Drug (ID: DG00385) and It's Reported Resistant Information
Name
Piperacillin/Tazobactam
Synonyms
Tazocin (TN); Zosyn (TN); Piperacillin-tazobactam; Piperacillin-tazobactam mixt.; Piperacillin-tazobactam mixture; NIOSH/XI0191450; Piperacillin sodium and tazobactam; DTXSID001016418; Tazobactam and piperacillin (JP17); Piperacillin-tazobactam mixt. (4:1); Tazobactam-piperacillin mixt. (1:4); XI01914500; D02505; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3-methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-, 4,4-dioxide, (2S-(2-alpha,3-beta,5-alpha))-, mixt. with (2S-(2-alpha,5-alpha,6-beta(S*)))-6-(((((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)phenylacetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid (1:4)
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Structure
Drug Resistance Disease(s)
Disease(s) with Clinically Reported Resistance for This Drug (6 diseases)
Bacterial infection [ICD-11: 1A00-1C4Z]
[1]
Malaria [ICD-11: 1F45]
[2]
Peritonitis [ICD-11: DC50]
[3]
Pneumonia [ICD-11: CA40]
[4]
Sclerosing cholangitis [ICD-11: DB96]
[5]
Ulcer [ICD-11: EH90]
[6]
Click to Show/Hide the Molecular Information and External Link(s) of This Drug
Formula
C33H38N9NaO12S2
IsoSMILES
CCN1CCN(C(=O)C1=O)C(=O)N[C@@H](C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)[O-].C[C@@]1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)O)CN3C=CN=N3.[Na+]
InChI
1S/C23H27N5O7S.C10H12N4O5S.Na/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28;1-10(5-13-3-2-11-12-13)8(9(16)17)14-6(15)4-7(14)20(10,18)19;/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34);2-3,7-8H,4-5H2,1H3,(H,16,17);/q;;+1/p-1/t13-,14+,15-,20+;7-,8+,10+;/m01./s1
InChIKey
TUPFOYXHAYOHIB-WZGOVNIISA-M
PubChem CID
23724843
Type(s) of Resistant Mechanism of This Drug
  DISM: Drug Inactivation by Structure Modification
Drug Resistance Data Categorized by Their Corresponding Diseases
ICD-01: Infectious/parasitic diseases
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Bacterial infection [ICD-11: 1A00-1C4Z]
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Drug Resistance Data Categorized by Their Corresponding Mechanisms
       Drug Inactivation by Structure Modification (DISM) Click to Show/Hide
Key Molecule: Beta-lactamase (BLA) [1]
Molecule Alteration Missense mutation
p.Y104A+p.N110D+p.E175Q+p.S179A
Resistant Disease Bacterial infection [ICD-11: 1A00-1C4Z]
Experimental Note Identified from the Human Clinical Data
In Vitro Model Escherichia coli TOP10 83333
Acinetobacter baumannii CIP70.10 470
Klebsiella pneumoniae kP3 1290996
Pseudomonas aeruginosa PU21 287
Experiment for
Molecule Alteration
Whole genome sequence assay; Allelic frequency measurement assay
Experiment for
Drug Resistance
MIC assay
Mechanism Description K. pneumoniae kP3 was resistant to all Beta-lactams, including carbapenems, and expressed the carbapenem-hydrolyzing Beta-lactamase OXA-181, which differs from OXA-48 by four amino acid substitutions. Compared to OXA-48, OXA-181 possessed a very similar hydrolytic profile.
Key Molecule: Beta-lactamase (BLA) [7], [8]
Molecule Alteration Expression
Up-regulation
Resistant Disease Bacterial infection [ICD-11: 1A00-1C4Z]
Experimental Note Identified from the Human Clinical Data
In Vitro Model Escherichia coli HB101 634468
Escherichia coli JM101 562
Experiment for
Molecule Alteration
Whole genome sequence assay
Mechanism Description Beta-lactamases (Beta-lactamhydrolase, EC 3.5.2.6), responsible for most of the resistance to Beta-lactam antibiotics, are often plasmid mediated.The OXA-1 beta-lactamase gene is part of Tn2603, which is borne on the R plasmid RGN238.
Key Molecule: Beta-lactamase (BLA) [9]
Molecule Alteration Missense mutation
p.V88L+p.M154L
Resistant Disease Bacterial infection [ICD-11: 1A00-1C4Z]
Experimental Note Identified from the Human Clinical Data
In Vitro Model Escherichia coli TOP10 83333
Escherichia coli ST648 562
Experiment for
Molecule Alteration
Whole genome sequence assay; Allelic frequency measurement assay
Experiment for
Drug Resistance
Etest assay
Mechanism Description NDM-5 differed from existing enzymes due to substitutions at positions 88 (Val - Leu) and 154 (Met - Leu) and reduced the susceptibility of Escherichia coli TOP10 transformants to expanded-spectrum cephalosporins and carbapenems when expressed under its native promoter.
Malaria [ICD-11: 1F45]
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Drug Resistance Data Categorized by Their Corresponding Mechanisms
       Drug Inactivation by Structure Modification (DISM) Click to Show/Hide
Key Molecule: CAM-1 carbapenemase (CAM1) [2]
Molecule Alteration Expression
Up-regulation
Resistant Disease Pseudomonas infection [ICD-11: 1F45.1]
Experimental Note Identified from the Human Clinical Data
In Vitro Model Escherichia coli TOP10 83333
Pseudomonas aeruginosa N17-01167 287
Pseudomonas aeruginosa N17-01173 287
Pseudomonas aeruginosa N17-02436 287
Pseudomonas aeruginosa N17-02437 287
Experiment for
Molecule Alteration
Whole genome sequencing assay
Experiment for
Drug Resistance
Vitek 2 assay; Etest assay
Mechanism Description A novel class B Beta-lactamase gene, blaCAM-1, exhibited resistance to imipenem, meropenem, doripenem, cefotaxime, ceftazidime, cefoxitin, piperacillin/tazobactam, ceftazidime/avibactam and ceftolozane/tazobactam.
References
Ref 1 Characterization of OXA-181, a carbapenem-hydrolyzing class D beta-lactamase from Klebsiella pneumoniae. Antimicrob Agents Chemother. 2011 Oct;55(10):4896-9. doi: 10.1128/AAC.00481-11. Epub 2011 Jul 18.
Ref 2 Identification of a novel metallo-Beta-lactamase, CAM-1, in clinical Pseudomonas aeruginosa isolates from Canada. J Antimicrob Chemother. 2019 Jun 1;74(6):1563-1567. doi: 10.1093/jac/dkz066.
Ref 3 Pathogen profile and drug resistance analysis of spontaneous peritonitis in cirrhotic patients .World J Gastroenterol. 2015 Sep 28;21(36):10409-17. doi: 10.3748/wjg.v21.i36.10409. 10.3748/wjg.v21.i36.10409
Ref 4 Pathogens and drug-resistance of hospital-acquired pneumonia in an EICU in Tianjin, ChinaInt J Biochem Mol Biol. 2021 Apr 15;12(2):49-54. eCollection 2021.
Ref 5 Treatment options for other hepatic malignancies .Liver Transpl. 2000 Nov;6(6 Suppl 2):S23-9. doi: 10.1053/jlts.2000.18687. 10.1053/jlts.2000.18687
Ref 6 Investigation and analysis of the characteristics and drug sensitivity of bacteria in skin ulcer infections .Chin J Traumatol. 2017 Aug;20(4):194-197. doi: 10.1016/j.cjtee.2016.09.005. Epub 2017 May 24. 10.1016/j.cjtee.2016.09.005
Ref 7 Precise insertion of antibiotic resistance determinants into Tn21-like transposons: nucleotide sequence of the OXA-1 beta-lactamase gene. Proc Natl Acad Sci U S A. 1987 Nov;84(21):7378-82. doi: 10.1073/pnas.84.21.7378.
Ref 8 Identifying novel Beta-lactamase substrate activity through in silico prediction of antimicrobial resistance. Microb Genom. 2021 Jan;7(1):mgen000500. doi: 10.1099/mgen.0.000500.
Ref 9 A novel variant, NDM-5, of the New Delhi metallo-Beta-lactamase in a multidrug-resistant Escherichia coli ST648 isolate recovered from a patient in the United Kingdom. Antimicrob Agents Chemother. 2011 Dec;55(12):5952-4. doi: 10.1128/AAC.05108-11. Epub 2011 Sep 19.

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