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: OFM

  • 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
S (Water solubility) 50 mg/mL Bocci G, Oprea TI, Benet LZ

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 235.81 27.61 94 5398 33742 63449788
Toxic epidermal necrolysis 157.89 27.61 65 5427 25269 63458261
Eosinophilia 123.74 27.61 53 5439 22703 63460827
Hepatocellular injury 102.02 27.61 49 5443 27332 63456198
Premature baby 89.24 27.61 41 5451 20694 63462836
Acute generalised exanthematous pustulosis 88.34 27.61 34 5458 11065 63472465
Stevens-Johnson syndrome 87.96 27.61 43 5449 24907 63458623
Rash maculo-papular 83.55 27.61 45 5447 31851 63451679
Septic shock 81.93 27.61 58 5434 66571 63416959
Pyrexia 69.62 27.61 136 5356 470342 63013188
Purpura 63.45 27.61 27 5465 11358 63472172
Multiple organ dysfunction syndrome 61.99 27.61 46 5446 56706 63426824
Patent ductus arteriosus 60.33 27.61 20 5472 4230 63479300
Agranulocytosis 59.02 27.61 33 5459 25101 63458429
Fatigue 55.98 27.61 6 5486 888022 62595508
Foetal exposure during pregnancy 54.17 27.61 34 5458 31928 63451602
Laryngeal stenosis 51.30 27.61 13 5479 1065 63482465
Hydrocephalus 48.55 27.61 18 5474 5282 63478248
Umbilical erythema 48.44 27.61 8 5484 72 63483458
Cholestasis 44.16 27.61 29 5463 29405 63454125
Acute kidney injury 42.30 27.61 79 5413 263336 63220194
Sepsis 41.08 27.61 58 5434 153065 63330465
Necrosis 40.78 27.61 16 5476 5471 63478059
Encephalopathy 39.26 27.61 30 5462 38590 63444940
Subperiosteal abscess 38.31 27.61 5 5487 5 63483525
Cross sensitivity reaction 38.14 27.61 12 5480 2150 63481380
Thrombocytopenia 37.25 27.61 55 5437 151102 63332428
Dermatitis bullous 37.14 27.61 17 5475 8491 63475039
Epidermolysis 36.35 27.61 9 5483 670 63482860
Lactic acidosis 35.14 27.61 28 5464 38259 63445271
Ventricular dysfunction 34.97 27.61 12 5480 2816 63480714
Disseminated intravascular coagulation 34.13 27.61 21 5471 19030 63464500
Dysbiosis 33.78 27.61 9 5483 897 63482633
Arthralgia 33.02 27.61 5 5487 569705 62913825
Petechiae 31.94 27.61 18 5474 13879 63469651
Toxic shock syndrome streptococcal 31.83 27.61 6 5486 121 63483409
Pulmonary necrosis 31.33 27.61 6 5486 132 63483398
Central nervous system necrosis 30.80 27.61 6 5486 145 63483385
Haemophagocytic lymphohistiocytosis 30.65 27.61 16 5476 10611 63472919
Stenotrophomonas infection 30.62 27.61 10 5482 2017 63481513
Clostridium bacteraemia 28.94 27.61 6 5486 200 63483330
Necrotising enterocolitis neonatal 28.68 27.61 6 5486 209 63483321
Oligohydramnios 28.67 27.61 13 5479 6353 63477177
Cyanosis 28.64 27.61 18 5474 16917 63466613
Hepatic failure 28.37 27.61 24 5468 35632 63447898
Respiratory acidosis 28.00 27.61 13 5479 6702 63476828
Toxic skin eruption 27.76 27.61 16 5476 12869 63470661

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 366.90 22.70 160 6457 32852 34917462
Hepatocellular injury 169.24 22.70 83 6534 22128 34928186
Rash maculo-papular 163.74 22.70 88 6529 28363 34921951
Toxic epidermal necrolysis 116.28 22.70 64 6553 21582 34928732
Eosinophilia 97.24 22.70 61 6556 26161 34924153
Clostridium difficile colitis 83.05 22.70 46 6571 15684 34934630
Haemophagocytic lymphohistiocytosis 74.18 22.70 40 6577 12933 34937381
Cholestasis 69.38 22.70 50 6567 26898 34923416
Hepatic cytolysis 67.36 22.70 39 6578 14457 34935857
Agranulocytosis 63.16 22.70 45 6572 23776 34926538
Acute kidney injury 56.54 22.70 155 6462 304833 34645481
Purpura 51.27 22.70 29 6588 10282 34940032
Toxic skin eruption 51.22 22.70 30 6587 11355 34938959
Urethral valves 47.52 22.70 11 6606 275 34950039
Acute generalised exanthematous pustulosis 44.71 22.70 23 6594 6753 34943561
Pyrexia 44.54 22.70 151 6466 332862 34617452
Klebsiella infection 39.74 22.70 23 6594 8508 34941806
Dermatitis bullous 38.60 22.70 21 6596 6901 34943413
Neutropenia 37.59 22.70 88 6529 156690 34793624
Thrombotic microangiopathy 37.54 22.70 24 6593 10606 34939708
Vasculitis necrotising 36.03 22.70 11 6606 809 34949505
Mixed liver injury 35.32 22.70 15 6602 2858 34947456
Drug ineffective 34.74 22.70 174 6443 456577 34493737
Thrombocytopenia 33.49 22.70 84 6533 156163 34794151
Death 31.83 22.70 18 6599 398031 34552283
Fatigue 30.73 22.70 16 6601 370637 34579677
Serratia sepsis 29.27 22.70 6 6611 83 34950231
Off label use 29.20 22.70 156 6461 419368 34530946
Nausea 29.18 22.70 14 6603 339894 34610420
Pancytopenia 29.14 22.70 59 6558 95098 34855216
ADAMTS13 activity decreased 28.88 22.70 6 6611 89 34950225
Systemic candida 28.55 22.70 14 6603 3712 34946602
Red blood cell schistocytes present 28.17 22.70 7 6610 238 34950076
Respiratory gas exchange disorder 28.05 22.70 8 6609 464 34949850
Bicytopenia 27.83 22.70 12 6605 2372 34947942
Septic shock 27.51 22.70 49 6568 71785 34878529
Rash 27.05 22.70 98 6519 222654 34727660
Haematoma muscle 26.80 22.70 10 6607 1358 34948956
Abscess 26.07 22.70 20 6597 11797 34938517
Gamma-glutamyltransferase increased 24.62 22.70 29 6588 29202 34921112
Face oedema 24.34 22.70 19 6598 11497 34938817
CD4 lymphocytes increased 23.71 22.70 6 6611 220 34950094
Serratia infection 23.04 22.70 8 6609 884 34949430
Cross sensitivity reaction 23.02 22.70 9 6608 1388 34948926

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 602.40 23.07 249 10338 63995 79669806
Hepatocellular injury 264.12 23.07 128 10459 47465 79686336
Rash maculo-papular 252.83 23.07 131 10456 55947 79677854
Toxic epidermal necrolysis 250.69 23.07 121 10466 44460 79689341
Eosinophilia 224.91 23.07 113 10474 45232 79688569
Agranulocytosis 126.00 23.07 77 10510 44953 79688848
Purpura 115.73 23.07 55 10532 19472 79714329
Acute generalised exanthematous pustulosis 109.66 23.07 51 10536 17203 79716598
Pyrexia 107.01 23.07 260 10327 678449 79055352
Cholestasis 106.14 23.07 73 10514 52036 79681765
Acute kidney injury 92.64 23.07 209 10378 519195 79214606
Clostridium difficile colitis 92.33 23.07 56 10531 32227 79701574
Hepatic cytolysis 87.84 23.07 51 10536 27100 79706701
Stevens-Johnson syndrome 82.42 23.07 56 10531 39110 79694691
Toxic skin eruption 80.52 23.07 45 10542 22248 79711553
Septic shock 80.32 23.07 90 10497 122711 79611090
Haemophagocytic lymphohistiocytosis 75.94 23.07 43 10544 21794 79712007
Fatigue 73.27 23.07 17 10570 929710 78804091
Dermatitis bullous 72.01 23.07 36 10551 14209 79719592
Thrombocytopenia 67.68 23.07 124 10463 265135 79468666
Neutropenia 57.04 23.07 121 10466 287589 79446212
Pain 55.11 23.07 13 10574 703789 79030012
Cross sensitivity reaction 54.58 23.07 20 10567 3692 79730109
Encephalopathy 53.92 23.07 55 10532 67342 79666459
Multiple organ dysfunction syndrome 51.06 23.07 71 10516 120175 79613626
Mixed liver injury 50.01 23.07 23 10564 7555 79726246
Nausea 48.67 23.07 34 10553 957162 78776639
Pseudomembranous colitis 47.40 23.07 20 10567 5354 79728447
Laryngeal stenosis 45.65 23.07 13 10574 1075 79732726
Thrombotic microangiopathy 42.80 23.07 29 10558 20140 79713661
Arthralgia 40.16 23.07 13 10574 571790 79162011
Hyperbilirubinaemia 39.92 23.07 30 10557 24488 79709313
Red blood cell schistocytes present 38.59 23.07 10 10577 579 79733222
Epidermolysis 38.08 23.07 11 10576 957 79732844
Hydrocephalus 34.97 23.07 19 10568 8881 79724920
Vasculitis necrotising 34.88 23.07 11 10576 1289 79732512
Anaphylactic shock 33.66 23.07 32 10555 35964 79697837
Bicytopenia 33.42 23.07 15 10572 4655 79729146
Klebsiella infection 31.92 23.07 22 10565 15698 79718103
Subperiosteal abscess 28.88 23.07 5 10582 38 79733763
Hepatic failure 28.78 23.07 38 10549 61174 79672627
Pancytopenia 28.59 23.07 66 10521 165679 79568122
Enterococcal infection 27.37 23.07 20 10567 15640 79718161
Ventricular dysfunction 26.89 23.07 14 10573 6009 79727792
ADAMTS13 activity decreased 26.79 23.07 6 10581 186 79733615
Respiratory gas exchange disorder 26.20 23.07 8 10579 843 79732958
Serratia sepsis 26.04 23.07 6 10581 212 79733589
Off label use 25.90 23.07 207 10380 907008 78826793
Rash 24.83 23.07 146 10441 578212 79155589
Brain oedema 24.66 23.07 23 10564 25240 79708561
Central nervous system necrosis 24.27 23.07 6 10581 287 79733514
Gamma-glutamyltransferase increased 24.26 23.07 33 10554 54647 79679154
CD4 lymphocytes increased 24.17 23.07 6 10581 292 79733509
Haematoma muscle 23.96 23.07 10 10577 2605 79731196
Neutrophil count increased 23.52 23.07 24 10563 29372 79704429
Nasopharyngitis 23.49 23.07 3 10584 253878 79479923
HIV associated nephropathy 23.44 23.07 6 10581 331 79733470

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
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
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 21586-011 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 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