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

Stem definitionDrug idCAS RN
antibiotics, 6-aminopenicillanic acid derivatives 720 61-72-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cloxacillin
  • Methocillin S
  • cloxacillin sodium
  • cloxacillin sodium salt
A semi-synthetic antibiotic that is a chlorinated derivative of OXACILLIN.
  • Molecular weight: 435.88
  • Formula: C19H18ClN3O5S
  • CLOGP: 2.52
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 2
  • TPSA: 112.74
  • ALOGS: -3.91
  • ROTB: 4

  • Status: OFM

  • 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) 4 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.01 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 75 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 76.40 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 40 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Sept. 17, 1974 FDA GLAXOSMITHKLINE

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
Acute kidney injury 74.01 30.30 48 789 235807 46449418
Allergy to metals 40.52 30.30 7 830 435 46684790
Iodine allergy 38.92 30.30 7 830 549 46684676
Cholestasis 33.75 30.30 14 823 26879 46658346
Rubber sensitivity 31.13 30.30 7 830 1689 46683536

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 153.70 35.24 55 1303 28433 29922687
Acute kidney injury 117.54 35.24 97 1261 273745 29677375
Hepatocellular injury 69.18 35.24 30 1328 25441 29925679
Toxic epidermal necrolysis 68.63 35.24 27 1331 17913 29933207
Cholestasis 44.58 35.24 22 1336 24928 29926192
Nephritis allergic 41.19 35.24 8 1350 371 29950749
Thrombocytopenia 39.25 35.24 39 1319 137005 29814115
Tubulointerstitial nephritis 38.72 35.24 18 1340 17873 29933247
Jaundice 36.42 35.24 21 1337 32465 29918655

Pharmacologic Action:

SourceCodeDescription
ATC J01CF02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
BETA-LACTAM ANTIBACTERIALS, PENICILLINS
Beta-lactamase resistant penicillins
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
CHEBI has role CHEBI:33282 antibacterials
CHEBI has role CHEBI:36047 antibacterial drugs

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
Acute bacterial sinusitis indication 75498004
Staphylococcal septicemia indication 111821004
Pharyngitis indication 405737000 DOID:2275
Infection due to Staphylococcus aureus indication 406602003
Continuation Therapy for Chronic Osteomyelitis indication
Staphylococcus Aureus Urinary Tract Infection indication
Continuation Therapy for Acute Osteomyelitis indication
Staphylococcus Epidermidis Urinary Tract Infection indication
Staphylococcus Aureus Bronchitis 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
Penicillin-binding protein Enzyme INHIBITOR CHEMBL CHEMBL
Beta-lactamase TEM Enzyme Ki 4.89 WOMBAT-PK
Beta-lactamase TEM Enzyme Ki 4.89 CHEMBL
Penicillin-binding protein 1A Enzyme WOMBAT-PK
Efflux transporter; SugE Unclassified IC50 8.40 CHEMBL
Beta-lactamase Enzyme IC50 8.40 CHEMBL
Beta-lactamase Enzyme IC50 7.59 CHEMBL

External reference:

IDSource
4019689 VUID
N0000147781 NUI
D07733 KEGG_DRUG
7081-44-9 SECONDARY_CAS_RN
4017893 VANDF
4019689 VANDF
C0009077 UMLSCUI
CHEBI:49566 CHEBI
CXN PDB_CHEM_ID
CHEMBL891 ChEMBL_ID
CHEMBL1200388 ChEMBL_ID
DB01147 DRUGBANK_ID
D003023 MESH_DESCRIPTOR_UI
6098 PUBCHEM_CID
11126 IUPHAR_LIGAND_ID
1533 INN_ID
O6X5QGC2VB UNII
2625 RXNORM
407 MMSL
4483 MMSL
d00152 MMSL
002691 NDDF
004835 NDDF
16492006 SNOMEDCT_US
373276005 SNOMEDCT_US
68422006 SNOMEDCT_US

Pharmaceutical products:

None