cloxacillin ๐Ÿถ Veterinary Use | 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
  • cloxacillin benzathine
A semi-synthetic antibiotic that is a chlorinated derivative of OXACILLIN.
  • Molecular weight: 435.88
  • Formula: C19H18ClN3O5S
  • CLOGP: 2.56
  • 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 Bocci G, Oprea TI, Benet LZ
EoM (Fraction excreted unchanged in urine) 75 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 76.40 ยตM/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 121.58 33.28 66 952 263349 63224655
Pemphigoid 57.94 33.28 15 1003 7329 63480675
Allergy to metals 57.50 33.28 10 1008 725 63487279
Iodine allergy 56.60 33.28 10 1008 794 63487210
Tubulointerstitial nephritis 51.04 33.28 17 1001 19886 63468118
Rubber sensitivity 45.98 33.28 10 1008 2321 63485683
Drug reaction with eosinophilia and systemic symptoms 42.24 33.28 17 1001 33819 63454185
Vascular purpura 38.63 33.28 8 1010 1470 63486534

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 218.74 40.09 76 1662 32936 34922257
Acute kidney injury 131.96 40.09 113 1625 304875 34650318
Hepatocellular injury 70.41 40.09 30 1708 22181 34933012
Cholestasis 58.66 40.09 28 1710 26920 34928273
Agranulocytosis 55.67 40.09 26 1712 23795 34931398
Toxic epidermal necrolysis 45.59 40.09 22 1716 21624 34933569
Nephritis allergic 44.96 40.09 9 1729 444 34954749
Eosinophilia 44.46 40.09 23 1715 26199 34928994
Thrombocytopenia 44.01 40.09 46 1692 156201 34798992
Rash maculo-papular 42.69 40.09 23 1715 28428 34926765
Tubulointerstitial nephritis 40.18 40.09 20 1718 21004 34934189

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 254.75 31.23 92 2651 64152 79677493
Acute kidney injury 235.19 31.23 170 2573 519234 79222411
Agranulocytosis 88.62 31.23 39 2704 44991 79696654
Tubulointerstitial nephritis 84.68 31.23 36 2707 38199 79703446
Cholestasis 83.17 31.23 39 2704 52070 79689575
Rash maculo-papular 68.57 31.23 35 2708 56043 79685602
Hepatocellular injury 67.94 31.23 33 2710 47560 79694085
Nephritis allergic 55.95 31.23 11 2732 719 79740926
Eosinophilia 54.54 31.23 28 2715 45317 79696328
Thrombocytopenia 46.21 31.23 51 2692 265208 79476437
Jaundice 42.23 31.23 25 2718 53324 79688321
Mixed liver injury 42.07 31.23 14 2729 7564 79734081
Cutaneous vasculitis 40.90 31.23 14 2729 8238 79733407
Vascular purpura 40.13 31.23 11 2732 3087 79738558
Pemphigoid 39.19 31.23 16 2727 15299 79726346
Toxic epidermal necrolysis 38.21 31.23 22 2721 44559 79697086
Renal tubular necrosis 34.61 31.23 17 2726 25022 79716623
Arterial angioplasty 34.41 31.23 5 2738 50 79741595
Gamma-glutamyltransferase increased 34.06 31.23 22 2721 54658 79686987
Hepatitis 31.25 31.23 21 2722 55706 79685939

FDA Adverse Event Reporting System (Pediatric)

None

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 bactericides
CHEBI has role CHEBI:36047 antibacterial drugs

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
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




๐Ÿถ Veterinary Drug Use

SpeciesUseRelation
Cattle Mastitis caused by Staphylococcus aureus Indication
Cattle Mastitis caused by Streptococcus agalactiae Indication

๐Ÿถ Veterinary products

ProductApplicantIngredients
Dry-Clox Intramammary Infusion Boehringer lngelheim Animal Health USA Inc. 1
Orbenin DC Intervet Inc. 1
Dariclox Intervet Inc. 1

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 CHEMBL
Beta-lactamase Enzyme IC50 7.59 CHEMBL
Penicillin-binding protein 1A Enzyme WOMBAT-PK
Beta-lactamase Enzyme IC50 8.40 CHEMBL
Beta-lactamase TEM Enzyme Ki 4.89 WOMBAT-PK
Efflux transporter; SugE Transporter IC50 8.40 CHEMBL

External reference:

IDSource
4019689 VUID
N0000147781 NUI
D07733 KEGG_DRUG
1043213 RXNORM
4017893 VANDF
4019689 VANDF
C0009077 UMLSCUI
CHEBI:49566 CHEBI
CXN PDB_CHEM_ID
CHEMBL891 ChEMBL_ID
CHEMBL1200388 ChEMBL_ID
D003023 MESH_DESCRIPTOR_UI
DB01147 DRUGBANK_ID
11126 IUPHAR_LIGAND_ID
1533 INN_ID
7081-44-9 SECONDARY_CAS_RN
O6X5QGC2VB UNII
6098 PUBCHEM_CID
407 MMSL
4483 MMSL
d00152 MMSL
002691 NDDF
004835 NDDF
004855 NDDF
16492006 SNOMEDCT_US
373276005 SNOMEDCT_US
68422006 SNOMEDCT_US
96066001 SNOMEDCT_US
CHEMBL3989531 ChEMBL_ID
23736-58-5 SECONDARY_CAS_RN

Pharmaceutical products:

None