Difference between revisions of "Ampicillin"

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(Edited the "Effects on Chloroplasts Division" Section by removing the "s" on Chloroplasts and the irrelevant last line of the section, which read "Ampicillin inhibits bacterial growth")
 
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'''Ampicillin''' is a [[beta-lactam antibiotic|beta-lactam]] [[antibiotic]] that has been used extensively to treat [[bacterium|bacterial]] [[infection]]s since 1961. Until the introduction of ampicillin by the British company, [[Beecham (pharmaceutical company)|Beecham]], penicillin therapies had only been effective against [[Gram-positive]] organisms such as [[Staphylococcus|staphylococci]] and [[Streptococcus|streptococci]]. Ampicillin (originally branded as 'Penbritin') also demonstrated activity against [[Gram-negative]] organisms such as ''[[H. influenzae]]'', [[coliform]]s and ''[[Proteus]]'' spp. Ampicillin was the first of a number of so-called broad spectrum penicillins subsequently introduced by Beecham. Ampicillin is part of the [[aminopenicillin]] family and is roughly equivalent to its successor, [[amoxicillin]] in terms of spectrum and level of activity<ref name=AHFS>{{ cite book | title= AHFS DRUG INFORMATION 2006 | publisher= American Society of Health-System Pharmacists | date= 2006 | edition= 2006}}</ref>. It can sometimes result in reactions that range in severity from a [[rash]] (in the case of patients that may unwittingly have [[Infectious mononucleosis|mononucleosis]]) to potentially lethal allergic reactions such as [[anaphylaxis]]. However, as with other penicillin drugs, it is relatively non-toxic and adverse effects of a serious nature are encountered only infrequently.
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'''Ampicillin''' is a [[beta-lactam antibiotic|beta-lactam]] [[antibiotic]] that has been used extensively to treat [[bacterium|bacterial]] [[infection]]s since 1961. Until the introduction of ampicillin by the British company [[Beecham (pharmaceutical company)|Beecham]], penicillin therapies had only been effective against [[Gram-positive]] organisms such as [[Staphylococcus|staphylococci]] and [[Streptococcus|streptococci]]. Ampicillin (originally branded as 'Penbritin') also demonstrated activity against [[Gram-negative]] organisms such as ''[[H. influenzae]]'', [[coliform]]s and ''[[Proteus]]'' spp. Ampicillin was the first of a number of so-called broad spectrum penicillins subsequently introduced by Beecham. Ampicillin is part of the [[aminopenicillin]] family and is roughly equivalent to its successor, [[amoxicillin]] in terms of spectrum and level of activity<ref name=AHFS>{{ cite book | title= AHFS DRUG INFORMATION 2006 | publisher= American Society of Health-System Pharmacists | year= 2006 | edition= 2006}}</ref>. It can sometimes result in reactions that range in severity from a [[rash]] (in the case of patients that may unwittingly have [[Infectious mononucleosis|mononucleosis]]) to potentially lethal allergic reactions such as [[anaphylaxis]]. However, as with other penicillin drugs, it is relatively non-toxic and adverse effects of a serious nature are encountered only infrequently.
  
 
==Mechanism of action==
 
==Mechanism of action==
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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.
 
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.
  
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Ampicillin acts as a competitive inhibitor of the enzyme [[DD-transpeptidase|transpeptidase]], which is needed by bacteria to make their [[cell wall]]s.<ref name=AHFS/> It inhibits the third and final stage of bacterial cell wall synthesis in [[binary fission]], which ultimately leads to cell [[lysis]].The holes that appear in the cell walls allow the body’s immune system to take over and fight off the bacteria. Ampicillin has received FDA approval for its action of mechanism.
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Ampicillin acts as a competitive inhibitor of the enzyme [[DD-transpeptidase|transpeptidase]], which is needed by bacteria to make their [[cell wall]]s.<ref name=AHFS/> 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 action of mechanism.
  
 
==== Effects on chloroplast division ====
 
==== Effects on chloroplast division ====
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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 ''[[Listeriosis|Listeria]]'' [[meningitis]]. It is used with [[flucloxacillin]] in the combination antibiotic [[co-fluampicil]] for [[Empirical|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 [[antibiotic resistance|resistant]] to Ampicillin necessitating combination therapy or use of other [[antibiotics]].
 
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 ''[[Listeriosis|Listeria]]'' [[meningitis]]. It is used with [[flucloxacillin]] in the combination antibiotic [[co-fluampicil]] for [[Empirical|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 [[antibiotic resistance|resistant]] to Ampicillin necessitating combination therapy or use of other [[antibiotics]].
  
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All ''[[Pseudomonas]]'' and most strains of ''[[Klebsiella]]'' and ''[[Aerobacter]]'' are considered resistant.<ref name=Mosby> {{ cite book | title=Mosby's Drug Consult 2006 | publisher= Mosby, Inc. | date= 2006 | edition= 16}}</ref>
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All ''[[Pseudomonas]]'' and most strains of ''[[Klebsiella]]'' and ''[[Aerobacter]]'' are considered resistant.<ref name=Mosby>{{ cite book | title=Mosby's Drug Consult 2006 | publisher= Mosby, Inc. | year= 2006 | edition= 16}}</ref>
  
 
===Use in research===
 
===Use in research===

Latest revision as of 15:47, 27 September 2010

Ampicillin
200px
200px
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
Pregnancy
category
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 Number 69-53-4
ATC code J01CA01 (WHO) S01AA19 QJ51CA01
PubChem CID 6249
DrugBank DB00415
ChemSpider 6013
UNII 7C782967RD
Chemical data
Formula C16H19N3O4S
Molar mass 349.41 g·mol−1[[Script error: No such module "String".]]
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  (verify)
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Ampicillin is a beta-lactam antibiotic that 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. Ampicillin 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 that may unwittingly have mononucleosis) to potentially lethal allergic reactions such as anaphylaxis. However, as with other penicillin drugs, it is relatively non-toxic and adverse effects of a serious nature are encountered only infrequently.

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. Ampicillin has received FDA approval for its action of mechanism.

Effects on chloroplast division

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 Lycopersicon esculentum L. (tomato) [2].

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]

Use in research

Ampicillin is often used as a selective agent in molecular biology to select for and 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 (typically 50–100 mg/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 (150 mg/ml).

References

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External links

Intracellular
inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin) · DADAL/AR inhibitors (Cycloserine) · bactoprenol inhibitors (Bacitracin)
Glycopeptide
inhibit PG chain elongation: Vancomycin# (Oritavancin, Telavancin) · Teicoplanin (Dalbavancin) · Ramoplanin
β-lactams/
(inhibit PBP
cross-links)
Combinations
Other

M: BAC

drug(J1p, w, n, m, vacc)

af:Ampisillien

ar:أمبيسيلين bs:Ampicilin cs:Ampicilin da:Ampicillin de:Ampicillin es:Ampicilina fa:آمپی‌سیلین fr:Ampicilline hr:Ampicilin it:Ampicillina kk:Ампициллин ht:Anpisilin hu:Ampicillin ja:アンピシリン pl:Ampicylina pt:Ampicilina ru:Ампициллин sk:Ampicilín sr:Ампицилин fi:Ampisilliini sv:Ampicillin th:แอมพิซิลลิน uk:Ампіцилін

zh:氨苄青黴素
  1. ↑ 1.0 1.1 AHFS DRUG INFORMATION 2006 (2006 ed.). American Society of Health-System Pharmacists. 2006. 
  2. ↑ 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]
  3. ↑ Mosby's Drug Consult 2006 (16 ed.). Mosby, Inc. 2006. 
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