive bacteria, in particular, species of staphylococci that are resistant to other penicillins.
Chemical data
- Formula
- C21H22N2O5S
- Molecular weight
- 414.5 g/mol
- 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
- 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
- InChIKey
- GPXLMGHLHQJAGZ-JTDSTZFVSA-N
- XLogP
- 2.9
- Polar surface area
- 121 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1965
- Admin. routes
- oral, parenteral
- Indications
- infection, osteomyelitis, bacterial disease, gram-positive bacterial infections
via ChEMBL · EBI
Research
1,061 papers- Nafcillin-Associated Hypokalemia.American journal of therapeutics · 2018
- Nafcillin-induced agranulocytosis.JAMA · 1975
- Nafcillin-associated hypokalemia.JAMA · 1979
- Pharmacokinetics of nafcillin.The Journal of pediatrics · 1979
- Nafcillin Augmentation of Daptomycin and Cathelicidin LL-37 Killing of Methicillin-resistant Staphylococcus epidermidis: Foundations of Successful Therapy of Endocarditis.International journal of antimicrobial agents · 2023
via PubMed
Wikidata facts
- Subclass of
- penicillin
- Mass
- 414.124943
- Has use
- medication
Show 7 more facts
- defined daily dose
- 3
- medical condition treated
- bacterial meningitis
- chemical formula
- C₂₁H₂₂N₂O₅S
- canonical SMILES
- CCOC1=C(C2=CC=CC=C2C=C1)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
- isomeric 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
- World Health Organisation international non-proprietary name
- nafcillin
- subject has role
- bactericide
via Wikidata · CC0
~3 min read
Encyclopedic overview
5 sectionsContents
- Indications
- Side-effects
- Interactions
- Mechanism of Action
- References
Nafcillin sodium is a narrow-spectrum, second-generation beta-lactam antibiotic of the penicillin class. As a beta-lactamase-resistant penicillin, it is used to treat infections caused by Gram-positive bacteria, in particular, species of staphylococci that are resistant to other penicillins.
Nafcillin is considered therapeutically equivalent to oxacillin, although one retrospective study found greater rates of hypokalemia and acute kidney injury in patients taking nafcillin compared to patients taking oxacillin.
Excerpted from Wikipedia’s “nafcillin” article, available under the CC BY-SA 4.0 licence.