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

Stem definitionDrug idCAS RN
antibiotics, cefalosporanic acid derivatives 537 79350-37-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cefixime
  • cefixim
  • cefiximine
  • cefixoral
A third-generation cephalosporin antibiotic that is stable to hydrolysis by beta-lactamases.
  • Molecular weight: 453.44
  • Formula: C16H15N5O7S2
  • CLOGP: -0.17
  • LIPINSKI: 1
  • HAC: 12
  • HDO: 4
  • TPSA: 184.51
  • ALOGS: -3.64
  • ROTB: 8
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.40 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 4 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.10 mg/mL Bocci G, Oprea TI, Benet LZ
EoM (Fraction excreted unchanged in urine) 41 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 29.33 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 47 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.24 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.31 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 3.20 hours Lombardo F, Berellini G, Obach RS

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 -2.777 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.839 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 0.378 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 2.099 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 48.100 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 52.930 % High 1
herg hERG pIC50 4.239 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 1.928 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 4.009 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 29.570 % High 1
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,AKT3,ALK,AURKA,AURKC,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,CSF1R,DDR1,DYRK1B,DYRK3,EGFR,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GRK3,GSK3B,HIPK2,IKBKB,ITK,JAK1,JAK2,KDR,KIT,MAP2K6,MAP3K14,MAP3K2,MAP3K21,MAP3K3,MAP3K7,MAP4K1,MAP4K3,MAPK1,MAPK10,MAPK12,MAPK7,MAPK9,MAPKAPK2,MAPKAPK5,MARK4,MTOR,NTRK1,NTRK2,PDK1,PDK2,PDK4,PIK3CA,PIK3CB,PIK3CD,PIK3CG,PIM1,PIM2,PIM3,PRKAA1,PRKCD,PRKDC,SGK1,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ULK1,ULK2,ZAP70 77
kinase-selectivity-class ACVR2B,AURKC,AXL,BRAF,CDK4,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,GRK2,IKBKB,JAK2,MAP2K6,MAP3K14,MAP3K2,MAPK12,MAPK7,MAPK8,PIM3,PRKAA1,PRKDC,STK33,SYK,TEK,TGFBR1,TTK,UHMK1 29
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 0.550 High 1
mh-clint Mouse hepatocyte intrinsic clearance 3.162 High 1
mppb Mouse plasma protein binding (% unbound) 61.480 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 0.207 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 34.890 % High 1
rh-clint Rat hepatocyte intrinsic clearance 1.135 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 92.670 % High 1
rppb Rat plasma protein binding (% unbound) 21.480 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 866.962 uM High 1

Approvals:

DateAgencyCompanyOrphan
April 28, 1989 FDA

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
Macular degeneration 75.07 16.88 41 6122 37929 90584355
Gastroenteritis staphylococcal 42.62 16.88 7 6156 79 90622205
Clostridium difficile infection 42.56 16.88 28 6135 36217 90586067
Clostridium difficile colitis 42.42 16.88 25 6138 26681 90595603
Secretion discharge 36.57 16.88 19 6144 15877 90606407
Paraesthesia oral 36.06 16.88 24 6139 31635 90590649
Toxic epidermal necrolysis 35.47 16.88 24 6139 32504 90589780
Vaginal flatulence 34.62 16.88 17 6146 12621 90609663
Female genital tract fistula 34.48 16.88 19 6144 17849 90604435
Drug hypersensitivity 34.12 16.88 88 6075 463521 90158763
Radiculopathy 33.86 16.88 19 6144 18486 90603798
Pulmonary congestion 33.00 16.88 19 6144 19414 90602870
Stevens-Johnson syndrome 32.81 16.88 22 6141 29354 90592930
Proctitis 31.60 16.88 17 6146 15242 90607042
Vaginal discharge 30.33 16.88 18 6145 19446 90602838
Dysbiosis 30.31 16.88 9 6154 1693 90620591
Chronic sinusitis 29.44 16.88 19 6144 23783 90598501
Mucocutaneous candidiasis 29.10 16.88 4 6159 11 90622273
Premature baby 28.53 16.88 19 6144 25058 90597226
Panic attack 27.67 16.88 19 6144 26346 90595938
Biopsy colon abnormal 27.58 16.88 5 6158 104 90622180
Procedural pain 25.83 16.88 20 6143 33340 90588944
Ankylosing spondylitis 25.44 16.88 14 6149 13119 90609165
Gastrointestinal mucosa hyperaemia 24.19 16.88 5 6158 210 90622074
Erythema 23.96 16.88 50 6113 229196 90393088
Movement disorder 23.79 16.88 18 6145 29001 90593283
Frequent bowel movements 23.69 16.88 24 6139 56911 90565373
Clostridium test positive 23.42 16.88 10 6153 5391 90616893
Vaginal infection 22.07 16.88 11 6152 8429 90613855
Pulmonary mass 21.73 16.88 17 6146 28755 90593529
Drug reaction with eosinophilia and systemic symptoms 21.50 16.88 20 6143 42738 90579546
Malignant melanoma in situ 21.10 16.88 6 6157 970 90621314
Foetal growth restriction 20.97 16.88 11 6152 9369 90612915
Candida test positive 20.72 16.88 6 6157 1033 90621251
Oligohydramnios 20.66 16.88 10 6153 7191 90615093
Apraxia 19.88 16.88 7 6156 2255 90620029
Febrile neutropenia 19.49 16.88 37 6126 158312 90463972
Meniscus injury 19.39 16.88 10 6153 8227 90614057
Haematochezia 19.37 16.88 24 6139 70889 90551395
COVID-19 19.02 16.88 38 6125 168805 90453479
Neutropenia 18.93 16.88 45 6118 224859 90397425
Oral candidiasis 18.63 16.88 17 6146 35438 90586846
Off label use 18.50 16.88 133 6030 1102119 89520165
Anaemia 18.18 16.88 59 6104 352743 90269541
Colitis 18.03 16.88 23 6140 69919 90552365
Abdominal pain 17.61 16.88 63 6100 395658 90226626
Disorientation 17.27 16.88 18 6145 44096 90578188
Acute generalised exanthematous pustulosis 17.09 16.88 11 6152 13692 90608592
Circumoral oedema 17.07 16.88 4 6159 301 90621983
Tubulointerstitial nephritis 17.06 16.88 14 6149 25329 90596955
Atypical mycobacterial pneumonia 16.96 16.88 3 6160 54 90622230

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
Oral pustule 41.97 20.68 8 2708 236 42618383
Tracheobronchitis bacterial 32.22 20.68 5 2711 41 42618578
Pyrexia 29.37 20.68 72 2644 393970 42224649
Psoriatic arthropathy 27.31 20.68 18 2698 24949 42593670
Pulmonary congestion 26.62 20.68 15 2701 15715 42602904
Heat exhaustion 25.06 20.68 5 2711 188 42618431
Urticaria 24.91 20.68 27 2689 74009 42544610
Clostridium difficile colitis 22.46 20.68 15 2701 21237 42597382
Septic shock 21.81 20.68 28 2688 91644 42526975
Tendon pain 21.33 20.68 8 2708 3292 42615327
Carnitine deficiency 20.92 20.68 4 2712 120 42618499

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
Clostridium difficile colitis 66.03 16.69 41 8221 43737 110537300
Pulmonary congestion 59.75 16.69 34 8228 30932 110550105
Secretion discharge 55.27 16.69 28 8234 20216 110560821
Toxic epidermal necrolysis 47.48 16.69 37 8225 56690 110524347
Panic attack 45.91 16.69 28 8234 28912 110552125
Oropharyngeal gonococcal infection 41.99 16.69 6 8256 21 110581016
Oral pustule 39.57 16.69 8 8254 273 110580764
Pulmonary mass 39.43 16.69 28 8234 37273 110543764
Stevens-Johnson syndrome 37.97 16.69 30 8232 46871 110534166
Movement disorder 37.73 16.69 27 8235 36377 110544660
Clostridium difficile infection 37.25 16.69 31 8231 52098 110528939
Clostridium test positive 35.50 16.69 17 8245 10876 110570161
Febrile neutropenia 35.34 16.69 75 8187 316692 110264345
Female genital tract fistula 34.20 16.69 19 8243 16500 110564537
Vaginal flatulence 33.74 16.69 17 8245 12127 110568910
Gastroenteritis staphylococcal 32.81 16.69 7 8255 312 110580725
Paraesthesia oral 32.68 16.69 24 8238 33647 110547390
Acute generalised exanthematous pustulosis 31.92 16.69 20 8242 21644 110559393
Dysbiosis 31.56 16.69 10 8252 2122 110578915
Erythema 31.34 16.69 68 8194 291379 110289658
Proctitis 31.08 16.69 18 8244 16909 110564128
Vaginal discharge 30.14 16.69 18 8244 17890 110563147
Macular degeneration 29.44 16.69 19 8243 21640 110559397
Radiculopathy 28.87 16.69 18 8244 19318 110561719
Oral candidiasis 28.67 16.69 25 8237 44735 110536302
Biopsy colon abnormal 27.74 16.69 5 8257 91 110580946
Chronic sinusitis 26.90 16.69 19 8243 25065 110555972
Pyrexia 26.75 16.69 135 8127 898130 109682907
Procedural pain 25.09 16.69 21 8241 35544 110545493
Pneumonia mycoplasmal 25.09 16.69 8 8254 1733 110579304
Tendon pain 24.10 16.69 11 8251 6315 110574722
Vaginal infection 23.34 16.69 11 8251 6793 110574244
Drug reaction with eosinophilia and systemic symptoms 22.22 16.69 29 8233 82066 110498971
Ankylosing spondylitis 21.97 16.69 14 8248 15598 110565439
Drug hypersensitivity 21.83 16.69 79 8183 454011 110127026
COVID-19 21.72 16.69 53 8209 245007 110336030
Neutropenia 21.35 16.69 69 8193 374551 110206486
Mucocutaneous candidiasis 21.14 16.69 4 8258 96 110580941
Tubulointerstitial nephritis 20.99 16.69 23 8239 54261 110526776
Agranulocytosis 20.21 16.69 24 8238 61736 110519301
Frequent bowel movements 18.98 16.69 25 8237 71365 110509672
Gastrointestinal mucosa hyperaemia 18.89 16.69 5 8257 563 110580474
Colitis 18.69 16.69 30 8232 102293 110478744
Candida test positive 18.60 16.69 6 8256 1349 110579688
Restless legs syndrome 18.33 16.69 15 8247 24611 110556426
Pseudomembranous colitis 17.91 16.69 9 8253 6382 110574655
Food protein-induced enterocolitis syndrome 17.59 16.69 3 8259 39 110580998
Haematochezia 17.30 16.69 31 8231 115493 110465544
Paralysis 17.15 16.69 12 8250 15588 110565449
Rash maculo-papular 16.73 16.69 24 8238 74198 110506839

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J01DD08 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER BETA-LACTAM ANTIBACTERIALS
Third-generation cephalosporins
ATC J01DD58 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER BETA-LACTAM ANTIBACTERIALS
Third-generation cephalosporins
ATC J01RA15 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
COMBINATIONS OF ANTIBACTERIALS
Combinations of antibacterials
ATC J01RA16 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
COMBINATIONS OF ANTIBACTERIALS
Combinations of antibacterials
MeSH PA D000097902 beta Lactam Antibiotics
MeSH PA D000097911 Third Generation Cephalosporins
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:35610 antineoplastic agent
CHEBI has role CHEBI:36047 antibacterial drug
CHEBI has role CHEBI:64946 anti-HIV agent
CHEBI has role CHEBI:88188 drug allergen

Related Drugs by ATC class:

J01DD Third-generation cephalosporins 17 drugs
cefcapenecefdinircefditoren pivoxilcefetametcefmenoximecefodizimecefoperazonecefotaximecefpiramidecefpodoxime proxetilcefsulodinceftazidime show all 17 →
J01RA Combinations of antibacterials 18 drugs
amikacinazithromycincefepimecefuroximeciprofloxacinfluconazolelevofloxacinmetronidazolenitazoxanidenorfloxacinnystatinofloxacin show all 18 →

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

DiseaseRelationSNOMED_IDDOID
Acute otitis media indication 3110003
Gonorrhea indication 15628003 DOID:7551
Haemophilus Influenzae Acute Otitis Media indication 19021002
Acute gonococcal cervicitis indication 20943002 DOID:10615
Acute gonococcal urethritis indication 29864006
Bronchitis indication 32398004 DOID:6132
Streptococcal tonsillitis indication 41582007
Upper respiratory infection indication 54150009
Urinary tract infectious disease indication 68566005
Tonsillitis indication 90176007 DOID:10456
Acute bacterial bronchitis indication 233598009
Escherichia coli urinary tract infection indication 301011002
Proteus urinary tract infection indication 301012009
Streptococcus pyogenes infection indication 302809008
Infective otitis media indication 312218008
Pharyngitis indication 405737000 DOID:2275
Acute exacerbation of chronic bronchitis indication 425748003
Moraxella Catarrhalis Acute Otitis Media indication 703469002
Haemophilus Influenzae Bronchitis indication
Haemophilus Influenzae Chronic Bronchitis indication
Streptococcus Pneumoniae Chronic Bronchitis indication
Streptococcus Pneumoniae Bronchitis indication
Pneumonia due to Escherichia coli off-label use 51530003
Acute bacterial sinusitis off-label use 75498004
Haemophilus Parahaemolyticus Pneumonia off-label use
Haemophilus Parainfluenzae Pneumonia off-label use
Impaired renal function disorder contraindication 197663003
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 2.45 acidic
pKa2 2.54 acidic
pKa3 3.24 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
500MG/5ML SUPRAX LUPIN LTD N202091 Feb. 20, 2013 RX FOR SUSPENSION ORAL 9233112 Dec. 14, 2028 METHODS FOR TREATING BACTERIAL INFECTIONS

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
D(2) dopamine receptor GPCR IC50 4.24 WOMBAT-PK
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1 Enzyme IC50 5.92 CHEMBL
Bacterial penicillin-binding protein Enzyme INHIBITOR CHEMBL CHEMBL
Streptokinase A Enzyme EC50 7.22 WOMBAT-PK

External reference:

IDSource
4019391 VUID
N0000147544 NUI
D00258 KEGG_DRUG
125110-14-7 SECONDARY_CAS_RN
25033 RXNORM
C0060400 UMLSCUI
CHEBI:472657 CHEBI
C04 PDB_CHEM_ID
CHEMBL1541 ChEMBL_ID
D020682 MESH_DESCRIPTOR_UI
DB00671 DRUGBANK_ID
10898 IUPHAR_LIGAND_ID
97I1C92E55 UNII
5362065 PUBCHEM_CID
233747 MMSL
4374 MMSL
d00072 MMSL
387536009 SNOMEDCT_US
96052006 SNOMEDCT_US
4019391 VANDF
002737 NDDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Cefixime Human Prescription Drug Label 1 59651-647 CAPSULE 400 mg ORAL ANDA 24 sections
Cefixime HUMAN PRESCRIPTION DRUG LABEL 1 64980-430 TABLET 400 mg ORAL ANDA 21 sections
Cefixime Human Prescription Drug Label 1 65862-751 POWDER, FOR SUSPENSION 100 mg ORAL ANDA 25 sections
Cefixime Human Prescription Drug Label 1 65862-752 POWDER, FOR SUSPENSION 200 mg ORAL ANDA 25 sections
CEFIXIME Human Prescription Drug Label 1 67877-584 CAPSULE 400 mg ORAL ANDA 24 sections
CEFIXIME HUMAN PRESCRIPTION DRUG LABEL 1 68180-405 POWDER, FOR SUSPENSION 100 mg ORAL ANDA 25 sections
CEFIXIME HUMAN PRESCRIPTION DRUG LABEL 1 68180-405 POWDER, FOR SUSPENSION 100 mg ORAL ANDA 25 sections
CEFIXIME HUMAN PRESCRIPTION DRUG LABEL 1 68180-407 POWDER, FOR SUSPENSION 200 mg ORAL ANDA 25 sections
CEFIXIME HUMAN PRESCRIPTION DRUG LABEL 1 68180-407 POWDER, FOR SUSPENSION 200 mg ORAL ANDA 25 sections
CEFIXIME HUMAN PRESCRIPTION DRUG LABEL 1 68180-416 CAPSULE 400 mg ORAL ANDA 25 sections
CEFIXIME HUMAN PRESCRIPTION DRUG LABEL 1 68180-416 CAPSULE 400 mg ORAL ANDA 25 sections
CEFIXIME HUMAN PRESCRIPTION DRUG LABEL 1 68180-423 CAPSULE 400 mg ORAL NDA authorized generic 25 sections
CEFIXIME HUMAN PRESCRIPTION DRUG LABEL 1 68180-423 CAPSULE 400 mg ORAL NDA authorized generic 25 sections
CEFIXIME HUMAN PRESCRIPTION DRUG LABEL 1 70518-2749 CAPSULE 400 mg ORAL ANDA 24 sections
CEFIXIME HUMAN PRESCRIPTION DRUG LABEL 1 70518-3221 CAPSULE 400 mg ORAL NDA authorized generic 25 sections
SUPRAX HUMAN PRESCRIPTION DRUG LABEL 1 70934-079 CAPSULE 400 mg ORAL NDA 28 sections
Cefixime 400 mg HUMAN PRESCRIPTION DRUG LABEL 1 83112-400 CAPSULE 400 mg ORAL ANDA 2 sections