Details of the Drug

General Information of Drug (ID: DMEB837)

Drug Name
Cefotaxime
Synonyms
Cefotaxima; Cefotaxima [INN-Spanish]; Cefotaxime [INN:BAN]; Cefotaxime acid; Cefotaximum; Cefotaximum [INN-Latin]; Cephotaxime; E-cefotaxime; Omnatax; RU 24662; RU 24756; cefotaxime; 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-7-(((2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-8-oxo-, (6R,7R)-; 60846-21-1; 63527-52-6; C16H17N5O7S2; CHEBI:204928; EINECS 264-299-1; HR 756; N2GI8B1GK7; Taxim; UNII-N2GI8B1GK7
Indication
Disease Entry ICD 11 Status REF
Bacteremia 1A73 Approved [1]
Bacterial arthritis N.A. Approved [1]
Bacterial infection 1A00-1C4Z Approved [2]
Escherichia coli meningitis N.A. Approved [1]
Meningococcal meningitis N.A. Approved [1]
Neonatal sepsis N.A. Approved [1]
Peritonitis N.A. Approved [1]
Staphylococcal pneumonia N.A. Approved [1]
⏷ Show the Full List of Indication(s)
Affected Organisms
Streptococcus pneumoniaeStreptococcus pyogenesStaphylococcus aureusEscherichia coliKlebsiella spp.Haemophilus influenzaeHaemophilus parainfluenzaeProteus mirabilisSerratia marcescensEnterobacter spp.Pseudomonas aeruginosaEnterococcusStaphylococcus epidermidisCitrobacter spp.Proteus vulgarisProvidencia stuartiiMorganella morganiiProvidencia rettgeriNeisseria gonorrhoeaeBacteroides spp.Clostridium spp.Peptostreptococcus spp.Peptococcus spp.Fusobacterium spp.Acinetobacter spp.
ATC Code
J01DD01: Cefotaxime
J01DD: Third-generation cephalosporins
J01D: OTHER BETA-LACTAM ANTIBACTERIALS
J01: ANTIBACTERIALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 455.5
Logarithm of the Partition Coefficient (xlogp) -1.4
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 12
ADMET Property
Absorption
The drug is rapidly absorbed following intramuscular injection []
Half-life
The concentration or amount of drug in body reduced by one-half in 1 hours [3]
Metabolism
The drug is metabolized via the kidneys []
Chemical Identifiers
Formula
C16H17N5O7S2
IUPAC Name
(6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Canonical SMILES
CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)C(=NOC)C3=CSC(=N3)N)SC1)C(=O)O
InChI
InChI=1S/C16H17N5O7S2/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26)/b20-9-/t10-,14-/m1/s1
InChIKey
GPRBEKHLDVQUJE-QSWIMTSFSA-N
Cross-matching ID
PubChem CID
5742673
ChEBI ID
CHEMBL1730
CAS Number
60846-21-1
UNII
N2GI8B1GK7
DrugBank ID
DB00493
VARIDT ID
D0D1HA
INTEDE ID
DR2226
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Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial DD-carboxypeptidase (Bact vanYB) TTLP6GN VANY_ENTFA Inhibitor [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Beta-lactamase (blaB) DEP0IWS A0A378EHS6_KLEPR Substrate [5]
Beta-lactamase (blaB) DEEAL81 BLA2_KLEPO Substrate [6], [7]
Beta-lactamase (blaB) DEKGVS4 PENA_BURM1 Substrate [8]
Beta-lactamase (blaB) DE7IH52 AMPC_CITFR Substrate [9], [10]
Beta-lactamase (blaB) DEAYSTX C0W968_9FIRM Substrate [11]
Beta-lactamase (blaB) DEITMS0 Q9XBM2_ACIFE Substrate [12]
Beta-lactamase (blaB) DE5HV8P A0A4Q5I6I2_9BACE Substrate [13]
Beta-lactamase (blaB) DE47ARF B5WXV2_9BACT Substrate [13]
Beta-lactamase (blaB) DEG2PK9 B5WXV3_BACOV Substrate [13]
Beta-lactamase (blaB) DEWHJ7A B5WXV7_BACT4 Substrate [13], [14]
Beta-lactamase (blaB) DEU1RXB BLAC_BACVU Substrate [13]
Beta-lactamase (blaB) DEMIUB2 BLAT_ECOLX Substrate [7]
Beta-lactamase (blaB) DEYIEO5 AMPC_SERMA Substrate [15]
Beta-lactamase (blaB) DEZLFV5 B8R6A5_9BURK Substrate [16]
Ampc beta-lactamase (ampC) DE0TCN3 B4EPS2_BURCJ Substrate [16]
PenA beta-lactamase (penA1) DE2ARDZ O08350_BURCE Substrate [17]
Beta-lactamase (blaB) DEVHXAU BLC2_SALTM Substrate [14]
Beta-lactamase (blaB) DEHJVX4 A0A414C8Y0_9BACT Substrate [13]
Beta-lactamase (blaB) DE5AHG6 BLAC_CITKO Substrate [18]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Cefotaxime
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Kanamycin DM2DMPO Moderate Increased risk of nephrotoxicity by the combination of Cefotaxime and Kanamycin. Bacterial infection [1A00-1C4Z] [19]
Streptomycin DME1LQN Moderate Increased risk of nephrotoxicity by the combination of Cefotaxime and Streptomycin. Bacterial infection [1A00-1C4Z] [19]
Gentamicin DMKINJO Moderate Increased risk of nephrotoxicity by the combination of Cefotaxime and Gentamicin. Bacterial infection [1A00-1C4Z] [19]
Netilmicin DMRD1QK Moderate Increased risk of nephrotoxicity by the combination of Cefotaxime and Netilmicin. Bacterial infection [1A00-1C4Z] [19]
Tobramycin DMUI0CH Moderate Increased risk of nephrotoxicity by the combination of Cefotaxime and Tobramycin. Bacterial infection [1A00-1C4Z] [19]
Coadministration of a Drug Treating the Disease Different from Cefotaxime (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Framycetin DMF8DNE Moderate Increased risk of nephrotoxicity by the combination of Cefotaxime and Framycetin. Alcoholic liver disease [DB94] [19]
Mycophenolic acid DMRBMAU Moderate Altered absorption of Cefotaxime due to GI flora changes caused by Mycophenolic acid. Crohn disease [DD70] [20]
Ethacrynic acid DM60QMR Moderate Increased risk of nephrotoxicity by the combination of Cefotaxime and Ethacrynic acid. Essential hypertension [BA00] [21]
Furosemide DMMQ8ZG Moderate Increased risk of nephrotoxicity by the combination of Cefotaxime and Furosemide. Heart failure [BD10-BD1Z] [21]
Bumetanide DMRV7H0 Moderate Increased risk of nephrotoxicity by the combination of Cefotaxime and Bumetanide. Heart failure [BD10-BD1Z] [21]
Givosiran DM5PFIJ Moderate Increased risk of nephrotoxicity by the combination of Cefotaxime and Givosiran. Inborn porphyrin/heme metabolism error [5C58] [22]
Probenecid DMMFWOJ Moderate Decreased elimination of Cefotaxime caused by Probenecid mediated competitive inhibition of renal tubular secretion. Inborn purine/pyrimidine/nucleotide metabolism error [5C55] [23]
Porfimer Sodium DM7ZWNY Moderate Increased risk of photosensitivity reactions by the combination of Cefotaxime and Porfimer Sodium. Lung cancer [2C25] [24]
Mycophenolate mofetil DMPQAGE Moderate Altered absorption of Cefotaxime due to GI flora changes caused by Mycophenolate mofetil. Transplant rejection [NE84] [20]
Plazomicin DMKMBES Moderate Increased risk of nephrotoxicity by the combination of Cefotaxime and Plazomicin. Urinary tract infection [GC08] [19]
⏷ Show the Full List of 10 DDI Information of This Drug

References

1 Cefotaxime FDA Label
2 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 064200.
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Extended-spectrum cephalosporinases: structure, detection and epidemiology. Future Microbiol. 2007 Jun;2:297-307.
5 Analysis of the drug-resistant characteristics of Klebsiella pneumoniae isolated from the respiratory tract and CTX-M ESBL genes. Genet Mol Res. 2015 Oct 5;14(4):12043-8.
6 Antibiotic resistance and production of extended-spectrum beta-lactamases amongst Klebsiella spp. from intensive care units in Europe. J Antimicrob Chemother. 1996 Sep;38(3):409-24.
7 Oral streptococcal strains isolated from odontogenic infections and their susceptibility to antibiotics. Rev Med Chir Soc Med Nat Iasi. 2006 Oct-Dec;110(4):1012-5.
8 Overcoming an extremely drug resistant (XDR) pathogen: avibactam restores susceptibility to ceftazidime for Burkholderia cepacia complex isolates from cystic fibrosis patients. ACS Infect Dis. 2017 Jul 14;3(7):502-511.
9 Citrobacter freundii bacteremia: Risk factors of mortality and prevalence of resistance genes. J Microbiol Immunol Infect. 2018 Aug;51(4):565-572.
10 Analyses of a ceftazidime-avibactam-resistant Citrobacter freundii isolate carrying blaKPC-2 reveals a heterogenous population and reversible genotype. mSphere. 2018 Sep 26;3(5). pii: e00408-18.
11 ACI-1 beta-lactamase is widespread across human gut microbiomes in Negativicutes due to transposons harboured by tailed prophages. Environ Microbiol. 2018 Jun;20(6):2288-2300.
12 ACI-1 from Acidaminococcus fermentans: characterization of the first beta-lactamase in Anaerobic cocci. Antimicrob Agents Chemother. 2000 Nov;44(11):3144-9.
13 Presence of the cfxA gene in Bacteroides distasonis. Res Microbiol. 2003 Jun;154(5):369-74.
14 Cephalosporinases associated with outer membrane vesicles released by Bacteroides spp. protect gut pathogens and commensals against beta-lactam antibiotics. J Antimicrob Chemother. 2015 Mar;70(3):701-9.
15 Determination of the antibiotic resistance rates of Serratia marcescens isolates obtained from various clinical specimens. Niger J Clin Pract. 2019 Jan;22(1):125-130.
16 Cell wall recycling-linked coregulation of AmpC and PenB beta-lactamases through ampD mutations in Burkholderia cenocepacia. Antimicrob Agents Chemother. 2015 Dec;59(12):7602-10.
17 Characterization of the penA and penR genes of Burkholderia cepacia 249 which encode the chromosomal class A penicillinase and its LysR-type transcriptional regulator. Antimicrob Agents Chemother. 1997 Nov;41(11):2399-405.
18 Novel TEM-type extended-spectrum beta-lactamase, TEM-134, in a Citrobacter koseri clinical isolate. Antimicrob Agents Chemother. 2005 Apr;49(4):1564-6.
19 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
20 Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
21 Chrysos G, Gargalianos P, Lelekis M, Stefanou J, Kosmidis J "Pharmacokinetic interactions of ceftazidime and frusemide." J Chemother 7 Suppl (1995): 107-10. [PMID: 8904125]
22 Cerner Multum, Inc. "Australian Product Information.".
23 Brown G, Zemcov SJ, Clarke AM "Effect of probenecid on cefazolin serum concentrations." J Antimicrob Chemother 31 (1993): 1009-11. [PMID: 8360120]
24 Blakely KM, Drucker AM, Rosen CF "Drug-induced photosensitivity-an update: Culprit drugs, prevention and management." Drug Saf 42 (2019): 827-47. [PMID: 30888626]