floxacillin 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, 6-aminopenicillanic acid derivatives 1183 5250-39-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • floxacillin
  • fluocloxacilin
  • flucloxacillin
  • fluoxacillin
  • flucloxacillin sodium
Antibiotic analog of CLOXACILLIN.
  • Molecular weight: 453.87
  • Formula: C19H17ClFN3O5S
  • CLOGP: 2.70
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 2
  • TPSA: 112.74
  • ALOGS: -3.92
  • ROTB: 3

Drug dosage:

DoseUnitRoute
2 g O
2 g P

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 146.96 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System) 4 Hosey CM, Chan R, Benet LZ
BA (Bioavailability) 55 % 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) 2.40 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.04 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.40 hours Lombardo F, Berellini G, Obach RS
S (Water solubility) 0.05 mg/mL Bocci G, Oprea TI, Benet LZ

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 -0.503 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 8.072 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 1.233 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 3.475 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 25.920 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 24.790 % High 1
herg hERG pIC50 4.305 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 3.083 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 3.357 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 12.960 % High 1
kinase-safety-class ACVR2A,ACVR2B,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK5,CDK9,DYRK1B,EGFR,EIF2AK3,ERBB2,GRK2,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,ZAP70 41
kinase-selectivity-class AXL,EIF2AK3,GRK2 3
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 1.936 High 1
mh-clint Mouse hepatocyte intrinsic clearance 12.823 High 1
mppb Mouse plasma protein binding (% unbound) 12.860 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 4.046 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 13.360 % High 1
rh-clint Rat hepatocyte intrinsic clearance 5.272 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 72.870 % High 1
rppb Rat plasma protein binding (% unbound) 9.740 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 959.401 uM High 1

Approvals:

DateAgencyCompanyOrphan
Jan. 1, 1962 YEAR INTRODUCED

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
Metabolic acidosis 555.20 24.40 200 7535 55476 90565236
Drug interaction 277.16 24.40 211 7524 276242 90344470
Pyroglutamic acidosis 268.88 24.40 52 7683 1228 90619484
Cellulitis 128.66 24.40 86 7649 91251 90529461
Pyroglutamate increased 109.79 24.40 20 7715 337 90620375
Swelling face 76.52 24.40 60 7675 81292 90539420
Acute kidney injury 65.37 24.40 106 7629 320281 90300431
Neutropenic sepsis 57.59 24.40 29 7706 18101 90602611
Toxic epidermal necrolysis 56.54 24.40 35 7700 32493 90588219
Jaundice 51.53 24.40 33 7702 32484 90588228
Lip swelling 46.39 24.40 33 7702 38577 90582135
Hiccups 46.20 24.40 15 7720 3011 90617701
Swollen tongue 45.59 24.40 35 7700 45921 90574791
Drug level decreased 44.49 24.40 20 7715 9710 90611002
Dermatitis allergic 44.40 24.40 24 7711 17303 90603409
Hypokalaemia 43.89 24.40 55 7680 131061 90489651
Sepsis 42.89 24.40 64 7671 179750 90440962
Eczema herpeticum 40.28 24.40 8 7727 217 90620495
Vascular device infection 37.61 24.40 19 7716 11933 90608779
Ejection fraction decreased 37.58 24.40 25 7710 26228 90594484
Rash erythematous 36.88 24.40 36 7699 65068 90555644
Perforation 35.03 24.40 11 7724 1983 90618729
Poor peripheral circulation 34.59 24.40 13 7722 4012 90616700
Mycobacterium marinum infection 32.21 24.40 7 7728 297 90620415
Anterior interosseous syndrome 30.70 24.40 4 7731 4 90620708
Clostridium difficile infection 30.36 24.40 25 7710 36220 90584492
Subclavian vein thrombosis 30.33 24.40 10 7725 2106 90618606
Diarrhoea 29.77 24.40 158 7577 939032 89681680
Rash 29.50 24.40 140 7595 795960 89824752
Epidermal necrosis 29.25 24.40 10 7725 2351 90618361
Polyhydramnios 28.66 24.40 10 7725 2498 90618214
Liver function test abnormal 28.58 24.40 28 7707 50817 90569895
Toxic shock syndrome 28.07 24.40 8 7727 1036 90619676
Vulvovaginal inflammation 27.67 24.40 8 7727 1090 90619622
Acute haemorrhagic oedema of infancy 27.04 24.40 4 7731 16 90620696
Depressed mood 27.01 24.40 27 7708 50195 90570517
Hepatic failure 26.39 24.40 24 7711 39704 90581008
Neuropathy peripheral 26.08 24.40 44 7691 136926 90483786
Strawberry tongue 25.42 24.40 4 7731 26 90620686
Pancytopenia 24.73 24.40 40 7695 120223 90500489

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
Metabolic acidosis 209.29 20.24 113 5640 51745 42563837
Pyroglutamic acidosis 191.66 20.24 39 5714 746 42614836
Drug interaction 172.51 20.24 195 5558 266804 42348778
Immunosuppressant drug level decreased 109.62 20.24 29 5724 1795 42613787
Pyroglutamate increased 97.02 20.24 19 5734 296 42615286
Drug reaction with eosinophilia and systemic symptoms 82.69 20.24 58 5695 42017 42573565
Drug level decreased 80.47 20.24 35 5718 9942 42605640
Stevens-Johnson syndrome 56.62 20.24 36 5717 22142 42593440
Acute kidney injury 46.44 20.24 131 5622 367206 42248376
Heart transplant rejection 36.94 20.24 12 5741 1522 42614060
Lip swelling 36.77 20.24 26 5727 19027 42596555
Genitalia external ambiguous 36.11 20.24 8 5745 232 42615350
Cellulitis 36.08 20.24 43 5710 61542 42554040
Congenital bladder anomaly 34.83 20.24 8 5745 274 42615308
Kounis syndrome 34.45 20.24 14 5739 3354 42612228
Staphylococcal bacteraemia 33.32 20.24 20 5733 11101 42604481
Foetal hypokinesia 32.25 20.24 8 5745 382 42615200
Transplant rejection 32.06 20.24 21 5732 13567 42602015
Neonatal respiratory depression 30.83 20.24 8 5745 458 42615124
Osteomyelitis salmonella 29.55 20.24 5 5748 32 42615550
Penile exfoliation 29.26 20.24 6 5747 119 42615463
Skin ulcer 27.97 20.24 25 5728 25576 42590006
Essential thrombocythaemia 27.15 20.24 6 5747 172 42615410
Acute encephalitis with refractory, repetitive partial seizures 27.14 20.24 5 5748 55 42615527
Inhibitory drug interaction 27.03 20.24 10 5743 1864 42613718
Blister 26.44 20.24 25 5728 27465 42588117
Rash 25.82 20.24 89 5664 276865 42338717
Liver injury 25.61 20.24 21 5732 19127 42596455
Drug level below therapeutic 25.58 20.24 14 5739 6531 42609051
Type IV hypersensitivity reaction 24.48 20.24 10 5743 2427 42613155
Angioedema 23.79 20.24 29 5724 42448 42573134
Tubulointerstitial nephritis 23.55 20.24 25 5728 31523 42584059
Gastric ulcer 20.27 20.24 18 5735 18244 42597338

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
Metabolic acidosis 702.05 18.88 307 13066 99437 110476489
Pyroglutamic acidosis 440.28 18.88 90 13283 1978 110573948
Drug interaction 432.02 18.88 406 12967 499777 110076149
Pyroglutamate increased 203.21 18.88 39 13334 611 110575315
Drug level decreased 149.51 18.88 63 13310 18485 110557441
Cellulitis 133.04 18.88 115 13258 125901 110450025
Immunosuppressant drug level decreased 105.21 18.88 30 13343 2741 110573185
Acute kidney injury 99.89 18.88 230 13143 635200 109940726
Lip swelling 80.86 18.88 59 13314 50608 110525318
Drug reaction with eosinophilia and systemic symptoms 78.75 18.88 71 13302 82024 110493902
Swelling face 77.27 18.88 74 13299 92247 110483679
Stevens-Johnson syndrome 66.76 18.88 51 13322 46850 110529076
Drug level below therapeutic 57.09 18.88 28 13345 11645 110564281
Jaundice 56.34 18.88 51 13322 59185 110516741
Rash 53.29 18.88 218 13155 820746 109755180
Dermatitis allergic 53.17 18.88 33 13340 21691 110554235
Swollen tongue 51.66 18.88 49 13324 60313 110515613
Clostridium difficile infection 49.81 18.88 45 13328 52084 110523842
Neutropenic sepsis 49.49 18.88 36 13337 30710 110545216
Toxic epidermal necrolysis 48.45 18.88 46 13327 56681 110519245
Angioedema 47.40 18.88 59 13314 98441 110477485
Rash erythematous 44.24 18.88 52 13321 81780 110494146
Liver function test abnormal 37.58 18.88 44 13329 68906 110507020
Tubulointerstitial nephritis 37.10 18.88 39 13334 54245 110521681
Mouth swelling 37.04 18.88 18 13355 7336 110568590
Skin ulcer 37.01 18.88 42 13331 63603 110512323
Heart transplant rejection 34.98 18.88 12 13361 2009 110573917
Hypokalaemia 32.97 18.88 70 13303 182378 110393548
Perforation 32.31 18.88 11 13362 1799 110574127
Eczema herpeticum 31.37 18.88 8 13365 478 110575448
Skin exfoliation 30.71 18.88 45 13328 87606 110488320
Vascular device infection 30.42 18.88 21 13352 16491 110559435
Penile exfoliation 30.26 18.88 6 13367 112 110575814
Poor peripheral circulation 29.68 18.88 13 13360 4184 110571742
Acidosis 28.80 18.88 23 13350 22508 110553418
Kounis syndrome 28.34 18.88 14 13359 5911 110570015
Osteomyelitis salmonella 28.31 18.88 5 13368 48 110575878
Staphylococcal bacteraemia 27.90 18.88 20 13353 16668 110559258
Polyhydramnios 27.80 18.88 10 13363 1923 110574003
Chromaturia 27.36 18.88 25 13348 29335 110546591
Epidermal necrosis 26.72 18.88 11 13362 3039 110572887
Anion gap increased 26.08 18.88 12 13361 4332 110571594
Infusion related reaction 25.96 18.88 7 13366 381155 110194771
Sinusitis 25.47 18.88 3 13370 296685 110279241
Type IV hypersensitivity reaction 25.18 18.88 13 13360 6020 110569906
Transplant rejection 25.03 18.88 22 13351 24545 110551381
Congenital bowing of long bones 24.92 18.88 4 13369 20 110575906
Anterior interosseous syndrome 24.30 18.88 4 13369 24 110575902
Subclavian vein thrombosis 24.09 18.88 10 13363 2822 110573104
Strawberry tongue 24.03 18.88 4 13369 26 110575900
Pharyngeal swelling 23.83 18.88 16 13357 12016 110563910
Ejection fraction decreased 23.80 18.88 27 13346 40853 110535073
Sepsis 23.60 18.88 90 13283 327256 110248670
Mycobacterium marinum infection 23.38 18.88 7 13366 758 110575168
Erythrodermic atopic dermatitis 23.30 18.88 4 13369 32 110575894
Anaphylactic reaction 23.17 18.88 46 13327 114254 110461672
Essential thrombocythaemia 22.86 18.88 6 13367 402 110575524
Dermatitis bullous 22.63 18.88 18 13355 17511 110558415
Toxic shock syndrome 22.37 18.88 8 13365 1512 110574414
Kussmaul respiration 22.09 18.88 6 13367 458 110575468
Pustule 22.04 18.88 10 13363 3494 110572432
Acute encephalitis with refractory, repetitive partial seizures 21.83 18.88 4 13369 48 110575878
Labelled drug-drug interaction medication error 21.73 18.88 22 13351 29280 110546646
Acute haemorrhagic oedema of infancy 21.68 18.88 4 13369 50 110575876
Skin reaction 21.68 18.88 19 13354 21125 110554801
Angiodermatitis 21.66 18.88 5 13368 196 110575730
Gait disturbance 21.16 18.88 4 13369 278204 110297722
Gastric ulcer 21.00 18.88 25 13348 39802 110536124
Repetitive strain injury 20.94 18.88 5 13368 227 110575699
Glutathione synthetase deficiency 20.76 18.88 4 13369 64 110575862
Lymphoedema 20.72 18.88 16 13357 14913 110561013
Hiccups 20.55 18.88 15 13358 12854 110563072
Dermatitis exfoliative generalised 20.32 18.88 14 13359 10958 110564968
Rash macular 19.94 18.88 24 13349 38662 110537264
Hepatic enzyme increased 19.85 18.88 7 13366 320885 110255041
Malaise 19.82 18.88 144 13229 671675 109904251
Completed suicide 19.50 18.88 3 13370 242378 110333548
Reperfusion arrhythmia 19.44 18.88 5 13368 309 110575617
Vulvovaginal inflammation 19.25 18.88 6 13367 743 110575183
Staphylococcal infection 19.06 18.88 32 13341 69912 110506014
Post inflammatory pigmentation change 19.04 18.88 6 13367 771 110575155
Catheter site hypersensitivity 18.95 18.88 4 13369 103 110575823

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J01CF05 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:35441 antiinfective agent
CHEBI has role CHEBI:36047 antibacterial drug

Related Drugs by ATC class:

J01CF Beta-lactamase resistant penicillins 5 drugs
cloxacillindicloxacillinmeticillinnafcillinoxacillin

Drug Use | Suggest Off label Use Form| |View source of the data|

None




🐶 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
Androgen receptor Nuclear hormone receptor IC50 6.25 WOMBAT-PK
Matrix metalloproteinase-9 Enzyme IC50 4.19 WOMBAT-PK
Penicillin-binding protein 1A Enzyme WOMBAT-PK

External reference:

IDSource
N0000167002 NUI
D01249 KEGG_DRUG
C0016267 UMLSCUI
CHEBI:5098 CHEBI
CHEMBL222645 ChEMBL_ID
D005436 MESH_DESCRIPTOR_UI
DB00301 DRUGBANK_ID
21319 PUBCHEM_CID
235750 RXNORM
003516 NDDF
003517 NDDF
387544009 SNOMEDCT_US
426208000 SNOMEDCT_US
96067005 SNOMEDCT_US
10910 IUPHAR_LIGAND_ID
2308 INN_ID
43B2M34G2V UNII

Pharmaceutical products:

None