OXACILLIN BENZATHINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C19H19N3O5S.C16H20N2
Molecular Weight	1043.216
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C(CNCC1=CC=CC=C1)NCC2=CC=CC=C2.[H][C@]34SC(C)(C)[C@@H](N3C(=O)[C@H]4NC(=O)C5=C(C)ON=C5C6=CC=CC=C6)C(O)=O.[H][C@]78SC(C)(C)[C@@H](N7C(=O)[C@H]8NC(=O)C9=C(C)ON=C9C%10=CC=CC=C%10)C(O)=O

InChI

InChIKey=YAYWMARUVKROAQ-VZHMHXRYSA-N

InChI=1S/2C19H19N3O5S.C16H20N2/c2*1-9-11(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;1-3-7-15(8-4-1)13-17-11-12-18-14-16-9-5-2-6-10-16/h2*4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26);1-10,17-18H,11-14H2/t2*13-,14+,17-;/m11./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

Molecular Formula	C16H20N2
Molecular Weight	240.3434
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 1971

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
[Evaluation of MRSA identification with latex agglutination kit for the detection of penicillin-binding protein 2].	2001	11682001
Linezolid: a review of its use in the management of serious gram-positive infections.	2001	11324682
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
Multi-resistance to antimicrobial agents for the ten most frequently isolated bacterial pathogens.	2001 Aug	11516938
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
A microdilution plating method for population analysis of antibiotic-resistant staphylococci.	2001 Fall	11759091
Antimicrobial susceptibility of quinupristin/dalfopristin tested against gram-positive cocci from Latin America: results from the global SMART (GSMART) surveillance study.	2001 Feb	11290311
High frequency of colonization and absence of identifiable risk factors for methicillin-resistant Staphylococcus aureus (MRSA)in intensive care units in Brazil.	2001 Feb	11290308
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
Generation of class-selective monoclonal antibodies against the penicillin group.	2001 Jul	11453774
In vitro antimicrobial activity of the aminoglycoside arbekacin tested against oxacillin-resistant Staphylococcus aureus isolated in Brazilian hospitals.	2001 Jun	11506776
Penicillin resistance in Streptococcus pneumoniae in Isparta.	2001 Mar	11264759
Application of ion-exchange cartridge clean-up in food analysis IV. Confirmatory assay of benzylpenicillin, phenoxymethylpenicillin, oxacillin, cloxacillin, nafcillin and dicloxacillin, in bovine tissues by liquid chromatography-electrospray ionization tandem mass spectrometry.	2001 Mar 16	11293583
Comparison of the Velogene Rapid MRSA Identification Assay, Denka MRSA-Screen Assay, and BBL Crystal MRSA ID System for rapid identification of methicillin-resistant Staphylococcus aureus.	2001 May-Jun	11448557
A sequence variant of Staphylococcus hominis with a high prevalence of oxacillin and fluoroquinolone resistance.	2001 Nov	11763241
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
Development of vancomycin and lysostaphin resistance in a methicillin-resistant Staphylococcus aureus isolate.	2001 Nov	11679550
Application of the IDSA guidelines for the use of antimicrobial agents in neutropenic patients: impact on reducing the use of glycopeptides.	2001 Oct	11776354
[Decreasing susceptibility to vancomycin in isogenic Staphylococcus aureus strains isolated from a single patient].	2001 Oct 13	11602171
The DUEL study: a multi-center in vitro evaluation of linezolid compared with other antibiotics in the Netherlands.	2001 Sep	11678931
Determination of benzylpenicillin, oxacillin, cloxacillin, and dicloxacillin in cows' milk by ion-pair high-performance liquid chromatography after precolumn derivatization.	2001 Sep	11605761
Cloning and sequencing of the gene, fmtC, which affects oxacillin resistance in methicillin-resistant Staphylococcus aureus.	2001 Sep 11	11557139
Molecular epidemiology of methicillin-resistant Staphylococcus aureus in Colombian hospitals: dominance of a single unique multidrug-resistant clone.	2001 Spring	11310800
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
Natural antibiotic susceptibility and biochemical profiles of Yersinia enterocolitica-like strains: Y. bercovieri, Y. mollaretii, Y. aldovae and 'Y. ruckeri'.	2002 Jan	11800473
An outbreak of community-acquired foodborne illness caused by methicillin-resistant Staphylococcus aureus.	2002 Jan	11749755
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

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 `Sat Dec 16 09:32:37 GMT 2023` Edited by `admin` on `Sat Dec 16 09:32:37 GMT 2023`
Record UNII	FUQ24YT1C9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXACILLIN BENZATHINE

Common Name

English

4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-6-(5-METHYL-3-PHENYL-4-ISOXAZOLECARBOXAMIDO)-7-OXO-, COMPD. WITH N,N'-DIBENZYLETHYLENEDIAMINE (2:1)

Systematic 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-(2.ALPHA.,5.ALPHA.,6.BETA.))-, COMPD. WITH N,N'-BIS(PHENYLMETHYL)-1,2-ETHANEDIAMINE (2:1)

Systematic 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)-, COMPD. WITH N,N'-BIS(PHENYLMETHYL)-1,2-ETHANEDIAMINE (2:1)

Systematic Name

English

ETHYLENEDIAMINE, N,N'-DIBENZYL-, BIS(3,3-DIMETHYL-6-(5-METHYL-3-PHENYL-4-ISOXAZOLECARBOXAMIDO)-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLATE)

Common Name

English

1,2-ETHANEDIAMINE, N,N'-BIS(PHENYLMETHYL)-, BIS((2S,5R,6R)-3,3-DIMETHYL-6-(((5-METHYL-3-PHENYL-4-ISOXAZOLYL)CARBONYL)AMINO)-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLATE)

Common Name

English

1,2-ETHANEDIAMINE, N,N'-BIS(PHENYLMETHYL)-, BIS((2S-(2.ALPHA.,5.ALPHA.,6.BETA.))-3,3-DIMETHYL-6-(((5-METHYL-3-PHENYL-4-ISOXAZOLYL)CARBONYL)AMINO)-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLATE)

Common Name

English

Code System Code Type Description

PUBCHEM

13175187