Piperacillin

IUPAC: (2S, 5R, 6R ) -6 - [(R) -2 - (4 -ethyl- 2, 3 - dioxopiperazine -1 - carboxamido) - 2- phenylacetamido ] -3,3 - dimethyl- 7 -oxo -4- thia- 1 -azabicyclo [3.2.0 ] heptane - 2-carboxylic acid

• 66258-76-2 ( piperacillin )
• 59703-84-3 ( piperacillin sodium salt)

J01CA12

White to almost white powder

β -lactam antibiotic

Inhibition of cell wall synthesis and Septumbildung

183-185 ° C ( decomposition) ( piperacillin sodium salt)

Slightly soluble in water, slightly soluble in methanol, sparingly soluble in ethyl acetate

Sodium salt

• > 10 g · kg -1 ( LD50, rat, oral)
• 9770 mg · kg -1 ( LD50, mouse, ip)
• 5 g · kg -1 ( LD50, mouse, i.v.)
• 2.7 g · kg -1 ( LD50, rat, i.v.)
• > 6 g · kg -1 ( LD50, dog, i.v.)
• > 4 g · kg -1 ( LD50, monkey, i.v.)

Template: Infobox chemical / molecular formula search available

Piperacillin is a β -lactam antibiotic used in its structural formula contains a four-membered lactam ring and belongs to the group of acylaminopenicillins. This ingredient has the broadest spectrum of activity of all penicillins ( including Pseudomonas and Enterobacteriaceae ).

• 2.1 pharmacokinetics

Clinical information

Spectrum

The spectrum of activity of piperacillin goes beyond that of benzylpenicillin. It is effective against gram- negative bacilli, enterobacteria and anaerobes. Activity against gram-positive cocci, is worse than that of benzylpenicillin, but is considered to be sufficient, and is comparable to that of amoxicillin.

Areas of application (indications )

For the treatment of acute and chronic bacterial infections of various localization and intensity caused by piperacillin - susceptible organisms, such as:

• Therapy of infections in which gram-negative rods are to be accepted as pathogens such as urogenital infections, including pyelonephritis, cystitis and urethritis. Piperacillin also is effective in acute uncomplicated infections caused by Neisseria gonorrhoeae, including prostatitis
• Intra-abdominal infections, such as infections of the biliary tract, peritonitis and intra-abdominal abscesses ( often caused by gram-negative and / or anaerobic organisms of the normal intestinal flora )
• Gynecological infections such as endometritis, abscesses and inflammation of the pelvis, pelvic inflammatory disease
• Pneumonia in ventilated patients or in pneumonia with Pseudomonas aeruginosa as a probable causative agent
• Severe sepsis, bacterial endocarditis
• Skin and soft tissue infections, including infections after accidents, surgeries and infected burns
• Bone and joint infections - including osteomyelitis
• Septicemia ( infection in the general term for the human organism, which is caused by bacteria and toxins in the blood)
• Nosocomial infections caused by the bacterium Pseudomonas aeruginosa, piperacillin here is the preferred penicillin calculated to chemotherapy ( initial therapy for not yet available, seed analysis, which is based on the expected spectrum of germs )

Contraindications ( contraindications)

Because of the risk of anaphylactic shock, piperacillin should not be used in patients with a history of penicillin hypersensitivity. A cross-allergy with other β -lactam antibiotics can be made. In patients with allergic diseases in medical history, such as bronchial asthma, allergic rhinitis, urticaria (hives), the risk of serious hypersensitivity reactions in injection or infusion treatment is increased, which is why piperacillin should be applied in such cases, according to strict indications with particular care.

• Use in pregnancy and lactation:

Since no experience regarding the use in human pregnancy and lactation are available, piperacillin should not be used during pregnancy and lactation.

Adverse effects (side effects)

The following is the important information on possible common side effects of piperacillin. These adverse effects do not occur, but they can. Each patient reacts differently to medications.

• Uncommon side effects:

Eruptions as external phenomena ( manifestations ) of a drug allergy or pseudo-allergy in the form of skin rash, skin redness, itching, and mucosal inflammation; Purpura ( speckled capillary bleeding into the skin, subcutaneous tissue ( subcutaneous ) or the mucous membranes, which occur at high doses ); Serum creatinine increase; Blood urea concentration increase; Headaches.

• Rare side effects:

Severe allergic reactions such as drug fever; joint pain; eosinophilia; angioneurotic edema ( Quincke's edema); Throat swelling; Serum sickness; Anaemia due to dissolution of red blood cells; allergic vasculitis; Inflammation of the kidneys; Erythema multiforme; Stevens -Johnson syndrome; a reduced hemoglobin level (anemia ); Lack of solid blood components; essential thrombocythemia that is, a strong increase of thrombocytes ( platelets) in your blood.

Pharmacological properties

Pharmacokinetics

The acylaminopenicillins are not β -lactamase - and acid- stable. You are not absorbed after oral administration and parenteral must - be administered - either intravenously or intramuscularly. After intravenous bolus injection of 1 gram of piperacillin plasma concentrations of 70 mg · L-1 to be measured, at higher dosage levels of 400 mg · L-1 or more may be achieved. The rapid penetration into the bacterial cell wall is a good Kryptizität is achieved. Peak plasma levels are lower after intravenous short infusion. The plasma protein binding is 20% and the bioavailability is 100 % for intravenous, 70 to 80 % for intramuscular administration. Since the active ingredient rapidly and mostly unchanged with an elimination half-life of 65 minutes to 80 % ( by glomerular filtration and tubular secretion ) renal, is eliminated to a level of 6 to 15% by biliary excretion, take the concentrations rapidly.

The combination of β -lactamase - labile piperacillin with a β - lactamase inhibitor such as tazobactam, the antibiotic resistance of bacteria against β -lactamase - labile penicillins can be overcome. β - lactamase inhibitors exert little or no direct antibacterial activity. You block specific, clinically commonly occurring β -lactamases irreversible. Most plasmidvermittelten penicillinases inhibited, less or not the chromosomally mediated cephalosporinases. The pharmacokinetic properties of the two combination partners are similar.

Trade names

Numerous generics (D)

Piperacillin / tazobactam (D, A, CH), Pipitaz (A), Tazobac (D, CH), Tazonam (A)