Ampicillin

Ampicillin

Ampicillin
Systematic (IUPAC) name
(2S,5R,6R)-6-([(2R)-2-amino-2-phenylacetyl]amino)
-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-
carboxylic acid
Clinical data
Trade names Principen among others
AHFS/Drugs.com
MedlinePlus
Licence data US FDA:
Pregnancy
category
Legal status
Routes of
administration
Oral, intravenous
Pharmacokinetic data
Bioavailability 40% (oral)
Protein binding 15 to 25%
Metabolism 12 to 50%
Biological half-life approx 1 hour
Excretion 75 to 85% renal
Identifiers
CAS Registry Number  YesY
ATC code J01 S01 QJ51
PubChem CID:
DrugBank  YesY
ChemSpider  YesY
UNII  YesY
KEGG  YesY
ChEBI  YesY
ChEMBL  YesY
Chemical data
Formula C16H19N3O4S
Molecular mass 349.41 g·mol−1
 YesY   

Ampicillin is an health system.[4] Its wholesale costs is between 0.13 and 1.20 USD for a vial of the intravenous solution as of 2014.[5] In the United States it is available as a generic medication and ten days of treatment is about 13 USD.[1]

Contents

  • Medical uses 1
  • Side effects 2
  • Mechanism of action 3
  • History 4
  • Cost 5
  • See also 6
  • References 7
  • External links 8

Medical uses

It is active against many Gram-positive and Gram-negative bacteria.

Ampicillin is active against Gram-(+) bacteria including Streptococcus pneumoniae, Streptococcus pyogenes, some isolates of Staphylococcus aureus (but not penicillin-resistant or methicillin-resistant strains), and some Enterococci. Activity against Gram-(-) bacteria includes Neisseria meningitidis, some Haemophilus influenzae, and some Enterobacteriaceae. Its spectrum of activity is enhanced by co-administration of sulbactam, a drug that inhibits beta lactamase, an enzyme produced by bacteria to inactivate ampicillin and related antibiotics.[6][7]

It is used for the treatment of infections known to be or highly likely to be caused by these bacteria. These include common respiratory infections including sinusitis, bronchitis, and pharyngitis, as well as otitis media. In combination with vancomycin (which provides coverage of ampicillin-resistant pneumococci), it is effective for the treatment of bacterial meningitis. It is also used for gastrointestinal infections caused by consuming contaminated water or food, such as Salmonella, Shigella, and Listeriosis.[8]

Ampicillin is a first-line agent for the treatment of infections caused by Enterococci. The bacteria are an important cause of healthcare-associated infections such as endocarditis, meningitis, and catheter-associated urinary tract infections that are typically resistant to other antibiotics.[8]

Side effects

Ampicillin is relatively non-toxic. Its most common side effects include rash, diarrhea, and nausea.[1] In very rare cases it causes severe side effects such as angioedema, anaphylaxis and Clostridium difficile diarrhea.

Mechanism of action

Ampicillin is in the penicillin group of beta-lactam antibiotics and is part of the aminopenicillin family. It is roughly equivalent to amoxicillin in terms of activity.[9]

Ampicillin is able to penetrate Gram-positive and some Gram-negative bacteria. It differs from penicillin G, or benzylpenicillin, only by the presence of an amino group. That amino group helps the drug penetrate the outer membrane of Gram-negative bacteria.

Ampicillin acts as an irreversible inhibitor of the enzyme transpeptidase, which is needed by bacteria to make their cell walls.[9] It inhibits the third and final stage of bacterial cell wall synthesis in binary fission, which ultimately leads to cell lysis; therefore ampicillin is usually bacteriocidal.[10][9]

History

Ampicillin has been used extensively to treat coliforms and Proteus spp.[11]

Cost

Its wholesale costs is between 0.13 and 1.20 USD for a vial of the intravenous solution as of 2014.[5] In the United States it is available as a generic medication and ten days of treatment is about 13 USD.[1]

See also

References

  1. ^ a b c d e f g
  2. ^
  3. ^
  4. ^
  5. ^ a b
  6. ^ Hauser AR (2013). Antibiotic Basics for Clinicians, 2nd ed. Lippincott, Williams, and Wikins, pp. 25-28
  7. ^
  8. ^ a b Finberg R, Fingeroth J in Longo DL, Fauci AS, Kasper DL, Hauser SL, Jameson JL, Loscalzo (eds.) (2012) Harrison's Principles of Internal Medicine, 18th ed., McGraw-Hill, Chapter 132.
  9. ^ a b c
  10. ^ a b Petri WA in Brunton LL, Chabner BA, Knollmann BC (eds.) (2011 ) Goodman and Gilman's The Pharmacological Basis of Therapeutics, 12th ed., Chapter 53. McGraw-Hill, New York.
  11. ^ a b

External links

  • Ampicillin bound to proteins in the PDB