oxacillin Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, 6-aminopenicillanic acid derivatives 2006 66-79-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • oxacillin sodium hydrate
  • oxacillin
  • oxazocilline
  • oxazocillin
  • oxacillin sodium
An antibiotic similar to FLUCLOXACILLIN used in resistant staphylococci infections.
  • Molecular weight: 401.44
  • Formula: C19H19N3O5S
  • CLOGP: 2.05
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 2
  • TPSA: 112.74
  • ALOGS: -3.67
  • ROTB: 4

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
2 g O
2 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 46 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 249.10 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 33 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.19 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 6.30 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.07 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.70 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
April 8, 1971 FDA SANDOZ

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC J01CF04 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
BETA-LACTAM ANTIBACTERIALS, PENICILLINS
Beta-lactamase resistant penicillins
FDA EPC N0000175497 Penicillin-class Antibacterial
FDA Chemical/Ingredient N0000011281 Penicillins
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
CHEBI has role CHEBI:36047 antibacterial drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Staphylococcal meningitis indication 12166008
Infection of skin AND/OR subcutaneous tissue indication 19824006
Staphylococcal pneumonia indication 22754005
Sinusitis indication 36971009
Lower respiratory tract infection indication 50417007
Staphylococcal infectious disease indication 56038003
Staphylococcal endocarditis indication 73028002
Acute bacterial sinusitis indication 75498004
Infection of bone indication 111253001
Staphylococcal septicemia indication 111821004
Pharyngitis indication 405737000 DOID:2275
Infection due to Staphylococcus aureus indication 406602003
Osteomyelitis due to Staphylococcus aureus indication 428783003
Sepsis due to Staphylococcus aureus indication 448417001
Staphylococcus Epidermidis Urinary Tract Infection indication
Staphylococcus Aureus Joint Infection indication
Staphylococcus Aureus Urinary Tract Infection indication
Continuation Therapy for Chronic Osteomyelitis indication
Staphylococcal Prosthetic Heart Valve Endocarditis indication
Staphylococcus Aureus Bronchitis indication
Continuation Therapy for Acute Osteomyelitis indication
Pyrexia of unknown origin off-label use 7520000
Cholangitis off-label use 82403002 DOID:9446
Bacterial endocarditis off-label use 301183007
Diabetic Foot Infection Due to Gram-Positive Bacteria off-label use
Kidney disease contraindication 90708001 DOID:557
Infectious mononucleosis contraindication 271558008 DOID:8568
Pseudomembranous enterocolitis contraindication 397683000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.76 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Prostaglandin G/H synthase 1 Enzyme IC50 7.02 WOMBAT-PK
Prostaglandin G/H synthase 2 Enzyme IC50 5.85 WOMBAT-PK
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A Enzyme IC50 5.04 WOMBAT-PK
Penicillin-binding protein Enzyme INHIBITOR CHEMBL CHEMBL
Penicillin-binding protein 1A Enzyme WOMBAT-PK

External reference:

IDSource
4019867 VUID
N0000147953 NUI
C0029983 UMLSCUI
D00929 KEGG_DRUG
83201006 SNOMEDCT_US
4019867 VANDF
7773 RXNORM
372868007 SNOMEDCT_US
d00115 MMSL
85724000 SNOMEDCT_US
004834 NDDF
CHEMBL693 ChEMBL_ID
CHEMBL819 ChEMBL_ID
DB00713 DRUGBANK_ID
G0V6C994Q5 UNII
7240-38-2 SECONDARY_CAS_RN
1372 INN_ID
0WO PDB_CHEM_ID
1S6 PDB_CHEM_ID
CHEBI:7809 CHEBI
D010068 MESH_DESCRIPTOR_UI
CHEMBL3989567 ChEMBL_ID
6196 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
OXACILLIN HUMAN PRESCRIPTION DRUG LABEL 1 0338-1013 INJECTION, SOLUTION 1 g INTRAVENOUS NDA 12 sections
OXACILLIN HUMAN PRESCRIPTION DRUG LABEL 1 0338-1015 INJECTION, SOLUTION 2 g INTRAVENOUS NDA 12 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-3099 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 13 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-3101 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 13 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-3103 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 11 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-9109 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 13 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-9111 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 13 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-9113 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 11 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 22607-699 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 13 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 25021-146 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 12 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 25021-162 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 13 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 25021-163 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 13 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 55150-127 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 12 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 55150-128 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 12 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 55150-129 POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 12 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 64679-698 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 12 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 64679-699 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 12 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 64679-700 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 12 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 66794-225 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 11 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 66794-226 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 11 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 66794-227 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 11 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 70655-099 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 12 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 70655-103 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 12 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 70655-109 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 12 sections