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
Meningitis 1D01 Approved [1]
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 455.5
Topological Polar Surface Area (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 [2]
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 [2]
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
GPRBEKHLDVQUJE-QSWIMTSFSA-N
InChIKey
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
Cross-matching ID
PubChem CID
5742673
ChEBI ID
CHEBI:204928
CAS Number
60846-21-1
DrugBank ID
DB00493
INTEDE ID
DR2226

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Beta-lactamase (blaB) DEP0IWS A0A378EHS6_KLEPR Substrate [4]
Beta-lactamase (blaB) DEEAL81 BLA2_KLEPO Substrate [5], [6]
Beta-lactamase (blaB) DEKGVS4 PENA_BURM1 Substrate [7]
Beta-lactamase (blaB) DE7IH52 AMPC_CITFR Substrate [8], [9]
Beta-lactamase (blaB) DEAYSTX C0W968_9FIRM Substrate [10]
Beta-lactamase (blaB) DEITMS0 Q9XBM2_ACIFE Substrate [11]
Beta-lactamase (blaB) DE5HV8P A0A4Q5I6I2_9BACE Substrate [12]
Beta-lactamase (blaB) DE47ARF B5WXV2_9BACT Substrate [12]
Beta-lactamase (blaB) DEG2PK9 B5WXV3_BACOV Substrate [12]
Beta-lactamase (blaB) DEWHJ7A B5WXV7_BACT4 Substrate [12], [13]
Beta-lactamase (blaB) DEU1RXB BLAC_BACVU Substrate [12]
Beta-lactamase (blaB) DEMIUB2 BLAT_ECOLX Substrate [6]
Beta-lactamase (blaB) DEYIEO5 AMPC_SERMA Substrate [14]
Beta-lactamase (blaB) DEZLFV5 B8R6A5_9BURK Substrate [15]
Ampc beta-lactamase (ampC) DE0TCN3 B4EPS2_BURCJ Substrate [15]
PenA beta-lactamase (penA1) DE2ARDZ O08350_BURCE Substrate [16]
Beta-lactamase (blaB) DEVHXAU BLC2_SALTM Substrate [13]
Beta-lactamase (blaB) DEHJVX4 A0A414C8Y0_9BACT Substrate [12]
Beta-lactamase (blaB) DE5AHG6 BLAC_CITKO Substrate [17]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Cefotaxime was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 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.
5 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.
6 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.
7 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.
8 Citrobacter freundii bacteremia: Risk factors of mortality and prevalence of resistance genes. J Microbiol Immunol Infect. 2018 Aug;51(4):565-572.
9 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.
10 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.
11 ACI-1 from Acidaminococcus fermentans: characterization of the first beta-lactamase in Anaerobic cocci. Antimicrob Agents Chemother. 2000 Nov;44(11):3144-9.
12 Presence of the cfxA gene in Bacteroides distasonis. Res Microbiol. 2003 Jun;154(5):369-74.
13 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.
14 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.
15 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.
16 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.
17 Novel TEM-type extended-spectrum beta-lactamase, TEM-134, in a Citrobacter koseri clinical isolate. Antimicrob Agents Chemother. 2005 Apr;49(4):1564-6.
18 Detection and characterization of beta-lactamase genes in subgingival bacteria from patients with refractory periodontitis. FEMS Microbiol Lett. 2005 Jan 15;242(2):319-24.
19 Antibiotic therapy for inducible AmpC beta-lactamase-producing Gram-negative bacilli: what are the alternatives to carbapenems, quinolones and aminoglycosides? Int J Antimicrob Agents. 2012 Oct;40(4):297-305.
20 Identification and functional characterization of arylamine N-acetyltransferases in eubacteria: evidence for highly selective acetylation of 5-aminosalicylic acid. J Bacteriol. 2001 Jun;183(11):3417-27.
21 Prevalence of antimicrobial resistance genes in Bacteroides spp. and Prevotella spp. Dutch clinical isolates. Clin Microbiol Infect. 2019 Sep;25(9):1156.e9-1156.e13.
22 War wound treatment complications due to transfer of an IncN plasmid harboring bla(OXA-181) from Morganella morganii to CTX-M-27-producing sequence type 131 Escherichia coli. Antimicrob Agents Chemother. 2015;59(6):3556-62.
23 Citrobacter koseri and Citrobacter amalonaticus isolates carry highly divergent beta-lactamase genes despite having high levels of biochemical similarity and 16S rRNA sequence homology. J Antimicrob Chemother. 2004 Jun;53(6):1076-80.