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) 0.10 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 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 54.10 17.87 83 4102 310604 63174233
Gastroenteritis staphylococcal 43.35 17.87 7 4178 73 63484764
Secretion discharge 32.64 17.87 16 4169 12215 63472622
Panic attack 31.11 17.87 19 4166 22312 63462525
Clostridium difficile infection 30.69 17.87 21 4164 29901 63454936
Pulmonary congestion 29.99 17.87 17 4168 17401 63467436
Mucocutaneous candidiasis 29.22 17.87 4 4181 11 63484826
Toxic epidermal necrolysis 28.91 17.87 19 4166 25315 63459522
Biopsy colon abnormal 27.51 17.87 5 4180 109 63484728
Dysbiosis 26.41 17.87 7 4178 899 63483938
Gastrointestinal mucosa hyperaemia 24.56 17.87 5 4180 201 63484636
Movement disorder 24.12 17.87 16 4169 21645 63463192
Vaginal infection 23.61 17.87 11 4174 7507 63477330
Foetal growth restriction 23.56 17.87 11 4174 7542 63477295
Premature baby 22.32 17.87 15 4170 20720 63464117
Oligohydramnios 22.14 17.87 10 4175 6356 63478481
Stevens-Johnson syndrome 22.07 17.87 16 4169 24934 63459903
Candida test positive 21.79 17.87 6 4179 890 63483947
Malignant melanoma in situ 21.56 17.87 6 4179 926 63483911
Pseudomembranous colitis 21.52 17.87 8 4177 3104 63481733
Pulmonary mass 21.16 17.87 15 4170 22581 63462256
Atypical mycobacterial pneumonia 19.65 17.87 3 4182 21 63484816
Disorientation 19.45 17.87 18 4167 39434 63445403
Neutropenia 18.92 17.87 38 4147 174967 63309870
Vanishing bile duct syndrome 18.26 17.87 5 4180 727 63484110
Circumoral oedema 18.12 17.87 4 4181 238 63484599
Meniscus injury 18.07 17.87 9 4176 7105 63477732

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 42.57 22.73 8 2002 243 34954678
Psoriatic arthropathy 30.16 22.73 17 1993 19781 34935140
Urticaria 25.31 22.73 24 1986 62353 34892568
Tendon pain 22.90 22.73 8 2002 2987 34951934
Acute generalised exanthematous pustulosis 22.86 22.73 10 2000 6766 34948155

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 51.62 17.14 24 5692 14998 79723674
Panic attack 48.89 17.14 27 5689 24189 79714483
Pulmonary congestion 48.71 17.14 28 5688 27072 79711600
Oral pustule 39.90 17.14 8 5708 273 79738399
Toxic epidermal necrolysis 38.22 17.14 29 5687 44552 79694120
Movement disorder 38.19 17.14 24 5692 27235 79711437
Drug hypersensitivity 38.15 17.14 73 5643 298843 79439829
Pulmonary mass 36.81 17.14 24 5692 29010 79709662
Clostridium difficile colitis 34.49 17.14 24 5692 32259 79706413
Acute generalised exanthematous pustulosis 34.17 17.14 19 5697 17235 79721437
Gastroenteritis staphylococcal 33.34 17.14 7 5709 301 79738371
Psoriatic arthropathy 31.24 17.14 33 5683 77966 79660706
Dysbiosis 28.23 17.14 8 5708 1211 79737461
Stevens-Johnson syndrome 28.22 17.14 23 5693 39143 79699529
Biopsy colon abnormal 27.70 17.14 5 5711 96 79738576
Pseudomembranous colitis 26.27 17.14 11 5705 5363 79733309
Agranulocytosis 25.43 17.14 23 5693 45007 79693665
Vaginal infection 25.31 17.14 11 5705 5869 79732803
Clostridium difficile infection 22.54 17.14 21 5695 42664 79696008
Pneumonia mycoplasmal 22.45 17.14 7 5709 1471 79737201
Mucocutaneous candidiasis 21.35 17.14 4 5712 95 79738577
Clostridium test positive 21.21 17.14 10 5706 6444 79732228
Urticaria 20.89 17.14 43 5673 185158 79553514
Febrile neutropenia 20.81 17.14 49 5667 230950 79507722
Drug reaction with eosinophilia and systemic symptoms 20.26 17.14 24 5692 64220 79674452
Candida test positive 20.04 17.14 6 5710 1100 79737572
Gastrointestinal mucosa hyperaemia 19.88 17.14 5 5711 480 79738192
Neutropenia 19.68 17.14 55 5661 287655 79451017
Tendon pain 19.31 17.14 9 5707 5649 79733023
Food protein-induced enterocolitis syndrome 17.72 17.14 3 5713 39 79738633
Pyrexia 17.42 17.14 95 5621 678614 79060058
Carnitine deficiency 17.19 17.14 4 5712 277 79738395

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
ATC J01RA16 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
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




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
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
125110-14-7 SECONDARY_CAS_RN
002737 NDDF

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 16714-766 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
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 43598-673 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
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
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 62250-663 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 62250-664 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 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
SUPRAX HUMAN PRESCRIPTION DRUG LABEL 1 68180-202 POWDER, FOR SUSPENSION 100 mg ORAL ANDA 27 sections