cefotaxime ๐Ÿถ Veterinary Use | 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: 0.33
  • 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 ยตM/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 199.82 26.88 81 4607 28343 50572093
Hepatocellular injury 101.36 26.88 49 4639 25898 50574538
Eosinophilia 87.56 26.88 40 4648 18612 50581824
Premature baby 85.06 26.88 39 4649 18298 50582138
Toxic epidermal necrolysis 77.04 26.88 38 4650 20954 50579482
Rash maculo-papular 65.77 26.88 37 4651 26604 50573832
Pyrexia 64.35 26.88 121 4567 380082 50220354
Septic shock 63.29 26.88 48 4640 57127 50543309
Patent ductus arteriosus 61.09 26.88 20 4668 3800 50596636
Acute generalised exanthematous pustulosis 57.69 26.88 24 4664 8914 50591522
Laryngeal stenosis 54.31 26.88 13 4675 784 50599652
Purpura 52.05 26.88 23 4665 9888 50590548
Foetal exposure during pregnancy 49.25 26.88 31 4657 27328 50573108
Umbilical erythema 47.89 26.88 8 4680 72 50600364
Fatigue 45.59 26.88 6 4682 707595 49892841
Agranulocytosis 45.54 26.88 27 4661 21394 50579042
Hydrocephalus 45.46 26.88 17 4671 4771 50595665
Necrosis 42.01 26.88 16 4672 4720 50595716
Encephalopathy 38.82 26.88 29 4659 33682 50566754
Subperiosteal abscess 37.97 26.88 5 4683 5 50600431
Thrombocytopenia 35.52 26.88 51 4637 127622 50472814
Ventricular dysfunction 35.06 26.88 12 4676 2609 50597827
Lactic acidosis 34.68 26.88 27 4661 33328 50567108
Multiple organ dysfunction syndrome 34.38 26.88 32 4656 50305 50550131
Acute kidney injury 34.04 26.88 69 4619 227989 50372447
Death neonatal 33.53 26.88 7 4681 225 50600211
Toxic shock syndrome streptococcal 32.79 26.88 6 4682 95 50600341
Haemophagocytic lymphohistiocytosis 32.76 26.88 16 4672 8617 50591819
Stenotrophomonas infection 31.86 26.88 10 4678 1659 50598777
Cholestasis 31.83 26.88 23 4665 25378 50575058
Pulmonary necrosis 31.76 26.88 6 4682 114 50600322
Central nervous system necrosis 30.88 26.88 6 4682 133 50600303
Cross sensitivity reaction 30.23 26.88 10 4678 1959 50598477
Petechiae 29.84 26.88 17 4671 12495 50587941
Oligohydramnios 29.08 26.88 13 4675 5737 50594699
Hepatic failure 29.02 26.88 24 4664 32259 50568177
Hyperleukocytosis 28.70 26.88 7 4681 457 50599979
Respiratory acidosis 28.49 26.88 13 4675 6015 50594421
Disseminated intravascular coagulation 27.33 26.88 18 4670 17117 50583319
Brain abscess 27.12 26.88 9 4679 1782 50598654

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 295.03 25.04 132 5650 27860 29540885
Rash maculo-papular 151.17 25.04 80 5702 24209 29544536
Hepatocellular injury 143.71 25.04 74 5708 21169 29547576
Eosinophilia 104.94 25.04 61 5721 22100 29546645
Toxic epidermal necrolysis 80.74 25.04 48 5734 18105 29550640
Agranulocytosis 56.43 25.04 40 5742 20300 29548445
Acute kidney injury 55.67 25.04 144 5638 265123 29303622
Haemophagocytic lymphohistiocytosis 55.27 25.04 31 5751 10473 29558272
Toxic skin eruption 54.64 25.04 30 5752 9727 29559018
Clostridium difficile colitis 53.73 25.04 33 5749 13179 29555566
Cholestasis 49.16 25.04 39 5743 23423 29545322
Urethral valves 47.28 25.04 11 5771 272 29568473
Purpura 45.21 25.04 26 5756 9206 29559539
Thrombotic microangiopathy 41.32 25.04 24 5758 8657 29560088
Pyrexia 38.24 25.04 133 5649 287489 29281256
Neutropenia 37.84 25.04 81 5701 131630 29437115
Klebsiella infection 36.79 25.04 21 5761 7328 29561417
Mixed liver injury 32.64 25.04 13 5769 2038 29566707
Haematoma muscle 29.98 25.04 10 5772 947 29567798
Nausea 29.41 25.04 10 5772 289245 29279500
ADAMTS13 activity decreased 29.22 25.04 6 5776 81 29568664
Rash 28.90 25.04 92 5690 189727 29379018
Systemic candida 28.83 25.04 13 5769 2767 29565978
Septic shock 28.61 25.04 47 5735 62513 29506232
Respiratory gas exchange disorder 28.33 25.04 8 5774 433 29568312
Death 28.22 25.04 16 5766 342068 29226677
Red blood cell schistocytes present 28.03 25.04 7 5775 235 29568510
Thrombocytopenia 27.91 25.04 73 5709 134750 29433995
Fatigue 27.32 25.04 14 5768 316807 29251938
Bicytopenia 27.07 25.04 11 5771 1816 29566929
Hepatic cytolysis 26.87 25.04 18 5764 8329 29560416
Drug ineffective 26.47 25.04 140 5642 363030 29205715
Gamma-glutamyltransferase increased 25.97 25.04 29 5753 26708 29542037
Vasculitis necrotising 25.84 25.04 8 5774 597 29568148
Face oedema 25.71 25.04 19 5763 10264 29558481
Acute generalised exanthematous pustulosis 25.42 25.04 15 5767 5568 29563177

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
Drug reaction with eosinophilia and systemic symptoms 488.28 22.04 208 8919 54009 64435596
Hepatocellular injury 235.90 22.04 119 9008 45116 64444489
Rash maculo-papular 220.01 22.04 115 9012 46911 64442694
Eosinophilia 197.98 22.04 100 9027 37976 64451629
Toxic epidermal necrolysis 154.35 22.04 84 9043 37082 64452523
Agranulocytosis 104.71 22.04 66 9061 38163 64451442
Purpura 97.55 22.04 48 9079 17198 64472407
Pyrexia 94.87 22.04 229 8898 558415 63931190
Acute kidney injury 82.48 22.04 190 8937 449050 64040555
Toxic skin eruption 78.38 22.04 43 9084 19241 64470364
Cholestasis 72.39 22.04 56 9071 44816 64444789
Septic shock 67.82 22.04 79 9048 105358 64384247
Clostridium difficile colitis 64.68 22.04 43 9084 27180 64462425
Fatigue 62.08 22.04 15 9112 748715 63740890
Acute generalised exanthematous pustulosis 61.73 22.04 33 9094 14025 64475580
Thrombocytopenia 57.72 22.04 109 9018 223692 64265913
Haemophagocytic lymphohistiocytosis 57.40 22.04 34 9093 17575 64472030
Neutropenia 53.68 22.04 110 9017 239514 64250091
Encephalopathy 51.70 22.04 52 9075 58767 64430838
Laryngeal stenosis 48.68 22.04 13 9114 794 64488811
Pseudomembranous colitis 44.55 22.04 19 9108 4897 64484708
Cross sensitivity reaction 44.26 22.04 17 9110 3350 64486255
Pain 44.06 22.04 12 9115 553499 63936106
Thrombotic microangiopathy 43.69 22.04 28 9099 16627 64472978
Nausea 43.59 22.04 29 9098 785771 63703834
Mixed liver injury 42.57 22.04 19 9108 5462 64484143
Dermatitis bullous 38.57 22.04 23 9104 12031 64477574
Hepatic cytolysis 37.80 22.04 24 9103 14025 64475580
Multiple organ dysfunction syndrome 33.34 22.04 55 9072 101358 64388247
Hyperbilirubinaemia 33.17 22.04 26 9101 21179 64468426
Hydrocephalus 31.04 22.04 17 9110 7574 64482031
Arthralgia 30.91 22.04 12 9115 442248 64047357
Anaphylactic shock 30.73 22.04 29 9098 30299 64459306
Bicytopenia 29.55 22.04 13 9114 3609 64485996
Klebsiella infection 29.19 22.04 20 9107 13261 64476344
Red blood cell schistocytes present 29.14 22.04 8 9119 542 64489063
Subperiosteal abscess 28.56 22.04 5 9122 38 64489567
Hepatic failure 28.30 22.04 37 9090 55357 64434248
Ventricular dysfunction 27.81 22.04 14 9113 5256 64484349
ADAMTS13 activity decreased 27.47 22.04 6 9121 155 64489450
Haematoma muscle 27 22.04 10 9117 1783 64487822
Respiratory gas exchange disorder 26.53 22.04 8 9119 757 64488848
Brain oedema 26.06 22.04 23 9104 22052 64467553
Stevens-Johnson syndrome 25.99 22.04 28 9099 34221 64455384
Neutrophil count increased 25.37 22.04 24 9103 25150 64464455
Rash 24.76 22.04 129 8998 458420 64031185
Gamma-glutamyltransferase increased 24.16 22.04 32 9095 48478 64441127
CD4 lymphocytes increased 24.14 22.04 6 9121 275 64489330
Central nervous system necrosis 24.08 22.04 6 9121 278 64489327
Vasculitis necrotising 23.88 22.04 8 9119 1064 64488541
Enterococcal infection 23.87 22.04 18 9109 13848 64475757
HIV associated nephropathy 23.73 22.04 6 9121 295 64489310
Erythema 23.68 22.04 69 9058 187001 64302604
Mucormycosis 23.46 22.04 14 9113 7327 64482278
Hyperlactacidaemia 23.04 22.04 12 9115 4832 64484773
CNS ventriculitis 22.95 22.04 6 9121 337 64489268

FDA Adverse Event Reporting System (Pediatric)

None

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 | Suggest Off label Use Form| |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




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 2.39 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
203117 RXNORM
4018466 VANDF
4019663 VANDF
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
5742673 PUBCHEM_CID
42787 MMSL
4378 MMSL
d00008 MMSL
002727 NDDF
004845 NDDF
3334000 SNOMEDCT_US
372704003 SNOMEDCT_US
41722006 SNOMEDCT_US

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