cloxacillin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 37 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 -0.553 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 7.015 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 1.312 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 3.589 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 27.360 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 21.950 % High 1
herg hERG pIC50 4.316 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 3.404 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 3.090 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 16.250 % High 1
kinase-selectivity-class AXL,GRK2,MAP2K6 3
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,MAPK10,MAPK7,MAPK9,MAPKAPK2,NTRK2,PDK1,PDK2,PDK4,PIK3CA,PIK3CB,PIK3CD,PIK3CG,PIM2,PRKDC,STK33,SYK,TEK,TGFBR1,TTK,ZAP70 45
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 1.626 High 1
mh-clint Mouse hepatocyte intrinsic clearance 12.618 High 1
mppb Mouse plasma protein binding (% unbound) 13.220 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 4.009 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 16.160 % High 1
rh-clint Rat hepatocyte intrinsic clearance 5.861 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 73.590 % High 1
rppb Rat plasma protein binding (% unbound) 12.680 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 959.401 uM High 1

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 164.87 27.93 88 1447 320299 90306613
Drug reaction with eosinophilia and systemic symptoms 75.31 27.93 28 1507 42730 90584182
Iodine allergy 55.07 27.93 10 1525 876 90626036
Pemphigoid 54.02 27.93 15 1520 9011 90617901
Allergy to metals 53.47 27.93 10 1525 1030 90625882
Agranulocytosis 51.09 27.93 20 1515 34982 90591930
Tubulointerstitial nephritis 49.78 27.93 18 1517 25325 90601587
Rubber sensitivity 43.46 27.93 10 1525 2827 90624085
Acute pulmonary oedema 39.85 27.93 12 1523 9568 90617344
Rash maculo-papular 38.17 27.93 17 1518 40916 90585996
Vascular purpura 36.89 27.93 8 1527 1730 90625182
Cutaneous vasculitis 34.23 27.93 10 1525 7183 90619729
Shunt infection 33.69 27.93 5 1530 124 90626788

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 260.61 41.55 92 2016 41983 42577244
Acute kidney injury 155.20 41.55 134 1974 367203 42252024
Rash maculo-papular 69.93 41.55 35 2073 37468 42581759
Hepatocellular injury 68.67 41.55 30 2078 23648 42595579
Agranulocytosis 61.30 41.55 30 2078 30582 42588645
Toxic epidermal necrolysis 58.96 41.55 28 2080 26722 42592505
Cholestasis 56.36 41.55 29 2079 32850 42586377
Thrombocytopenia 53.81 41.55 56 2052 190223 42429004
Eosinophilia 50.62 41.55 27 2081 32872 42586355

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 335.62 27.80 119 3533 81976 110503671
Acute kidney injury 306.79 27.80 213 3439 635217 109950430
Agranulocytosis 112.32 27.80 50 3602 61710 110523937
Rash maculo-papular 106.58 27.80 51 3601 74171 110511476
Eosinophilia 80.68 27.80 39 3613 57897 110527750
Tubulointerstitial nephritis 80.02 27.80 38 3614 54246 110531401
Cholestasis 79.63 27.80 40 3612 64478 110521169
Hepatocellular injury 67.22 27.80 33 3619 50609 110535038
Jaundice 56.73 27.80 31 3621 59205 110526442
Thrombocytopenia 55.92 27.80 63 3589 348822 110236825
Nephritis allergic 52.11 27.80 11 3641 1068 110584579
Toxic epidermal necrolysis 49.69 27.80 28 3624 56699 110528948
Cutaneous vasculitis 46.36 27.80 17 3635 12712 110572935
Mixed liver injury 39.84 27.80 15 3637 12064 110573583
Vascular purpura 38.43 27.80 11 3641 3760 110581887
Varicella zoster pneumonia 36.69 27.80 7 3645 407 110585240
Pemphigoid 35.92 27.80 16 3636 19691 110565956
Gamma-glutamyltransferase increased 34.98 27.80 23 3629 61286 110524361
Renal tubular necrosis 34.96 27.80 18 3634 30457 110555190
Arterial angioplasty 34.61 27.80 5 3647 50 110585597
Enterobacter pneumonia 34.04 27.80 7 3645 598 110585049
Duodenal stenosis 30.70 27.80 7 3645 970 110584677

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 D000890 Anti-Infective Agents
MeSH PA D000900 Anti-Bacterial Agents
CHEBI has role CHEBI:33282 antibacterial agent
CHEBI has role CHEBI:36047 antibacterial drug

Related Drugs by ATC class:

J01CF Beta-lactamase resistant penicillins 5 drugs
dicloxacillinfloxacillinmeticillinnafcillinoxacillin

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




🐶 Veterinary Drug Use

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

🐶 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
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
4017893 VANDF
4019689 VANDF

Pharmaceutical products:

None