Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H19N3O5S |
| Molecular Weight | 401.436 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=C(C(=O)N[C@H]2[C@H]3SC(C)(C)[C@@H](N3C2=O)C(O)=O)C(=NO1)C4=CC=CC=C4
InChI
InChIKey=UWYHMGVUTGAWSP-JKIFEVAISA-N
InChI=1S/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1
| Molecular Formula | C19H19N3O5S |
| Molecular Weight | 401.436 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050640s017lbl.pdf
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050640s017lbl.pdf
Oxacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Oxacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Oxacillin results from the inhibition of cell wall synthesis and is mediated through Oxacillin binding to penicillin binding proteins (PBPs). Oxacillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Oxacillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that Oxacillin interferes with an autolysin inhibitor. Oxacillin is used in the treatment of resistant staphylococci infections. Oxacillin sodium was marketed under the trade name Bactocill.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL5658 |
100.0 µM [IC50] | ||
Target ID: CHEMBL2362973 |
0.42 nM [IC50] | ||
Target ID: CHEMBL352 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Oxacillin Approved UseOxacillin is indicated in the treatment of infections caused by penicillinase producing
staphylococci which have demonstrated susceptibility to the drug. Launch Date1971 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
43 μg/mL |
500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
OXACILLIN serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
125.9 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6619039 |
30 mg/kg bw single, intravenous dose: 30 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
OXACILLIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.42 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6619039 |
30 mg/kg bw single, intravenous dose: 30 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
OXACILLIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
25 min |
500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
OXACILLIN serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
6% |
500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
OXACILLIN serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
175 mg/kg/day 1 times / day multiple, intravenous Studied dose Dose: 175 mg/kg/day, 1 times / day Route: intravenous Route: multiple Dose: 175 mg/kg/day, 1 times / day Sources: |
unhealthy, mean age 4.96 years Health Status: unhealthy Age Group: mean age 4.96 years Sex: M+F Sources: |
Other AEs: Neutropenia... |
175 mg/kg/day 1 times / day multiple, intravenous Studied dose Dose: 175 mg/kg/day, 1 times / day Route: intravenous Route: multiple Dose: 175 mg/kg/day, 1 times / day Sources: |
unhealthy, mean age 4.96 years Health Status: unhealthy Age Group: mean age 4.96 years Sex: M+F Sources: |
Other AEs: Elevated liver enzymes... |
2 g 4 times / day multiple, intravenous Studied dose Dose: 2 g, 4 times / day Route: intravenous Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy, mean age 49.2 years Health Status: unhealthy Age Group: mean age 49.2 years Sex: M+F Sources: |
Other AEs: Nausea, Headache... Other AEs: Nausea (grade 1-2, 5.7%) Sources: Headache (grade 1-2, 3.8%) Vomiting (grade 1-2, 1.9%) Hypertension (grade 1-2, 0.2%) Diarrhea (grade 1-2, 2.9%) Pain localized (grade 1-2, 0.7%) Dyspepsia (grade 1-2, 1.7%) Insomnia (grade 1-2, 2.1%) Dizziness (grade 1-2, 0.7%) Abdominal pain (grade 1-2, 1.2%) Constipation (grade 1-2, 3.1%) Pruritus (grade 1-2, 2.1%) Fever (grade 1-2, 2.6%) |
12 g/day 1 times / day multiple, intravenous Studied dose Dose: 12 g/day, 1 times / day Route: intravenous Route: multiple Dose: 12 g/day, 1 times / day Sources: |
unhealthy, mean age 51 years Health Status: unhealthy Age Group: mean age 51 years Sex: M+F Sources: |
Disc. AE: Transaminases increased, Leukopenia... Other AEs: Rash, Transaminases increased... AEs leading to discontinuation/dose reduction: Transaminases increased (11.8%) Other AEs:Leukopenia (3%) Blood sodium decreased (3%) Rash (3%) Rash (3%) Sources: Transaminases increased (18%) Creatinine serum increased (3%) Leukopenia (3%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Neutropenia | 12.5% | 175 mg/kg/day 1 times / day multiple, intravenous Studied dose Dose: 175 mg/kg/day, 1 times / day Route: intravenous Route: multiple Dose: 175 mg/kg/day, 1 times / day Sources: |
unhealthy, mean age 4.96 years Health Status: unhealthy Age Group: mean age 4.96 years Sex: M+F Sources: |
| Elevated liver enzymes | 12.5% | 175 mg/kg/day 1 times / day multiple, intravenous Studied dose Dose: 175 mg/kg/day, 1 times / day Route: intravenous Route: multiple Dose: 175 mg/kg/day, 1 times / day Sources: |
unhealthy, mean age 4.96 years Health Status: unhealthy Age Group: mean age 4.96 years Sex: M+F Sources: |
| Hypertension | grade 1-2, 0.2% | 2 g 4 times / day multiple, intravenous Studied dose Dose: 2 g, 4 times / day Route: intravenous Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy, mean age 49.2 years Health Status: unhealthy Age Group: mean age 49.2 years Sex: M+F Sources: |
| Dizziness | grade 1-2, 0.7% | 2 g 4 times / day multiple, intravenous Studied dose Dose: 2 g, 4 times / day Route: intravenous Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy, mean age 49.2 years Health Status: unhealthy Age Group: mean age 49.2 years Sex: M+F Sources: |
| Pain localized | grade 1-2, 0.7% | 2 g 4 times / day multiple, intravenous Studied dose Dose: 2 g, 4 times / day Route: intravenous Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy, mean age 49.2 years Health Status: unhealthy Age Group: mean age 49.2 years Sex: M+F Sources: |
| Abdominal pain | grade 1-2, 1.2% | 2 g 4 times / day multiple, intravenous Studied dose Dose: 2 g, 4 times / day Route: intravenous Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy, mean age 49.2 years Health Status: unhealthy Age Group: mean age 49.2 years Sex: M+F Sources: |
| Dyspepsia | grade 1-2, 1.7% | 2 g 4 times / day multiple, intravenous Studied dose Dose: 2 g, 4 times / day Route: intravenous Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy, mean age 49.2 years Health Status: unhealthy Age Group: mean age 49.2 years Sex: M+F Sources: |
| Vomiting | grade 1-2, 1.9% | 2 g 4 times / day multiple, intravenous Studied dose Dose: 2 g, 4 times / day Route: intravenous Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy, mean age 49.2 years Health Status: unhealthy Age Group: mean age 49.2 years Sex: M+F Sources: |
| Insomnia | grade 1-2, 2.1% | 2 g 4 times / day multiple, intravenous Studied dose Dose: 2 g, 4 times / day Route: intravenous Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy, mean age 49.2 years Health Status: unhealthy Age Group: mean age 49.2 years Sex: M+F Sources: |
| Pruritus | grade 1-2, 2.1% | 2 g 4 times / day multiple, intravenous Studied dose Dose: 2 g, 4 times / day Route: intravenous Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy, mean age 49.2 years Health Status: unhealthy Age Group: mean age 49.2 years Sex: M+F Sources: |
| Fever | grade 1-2, 2.6% | 2 g 4 times / day multiple, intravenous Studied dose Dose: 2 g, 4 times / day Route: intravenous Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy, mean age 49.2 years Health Status: unhealthy Age Group: mean age 49.2 years Sex: M+F Sources: |
| Diarrhea | grade 1-2, 2.9% | 2 g 4 times / day multiple, intravenous Studied dose Dose: 2 g, 4 times / day Route: intravenous Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy, mean age 49.2 years Health Status: unhealthy Age Group: mean age 49.2 years Sex: M+F Sources: |
| Constipation | grade 1-2, 3.1% | 2 g 4 times / day multiple, intravenous Studied dose Dose: 2 g, 4 times / day Route: intravenous Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy, mean age 49.2 years Health Status: unhealthy Age Group: mean age 49.2 years Sex: M+F Sources: |
| Headache | grade 1-2, 3.8% | 2 g 4 times / day multiple, intravenous Studied dose Dose: 2 g, 4 times / day Route: intravenous Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy, mean age 49.2 years Health Status: unhealthy Age Group: mean age 49.2 years Sex: M+F Sources: |
| Nausea | grade 1-2, 5.7% | 2 g 4 times / day multiple, intravenous Studied dose Dose: 2 g, 4 times / day Route: intravenous Route: multiple Dose: 2 g, 4 times / day Sources: |
unhealthy, mean age 49.2 years Health Status: unhealthy Age Group: mean age 49.2 years Sex: M+F Sources: |
| Transaminases increased | 11.8% Disc. AE |
12 g/day 1 times / day multiple, intravenous Studied dose Dose: 12 g/day, 1 times / day Route: intravenous Route: multiple Dose: 12 g/day, 1 times / day Sources: |
unhealthy, mean age 51 years Health Status: unhealthy Age Group: mean age 51 years Sex: M+F Sources: |
| Transaminases increased | 18% | 12 g/day 1 times / day multiple, intravenous Studied dose Dose: 12 g/day, 1 times / day Route: intravenous Route: multiple Dose: 12 g/day, 1 times / day Sources: |
unhealthy, mean age 51 years Health Status: unhealthy Age Group: mean age 51 years Sex: M+F Sources: |
| Creatinine serum increased | 3% | 12 g/day 1 times / day multiple, intravenous Studied dose Dose: 12 g/day, 1 times / day Route: intravenous Route: multiple Dose: 12 g/day, 1 times / day Sources: |
unhealthy, mean age 51 years Health Status: unhealthy Age Group: mean age 51 years Sex: M+F Sources: |
| Leukopenia | 3% | 12 g/day 1 times / day multiple, intravenous Studied dose Dose: 12 g/day, 1 times / day Route: intravenous Route: multiple Dose: 12 g/day, 1 times / day Sources: |
unhealthy, mean age 51 years Health Status: unhealthy Age Group: mean age 51 years Sex: M+F Sources: |
| Rash | 3% | 12 g/day 1 times / day multiple, intravenous Studied dose Dose: 12 g/day, 1 times / day Route: intravenous Route: multiple Dose: 12 g/day, 1 times / day Sources: |
unhealthy, mean age 51 years Health Status: unhealthy Age Group: mean age 51 years Sex: M+F Sources: |
| Blood sodium decreased | 3% Disc. AE |
12 g/day 1 times / day multiple, intravenous Studied dose Dose: 12 g/day, 1 times / day Route: intravenous Route: multiple Dose: 12 g/day, 1 times / day Sources: |
unhealthy, mean age 51 years Health Status: unhealthy Age Group: mean age 51 years Sex: M+F Sources: |
| Leukopenia | 3% Disc. AE |
12 g/day 1 times / day multiple, intravenous Studied dose Dose: 12 g/day, 1 times / day Route: intravenous Route: multiple Dose: 12 g/day, 1 times / day Sources: |
unhealthy, mean age 51 years Health Status: unhealthy Age Group: mean age 51 years Sex: M+F Sources: |
| Rash | 3% Disc. AE |
12 g/day 1 times / day multiple, intravenous Studied dose Dose: 12 g/day, 1 times / day Route: intravenous Route: multiple Dose: 12 g/day, 1 times / day Sources: |
unhealthy, mean age 51 years Health Status: unhealthy Age Group: mean age 51 years Sex: M+F Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Susceptibility of bacterial isolates to cefepime in comparison to other broad spectrum antimicrobial agents at a tertiary care center in Lebanon. | 2002-03-26 |
|
| Simultaneous detection of the mecA and ileS-2 genes in coagulase-negative staphylococci isolated from Brazilian hospitals by multiplex PCR. | 2002-03 |
|
| A European study on the relationship between antimicrobial use and antimicrobial resistance. | 2002-03 |
|
| In vitro antibacterial activities of DQ-113, a potent quinolone, against clinical isolates. | 2002-03 |
|
| Comparative antimicrobial spectrum and activity of BMS284756 (T-3811; a desfluoroquinolone) tested against an international collection of staphylococci and enterococci, including in vitro test development and intermethod comparisons. | 2002-02 |
|
| Emergence of mupirocin-resistant Staphylococcus aureus in chronic peritoneal dialysis patients using mupirocin prophylaxis to prevent exit-site infection. | 2002-01-11 |
|
| Higher occurrence of hepatotoxicity and rash in patients treated with oxacillin, compared with those treated with nafcillin and other commonly used antimicrobials. | 2002-01-01 |
|
| A comparison of PCR detection of mecA with two standard methods of oxacillin disk susceptibility testing for coagulase-negative staphylococci. | 2002-01 |
|
| Natural antibiotic susceptibility and biochemical profiles of Yersinia enterocolitica-like strains: Y. bercovieri, Y. mollaretii, Y. aldovae and 'Y. ruckeri'. | 2002-01 |
|
| Prediction of mecA-positive coagulase-negative staphylococci: assessment of different phenotypic methods, breakpoints, culture media and culture conditions. | 2002-01 |
|
| An outbreak of community-acquired foodborne illness caused by methicillin-resistant Staphylococcus aureus. | 2002-01 |
|
| Antimicrobial drug resistance in pathogens causing nosocomial infections at a university hospital in Taiwan, 1981-1999. | 2002-01 |
|
| Surveillance for antimicrobial resistance in Croatia. | 2002-01 |
|
| Vancomycin-intermediate Staphylococcus aureus in a home health-care patient. | 2001-12-19 |
|
| Antibiotic resistance in coagulase-negative staphylococci isolated from Cope's gray treefrogs (Hyla chrysoscelis). | 2001-12-18 |
|
| Therapeutic options for Gram-positive infections. | 2001-12 |
|
| Economic evaluation of linezolid, flucloxacillin and vancomycin in the empirical treatment of cellulitis in UK hospitals: a decision analytical model. | 2001-12 |
|
| Evaluation of a reverse hybridization blot test for detection of oxacillin-resistant Staphylococcus aureus. | 2001-12 |
|
| Natural antibiotic susceptibility of strains of the Enterobacter cloacae complex. | 2001-12 |
|
| Susceptibility of Arcobacter butzleri isolates to 23 antimicrobial agents. | 2001-12 |
|
| Crystallization and preliminary X-ray study of OXA-1, a class D beta-lactamase. | 2001-12 |
|
| Changing pattern of antibiotic resistance in methicillin-resistant Staphylococcus aureus from German hospitals. | 2001-11 |
|
| Evaluation of the MRSA-Screen Test in detecting oxacillin resistance in community and hospital isolates of Staphylococcus aureus. | 2001-11 |
|
| Microbiology of normal external auditory canal. | 2001-11 |
|
| A sequence variant of Staphylococcus hominis with a high prevalence of oxacillin and fluoroquinolone resistance. | 2001-11 |
|
| Direct detection of mecA, nuc and 16S rRNA genes in BacT/Alert blood culture bottles. | 2001-11 |
|
| Molecular characterization of a chromosomal locus in Staphylococcus aureus that contributes to oxidative defence and is highly induced by the cell-wall-active antibiotic oxacillin. | 2001-11 |
|
| Antimicrobial susceptibility of staphylococci isolated from the faeces of wild turkeys (Meleagris gallopavo). | 2001-11 |
|
| Development of vancomycin and lysostaphin resistance in a methicillin-resistant Staphylococcus aureus isolate. | 2001-11 |
|
| [Decreasing susceptibility to vancomycin in isogenic Staphylococcus aureus strains isolated from a single patient]. | 2001-10-13 |
|
| In vitro susceptibility of gram-positive cocci isolated from skin and respiratory tract to azithromycin and twelve other antimicrobial agents. | 2001-10 |
|
| Application of the IDSA guidelines for the use of antimicrobial agents in neutropenic patients: impact on reducing the use of glycopeptides. | 2001-10 |
|
| Antibacterial action of several tannins against Staphylococcus aureus. | 2001-10 |
|
| Glycopeptide susceptibility profiles of nosocomial multiresistant Staphylococcus haemolyticus isolates. | 2001-09 |
|
| [Multicenter study in southern South America of the in vitro activity of telithromycin in strains with defined resistance phenotypes isolated from community-acquired respiratory infections]. | 2001-09 |
|
| Frequency of isolation and antimicrobial resistance of gram-negative and gram-positive bacteria from patients in intensive care units of 25 European university hospitals participating in the European arm of the SENTRY Antimicrobial Surveillance Program 1997-1998. | 2001-09 |
|
| The DUEL study: a multi-center in vitro evaluation of linezolid compared with other antibiotics in the Netherlands. | 2001-09 |
|
| [Evaluation of the E-test and the ATB-PNEUMo battery for determining the beta-lactam MIC for Streptococcus pneumoniae in daily practice]. | 2001-09 |
|
| Staphylococcus lugdunensis: an emerging cause of ventriculoperitoneal shunt infections. | 2001-09 |
|
| Determination of benzylpenicillin, oxacillin, cloxacillin, and dicloxacillin in cows' milk by ion-pair high-performance liquid chromatography after precolumn derivatization. | 2001-09 |
|
| Pathogen frequency and resistance patterns in Brazilian hospitals: summary of results from three years of the SENTRY Antimicrobial Surveillance Program. | 2001-08 |
|
| Oxacillin susceptibility testing of Staphylococcus saprophyticus using disk diffusion, agar dilution, broth microdilution, and the Vitek GPS-105 card. | 2001-08 |
|
| RU-79115 (Aventis Pharma). | 2001-06 |
|
| Multicenter surveillance of antimicrobial resistance of major bacterial pathogens in intensive care units in 2000 in Taiwan. | 2001 |
|
| A microdilution plating method for population analysis of antibiotic-resistant staphylococci. | 2001 |
|
| Low prevalence of methicillin-resistant strains among Staphylococcus aureus colonizing young and healthy members of the community in Portugal. | 2001 |
|
| Incidence of Chlamydia trachomatis and other potential pathogens in neonatal conjunctivitis. | 2001 |
|
| Antibacterials for the prophylaxis and treatment of bacterial endocarditis in children. | 2001 |
|
| [Evaluation of MRSA identification with latex agglutination kit for the detection of penicillin-binding protein 2]. | 2001 |
|
| [Monitoring of uropathogens and their susceptibility to antibiotics]. | 2001 |
Sample Use Guides
Oxacillin Injection, USP supplied as a premixed frozen solution is to be administered as a
continuous or intermittent intravenous infusion. The usual dose recommendation is as
follows:
Adults
250-500 mg I.V. every 4-6 hours (mild to moderate infections)
1 gram I.V. every 4-6 hours (severe infections)
Route of Administration:
Intravenous
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 09:59:47 GMT 2025
by
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on
Wed Apr 02 09:59:47 GMT 2025
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| Record UNII |
UH95VD7V76
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| Record Status |
Validated (UNII)
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| Record Version |
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WHO-VATC |
QJ01CF04
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NDF-RT |
N0000011281
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NDF-RT |
N0000011281
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WHO-VATC |
QG51AG04
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N0000175497
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J01CF04
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N0000011281
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N0000011281
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N0000011281
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LIVERTOX |
NBK548078
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NCI_THESAURUS |
C1500
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NDF-RT |
N0000011281
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NDF-RT |
N0000011281
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N0000011281
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WHO-VATC |
QJ51CF04
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NDF-RT |
N0000011281
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m8273
Created by
admin on Wed Apr 02 09:59:47 GMT 2025 , Edited by admin on Wed Apr 02 09:59:47 GMT 2025
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PRIMARY | Merck Index | ||
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Oxacillin
Created by
admin on Wed Apr 02 09:59:47 GMT 2025 , Edited by admin on Wed Apr 02 09:59:47 GMT 2025
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PRIMARY |
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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ENZYME->SUBSTRATE |
Leads to resistance to the antibiotic.
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BINDER->LIGAND |
BINDING
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Biological Half-life | PHARMACOKINETIC |
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