General Information of Drug (ID: DR2226)
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 Meningitis [ICD11: 1A62] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 455.5 Topological Polar Surface Area 227
Heavy Atom Count 30 Rotatable Bond Count 8
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 12
Cross-matching ID
PubChem CID
5742673
ChEBI ID
CHEBI:204928
CAS Number
60846-21-1
Formula
C16H17N5O7S2
Canonical SMILES
CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)C(=NOC)C3=CSC(=N3)N)SC1)C(=O)O
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Desacetylcefotaxime DM000748
9576239
Oxidation - Deacetylation 1 [20] , [24]
Deacetylcefotaxime lactone DM000749
13080558
Unclear 2 [20] , [24]
Desacetylcefotaxime lactone M2 DM000750
14673053
Unclear 3 [20]
Desacetylcefotaxime lactone M3 DM000751
156028121
Unclear 3 [20]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000583 Cefotaxime Desacetyl-cefotaxime Oxidation - Deacetylation blaB [20], [24]
MR000580 Desacetyl-cefotaxime Deacetylcefotaxime lactone Unclear Unclear [20], [24]
MR000581 Deacetylcefotaxime lactone Desacetylcefotaxime lactone M2 Unclear Unclear [20]
MR000582 Deacetylcefotaxime lactone Desacetylcefotaxime lactone M3 Unclear Unclear [20]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
#NAME? DMEN832 Lactococcus garvieae Not Available Not Available [2]
Ampc beta-lactamase (ampC) DME1191 Burkholderia cenocepacia
B4EPS2_BURCJ
3.5.2.6
[3]
Beta-lactamase (bla OXA-17) DMEN835 Pseudomonas aeruginosa Not Available Not Available [4]
Beta-lactamase (blaB) DME1020 Acidaminococcus fermentans
Q9XBM2_ACIFE
3.5.2.6
[5]
Beta-lactamase (blaB) DME1094 Citrobacter freundii
AMPC_CITFR
3.5.2.6
[6] , [7]
Beta-lactamase (blaB) DME1231 Serratia marcescens
AMPC_SERMA
3.5.2.6
[8]
Beta-lactamase (blaB) DME1024 Klebsiella variicola
BLA2_KLEPO
3.5.2.6
[9] , [10]
Beta-lactamase (blaB) DME1223 Escherichia coli
BLAT_ECOLX
3.5.2.6
[10]
Beta-lactamase (blaB) DME1311 Salmonella enterica
BLC2_SALTM
3.5.2.6
[11]
Beta-lactamase (blaB) DME1223 Escherichia coli
BLAT_ECOLX
3.5.2.6
[12]
Beta-lactamase (blaB) DME1014 Acidaminococcus intestini
C0W968_9FIRM
3.5.2.6
[13]
Beta-lactamase (blaB) DME1733 Citrobacter koseri
BLAC_CITKO
3.5.2.6
[14]
Beta-lactamase (blaB) DME1023 Klebsiella pneumoniae
A0A378EHS6_KLEPR
3.5.2.6
[15]
Beta-lactamase (blaB) DME1215 Bacteroides caccae
A0A4Q5I6I2_9BACE
3.5.2.6
[16]
Beta-lactamase (blaB) DME1216 Parabacteroides distasonis
B5WXV2_9BACT
3.5.2.6
[16]
Beta-lactamase (blaB) DME1217 Parabacteroides merdae
A0A414C8Y0_9BACT
3.5.2.6
[16]
Beta-lactamase (blaB) DME1218 Bacteroides ovatus
B5WXV3_BACOV
3.5.2.6
[16]
Beta-lactamase (blaB) DME1219 Bacteroides thetaiotaomicron
B5WXV7_BACT4
3.5.2.6
[16] , [11]
Beta-lactamase (blaB) DME1220 Bacteroides vulgatus
BLAC_BACVU
3.5.2.6
[16]
Beta-lactamase (blaB) DME2100 Burkholderia multivorans
PENA_BURM1
3.5.2.6
[17]
Beta-lactamase (blaB) DME1312 Burkholderia cenocepacia
B8R6A5_9BURK
3.5.2.6
[3]
Beta-lactamase (blaCTX-M-19) DMEN833 Escherichia coli
S0F1K6_ECOLX
3.5.2.6
[18]
beta-lactamase CTX-M-10 (CTX-M-10) DMEN836 Escherichia coli Not Available Not Available [19]
Dehydropeptidase-I (DPEP1) DME0117 Homo sapiens
DPEP1_HUMAN
3.4.13.19
[20]
extended-spectrum -lactamase 1 (PME-1) DMEN834 Pseudomonas aeruginosa Not Available Not Available [21]
KPC-type -lactamase (KPCB) DMEN839 Bacteroides fragilis Not Available Not Available [22]
PenA beta-lactamase (penA1) DME1559 Burkholderia cepacia
O08350_BURCE
3.5.2.6
[23]
⏷ Show the Full List of 27  DME(s)
References
1 Cefotaxime was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Dual functional roles of a novel bifunctional -lactamase/esterase from Lactococcus garvieae
3 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.
4 OXA-17, a further extended-spectrum variant of OXA-10 beta-lactamase, isolated from Pseudomonas aeruginosa
5 ACI-1 from Acidaminococcus fermentans: characterization of the first beta-lactamase in Anaerobic cocci. Antimicrob Agents Chemother. 2000 Nov;44(11):3144-9.
6 Citrobacter freundii bacteremia: Risk factors of mortality and prevalence of resistance genes. J Microbiol Immunol Infect. 2018 Aug;51(4):565-572.
7 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.
8 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.
9 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.
10 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.
11 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.
12 Single amino acid substitution between SHV-1 beta-lactamase and cefotaxime-hydrolyzing SHV-2 enzyme
13 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.
14 Novel TEM-type extended-spectrum beta-lactamase, TEM-134, in a Citrobacter koseri clinical isolate. Antimicrob Agents Chemother. 2005 Apr;49(4):1564-6.
15 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.
16 Presence of the cfxA gene in Bacteroides distasonis. Res Microbiol. 2003 Jun;154(5):369-74.
17 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.
18 Role of a mutation at position 167 of CTX-M-19 in ceftazidime hydrolysis
19 Nucleotide sequence and characterization of a novel cefotaxime-hydrolyzing beta-lactamase (CTX-M-10) isolated in Spain
20 Metabolism of cefotaxime in animals and humans Rev Infect Dis. 1982 Sep-Oct;4 Suppl:S325-32. doi: 10.1093/clinids/4.supplement_2.s325.
21 PME-1, an extended-spectrum -lactamase identified in Pseudomonas aeruginosa
22 In silico identification and experimental validation of hits active against KPC-2 -lactamase
23 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.
24 Molecularly Imprinted Polymers as Solid-Phase Microextraction Fibers for the Isolation of Selected Antibiotics from Human Plasma. Materials (Basel). 2021 Aug 27;14(17):4886. doi: 10.3390/ma14174886.

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