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

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

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 8228	100.0 µM [IC50]
Penicillin-binding protein 31 Target ID: CHEMBL2362973 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421	Inhibitor 8228	0.42 nM [IC50]
Staphylococcus aureus 65 Target ID: CHEMBL352 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050640s017lbl.pdf	Inhibitor 8228

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 8360	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
Rapid detection of the methicillin-resistance gene, mecA, in coagulase-negative Staphylococci.	2001	11515759
Linezolid: a review of its use in the management of serious gram-positive infections.	2001	11324682
Chronic granulomatous disease: a case report.	2001 Apr	11393130
[Choice of the NaCl concentration for optimizing the detection of methicillin resistance in Staphylococcus using the gel diffusion method].	2001 Apr	11367555
Prevalence of penicillin-resistant Streptococcus pneumoniae in Kuwait.	2001 Apr	11330362
Simultaneous determination of five beta-lactam antibiotics in bovine milk using liquid chromatography coupled with electrospray ionization tandem mass spectrometry.	2001 Apr 1	11321318
Pathogen frequency and resistance patterns in Brazilian hospitals: summary of results from three years of the SENTRY Antimicrobial Surveillance Program.	2001 Aug	11712965
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
Antibiotic resistance in coagulase-negative staphylococci isolated from Cope's gray treefrogs (Hyla chrysoscelis).	2001 Dec 18	11750814
Antimicrobial susceptibility of quinupristin/dalfopristin tested against gram-positive cocci from Latin America: results from the global SMART (GSMART) surveillance study.	2001 Feb	11290311
[Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine].	2001 Feb	11265221
Quinupristin/dalfopristin: a therapeutic review.	2001 Jan	11219478
Prevalence and characteristics of Pasteurella multocida in commercial turkeys.	2001 Jan-Mar	11332480
Methicillin-resistant Staphylococcus aureus in the hospitals of central Greece.	2001 Jul	11463528
Solid-phase extraction followed by liquid chromatography-mass spectrometry for trace determination of beta-lactam antibiotics in bovine milk.	2001 Jul	11453792
Investigation of oxacillin-hydrolyzing beta-lactamase in borderline methicillin-resistant clinical isolates of Staphylococcus aureus.	2001 Jul-Aug	11399858
RU-79115 (Aventis Pharma).	2001 Jun	11572652
Plasmid and chromosomal basis of tolerance to cadmium and resistance to antibiotics in normal bovine duodenal bacterial flora.	2001 Jun	11383651
Filamentous forms of Escherichia coli in cerebrospinal fluid.	2001 Jun	11371248
Cutaneous leucocytoclastic vasculitis associated with oxacillin.	2001 Mar	11337188
Penicillin resistance in Streptococcus pneumoniae in Isparta.	2001 Mar	11264759
Association between antibiotic resistance and the expression of Dr adhesin among uropathogenic Escherichia coli.	2001 Mar-Apr	11173810
Community-acquired, non-multiresistant oxacillin-resistant Staphylococcus aureus (NORSA) in South Western Sydney.	2001 May	11358055
A sequence variant of Staphylococcus hominis with a high prevalence of oxacillin and fluoroquinolone resistance.	2001 Nov	11763241
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
Streptococcal meningitis in adults: therapeutic outcomes and prognostic factors.	2001 Oct	11532551
[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
Staphylococcus aureus in lower respiratory infections: clinical relevance of antimicrobial resistance.	2001 Sep	11562899
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
Molecular epidemiology of methicillin-resistant Staphylococcus aureus in Colombian hospitals: dominance of a single unique multidrug-resistant clone.	2001 Spring	11310800
A comparison of PCR detection of mecA with two standard methods of oxacillin disk susceptibility testing for coagulase-negative staphylococci.	2002 Jan	11800477
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

Substance Class	Chemical Created by `admin` on `Thu Jul 06 23:21:29 UTC 2023` Edited by `admin` on `Thu Jul 06 23:21:29 UTC 2023`
Record UNII	UH95VD7V76
Record Status	`Validated (UNII)`
Record Version

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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