Pivampicillin
- Atc Codes:J01CA02
- CAS Codes:26309-95-5#33817-20-8#39030-72-3
- PHARMGKB ID:26309-95-5#33817-20-8#39030-72-3
Table of contents
- Brand Names
- Chemistry
- Pharmacologic Category
- Mechanism of Action
- Therapeutic Use
- Pregnancy and Lactation Implications
- Contraindications
- Warnings and Precautions
- Adverse Reactions
- Drug Interactions
- Nutrition/Nutraceutical Interactions
- Dosage
- Pharmacokinetics and Pharmacodynamics
- Special Considerations
Brand Names
Europe
Denmark: Pondocillin; Greece: Pondocillin; Sweden: Pondocillin.
Drug combinations
Chemistry
Pivampicillin Hydrochloride: C~22~H~29~N~3~O~6~S HCl. Mw: 500.01. 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, monohydrochloride, [2S-[2α,5α,6β(S*)]]-. CAS-26309-95-5; CAS-33817-20-8 (pivampicillin)(1970).
Pivampicillin Pamoate: (C~22~H~29~N~3~O~6~S)~2~ C~23~H~16~O~6~. Mw: 1315.46. (1) 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, [2S-[(2α,5α,6β(S*)])]-, 4,4′-methylenebis[3-hydroxy-2-naphthalenecarboxylate] (2:1); (2) Hydroxymethyl D-(-)-6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate (ester) compound with 4,4′-methylenebis[3-hydroxy-2-naphthoic acid] (2:1). CAS-39030-72-3 (1973).
Pharmacologic Category
Extended-spectrum Penicillins. (ATC-Code: J01CA02).
Mechanism of action
Prodrug converted to microbiologically active component (ampicillin) which inhibits bacterial cell wall synthesis by binding to one or more penicillin-binding proteins which in turn inhibits final transpeptidation step of peptidoglycan synthesis in bacterial cell walls, thus inhibiting cell wall biosynthesis.
Therapeutic use
Treatment of susceptible bacterial infections (non-β-lactamase-producing organisms). Susceptible bacterial infections caused by streptococci, pneumococci, non-penicillinase-producing staphylococci, H. influenzae, N. gonorrhoeae, E. coli, P. mirabilis, Listeria, Salmonella, Shigella, Enterobacter, and Klebsiella.
Pregnancy and lactiation implications
Safety not established. Ampicillin component crosses human placenta, also enters breast milk. Unknown if pivalic acid component secreted into breast milk (use caution).
Unlabeled use
Contraindications
Hypersensitivity to ampicillin, pivalic acid, any component of the formulation, or other penicillins or cephalosporins. In secondary infections associated with mononucleosis or lymphatic leukemia. Infections due to β-lactamase-producing bacteria.
Warnings and precautions
Increase in carnitine excretion in urine as conjugate with pivalic acid, and thus decrease in serum carnitine levels, seen in patients. Prolonged use may result in fungal or bacterial superinfection, including C. difficile-associated diarrhea and pseudomembranous colitis. Avoid use in porphyria (considered unsafe). Concurrent treatment with medications liberating pivalic acid (e.g. valproate) should be avoided. Suspension not recommended for treatment of severe infections in children.