oxacillin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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: 2.09
  • 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 µM/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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 -0.699 Moderate 0.78
caco2-efflux Caco-2 efflux ratio (BA/AB) 5.916 Moderate 0.78
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 1.535 10^-6 cm/s Moderate 0.78
dh-clint Dog hepatocyte intrinsic clearance 2.799 uL/min/10^6 cells Moderate 0.78
dppb Dog plasma protein binding (% unbound) 36.530 % Moderate 0.78
fcs-ppb Fetal calf serum protein binding (% unbound) 28.660 % Moderate 0.78
herg hERG pIC50 4.339 pIC50 Moderate 0.78
hh-clint Human hepatocyte intrinsic clearance 2.065 uL/min/10^6 cells Moderate 0.78
hlm-clint Human liver microsomal intrinsic clearance 2.999 uL/min/mg protein Moderate 0.78
hppb Human plasma protein binding (% unbound) 23.150 % Moderate 0.78
kinase-safety-class ACVR2A,ACVR2B,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,GRK2,GRK3,GSK3B,ITK,JAK2,JAK3,MAP2K6,MAP3K21,MAP3K7,MAPK7,MAPK9,MAPKAPK2,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CB,PIK3CD,PIK3CG,PIM2,PRKDC,SIK2,STK33,SYK,TEK,TTK,ZAP70 44
kinase-selectivity-class ACVR2B,AXL,GRK2,MAP2K6 4
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 1.923 Moderate 0.78
mh-clint Mouse hepatocyte intrinsic clearance 8.414 Moderate 0.78
mppb Mouse plasma protein binding (% unbound) 20.040 Moderate 0.78
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 3.963 Moderate 0.78
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 22.500 % Moderate 0.78
rh-clint Rat hepatocyte intrinsic clearance 4.276 uL/min/10^6 cells Moderate 0.78
rh-fuinc Rat hepatocyte fraction unbound in incubation 79.020 % Moderate 0.78
rppb Rat plasma protein binding (% unbound) 18.850 % Moderate 0.78
solubility-dd Solubility at pH 7.4 in DMSO 952.796 uM Moderate 0.78

Approvals:

DateAgencyCompanyOrphan
April 8, 1971 FDA SANDOZ

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug reaction with eosinophilia and systemic symptoms 96.14 43.39 28 699 42730 90584990
Toxic epidermal necrolysis 71.71 43.39 21 706 32507 90595213

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug reaction with eosinophilia and systemic symptoms 105.84 35.41 43 1390 42032 42577870
Eosinophilia 51.14 35.41 24 1409 32875 42587027
Acute kidney injury 43.23 35.41 57 1376 367280 42252622
Eosinophilic myocarditis 38.53 35.41 9 1424 1364 42618538
Toxic skin eruption 37.75 35.41 15 1418 13715 42606187
Renal tubular necrosis 36.79 35.41 16 1417 18338 42601564

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug reaction with eosinophilia and systemic symptoms 196.19 35.64 69 2000 82026 110505204
Eosinophilia 91.49 35.64 36 2033 57900 110529330
Acute kidney injury 76.01 35.64 75 1994 635355 109951875
Toxic epidermal necrolysis 52.03 35.64 24 2045 56703 110530527
Staphylococcal infection 44.35 35.64 23 2046 69921 110517309
Drug resistance 42.97 35.64 21 2048 56353 110530877
Eosinophilic myocarditis 40.03 35.64 9 2060 2076 110585154
Toxic skin eruption 39.56 35.64 16 2053 27499 110559731
Renal tubular necrosis 37.98 35.64 16 2053 30459 110556771
Device related infection 37.10 35.64 17 2052 39502 110547728

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J01CF04 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
BETA-LACTAM ANTIBACTERIALS, PENICILLINS
Beta-lactamase resistant penicillins
FDA CS M0016152 Penicillins
FDA EPC N0000175497 Penicillin-class Antibacterial
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000900 Anti-Bacterial Agents
CHEBI has role CHEBI:33282 antibacterial agent
CHEBI has role CHEBI:35441 antiinfective agent
CHEBI has role CHEBI:36047 antibacterial drug

Related Drugs by ATC class:

J01CF Beta-lactamase resistant penicillins 5 drugs
cloxacillindicloxacillinfloxacillinmeticillinnafcillin

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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 2 Enzyme IC50 5.85 WOMBAT-PK
Prostaglandin G/H synthase 1 Enzyme IC50 7.02 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
D00929 KEGG_DRUG
7240-38-2 SECONDARY_CAS_RN
4018149 VANDF
4019867 VANDF
C0029983 UMLSCUI
CHEBI:7809 CHEBI
CHEMBL819 ChEMBL_ID
CHEMBL3989567 ChEMBL_ID
D010068 MESH_DESCRIPTOR_UI
DB00713 DRUGBANK_ID
6196 PUBCHEM_CID
10943 IUPHAR_LIGAND_ID
1372 INN_ID
UH95VD7V76 UNII
7773 RXNORM
4479 MMSL
5207 MMSL
d00115 MMSL
002690 NDDF
004834 NDDF
372868007 SNOMEDCT_US
83201006 SNOMEDCT_US
85724000 SNOMEDCT_US
0WO PDB_CHEM_ID
1S6 PDB_CHEM_ID
UH95VD7V76 INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
OXACILLIN HUMAN PRESCRIPTION DRUG LABEL 1 0338-1013 INJECTION, SOLUTION 1 g INTRAVENOUS NDA 24 sections
OXACILLIN HUMAN PRESCRIPTION DRUG LABEL 1 0338-1015 INJECTION, SOLUTION 2 g INTRAVENOUS NDA 24 sections
Oxacillin Human Prescription Drug Label 1 55150-127 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 22 sections
Oxacillin Human Prescription Drug Label 1 55150-128 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 22 sections
Oxacillin Human Prescription Drug Label 1 55150-129 POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 22 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 63323-811 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 23 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 63323-812 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 12 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 63323-813 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 12 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 64679-698 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 20 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 64679-698 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 20 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 64679-699 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 20 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 64679-699 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 20 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 64679-700 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 19 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 64679-700 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 19 sections
Oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 72485-409 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 24 sections
oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 83270-306 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 21 sections
oxacillin HUMAN PRESCRIPTION DRUG LABEL 1 83270-307 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 21 sections