II. Indications
- Serious Gram Negative Bacterial infection
- Use alone or in combination with Aminoglycosides
III. Medications
- Alpha carboxy Penicillin
- Carbenicillin
- Discontinued in U.S. as of 2008
- Ticarcillin (Ticar)
- Withdrawn from U.S. market as of 2015
- Ticarcillin clavulanate (Timentin)
- Withdrawn from U.S. market as of 2015
- Carbenicillin
- Acylamino-Penicillin
- Mezlocillin (Mezlin)
- Discontinued in U.S.
- Piperacillin (Pipracil)
- Not typically used without tazobactam
- Piperacillin Tazobactam (Zosyn)
- Only Extended Spectrum Penicillin still available in the United States as of 2023
- Mezlocillin (Mezlin)
- Other structures
- Pivmecillinam (Selexid, Pivya)
- FDA approved in 2024 for simple cystitis in women
- Pivmecillinam (Selexid, Pivya)
IV. Mechanism
- Similar to Natural Penicillins
- Greater penetration through Gram Negative membrane
- High affinity for Penicillin binding Proteins
- Beta Lactamase resistance with Clavulanate, Tazobactam
V. Mechanism: Bacterial Resistance
- Beta Lactamase (except with Clavulanate or Tazobactam)
- Alteration of Penicillin binding Proteins (Pseudomonas)
VI. Dosing: Parenteral
-
Piperacillin Tazobactam (Zosyn)
- Adult: 3.375 g IV q6 hours
- Ticarcillin Clavulanate (Timentin, not available in U.S.)
- Listed for historical purposes, and for use outside the U.S.
- Adult: 3.1 g IV q4-6h
- Child: 50 mg/kg up to 3.1 g IV q4-6 hours
VII. Adverse Effects
- Many side effects in addition to Natural Penicillins
- High Sodium load (Carbenicillin)
- Platelet Dysfunction
VIII. Activity Spectrum
- Similar to Natural Penicillins and Aminopenicillins
- Expanded Gram Negative coverage
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| Definition (NCI) | A broad-spectrum, semi-synthetic penicillin antibiotic with bactericidal and beta-lactamase resistant activity. Carbenicillin acylates the penicillin-sensitive transpeptidase C-terminal domain by opening the lactam ring. This inactivation prevents the cross-linkage of peptidoglycan strands, thereby inhibiting the third and last stage of bacterial cell wall synthesis. This leads to incomplete bacterial cell wall synthesis and eventually causes cell lysis. |
| Definition (MSH) | Broad-spectrum semisynthetic penicillin derivative used parenterally. It is susceptible to gastric juice and penicillinase and may damage platelet function. |
| Concepts | Antibiotic (T195) , Organic Chemical (T109) |
| MSH | D002228 |
| SnomedCT | 34731007, 372713001 |
| LNC | LP16062-9, MTHU007966 |
| English | Carbenicillin, Carboxybenzyl Penicillin, Penicillin, Carboxybenzyl, 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((carboxyphenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-, carbenicillin, Carbenicillin [Chemical/Ingredient], Carbenicillin (product), Carbenicillin (substance), CARBENICILLIN |
| Swedish | Karbenicillin |
| Czech | karbenicilin |
| Finnish | Karbenisilliini |
| Russian | KARBOKSIBENZILPENITSILLIN, KARBENITSILLIN, КАРБЕНИЦИЛЛИН, КАРБОКСИБЕНЗИЛПЕНИЦИЛЛИН |
| Japanese | カルベニシリン, カルボキシベンジルペニシリン, カルベニシリンナトリウム |
| Croatian | CARBENICILLIN |
| Polish | Karbenicylina |
| Spanish | Carboxibencilpenicilina, carbenicilina (producto), carbenicilina (sustancia), carbenicilina, Carbenicilina, Carboxibencil Penicilina |
| French | Carbénicilline |
| German | Carbenicillin, Carboxybenzylpenizillin |
| Italian | Carbenicillina |
| Portuguese | Carbenicilina, Carboxibenzilpenicilina |
Ontology: Piperacillin (C0031955)
| Definition (NCI) | A broad-spectrum semisynthetic, ampicillin-derived ureidopenicillin antibiotic. Piperacillin binds to penicillin binding proteins (PBP), the enzymes that catalyze the synthesis of peptidoglycan, a critical component of the bacterial cell wall. This blockade leads to the interruption of cell wall synthesis, consequently, leading to bacterial cell growth inhibition and cell lysis. |
| Definition (MSH) | Semisynthetic, broad-spectrum, AMPICILLIN derived ureidopenicillin antibiotic proposed for PSEUDOMONAS infections. It is also used in combination with other antibiotics. |
| Concepts | Antibiotic (T195) , Organic Chemical (T109) |
| MSH | D010878 |
| SnomedCT | 372836004, 74575000 |
| LNC | LP16256-7, MTHU008471 |
| English | Pipercillin, 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)phenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta(S*)))-, piperacillin, piperacillin (medication), Piperacillin [Chemical/Ingredient], pipercillin, (2S,5R,6R)-6-((R)-2-(4-Ethyl-2,3-dioxo-1-piperazinecarboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid Monohydrate, PIPERACILLIN, Piperacillin (product), Piperacillin (substance), Piperacillin |
| Swedish | Piperacillin |
| Czech | piperacilin |
| Finnish | Piperasilliini |
| Russian | PIPERATSILLIN, ПИПЕРАЦИЛЛИН |
| Japanese | ピシリアント, プランジン, ホモスリン, ペンマリン, ペントシリン, ピペラシリンナトリウム, ピペユンシン, アルカベミン, ピペラシリン |
| Italian | Pipercillina, Piperacillina |
| Croatian | PIPERACILIN |
| Polish | Piperacylina |
| Spanish | piperacilina (producto), piperacilina (sustancia), piperacilina, Piperacilina |
| French | Pipéracilline |
| German | Piperacillin |
| Portuguese | Piperacilina |
Ontology: Ticarcillin (C0040193)
| Definition (NCI) | A broad-spectrum, semi-synthetic penicillin antibiotic with bactericidal activity. Similar to carbenicillin in action, ticarcillin inactivates the penicillin-sensitive transpeptidase C-terminal domain by opening the lactam ring. This inactivation prevents the cross-linkage of peptidoglycan strands, thereby inhibiting the third and last stage of bacterial cell wall synthesis. This leads to incomplete bacterial cell wall synthesis and eventually causes cell lysis. |
| Definition (MSH) | An antibiotic derived from penicillin similar to CARBENICILLIN in action. |
| Concepts | Antibiotic (T195) , Organic Chemical (T109) |
| MSH | D013982 |
| SnomedCT | 1148001, 372577006 |
| LNC | LP16291-4, MTHU008492 |
| English | Ticarcillin, 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((carboxy-3-thienylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta(S*)))-, ticarcillin, Ticarcillin [Chemical/Ingredient], ticarcillin (medication), TICARCILLIN, Ticarcillin (product), Ticarcillin (substance), Ticarcillin, NOS |
| Swedish | Ticarcillin |
| Czech | tikarcilin |
| Finnish | Tikarsilliini |
| Russian | TIKARTSILLIN, BRL 2288, ТИКАРЦИЛЛИН |
| Japanese | チカルシリン, チカルシリンナトリウム |
| Polish | Tikarcylina |
| Spanish | ticarcilina (producto), ticarcilina (sustancia), ticarcilina, Ticarcilina |
| French | Ticarcilline |
| German | Ticarcillin |
| Italian | Ticarcillina |
| Portuguese | Ticarcilina |
Ontology: Timentin (C0076686)
| Concepts | Antibiotic (T195) , Organic Chemical (T109) |
| MSH | C043215 |
| English | Timentin, Timentin ADD-Vantage, timentin |
