cefixime 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: 0.25
  • 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 ┬ÁM/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 66.05 21.03 79 3027 265163 53080797
Gastroenteritis staphylococcal 43.40 21.03 7 3099 83 53345877
Secretion discharge 33.64 21.03 15 3091 10491 53335469
Panic attack 31.35 21.03 18 3088 21400 53324560
Mucocutaneous candidiasis 30.61 21.03 4 3102 8 53345952
Dysbiosis 29.89 21.03 7 3099 615 53345345
Biopsy colon abnormal 27.44 21.03 5 3101 126 53345834
Movement disorder 25.48 21.03 15 3091 18666 53327294
Gastrointestinal mucosa hyperaemia 25.45 21.03 5 3101 190 53345770
Pulmonary congestion 24.77 21.03 14 3092 16142 53329818
Oligohydramnios 23.79 21.03 10 3096 6066 53339894
Vaginal infection 23.08 21.03 10 3096 6531 53339429
Foetal growth restriction 22.19 21.03 10 3096 7164 53338796
Premature baby 22.14 21.03 14 3092 19787 53326173
Pulmonary mass 22.00 21.03 14 3092 19990 53325970
Candida test positive 21.85 21.03 6 3100 998 53344962
Disorientation 21.43 21.03 18 3088 39341 53306619

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 44.37 25.15 8 1423 254 32511841
Psoriatic arthropathy 36.14 25.15 17 1414 17843 32494252

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 (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

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

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
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
SUPRAX HUMAN PRESCRIPTION DRUG LABEL 1 70934-079 CAPSULE 400 mg ORAL NDA 28 sections