Piperacillin/tazobactam

Overview

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.[1][2] WP

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.[1][3] WP

Piperacillin/tazobactam was approved for medical use in the United States in 1993. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.[1][2][4] WP

Uses, dosage and effects

Medical uses

Its main uses are in intensive care medicine (pneumonia, peritonitis), some diabetes-related foot infections, and empirical therapy in febrile neutropenia (e.g., after chemotherapy). The drug is administered intravenously every 6 or 8 hr, typically over 3–30 min. It may also be administered by continuous infusion over four hours. Prolonged infusions are thought to maximize the time that serum concentrations are above the minimum inhibitory concentration (MIC) of the bacteria implicated in infection. WP⚠ Wikipedia itself has flagged this text: citation needed.

Piperacillin-tazobactam is recommended by the National Institute for Health and Care Excellence as first-line therapy for the treatment of bloodstream infections in neutropenic cancer patients.[5] WP

For β-lactam antipseudomonal antibiotics, including piperacillin/tazobactam, prolonged intravenous infusion is associated with lower mortality than bolus intravenous infusion in persons with sepsis due to Pseudomonas aeruginosa.[6] WP

Piperacillin/tazobactam may be used for low to mid-severity infections with gram-negative rod bacteria that produce extended-spectrum beta-lactamases (ESBLs). It is not suitable for any life-threatening infection with ESBL-producing organisms.[7] WP

Risks and side effects

Adverse effects

The most common adverse effect is diarrhea (7–11%). Another adverse effect is inhibition of platelets which is also known as thrombocytopenia.[8][9] WP

Contraindications

Piperacillin/tazobactam is contraindicated when a patient has hypersensitivity to penicillins, cephalosporins, beta-lactamase inhibitors or any component of the formulation.[10] WP

Legal status

Brand names

The combination is marketed in various countries under brand names including Tazam, Tazocin, Zosyn, Tazovex, Tazact, Biopiper TZ, Brodactam, Piptaz, Maxitaz, Kilbac, Trezora, Du-Tazop, Tazopen, Sytaz, Tazin, and Inzalin TZ. WP⚠ Wikipedia itself has flagged this text: citation needed.

2017 shortage

Various sources have referred to a shortage of the drug since May 2017, citing various reasons, including an earthquake in China and other issues at the major production facility in 海正 (Hisun); increased demand; withdrawal of funding by a major pharmaceutical company.[11] WP

Chemistry

Formula

C33H39N9O12S2 PC

CAS number

123683-33-0 PC

Molar mass (g/mol)

817.9 PC

IUPAC name (computed by PubChem)

(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 PC

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 PC

InChIKey

LITBAYYWXZOHAW-XDZRHBBOSA-N PC

PubChem CID

9918881

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other Piperacillin Sodium and Tazobactam Sodium
2. Other British national formulary: BNF 69. 2015
3. Other Piperacillin / tazobactam (Zosyn) Use During Pregnancy
4. Other World Health Organization model list of essential medicines: 21st list 2019. 2019
5. Journal / agency National Collaborating Centre for Cancer (UK). Neutropenic Sepsis: Prevention and Management of Neutropenic Sepsis in Cancer Patients - National Library of Medicine - PubMed Health. 2012. PMID 26065059
6. Journal / agency Vardakas KZ, Voulgaris GL, Maliaros A, Samonis G, Falagas ME. Prolonged versus short-term intravenous infusion of antipseudomonal β-lactams for patients with sepsis: a systematic review and meta-analysis of randomised trials. Lancet Infect Dis. January 2018. doi:10.1016/S1473-3099(17)30615-1 · PMID 29102324
7. Other Munoz-Price, L (2017). "Chapter 185: Antibiotic Resistance". Principles and Practice of Hospital Medicine (2nd ed.). New York: McGraw-Hill Education
8. Other Piperacillin and Tazobactam Sodium
9. Journal / agency Rousan TA, Aldoss IT, Cowley BD Jr, Curtis BR, Bougie DW, Aster RH, George JN. Recurrent acute thrombocytopenia in the hospitalized patient: Sepsis, DIC, HIT, or antibiotic-induced thrombocytopenia. American Journal of Hematology. January 2010. doi:10.1002/ajh.21536 · PMID 19802882 · PMC4410979
10. Journal / agency Piperacillin and Tazobactam Injection. 15 October 2016
11. Other Drug Shortages › Piperacillin Tazobactam Injection. 10 July 2017

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.