Ampicillin

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Ampicillin
Ampicillin Structural Formulae V.1.svg
Ampicillin 3d structure pdb.gif
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
AHFS/Drugs.com monograph
MedlinePlus a685002
Pregnancy cat.
Legal status
?
Routes Oral, intravenous
Pharmacokinetic data
Bioavailability 40% (oral)
Protein binding 15 to 25%
Metabolism 12 to 50%
Half-life approx 1 hour
Excretion 75 to 85% renal
Identifiers
CAS number 69-53-4 YesY
ATC code J01CA01 S01AA19 QJ51CA01
PubChem CID 6249
DrugBank DB00415
ChemSpider 6013 YesY
UNII 7C782967RD YesY
KEGG D00204 YesY
ChEBI CHEBI:28971 YesY
ChEMBL CHEMBL174 YesY
Chemical data
Formula C16H19N3O4S 
Mol. mass 349.41 g·mol−1
 YesY (what is this?)  (verify)

Ampicillin is an antibiotic useful for the treatment of a number of bacterial infections. It is a beta-lactam antibiotic that is part of the aminopenicillin family and is roughly equivalent to amoxicillin in terms of activity.[1] It is either taken by mouth or through a vein. It is active against many Gram-positive and Gram-negative bacteria.

It is effective for ear infections and respiratory infections such as sinusitis caused by bacteria, acute exacerbations of COPD, and epiglottitis. It is also sometimes used for the treatment of urinary tract infections, meningitis, and salmonella infections, but resistance to ampicillin is increasingly common among the bacteria responsible for these infections.[2][3]

Common side effects include rash, diarrhea, nausea and vomiting.[4] It is not useful for the treatment of viral infections.

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[5]

Medical uses[edit]

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.[3]

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.[3]

Side effects[edit]

Ampicillin is relatively non-toxic. Its most common side effects include rash, diarrhea, nausea and vomiting.[4] In very rare cases it causes severe side effects such as angioedema, anaphylaxis and Clostridium difficile diarrhea.

Mechanism of action[edit]

Belonging to the penicillin group of beta-lactam antibiotics, 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.[1] It inhibits the third and final stage of bacterial cell wall synthesis in binary fission, which ultimately leads to cell lysis. Ampicillin is bacteriocidal.[2]

History[edit]

Ampicillin has been used extensively to treat bacterial infections since 1961.[8] Until the introduction of ampicillin by the British company Beecham, penicillin therapies had only been effective against Gram-positive organisms such as staphylococci and streptococci.[2] Ampicillin (originally branded as 'Penbritin') also demonstrated activity against Gram-negative organisms such as H. influenzae, coliforms and Proteus spp.[8]

References[edit]

  1. ^ a b AHFS DRUG INFORMATION 2006 (2006 ed.). American Society of Health-System Pharmacists. 2006. 
  2. ^ a b c Petri WA in Brunton LL, Chabner BA, Knollmann BC, Ed. Goodman and Gilman's The Pharmacological Basis of Therapeutics, 12th ed., Chapter 53. McGraw-Hill, 2011 New York.
  3. ^ a b c Finberg R, Fingeroth J in Longo DL, Fauci AS, Kasper DL, Hauser SL, Jameson JL, Loscalzo, Ed. Harrison's Principles of Internal Medicine, 18th ed., McGraw-Hill, 2012, Chapter 132.
  4. ^ a b "www.accessdata.fda.gov". 
  5. ^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014. 
  6. ^ Hauser AR. Antibiotic Basics for Clinicians, 2nd ed. Lippincott, Williams, and Wikins (2013), pp 25-28
  7. ^ Akova M (January 2008). "Sulbactam-containing beta-lactamase inhibitor combinations". Clin. Microbiol. Infect. 14 Suppl 1: 185–8. doi:10.1111/j.1469-0691.2007.01847.x. PMID 18154545. 
  8. ^ a b ACRED P, BROWN DM, TURNER DH, WILSON MJ (April 1962). "Pharmacology and chemotherapy of ampicillin--a new broad-spectrum penicillin". Br J Pharmacol Chemother 18: 356–69. doi:10.1111/j.1476-5381.1962.tb01416.x. PMC 1482127. PMID 13859205. 

External links[edit]