cefixime ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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) 0.06 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 41 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 29.33 ยตM/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

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
Drug hypersensitivity 63.75 20.26 80 3229 250930 50350885
Gastroenteritis staphylococcal 43.67 20.26 7 3302 70 50601745
Secretion discharge 32.98 20.26 15 3294 9776 50592039
Panic attack 31.11 20.26 18 3291 19324 50582491
Mucocutaneous candidiasis 30.15 20.26 4 3305 8 50601807
Pulmonary congestion 29.44 20.26 16 3293 15231 50586584
Dysbiosis 28.67 20.26 7 3302 653 50601162
Biopsy colon abnormal 27.55 20.26 5 3304 109 50601706
Gastrointestinal mucosa hyperaemia 25.06 20.26 5 3304 183 50601632
Movement disorder 24.67 20.26 15 3294 17617 50584198
Oligohydramnios 23.20 20.26 10 3299 5740 50596075
Vaginal infection 22.42 20.26 10 3299 6226 50595589
Malignant melanoma in situ 22.33 20.26 6 3303 819 50600996
Candida test positive 22.05 20.26 6 3303 858 50600957
Foetal growth restriction 21.84 20.26 10 3299 6617 50595198
Premature baby 21.63 20.26 14 3295 18323 50583492
Pulmonary mass 21.38 20.26 14 3295 18691 50583124
Disorientation 21.23 20.26 18 3291 35466 50566349
Drug reaction with eosinophilia and systemic symptoms 20.33 20.26 16 3293 28408 50573407

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 43.95 24.91 8 1425 243 29572851
Psoriatic arthropathy 37.75 24.91 17 1416 14674 29558420

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
Secretion discharge 54.52 18.90 23 4406 11941 64482362
Panic attack 50.76 18.90 26 4403 20927 64473376
Drug hypersensitivity 48.54 18.90 70 4359 237745 64256558
Pulmonary congestion 44.81 18.90 25 4404 23855 64470448
Psoriatic arthropathy 44.75 18.90 31 4398 43250 64451053
Movement disorder 41.19 18.90 23 4406 21977 64472326
Oral pustule 40.33 18.90 8 4421 270 64494033
Pulmonary mass 39.31 18.90 23 4406 23993 64470310
Clostridium difficile colitis 39.18 18.90 24 4405 27199 64467104
Gastroenteritis staphylococcal 34.31 18.90 7 4422 273 64494030
Dysbiosis 31.02 18.90 8 4421 887 64493416
Biopsy colon abnormal 27.91 18.90 5 4424 96 64494207
Agranulocytosis 25.33 18.90 21 4408 38208 64456095
Mucocutaneous candidiasis 24.76 18.90 4 4425 40 64494263
Acute generalised exanthematous pustulosis 24.43 18.90 14 4415 14044 64480259
Pseudomembranous colitis 24.23 18.90 10 4419 4906 64489397
Vaginal infection 24.23 18.90 10 4419 4910 64489393
Drug reaction with eosinophilia and systemic symptoms 22.65 18.90 23 4406 54194 64440109
Gastrointestinal mucosa hyperaemia 20.76 18.90 5 4424 419 64493884
Candida test positive 20.49 18.90 6 4423 1064 64493239
Psoriasis 18.98 18.90 24 4405 71679 64422624

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 J01RA15 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
COMBINATIONS OF ANTIBACTERIALS
Combinations of antibacterials
CHEBI has role CHEBI:36047 antibacterial drugs
CHEBI has role CHEBI:88188 allergenic drug
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents

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

DiseaseRelationSNOMED_IDDOID
Acute otitis media indication 3110003
Gonorrhea indication 15628003 DOID:7551
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
Haemophilus Influenzae Acute Otitis Media indication
Haemophilus Influenzae Chronic Bronchitis indication
Streptococcus Pneumoniae Chronic Bronchitis indication
Haemophilus Influenzae Bronchitis indication
Moraxella Catarrhalis Acute Otitis Media 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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ 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
25033 RXNORM
4019391 VANDF
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
002737 NDDF
387536009 SNOMEDCT_US
96052006 SNOMEDCT_US
125110-14-7 SECONDARY_CAS_RN

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Cefixime HUMAN PRESCRIPTION DRUG LABEL 1 16714-766 POWDER, FOR SUSPENSION 100 mg ORAL ANDA 27 sections
Cefixime HUMAN PRESCRIPTION DRUG LABEL 1 16714-767 POWDER, FOR SUSPENSION 200 mg ORAL ANDA 27 sections
SUPRAX HUMAN PRESCRIPTION DRUG LABEL 1 27437-201 TABLET 400 mg ORAL ANDA 27 sections
SUPRAX HUMAN PRESCRIPTION DRUG LABEL 1 27437-203 TABLET, CHEWABLE 100 mg ORAL ANDA 19 sections
SUPRAX HUMAN PRESCRIPTION DRUG LABEL 1 27437-203 TABLET, CHEWABLE 100 mg ORAL ANDA 19 sections
SUPRAX HUMAN PRESCRIPTION DRUG LABEL 1 27437-205 TABLET, CHEWABLE 200 mg ORAL ANDA 19 sections
SUPRAX HUMAN PRESCRIPTION DRUG LABEL 1 27437-205 TABLET, CHEWABLE 200 mg ORAL ANDA 19 sections
SUPRAX HUMAN PRESCRIPTION DRUG LABEL 1 27437-206 POWDER, FOR SUSPENSION 200 mg ORAL ANDA 27 sections
SUPRAX HUMAN PRESCRIPTION DRUG LABEL 1 27437-207 POWDER, FOR SUSPENSION 500 mg ORAL NDA 27 sections
SUPRAX HUMAN PRESCRIPTION DRUG LABEL 1 27437-208 CAPSULE 400 mg ORAL NDA 27 sections
Cefixime HUMAN PRESCRIPTION DRUG LABEL 1 43598-673 POWDER, FOR SUSPENSION 100 mg ORAL ANDA 22 sections
Cefixime HUMAN PRESCRIPTION DRUG LABEL 1 43598-674 POWDER, FOR SUSPENSION 200 mg ORAL ANDA 22 sections
SUPRAX HUMAN PRESCRIPTION DRUG LABEL 1 54348-797 CAPSULE 400 mg ORAL ANDA 27 sections
Cefixime HUMAN PRESCRIPTION DRUG LABEL 1 62250-663 POWDER, FOR SUSPENSION 100 mg ORAL ANDA 27 sections
Cefixime HUMAN PRESCRIPTION DRUG LABEL 1 62250-664 POWDER, FOR SUSPENSION 200 mg ORAL ANDA 27 sections
Cefixime HUMAN PRESCRIPTION DRUG LABEL 1 62250-668 POWDER, FOR SUSPENSION 500 mg ORAL ANDA 27 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 67877-584 CAPSULE 400 mg ORAL ANDA 24 sections
SUPRAX HUMAN PRESCRIPTION DRUG LABEL 1 68180-202 POWDER, FOR SUSPENSION 100 mg ORAL ANDA 27 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 68180-416 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 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
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