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piperacillin/tazobactam

Structure via PubChem · Public domain (PubChem)

EntityQ7197337· pop 16· linked from 214 articles

piperacillin/tazobactam

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Also known as Tazocin, Zosyn

Piperacillin/tazobactam, sold under the brand name Tazocin among others, is a combination medication containing the antibiotic piperacillin and the β-lactamase inhibitor tazobactam. The combination has activity against many Gram-positive and Gram-negative bacteria including Pseudomonas aeruginosa. It is used to treat pelvic inflammatory disease, intra-abdominal infection, pneumonia, cellulitis, and sepsis. It is given by injection into a vein.

Chemical data

Formula
C33H39N9O12S2
Molecular weight
817.9 g/mol
IUPAC name
(2S,5R,6R)-6-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;(2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILES
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
InChIKey
LITBAYYWXZOHAW-XDZRHBBOSA-N
Polar surface area
313 Ų
H-bond donors
4
H-bond acceptors
15
Formal charge
0

via PubChem

Drug data · ChEMBL

Molecule type
Small molecule

via ChEMBL · EBI

Research

7,531 papers

via PubMed

Wikidata facts

Subclass of
combination drug
Mass
817.21596
Show 4 more facts
chemical formula
C₃₃H₃₉N₉O₁₂S₂
canonical SMILES
CCN1CCN(C(=O)C1=O)C(=O)NC(C2=CC=CC=C2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O.CC1(C(N2C(S1(=O)=O)CC2=O)C(=O)O)CN3C=CN=N3
isomeric SMILES
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
subject has role
essential medicine
Sources (2)

via Wikidata · CC0

~5 min read

Encyclopedic overview

8 sections
Contents
  • Medical uses
  • Route of administration
  • Adverse effects
  • Contraindications
  • Society and culture
  • Brand names
  • 2017 shortage
  • References

Piperacillin/tazobactam, sold under the brand name Tazocin among others, is a combination medication containing the antibiotic piperacillin and the β-lactamase inhibitor tazobactam. The combination has activity against many Gram-positive and Gram-negative bacteria including Pseudomonas aeruginosa. It is used to treat pelvic inflammatory disease, intra-abdominal infection, pneumonia, cellulitis, and sepsis. It is given by injection into a vein.

Common adverse effects include headache, trouble sleeping, rash, nausea, constipation, and diarrhea. Serious adverse effects include Clostridioides difficile infection and allergic reactions including anaphylaxis. Those who are allergic to other β-lactam are more likely to be allergic to piperacillin/tazobactam. Use in pregnancy or breastfeeding appears to generally be safe. Its mechanism usually results in bacterial death through blocking their ability to make a cell wall.

Excerpted from Wikipedia’s “piperacillin/tazobactam” article, available under the CC BY-SA 4.0 licence.

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