Ampicillin
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Ampicillin
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| 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 |
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| Identifiers | |
| CAS number | |
| ATC code | J01 S01 QJ51 |
| PubChem | |
| DrugBank | |
| ChemSpider | |
| Chemical data | |
| Formula | C16H19N3O4S |
| Mol. mass | 349.406 g/mol |
| Pharmacokinetic data | |
| Bioavailability | 40% (oral) |
| Protein binding | 15 to 25% |
| Metabolism | 12 to 50% |
| Half life | approx 1 hour |
| Excretion | 75 to 85% renal |
| Therapeutic considerations | |
| Pregnancy cat. | |
| Legal status | |
| Routes | Oral, intravenous |
Ampicillin is a beta-lactam antibiotic that has been used extensively to treat bacterial infections since 1961. It is considered part of the aminopenicillin family and is roughly equivalent to amoxicillin in terms of spectrum and level of activity[1]. It can sometimes result in non-allergic reactions that range in severity from a rash (e.g., patients with mononucleosis) to potentially lethal anaphylaxis.
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[edit] Mechanism of action
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 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 a competitive 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.
[edit] Effects on chloroplasts division
Ampicillin, like other β-lactam antibiotics, not only block 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 Lycopersicon esculentum L. (tomato) [2].
[edit] Application
Ampicillin is closely related to amoxicillin, another type of penicillin, and both are used to treat urinary tract infections, otitis media, uncomplicated community-acquired pneumonia, Haemophilus influenzae, 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 the Staphylococcus aureus bacterium. Of concern is the number of bacteria that become resistant to Ampicillin necessitating combination therapy or use of other antibiotics.
All Pseudomonas and most strains of Klebsiella and Aerobacter are considered resistant.[3]
[edit] Use in research
Ampicillin is often used as a selective agent in molecular biology to confirm the uptake of genes (e.g., of plasmids) by bacteria (e.g., E. coli). A gene that is to be inserted into a bacterium is coupled to a gene coding for an ampicillin resistance (in E. coli, usually the bla (TEM-1) gene, coding for β-lactamase). The treated bacteria are then grown in a medium containing ampicillin (50-100mg/L). Only the bacteria that successfully take up the desired genes become ampicillin resistant, and therefore contain the other desired gene as well. It can be used with Cloaxicillin as well. As a powder ampicillin is white with slight yellow cast and is soluble in water (150mg/ml).
[edit] External links
[edit] References
- ^ a b AHFS DRUG INFORMATION 2006 (2006 ed ed.). American Society of Health-System Pharmacists. 2006.
- ^ Britta Kasten und Ralf Reski (1997): β-lactam antibiotics inhibit chloroplast division in a moss (Physcomitrella patens) but not in tomato (Lycopersicon esculentum). Journal of Plant Physiology 150, 137-140. [1]
- ^ Mosby's Drug Consult 2006 (16 ed ed.). Mosby, Inc.. 2006.
