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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 of OXACILLIN

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

HIDE SMILES / InChI

Molecular Formula C19H19N3O5S
Molecular Weight 401.436
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Oxacillin
PubMed

PubMed

TitleDatePubMed
[Monitoring of uropathogens and their susceptibility to antibiotics].
2001
Oxacillin susceptibility testing of Staphylococcus saprophyticus using disk diffusion, agar dilution, broth microdilution, and the Vitek GPS-105 card.
2001 Aug
Optimizing antibiotic therapy in the intensive care unit setting.
2001 Aug
RU-79115 (Aventis Pharma).
2001 Jun
Antibacterial action of several tannins against Staphylococcus aureus.
2001 Oct
Staphylococcus aureus in lower respiratory infections: clinical relevance of antimicrobial resistance.
2001 Sep
Cloning and sequencing of the gene, fmtC, which affects oxacillin resistance in methicillin-resistant Staphylococcus aureus.
2001 Sep 11
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 Tue Mar 06 11:23:12 UTC 2018
Edited
by admin
on Tue Mar 06 11:23:12 UTC 2018
Record UNII
UH95VD7V76
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXACILLIN
INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
OXACILINA
Brand Name English
OXACILLIN [MI]
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 [WHO-DD]
Common Name English
OXACILLIN [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ01CF04
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
NDF-RT N0000011281
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
NDF-RT N0000011281
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
WHO-VATC QG51AG04
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
NDF-RT N0000175497
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
WHO-ATC J01CF04
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
NDF-RT N0000011281
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
NDF-RT N0000011281
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
NDF-RT N0000011281
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
LIVERTOX 717
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
NDF-RT N0000011281
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
NDF-RT N0000011281
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
NDF-RT N0000011281
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
WHO-VATC QJ51CF04
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
NDF-RT N0000011281
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
Code System Code Type Description
RXCUI
7773
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
PRIMARY RxNorm
NCI_THESAURUS
C62063
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
PRIMARY
EPA CompTox
66-79-5
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
PRIMARY
MESH
D010068
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
PRIMARY
EVMPD
SUB09484MIG
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
PRIMARY
ChEMBL
CHEMBL819
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
PRIMARY
WIKIPEDIA
OXACILLIN
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
PRIMARY
DRUG BANK
DB00713
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
PRIMARY
PUBCHEM
6196
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
PRIMARY SWITZERF
INN
1372
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
PRIMARY
LactMed
66-79-5
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
PRIMARY
ECHA (EC/EINECS)
200-635-5
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
PRIMARY
CAS
66-79-5
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
PRIMARY
MERCK INDEX
M8273
Created by admin on Tue Mar 06 11:23:12 UTC 2018 , Edited by admin on Tue Mar 06 11:23:12 UTC 2018
PRIMARY Merck Index
Related Record Type Details
ACTIVE MOIETY