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. A (Au), B (U.S.)
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 its successor, amoxicillin in terms of spectrum and level of activity.[1]

It can sometimes result in reactions that range in severity from a rash (in the case of patients who may unwittingly have mononucleosis) to potentially lethal allergic reactions such as anaphylaxis. However, as with other penicillin drugs, it is relatively nontoxic, and adverse effects of a serious nature are encountered only rarely.

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.[2]

Medical uses[edit]

Ampicillin is closely related to amoxicillin, another type of penicillin, and both are used to treat urinary tract infections, otitis media, H. influenzae infection, salmonellosis, and Listeria meningitis. It is used with flucloxacillin in the combination antibiotic co-fluampicil for empiric treatment of cellulitis, providing cover against group A streptococcal infection whilst the flucloxacillin acts against Staphylococcus aureus. Of concern is the number of bacteria that have become resistant to ampicillin, necessitating combination therapy or use of other antibiotics.

All Pseudomonas species and most strains of Klebsiella and Aerobacter are considered resistant.[3] Additionally, resistance to ampicillin is seen in enterobacter, citrobacter, serratia, indole-positive proteus species, and other hospital-acquired gram negative infections.[4]

An ampicillin resistance gene (abbreviated ampR) is commonly used as a selectable marker in routine biotechnology. Due to concerns over horizontal gene transfer to pathogenic organisms in the wild, the European Food Safety Authority restricts use of this gene (among other resistance genes) in commercial genetically modified organisms. The enzyme responsible for degrading ampicillin is called beta-lactamase, in reference to the beta-lactam structure of ampicillin and related drugs.

Spectrum of bacterial susceptibility[edit]

Ampicillin has a broad spectrum of activity and has been used to treat bacteria responsible for causing infections in the genitourinary and lower respiratory tract. The following represents ampicillin MIC susceptibility data for a few medically significant microorganisms.

  • Escherichia coli: 0.5 μg/mL - 1024 μg/mL
  • Haemophilus influenzae: 0.07 μg/mL - 128 μg/mL
  • Streptococcus pneumoniae: 1 μg/mL - >50 μg/mL

[5]

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 has received FDA approval for its mechanism of action.

Effects on chloroplast division[edit]

Ampicillin, like other β-lactam antibiotics, not only blocks the division of bacteria, but also the division of chloroplasts of the glaucophytes (called cyanelles) and chloroplasts of the moss Physcomitrella patens, a bryophyte. In contrast, it has no effect on the plastids of the higher-developed vascular plant Solanum lycopersicum (tomato).[6]

History[edit]

Ampicillin has been used extensively to treat bacterial infections since 1961. 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. Ampicillin (originally branded as 'Penbritin') also demonstrated activity against Gram-negative organisms such as H. influenzae, coliforms and Proteus spp. Ampicillin was the first of a number of so-called broad-spectrum penicillins subsequently introduced by Beecham.

References[edit]

  1. ^ a b AHFS DRUG INFORMATION 2006 (2006 ed.). American Society of Health-System Pharmacists. 2006. 
  2. ^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014. 
  3. ^ Mosby's Drug Consult 2006 (16 ed.). Mosby, Inc. 2006. 
  4. ^ Katzung, Bertram G. (2007). Basic and Clinical Pharmacology, 10th edition. New York, NY: McGraw Hill Medical. p. 733. ISBN 978-0-07-145153-6. 
  5. ^ http://www.toku-e.com/Assets/MIC/Ampicillin%20anhydrous.pdf
  6. ^ Britta Kasten und Ralf Reski (1997): β-lactam antibiotics inhibit chloroplast division in a moss (Physcomitrella patens) but not in tomato (Solanum lycopersicum). Journal of Plant Physiology 150, 137-140. [1]

External links[edit]