OXACILLIN

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

Structure Search

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C3=C(C)ON=C3C4=CC=CC=C4)C(O)=O

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

HIDE SMILES / InChI

Description
Sources: https://www.drugbank.ca/drugs/DB00713
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Prostaglandin E synthase 9 Target ID: CHEMBL5658 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19017494	Inhibitor 8297	100.0 µM [IC50]
Penicillin-binding protein 31 Target ID: CHEMBL2362973 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421	Inhibitor 8297	0.42 nM [IC50]
Staphylococcus aureus 67 Target ID: CHEMBL352 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050640s017lbl.pdf	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Infections caused by penicillinase-producing staphylococci 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050640s017lbl.pdf	Curative		Approved 8429	Oxacillin Approved Use Oxacillin is indicated in the treatment of infections caused by penicillinase producing staphylococci which have demonstrated susceptibility to the drug. Launch Date 3.9830401E10

C_max

Value	Dose	Co-administered	Analyte	Population
43 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050640s010lbl.pdf	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

T_1/2

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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050640s010lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
6% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050640s010lbl.pdf	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: https://pubmed.ncbi.nlm.nih.gov/7172968/	unhealthy, mean age 4.96 years n = 8 Health Status: unhealthy Condition: sternal osteomyelitis Age Group: mean age 4.96 years Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/7172968/	Other AEs: Elevated liver enzymes... Other AEs: Elevated liver enzymes (12.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/7172968/
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: https://pubmed.ncbi.nlm.nih.gov/7172968/	unhealthy, mean age 4.96 years n = 8 Health Status: unhealthy Condition: submandibular adenitis Age Group: mean age 4.96 years Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/7172968/	Other AEs: Neutropenia... Other AEs: Neutropenia (12.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/7172968/
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 Co-administed with:: dicloxacillin(500 mg orally; 4 per day) Sources: https://pubmed.ncbi.nlm.nih.gov/11083648/	unhealthy, mean age 49.2 years n = 419 Health Status: unhealthy Condition: complicated skin and soft tissue infections Age Group: mean age 49.2 years Sex: M+F Population Size: 419 Sources: https://pubmed.ncbi.nlm.nih.gov/11083648/	Other AEs: Nausea, Headache... Other AEs: Nausea (grade 1-2, 5.7%) 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%) Sources: https://pubmed.ncbi.nlm.nih.gov/11083648/
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: https://pubmed.ncbi.nlm.nih.gov/24936596/	unhealthy, mean age 51 years n = 34 Health Status: unhealthy Condition: complicated bacteremia Age Group: mean age 51 years Sex: M+F Population Size: 34 Sources: https://pubmed.ncbi.nlm.nih.gov/24936596/	Disc. AE: Transaminases increased, Leukopenia... Other AEs: Rash, Transaminases increased... AEs leading to discontinuation/dose reduction: Transaminases increased (11.8%) Leukopenia (3%) Blood sodium decreased (3%) Rash (3%) Other AEs: Rash (3%) Transaminases increased (18%) Creatinine serum increased (3%) Leukopenia (3%) Sources: https://pubmed.ncbi.nlm.nih.gov/24936596/

AEs

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:7809	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7809
ZINC	ZINC000003875439	http://zinc15.docking.org/substances/ZINC000003875439

PubMed

Title	Date	PubMed
Incidence of Chlamydia trachomatis and other potential pathogens in neonatal conjunctivitis.	2001	11724670
Antibacterials for the prophylaxis and treatment of bacterial endocarditis in children.	2001	11706922
[Evaluation of MRSA identification with latex agglutination kit for the detection of penicillin-binding protein 2].	2001	11682001
Rapid detection of the methicillin-resistance gene, mecA, in coagulase-negative Staphylococci.	2001	11515759
Pathogen frequency and resistance patterns in Brazilian hospitals: summary of results from three years of the SENTRY Antimicrobial Surveillance Program.	2001 Aug	11712965
[Coagulase negative staphylococci isolated on blood cultures].	2001 Aug	11550419
Optimizing antibiotic therapy in the intensive care unit setting.	2001 Aug	11511331
Therapeutic options for Gram-positive infections.	2001 Dec	11926437
Economic evaluation of linezolid, flucloxacillin and vancomycin in the empirical treatment of cellulitis in UK hospitals: a decision analytical model.	2001 Dec	11926436
Evaluation of a reverse hybridization blot test for detection of oxacillin-resistant Staphylococcus aureus.	2001 Dec	11837648
Natural antibiotic susceptibility of strains of the Enterobacter cloacae complex.	2001 Dec	11738341
Susceptibility of Arcobacter butzleri isolates to 23 antimicrobial agents.	2001 Dec	11737626
Crystallization and preliminary X-ray study of OXA-1, a class D beta-lactamase.	2001 Dec	11717515
Antibiotic resistance in coagulase-negative staphylococci isolated from Cope's gray treefrogs (Hyla chrysoscelis).	2001 Dec 18	11750814
A microdilution plating method for population analysis of antibiotic-resistant staphylococci.	2001 Fall	11759091
Low prevalence of methicillin-resistant strains among Staphylococcus aureus colonizing young and healthy members of the community in Portugal.	2001 Fall	11759085
Susceptibility of bacterial isolates to cefepime in comparison to other broad spectrum antimicrobial agents at a tertiary care center in Lebanon.	2001 Jan-Feb	11910959
Changing pattern of antibiotic resistance in methicillin-resistant Staphylococcus aureus from German hospitals.	2001 Nov	11842987
Evaluation of the MRSA-Screen Test in detecting oxacillin resistance in community and hospital isolates of Staphylococcus aureus.	2001 Nov	11827417
Microbiology of normal external auditory canal.	2001 Nov	11801996
A sequence variant of Staphylococcus hominis with a high prevalence of oxacillin and fluoroquinolone resistance.	2001 Nov	11763241
Direct detection of mecA, nuc and 16S rRNA genes in BacT/Alert blood culture bottles.	2001 Nov	11750172
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 Nov	11700354
Antimicrobial susceptibility of staphylococci isolated from the faeces of wild turkeys (Meleagris gallopavo).	2001 Nov	11696101
Development of vancomycin and lysostaphin resistance in a methicillin-resistant Staphylococcus aureus isolate.	2001 Nov	11679550
Emergence of mupirocin-resistant Staphylococcus aureus in chronic peritoneal dialysis patients using mupirocin prophylaxis to prevent exit-site infection.	2001 Nov-Dec	11783763
Vancomycin-intermediate Staphylococcus aureus in a home health-care patient.	2001 Nov-Dec	11747733
In vitro susceptibility of gram-positive cocci isolated from skin and respiratory tract to azithromycin and twelve other antimicrobial agents.	2001 Oct	11779453
Application of the IDSA guidelines for the use of antimicrobial agents in neutropenic patients: impact on reducing the use of glycopeptides.	2001 Oct	11776354
Glycopeptide susceptibility profiles of nosocomial multiresistant Staphylococcus haemolyticus isolates.	2001 Sep	11810575
[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 Sep	11753448
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 Sep	11714042
The DUEL study: a multi-center in vitro evaluation of linezolid compared with other antibiotics in the Netherlands.	2001 Sep	11678931
[Evaluation of the E-test and the ATB-PNEUMo battery for determining the beta-lactam MIC for Streptococcus pneumoniae in daily practice].	2001 Sep	11642017
Determination of benzylpenicillin, oxacillin, cloxacillin, and dicloxacillin in cows' milk by ion-pair high-performance liquid chromatography after precolumn derivatization.	2001 Sep	11605761
Selection of high-level oxacillin resistance in heteroresistant Staphylococcus aureus by fluoroquinolone exposure.	2001 Sep	11533002
Epigallocatechin gallate synergy with ampicillin/sulbactam against 28 clinical isolates of methicillin-resistant Staphylococcus aureus.	2001 Sep	11533000
Cloning and sequencing of the gene, fmtC, which affects oxacillin resistance in methicillin-resistant Staphylococcus aureus.	2001 Sep 11	11557139
Multicenter surveillance of antimicrobial resistance of major bacterial pathogens in intensive care units in 2000 in Taiwan.	2001 Winter	11822777
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 Feb	11892893
A comparison of PCR detection of mecA with two standard methods of oxacillin disk susceptibility testing for coagulase-negative staphylococci.	2002 Jan	11800477
Natural antibiotic susceptibility and biochemical profiles of Yersinia enterocolitica-like strains: Y. bercovieri, Y. mollaretii, Y. aldovae and 'Y. ruckeri'.	2002 Jan	11800473
Prediction of mecA-positive coagulase-negative staphylococci: assessment of different phenotypic methods, breakpoints, culture media and culture conditions.	2002 Jan	11751789
An outbreak of community-acquired foodborne illness caused by methicillin-resistant Staphylococcus aureus.	2002 Jan	11749755
Antimicrobial drug resistance in pathogens causing nosocomial infections at a university hospital in Taiwan, 1981-1999.	2002 Jan	11749750
Surveillance for antimicrobial resistance in Croatia.	2002 Jan	11749742
Higher occurrence of hepatotoxicity and rash in patients treated with oxacillin, compared with those treated with nafcillin and other commonly used antimicrobials.	2002 Jan 1	11731945
Simultaneous detection of the mecA and ileS-2 genes in coagulase-negative staphylococci isolated from Brazilian hospitals by multiplex PCR.	2002 Mar	11929693
A European study on the relationship between antimicrobial use and antimicrobial resistance.	2002 Mar	11927025
In vitro antibacterial activities of DQ-113, a potent quinolone, against clinical isolates.	2002 Mar	11850285

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

Minimum inhibitory concentration that inhibited 90% of the coagulase-negative staphylococci isolates from bovine clinical and subclinical mastitis tested was 0.38 ug/ml for oxacillin

Name

Type

Language

OXACILLIN

Official Name

English

OXACILINA

Brand Name

English

OXACILLIN [MI]

Common Name

English

Oxacillin [WHO-DD]

Common Name

English

OXACILLIN [MART.]

Common Name

English

OXACILLIN [VANDF]

Common Name

English

4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-6-(((5-METHYL-3-PHENYL-4-ISOXAZOLYL)CARBONYL)AMINO)-7-OXO-,(2S,5R,6R)-

Common Name

English

OXAZOCILLINE

Common Name

English

oxacillin [INN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ01CF04