Substance
ID:490
Names and Identifiers
IUPAC Traditional name
(2S,5R,6R)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Brand Name
NaphcillinNafcilin-1Nafcillin sodium for injectionNallpenUnipenNallpen In Plastic Container
Synonyms
Nafcillin sodium saltNafcillinum [INN-Latin]Nafcillin SodiumNafcillinNafcilina [INN-Spanish]Nafcilline [INN-French]
IUPAC name
(2S,5R,6R)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Properties
Physical Property
Solubility
Soluble
Hydrophobicity(logP)
3.3
Molecule Details
Drug Groups
approved
Description
A semi-synthetic antibiotic related to penicillin. [PubChem]
Indication
For the treatment of infections caused by penicillinase-producing staphylococci which have demonstrated susceptibility to the drugs.
Pharmacology
Nafcillin is a semisynthetic antibiotic substance derived from 6-amino-penicillanic acid. The drugs in this class are highly resistant to inactivation by staphylococcal penicillinase and are active against penicillinase-producing and non penicillinase-producing strains of Staphylococcus aureus. The penicillinase- resistant penicillins are active in vitro against a variety of other bacteria.
Toxicity
Serious toxicity is unlikely following large doses of nafcillin. Acute ingestion of large doses of nafcillin may cause nausea, vomiting, diarrhea and abdominal pain. Acute oliguric renal failure and hematuria may occur following large doses.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation
Hepatic metabolism accounts for less than 30% of the biotransformation of most penicillins.
Half Life
The serum half-life of nafcillin administered by the intravenous route ranged from 33 to 61 minutes as measured in three separate studies.
Protein Binding
89.9 ±1.5%
Elimination
Nafcillin is primarily eliminated by nonrenal routes, namely hepatic inactivation and excretion in the bile.
External Links
Molecular Spectra
No Data Available
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References
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