cefepime Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, cefalosporanic acid derivatives 535 88040-23-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cefepime dihydrochloride hydrate
  • cefepime
  • cefepime hydrochloride
  • cefimen
  • tsefepim
  • cefepime HCl
A fourth-generation cephalosporin antibacterial agent that is used in the treatment of infections, including those of the abdomen, urinary tract, respiratory tract, and skin. It is effective against PSEUDOMONAS AERUGINOSA and may also be used in the empiric treatment of FEBRILE NEUTROPENIA.
  • Molecular weight: 480.56
  • Formula: C19H24N6O5S2
  • CLOGP: -5.97
  • LIPINSKI: 1
  • HAC: 11
  • HDO: 2
  • TPSA: 150.04
  • ALOGS: -4.49
  • ROTB: 7

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
4 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 85 % Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability) 99 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.28 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2.20 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.78 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.90 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 18, 1996 FDA HOSPIRA INC

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
Acute kidney injury 348.39 66.71 102 708 28020 2329255
Status epilepticus 322.92 66.71 61 749 2417 2354858
Encephalopathy 303.04 66.71 64 746 4497 2352778
Myoclonus 206.10 66.71 42 768 2441 2354834
Neurotoxicity 158.86 66.71 33 777 2097 2355178
Sepsis 142.42 66.71 47 763 18441 2338834
Pyrexia 137.52 66.71 61 749 53647 2303628
Drug reaction with eosinophilia and systemic symptoms 132.50 66.71 34 776 5484 2351791
Mental status changes 132.11 66.71 34 776 5548 2351727
Tubulointerstitial nephritis 131.89 66.71 29 781 2409 2354866
Klebsiella infection 124.28 66.71 23 787 794 2356481
Thrombocytopenia 113.37 66.71 40 770 19091 2338184
Rash 112.91 66.71 55 755 59503 2297772
Confusional state 111.21 66.71 42 768 24302 2332973
Febrile neutropenia 105.43 66.71 33 777 10849 2346426
Drug hypersensitivity 100.18 66.71 47 763 46596 2310679
Clostridium difficile infection 90.19 66.71 22 788 2868 2354407
Drug resistance 87.12 66.71 21 789 2603 2354672
Blood creatinine increased 81.70 66.71 27 783 10506 2346769
Renal failure 72.08 66.71 28 782 17321 2339954
Pancytopenia 67.84 66.71 24 786 11428 2345847

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
Acute kidney injury 339.02 52.68 122 783 34822 1711054
Encephalopathy 249.74 52.68 61 844 4391 1741485
Myoclonus 189.00 52.68 43 862 2252 1743624
Tubulointerstitial nephritis 137.68 52.68 35 870 2923 1742953
Neurotoxicity 129.83 52.68 31 874 1993 1743883
Rash 126.59 52.68 63 842 38630 1707246
Drug ineffective 125.50 52.68 74 831 63727 1682149
Acute generalised exanthematous pustulosis 125.16 52.68 27 878 1095 1744781
Confusional state 121.05 52.68 51 854 21227 1724649
Status epilepticus 119.18 52.68 29 876 2017 1743859
Septic shock 110.75 52.68 37 868 8072 1737804
Pyrexia 110.19 52.68 61 844 46339 1699537
Thrombocytopenia 76.21 52.68 37 868 21212 1724664
Multiple organ dysfunction syndrome 76.06 52.68 29 876 9213 1736663
Clostridium difficile colitis 74.59 52.68 19 886 1585 1744291
Febrile neutropenia 74.36 52.68 30 875 11070 1734806
Drug reaction with eosinophilia and systemic symptoms 72.53 52.68 24 881 5046 1740830
Renal tubular necrosis 64.72 52.68 18 887 2101 1743775
Mental status changes 64.47 52.68 23 882 6052 1739824
Haemodialysis 60.97 52.68 18 887 2598 1743278
Neutropenia 60.03 52.68 30 875 18230 1727646
Enterococcal infection 58.70 52.68 14 891 887 1744989
Clostridium difficile infection 58.40 52.68 16 889 1765 1744111
Toxic epidermal necrolysis 58.27 52.68 17 888 2354 1743522
Botulism 55.95 52.68 8 897 23 1745853
Meningitis candida 54.10 52.68 7 898 6 1745870
Pancytopenia 53.71 52.68 24 881 11333 1734543
Drug resistance 53.09 52.68 17 888 3213 1742663
Drug hypersensitivity 53.07 52.68 26 879 15109 1730767

Pharmacologic Action:

SourceCodeDescription
ATC J01DE01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER BETA-LACTAM ANTIBACTERIALS
Fourth-generation cephalosporins
ATC J01RA06 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
COMBINATIONS OF ANTIBACTERIALS
Combinations of antibacterials
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
CHEBI has role CHEBI:36047 antibacterial drug
FDA EPC N0000175488 Cephalosporin Antibacterial
FDA CS M0003827 Cephalosporins

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Infection due to Pseudomonas aeruginosa indication 11218009
Pneumonia due to Streptococcus indication 34020007
Pneumonia due to Pseudomonas indication 41381004
Bacterial pneumonia indication 53084003 DOID:874
Klebsiella cystitis indication 60867007
Infectious disease of abdomen indication 128070006
Bacterial infection due to Klebsiella pneumoniae indication 186435004
Bacterial peritonitis indication 197171003
Pneumococcal pneumonia indication 233607000
Escherichia coli urinary tract infection indication 301011002
Proteus urinary tract infection indication 301012009
Streptococcus pyogenes infection indication 302809008
Bacterial urinary infection indication 312124009
Infection due to Staphylococcus aureus indication 406602003
Urinary tract infection caused by Klebsiella indication 369001000119100
Complicated Proteus UTI indication
E. Coli Pyelonephritis indication
Complicated Urinary Tract Infections indication
Complicated Bacteroides Peritonitis indication
Complicated Streptococcus Peritonitis indication
Klebsiella Pyelonephritis indication
Complicated E. Coli Peritonitis indication
Enterobacter Pneumonia indication
Complicated Klebsiella Peritonitis indication
Proteus Pyelonephritis indication
Myoclonus contraindication 17450006
Colitis contraindication 64226004 DOID:0060180
Blood coagulation disorder contraindication 64779008 DOID:1247
Factor II deficiency contraindication 73975000
Disorder of brain contraindication 81308009 DOID:936
Seizure disorder contraindication 128613002
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 2.32 acidic
pKa2 13.31 acidic
pKa3 3.1 Basic

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
Bacterial penicillin-binding protein Enzyme INHIBITOR CHEMBL CHEMBL

External reference:

IDSource
D000077723 MESH_DESCRIPTOR_UI
4024049 VUID
N0000022054 NUI
C0055003 UMLSCUI
D01157 KEGG_DRUG
370371004 SNOMEDCT_US
d03882 MMSL
20481 RXNORM
96048006 SNOMEDCT_US
4024049 VANDF
004974 NDDF
807PW4VQE3 UNII
6092 INN_ID
CHEMBL186 ChEMBL_ID
123171-59-5 SECONDARY_CAS_RN
9WT PDB_CHEM_ID
DB01413 DRUGBANK_ID
CHEBI:478164 CHEBI
CHEMBL1200962 ChEMBL_ID
5479537 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
CEFEPIME HYDROCHLORIDE AND DEXTROSE HUMAN PRESCRIPTION DRUG LABEL 1 0264-3193 INJECTION, SOLUTION 1 g INTRAVENOUS NDA 19 sections
CEFEPIME HYDROCHLORIDE AND DEXTROSE HUMAN PRESCRIPTION DRUG LABEL 1 0264-3195 INJECTION, SOLUTION 2 g INTRAVENOUS NDA 19 sections
Cefepime HUMAN PRESCRIPTION DRUG LABEL 1 0338-1301 INJECTION, SOLUTION 1 g INTRAVENOUS NDA 18 sections
Cefepime Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-3222 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 14 sections
Cefepime Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-3223 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 14 sections
cefepime HUMAN PRESCRIPTION DRUG LABEL 1 25021-121 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 17 sections
cefepime HUMAN PRESCRIPTION DRUG LABEL 1 25021-122 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 17 sections
Cefepime HUMAN PRESCRIPTION DRUG LABEL 1 44567-240 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 17 sections
Cefepime HUMAN PRESCRIPTION DRUG LABEL 1 44567-241 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 17 sections
Cefepime HUMAN PRESCRIPTION DRUG LABEL 1 60505-6144 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 17 sections
Cefepime HUMAN PRESCRIPTION DRUG LABEL 1 60505-6145 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 17 sections
Cefepime HUMAN PRESCRIPTION DRUG LABEL 1 60505-6146 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 17 sections
Cefepime HUMAN PRESCRIPTION DRUG LABEL 1 60505-6147 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 17 sections
Cefepime HUMAN PRESCRIPTION DRUG LABEL 1 63323-326 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 17 sections
Cefepime HUMAN PRESCRIPTION DRUG LABEL 1 63323-340 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 17 sections
CEFEPIME HUMAN PRESCRIPTION DRUG LABEL 1 66288-8100 INJECTION, POWDER, FOR SOLUTION 100 g INTRAVENOUS ANDA 18 sections
Cefepime HUMAN PRESCRIPTION DRUG LABEL 1 66794-209 INJECTION, POWDER, FOR SOLUTION 10 g INTRAMUSCULAR ANDA 15 sections
Cefepime HUMAN PRESCRIPTION DRUG LABEL 1 66794-210 INJECTION, POWDER, FOR SOLUTION 20 g INTRAVENOUS ANDA 15 sections
Cefepime HUMAN PRESCRIPTION DRUG LABEL 1 67184-1002 INJECTION, POWDER, FOR SOLUTION 500 mg INTRAVENOUS ANDA 17 sections
Cefepime HUMAN PRESCRIPTION DRUG LABEL 1 67184-1003 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 17 sections
Cefepime HUMAN PRESCRIPTION DRUG LABEL 1 67184-1004 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 17 sections
Cefepime HUMAN PRESCRIPTION DRUG LABEL 1 71288-008 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 17 sections
Cefepime HUMAN PRESCRIPTION DRUG LABEL 1 71288-009 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 17 sections