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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

[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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
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

Targets

Primary TargetPharmacologyConditionPotency
100.0 µM [IC50]
0.42 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Oxacillin

Cmax

ValueDoseCo-administeredAnalytePopulation
43 μg/mL
500 mg single, intravenous
OXACILLIN serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
125.9 mg × h/L
30 mg/kg bw single, intravenous
OXACILLIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
0.42 h
30 mg/kg bw single, intravenous
OXACILLIN plasma
Homo sapiens
25 min
500 mg single, intravenous
OXACILLIN serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
6%
500 mg single, intravenous
OXACILLIN serum
Homo sapiens

Doses

AEs

Sourcing

PubMed

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
Record UNII
UH95VD7V76
Record Status Validated (UNII)
Record Version