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

Stem definitionDrug idCAS RN
antibiotics, cefalosporanic acid derivatives 546 63527-52-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • cefotaxime
  • cefotaxime sodium
  • cephotaxime
  • cefotaxime sodium salt
Semisynthetic broad-spectrum cephalosporin.
  • Molecular weight: 455.46
  • Formula: C16H17N5O7S2
  • CLOGP: 0.14
  • LIPINSKI: 1
  • HAC: 12
  • HDO: 3
  • TPSA: 173.51
  • ALOGS: -3.49
  • ROTB: 8

  • 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) 30 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 376.38 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 0.19 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2.70 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.60 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.20 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
March 11, 1981 FDA SANOFI AVENTIS US

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 reaction with eosinophilia and systemic symptoms 212.46 25.53 91 5424 32709 53310842
Hepatocellular injury 100.79 25.53 53 5462 29933 53313618
Eosinophilia 99.17 25.53 47 5468 21288 53322263
Premature baby 87.09 25.53 42 5473 19759 53323792
Toxic epidermal necrolysis 83.06 25.53 43 5472 23507 53320044
Patent ductus arteriosus 81.40 25.53 26 5489 4092 53339459
Septic shock 69.67 25.53 55 5460 62174 53281377
Acute generalised exanthematous pustulosis 64.73 25.53 28 5487 10253 53333298
Pyrexia 63.77 25.53 133 5382 403060 52940491
Rash maculo-papular 58.22 25.53 37 5478 29712 53313839
Fatigue 54.76 25.53 6 5509 730500 52613051
Purpura 53.77 25.53 25 5490 10828 53332723
Laryngeal stenosis 52.75 25.53 13 5502 793 53342758
Foetal exposure during pregnancy 50.69 25.53 36 5479 34679 53308872
Hydrocephalus 45.65 25.53 18 5497 5218 53338333
Umbilical erythema 45.31 25.53 8 5507 91 53343460
Agranulocytosis 42.67 25.53 28 5487 23721 53319830
Encephalopathy 42.17 25.53 33 5482 36775 53306776
Thrombocytopenia 41.85 25.53 61 5454 138666 53204885
Multiple organ dysfunction syndrome 41.48 25.53 39 5476 55638 53287913
Haemophagocytic lymphohistiocytosis 39.00 25.53 19 5496 9118 53334433
Necrosis 38.76 25.53 16 5499 5215 53338336
Subperiosteal abscess 37.42 25.53 5 5510 5 53343546
Sepsis 35.22 25.53 58 5457 146371 53197180
Necrotising enterocolitis neonatal 34.12 25.53 7 5508 184 53343367
Lactic acidosis 33.46 25.53 29 5486 37224 53306327
Brain abscess 33.26 25.53 11 5504 1930 53341621
Sepsis neonatal 32.60 25.53 8 5507 479 53343072
Acute kidney injury 32.36 25.53 77 5438 253791 53089760
Ventricular dysfunction 32.34 25.53 12 5503 2951 53340600
Death neonatal 32.02 25.53 7 5508 251 53343300
Petechiae 31.90 25.53 19 5496 13586 53329965
Toxic shock syndrome streptococcal 31.74 25.53 6 5509 102 53343449
Neutropenia 31.68 25.53 58 5457 159127 53184424
Cholestasis 31.30 25.53 25 5490 28670 53314881
Pulmonary necrosis 30.72 25.53 6 5509 122 53343429
Hepatic failure 30.40 25.53 27 5488 35779 53307772
Stenotrophomonas infection 30.39 25.53 10 5505 1726 53341825
Disseminated intravascular coagulation 30.05 25.53 21 5494 19698 53323853
Central nervous system necrosis 29.61 25.53 6 5509 148 53343403
Arthralgia 29.58 25.53 5 5510 439778 52903773
Cross sensitivity reaction 28.59 25.53 10 5505 2077 53341474
Intraventricular haemorrhage neonatal 28.35 25.53 6 5509 184 53343367
Clostridium bacteraemia 27.93 25.53 6 5509 198 53343353
Hyperleukocytosis 27.20 25.53 7 5508 509 53343042
Oligohydramnios 27.03 25.53 13 5502 6063 53337488
Respiratory acidosis 26.41 25.53 13 5502 6375 53337176

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
Drug reaction with eosinophilia and systemic symptoms 283.66 23.11 137 6608 32348 32474433
Rash maculo-papular 149.29 23.11 85 6660 27937 32478844
Hepatocellular injury 130.03 23.11 75 6670 25243 32481538
Eosinophilia 104.90 23.11 65 6680 24893 32481888
Toxic epidermal necrolysis 92.57 23.11 56 6689 20537 32486244
Agranulocytosis 64.55 23.11 47 6698 23430 32483351
Haemophagocytic lymphohistiocytosis 56.59 23.11 33 6712 11302 32495479
Clostridium difficile colitis 51.90 23.11 34 6711 14297 32492484
Pyrexia 49.61 23.11 162 6583 319806 32186975
Purpura 48.24 23.11 29 6716 10496 32496285
Toxic skin eruption 48.12 23.11 30 6715 11584 32495197
Acute kidney injury 46.74 23.11 150 6595 293318 32213463
Klebsiella infection 44.47 23.11 25 6720 7987 32498794
Cholestasis 40.40 23.11 38 6707 26995 32479786
Fatigue 37.63 23.11 13 6732 350688 32156093
Face oedema 35.62 23.11 25 6720 11750 32495031
Thrombotic microangiopathy 35.56 23.11 23 6722 9459 32497322
Neutropenia 34.69 23.11 85 6660 142090 32364691
Death 33.47 23.11 19 6726 382498 32124283
Septic shock 32.14 23.11 54 6691 68935 32437846
Nausea 30.94 23.11 14 6731 320835 32185946
Brain abscess 30.52 23.11 14 6731 2920 32503861
Learning disorder 30.49 23.11 10 6735 846 32505935
Thrombocytopenia 30.34 23.11 83 6662 148216 32358565
Haematoma muscle 28.66 23.11 10 6735 1022 32505759
CNS ventriculitis 27.36 23.11 7 6738 244 32506537
ADAMTS13 activity decreased 27.19 23.11 6 6739 109 32506672
Respiratory gas exchange disorder 27.15 23.11 8 6737 475 32506306
Systemic candida 27.06 23.11 13 6732 3008 32503773
Rash 26.24 23.11 99 6646 209234 32297547
Hyperthermia 26.16 23.11 20 6725 10708 32496073
Gamma-glutamyltransferase increased 26.01 23.11 32 6713 30750 32476031
Red blood cell schistocytes present 25.81 23.11 7 6738 307 32506474
Drug ineffective 25.71 23.11 151 6594 383326 32123455
Neonatal disorder 25.49 23.11 9 6736 952 32505829
Bicytopenia 25.31 23.11 11 6734 2020 32504761
Vasculitis necrotising 24.90 23.11 8 6737 634 32506147
Pancytopenia 24.88 23.11 57 6688 91178 32415603
Acute generalised exanthematous pustulosis 24.69 23.11 16 6729 6597 32500184
Hepatic cytolysis 23.61 23.11 17 6728 8316 32498465

Pharmacologic Action:

SourceCodeDescription
ATC J01DD01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER BETA-LACTAM ANTIBACTERIALS
Third-generation cephalosporins
ATC J01DD51 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER BETA-LACTAM ANTIBACTERIALS
Third-generation cephalosporins
FDA CS M0003827 Cephalosporins
FDA EPC N0000175488 Cephalosporin Antibacterial
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
CHEBI has role CHEBI:36047 antibacterial drugs
CHEBI has role CHEBI:88188 allergenic drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Streptococcal meningitis indication 4510004 DOID:11574
Septicemia due to Escherichia coli indication 9323009
Bacterial septicemia indication 10001005 DOID:0040085
Infection of skin AND/OR subcutaneous tissue indication 19824006
Staphylococcal pneumonia indication 22754005
Streptococcal septicemia indication 29577008
Pneumonia due to Streptococcus indication 34020007
Neonatal conjunctivitis indication 34298002 DOID:9699
Pneumonia due to Pseudomonas indication 41381004
Bacterial arthritis indication 48245008
Peritonitis indication 48661000
Lower respiratory tract infection indication 50417007
Pneumonia due to Escherichia coli indication 51530003
Bacterial pneumonia indication 53084003 DOID:874
Klebsiella cystitis indication 60867007
Haemophilus influenzae pneumonia indication 70036007
Bacterial infection due to Serratia indication 71120004
Septicemia due to Serratia indication 82091000
Bacterial meningitis indication 95883001 DOID:9470
Infection of bone indication 111253001
Female genital tract infection indication 125585007
Infectious disease of abdomen indication 128070006
Bacterial infection due to Klebsiella pneumoniae indication 186435004
Meningococcal meningitis indication 192644005
Escherichia coli meningitis indication 192655005
Proteus pneumonia indication 195888009
Sepsis of the newborn indication 206376005
Neonatal pneumonia indication 233619008
Neonatal meningitis indication 276674008
Escherichia coli urinary tract infection indication 301011002
Proteus urinary tract infection indication 301012009
Bacterial urinary infection indication 312124009
Meningitis due to Klebsiella mobilis indication 420585007
Sepsis due to Staphylococcus aureus indication 448417001
Cesarean Section Infection Prevention indication
Streptococcal Peritonitis indication
E. Coli Peritonitis indication
E. Coli Endometritis indication
Haemophilus Influenzae Type B Infections indication
Neonatal Group B Streptococcal Septicemia indication
Klebsiella Endometritis indication
Proteus Endometritis indication
Enterococcus Pelvic Cellulitis indication
Prevention of Perioperative Infection indication
Proteus Mirabilis Osteomyelitis indication
Bacteroides Pelvic Cellulitis indication
Klebsiella Pelvic Inflammatory Disease indication
Staphylococcus Endometritis indication
H. Influenzae Meningitis indication
Clostridium Pelvic Inflammatory Disease indication
Haemophilus Parainfluenzae Pneumonia indication
Bacteroides Pelvic Inflammatory Disease indication
Staphylococcus Pelvic Inflammatory Disease indication
Proteus Peritonitis indication
Clostridium Endometritis indication
Staphylococcus Epidermidis Urinary Tract Infection indication
Enterococcus Pelvic Inflammatory Disease indication
Morganella Morganii Urinary Tract Infection indication
Fusobacterium Pelvic Inflammatory Disease indication
Streptococcus Osteomyelitis indication
Enterococcus Urinary Tract Infection indication
Clostridium Pelvic Cellulitis indication
Serratia Urinary Tract Infection indication
Enterobacter Pneumonia indication
Enterobacter Pelvic Inflammatory Disease indication
Bacteroides Endometritis indication
Providencia Urinary Tract Infection indication
Citrobacter Urinary Tract Infection indication
Fusobacterium Endometritis indication
Proteus Pelvic Inflammatory Disease indication
Clostridium Peritonitis indication
Staphylococcus Aureus Urinary Tract Infection indication
E. Coli Pelvic Inflammatory Disease indication
E. Coli Pelvic Cellulitis indication
Enterobacter Endometritis indication
Pseudomonas Aeruginosa Urinary Tract Infection indication
Klebsiella Pneumoniae Peritonitis indication
Enterococcus Endometritis indication
Pyrexia of unknown origin off-label use 7520000
Acute gonococcal cervicitis off-label use 20943002 DOID:10615
Lyme disease off-label use 23502006 DOID:11729
Acute gonococcal urethritis off-label use 29864006
Lyme arthritis off-label use 33937009
Pseudotuberculosis off-label use 36753006
Gonorrhea of rectum off-label use 42746002
Lyme carditis off-label use 77863005
Infection by Yersinia enterocolitica off-label use 80960004
Ventilator-acquired pneumonia off-label use 429271009
Disseminated Gonococcal Infection off-label use
Lyme Disease of the Central Nervous System off-label use
Acute nephropathy contraindication 58574008
Pseudomembranous enterocolitis contraindication 397683000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.39 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
Peptidoglycan synthase FtsI Enzyme INHIBITOR IC50 6.24 WOMBAT-PK CHEMBL
Penicillin-binding protein 1A Enzyme INHIBITOR IC50 6.51 WOMBAT-PK CHEMBL
Penicillin-binding protein 1B Enzyme INHIBITOR IC50 5.66 WOMBAT-PK CHEMBL
Penicillin-binding protein 2 Enzyme INHIBITOR IC50 4.62 WOMBAT-PK CHEMBL
Beta-lactamase Enzyme Ki 6.30 CHEMBL
Beta-lactamase Enzyme Ki 5.60 CHEMBL

External reference:

IDSource
4019663 VUID
N0000147755 NUI
D00919 KEGG_DRUG
64485-93-4 SECONDARY_CAS_RN
C0007554 UMLSCUI
CHEBI:3498 CHEBI
CE3 PDB_CHEM_ID
CHEMBL1010 ChEMBL_ID
CHEMBL1730 ChEMBL_ID
D002439 MESH_DESCRIPTOR_UI
DB00493 DRUGBANK_ID
10893 IUPHAR_LIGAND_ID
4504 INN_ID
N2GI8B1GK7 UNII
10695961 PUBCHEM_CID
203117 RXNORM
42787 MMSL
4378 MMSL
d00008 MMSL
002727 NDDF
004845 NDDF
3334000 SNOMEDCT_US
372704003 SNOMEDCT_US
41722006 SNOMEDCT_US
4018466 VANDF
4019663 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Cefotaxime HUMAN PRESCRIPTION DRUG LABEL 1 0143-9930 INJECTION, POWDER, FOR SOLUTION 500 mg INTRAMUSCULAR ANDA 24 sections
Cefotaxime HUMAN PRESCRIPTION DRUG LABEL 1 0143-9931 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 24 sections
Cefotaxime HUMAN PRESCRIPTION DRUG LABEL 1 0143-9933 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 24 sections
Cefotaxime HUMAN PRESCRIPTION DRUG LABEL 1 0143-9935 INJECTION 10 g INTRAVENOUS ANDA 24 sections
Cefotaxime HUMAN PRESCRIPTION DRUG LABEL 1 21586-011 POWDER, FOR SOLUTION 1 g INTRAMUSCULAR Unapproved drug for use in drug shortage 2 sections
Cefotaxime HUMAN PRESCRIPTION DRUG LABEL 1 21586-012 POWDER, FOR SOLUTION 2 g INTRAMUSCULAR Unapproved drug for use in drug shortage 2 sections
CEFOTAXIME HUMAN PRESCRIPTION DRUG LABEL 1 55648-947 INJECTION, POWDER, FOR SOLUTION 500 mg INTRAMUSCULAR ANDA 11 sections
CEFOTAXIME HUMAN PRESCRIPTION DRUG LABEL 1 55648-948 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 11 sections
CEFOTAXIME HUMAN PRESCRIPTION DRUG LABEL 1 55648-986 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 11 sections
Cefotaxime HUMAN PRESCRIPTION DRUG LABEL 1 64679-947 INJECTION, POWDER, FOR SOLUTION 500 mg INTRAMUSCULAR ANDA 20 sections
Cefotaxime HUMAN PRESCRIPTION DRUG LABEL 1 64679-948 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 20 sections
Cefotaxime HUMAN PRESCRIPTION DRUG LABEL 1 64679-986 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 20 sections