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IV injections must be given slowly, as rapid IV injections can lead to convulsive [[seizures]].<ref name="AHFS2015" /><ref name=":3" />
IV injections must be given slowly, as rapid IV injections can lead to convulsive [[seizures]].<ref name="AHFS2015" /><ref name=":3" />

=== Specific populations===
Ampicillin is one of the most commonly used drugs in pregnancy,<ref name=":4">{{cite book|url=https://books.google.com/books?id=apoTV0TZHRQC&lpg=PT47&dq=ampicillin%20pregnancy&pg=PT47#v=onepage&q=ampicillin%20pregnancy&f=false|title=The Complete Guide to Medications During Pregnancy and Breastfeeding: Everything You Need to Know to Make the Best Choices for You and Your Baby|last1=Weiner|first1=Carl P.|last2=Rope|first2=Kate|publisher=St. Martin's Press|year=2013|isbn=978-1-250-03720-6|pages=47–49|ref=harv}}</ref> and has been found to be generally harmless both by the [[Food and Drug Administration]] in the U.S. (which classified it as [[Pregnancy category#United States|category B]]) and the [[Therapeutic Goods Administration]] in Australia (which classified it as [[Pregnancy category#Australia|category A]]).<ref name="AHFS2015" /><ref>{{cite web|url=https://www.tga.gov.au/prescribing-medicines-pregnancy-database|title=Prescribing medicines in pregnancy database|last=Administration|first=Australian Government Department of Health Therapeutic Goods|date=25 October 2017|work=Therapeutic Goods Administration (TGA)|publisher=Australian Government Department of Health|accessdate=23 February 2018}} {{Small|Note: scroll down to "Seach by name" and type "ampicillin" into the search bar. Requires JavaScript to be enabled.}} <!-- If you can find a way to link directly to the "ampicillin" entry, please replace the URL (and title, if needed) and remove the appended note. --></ref> It is the drug of choice for treating ''[[Listeria monocytogenes]]'' in pregnant women, either alone or combined with an aminoglycoside.<ref name="AHFS2015" /> Pregnancy increases the [[Clearance (pharmacology)|clearance]] of ampicillin by up to 50%, and a higher dose is thus needed to reach therapeutic levels.<ref name=":4" /><ref name=":5">{{cite book|url=https://books.google.com/books?id=wysQmU5bYAAC&pg=PA172|title=Infectious Diseases in Critical Care|last1=Rello|first1=Jordi|last2=Kollef|first2=Martin H.|last3=Díaz|first3=Emilio|last4=Rodríguez|first4=Alejandro|publisher=Springer Science & Business Media|year=2010|isbn=978-3-540-34406-3|pages=172|ref=harv}}</ref>

Ampicillin crosses the [[placenta]] and remains in the [[amniotic fluid]] at 50–100% of the concentration in maternal [[Plasma (blood)|plasma]]; this can lead to high concentrations of ampicillin in the newborn.<ref name=":5" />

While lactating mothers secrete some ampicillin into their breast milk, the amount is minimal.<ref name="AHFS2015" /><ref name=":4" />

In neonates, ampicillin has a longer half-life and lower plasma protein binding.<ref>{{cite book|url=https://books.google.com/books?id=CtfIAgAAQBAJ&pg=PA26|title=Essential Drug Data for Rational Therapy in Veterinary Practice|last=Eghianruwa|first=Kingsley|publisher=AuthorHouse|year=2014|isbn=978-1-4918-0010-2|location=|pages=26|ref=harv}}</ref> The renal clearance is lower, as renal function has not fully developed.<ref name="AHFS2015" />


==Side effects==
==Side effects==

Revision as of 01:16, 23 February 2018

Not to be confused with Amoxicillin.

Ampicillin
Clinical data
Trade namesPrincipen, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa685002
License data
Pregnancy
category
  • AU: A
Routes of
administration		By mouth, intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability40% (oral)
Protein binding15 to 25%
Metabolism12 to 50%
Elimination half-lifeapprox 1 hour
Excretion75 to 85% renal
Identifiers
  • (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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.645 Edit this at Wikidata
Chemical and physical data
FormulaC16H19N3O4S
Molar mass349.41 g/mol g·mol−1
3D model (JSmol)
  • O=C(O)[C@@H]2N3C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)N)[C@H]3SC2(C)C
  • InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1 checkY
  • Key:AVKUERGKIZMTKX-NJBDSQKTSA-N checkY
  (verify)

Ampicillin is an antibiotic used to prevent and treat a number of bacterial infections, such as respiratory tract infections, urinary tract infections, meningitis, salmonellosis, and endocarditis.[3] It may also be used to prevent group B streptococcal infection in newborns.[3] It is used by mouth, by injection into a muscle, or intravenously.[3] Like all antibiotics, it is not useful for the treatment of viral infections.

Common side effects include rash, nausea, and diarrhea.[3] It should not be used in people who are allergic to penicillin.[3] Serious side effects may include Clostridium difficile colitis or anaphylaxis.[3] While usable in those with kidney problems, the dose may need to be decreased.[3] Its use during pregnancy and breastfeeding appears to be generally safe.[3][4]

Ampicillin was discovered in 1958 and came into commercial use in 1961.[5][6] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[7] Its wholesale cost in the developing world is between US$0.13 and 1.20 for a vial of the intravenous solution as of 2014.[8] In the United States, it is available as a generic medication and 10 days of treatment cost about $13.[3]

Medical uses

Diseases

Ampicillin used to also be used to treat gonorrhea, but there are now too may strains resistant to penicillins.[3]

Bacteria

Ampicillin is used to treat infections by many Gram-positive and Gram-negative bacteria. It was the first "broad spectrum" penicillin with activity against Gram-positive bacteria, including Streptococcus pneumoniae, Streptococcus pyogenes, some isolates of Staphylococcus aureus (but not penicillin-resistant or methicillin-resistant strains), Trueperella, and some Enterococcus. It is one of the few antibiotics that works against multidrug resistant Enterococcus faecalis and E. faecium.[14] Activity against Gram-negative bacteria includes Neisseria meningitidis, some Haemophilus influenzae, and some of the Enterobacteriaceae (though most Enterobacteriaceae and Pseudomonas are resistant).[14][15] 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.[16][17] It is sometimes used in combination with other antibiotics that have different mechanisms of action, like vancomycin, linezolid, daptomycin, and tigecycline.[18][19]

Available forms

Ampicillin can be administered by mouth, an intramuscular injection (shot) or by intravenous infusion.[3] The oral form, available as capsules or oral suspensions, is not given as an initial treatment for severe infections, but rather as a follow-up to an IM or IV injection.[11][3] For IV and IM injections, ampicillin is kept as a powder that must be reconstituted.[20] Its shelf-life once reconstituted depends on which reconstituting agent is used: for sterile water, saline, or lactated-ringer's solution (LRS), the mixture can be kept in the fridge for up to 8 hours, and 24–72 hours at room temperature (24 hours for LRS, 24–48 hours for saline, and 48–72 hours for sterile water). If reconstituted with 5% dextrose, the solution is stable only for 1 or 2 hours, whether in the fridge or left out.[21]

IV injections must be given slowly, as rapid IV injections can lead to convulsive seizures.[3][21]

Specific populations

Ampicillin is one of the most commonly used drugs in pregnancy,[22] and has been found to be generally harmless both by the Food and Drug Administration in the U.S. (which classified it as category B) and the Therapeutic Goods Administration in Australia (which classified it as category A).[3][23] It is the drug of choice for treating Listeria monocytogenes in pregnant women, either alone or combined with an aminoglycoside.[3] Pregnancy increases the clearance of ampicillin by up to 50%, and a higher dose is thus needed to reach therapeutic levels.[22][24]

Ampicillin crosses the placenta and remains in the amniotic fluid at 50–100% of the concentration in maternal plasma; this can lead to high concentrations of ampicillin in the newborn.[24]

While lactating mothers secrete some ampicillin into their breast milk, the amount is minimal.[3][22]

In neonates, ampicillin has a longer half-life and lower plasma protein binding.[25] The renal clearance is lower, as renal function has not fully developed.[3]

Side effects

Ampicillin is comparatively less toxic than other antibiotics. In very rare cases, it causes severe side effects such as angioedema, anaphylaxis, and C. difficile infection. Some develop black 'furry' tongue'. The most serious adverse effects are seizures, serum sickness, anaphylaxis, pseudomembranous colitis. The most common side effects to be expected in ten percent of users are diarrhea and rash. Less common side effects can be nausea, vomiting, itching, blood dyscrasias, and mild allergic reactions. Other conditions may develop up several weeks after treatment.[3][9]

Interactions

Ampicillin reacts with probenecid to decrease renal excretion. Large doses of ampicillin can increase the risk of bleeding with concurrent use of warfarin. Ampicillin use can make oral contraceptives less effective.[3][9]

Mechanisms

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.[3]

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.[26]

Ampicillin acts as an irreversible inhibitor of the enzyme transpeptidase, which is needed by bacteria to make the cell wall.[3] 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 bacteriolytic.[3][27]

History

Ampicillin has been used extensively to treat bacterial infections since 1961.[28] 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.[27] Ampicillin (originally branded as 'Penbritin') also demonstrated activity against Gram-negative organisms such as H. influenzae, coliforms, and Proteus spp.[28]

Cost

Its wholesale costs is between US$0.13 and 1.20 for a vial of the intravenous solution as of 2014.[8] In the United States, it is available as a generic medication and 10 days of treatment cost about $13.[3]

See also

References

  1. ^ Drugs.com International trade names for Ampicillin Archived 16 February 2016 at the Wayback Machine Retrieved 14 January 2015
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ a b c d e f g h i j k l m n o p q r s t u v w x y z aa "Ampicillin". The American Society of Health-System Pharmacists. Archived from the original on 12 July 2015. Retrieved 1 August 2015. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  4. ^ "Ampicillin use while Breastfeeding". March 2015. Archived from the original on 23 September 2015. Retrieved 1 August 2015. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  5. ^ Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 490. ISBN 9783527607495. Archived from the original on 20 December 2016. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  6. ^ Ravina, Enrique (2011). The evolution of drug discovery : from traditional medicines to modern drugs (1 ed.). Weinheim: Wiley-VCH. p. 262. ISBN 9783527326693. Archived from the original on 9 August 2016. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  7. ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived from the original (PDF) on 13 December 2016. Retrieved 8 December 2016. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  8. ^ a b "Ampicillin". International Drug Price Indicator Guide. Archived from the original on 5 March 2017. Retrieved 1 August 2015. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  9. ^ a b c d "Ampicillin". Davis. 2017. Archived from the original on 25 February 2017. Retrieved 22 March 2017. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  10. ^ a b c d US National Library of Medicine. "AMPICILLIN- ampicillin sodium injection, powder, for solution". DailyMed. Retrieved 21 August 2017.
  11. ^ a b WebMD. "ampicillin (Rx)". Medscape. Retrieved 22 August 2017.
  12. ^ Finberg, Robert; Fingeroth, Joyce (2012). "Chapter 132: Infections in Transplant Recipients". In Longo, Dan; Fauci, Anthony; Kasper, Dennis; Hauser, Stephen; Jameson, J.; Loscalzo, Joseph (eds.). Harrison's Principles of Internal Medicine: Volume 1 (18th ed.). McGraw-Hill Medical. ISBN 978-0-07-174887-2. {{cite book}}: Invalid |ref=harv (help)
  13. ^ US National Library of Medicine. "AMPICILLIN- ampicillin injection, powder, for suspension". DailyMed. Retrieved 21 August 2017.
  14. ^ a b Magdesian, K. Gary (2017). Equine Pharmacology, an Issue of Veterinary Clinics of North America: Equine Practice, E-Book. Elsevier Health Sciences. p. 59. ISBN 978-0-323-52438-4. {{cite book}}: Invalid |ref=harv (help)
  15. ^ Papich, Mark G. (2015). Saunders Handbook of Veterinary Drugs: Small and Large Animal. Elsevier Health Sciences. pp. 43–47. ISBN 978-0-323-24485-5. {{cite book}}: Invalid |ref=harv (help)
  16. ^ Hauser, Alan R. (2012). Antibiotic Basics for Clinicians: The ABCs of Choosing the Right Antibacterial Agent. Lippincott Williams & Wilkins. pp. 25–28. ISBN 978-1-4511-1221-4. {{cite book}}: Invalid |ref=harv (help)
  17. ^ 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.
  18. ^ Suleyman, G; Zervos, MJ (2016). "Safety and efficacy of commonly used antimicrobial agents in the treatment of enterococcal infections: a review". Expert opinion on drug safety. 15 (2): 153–67. doi:10.1517/14740338.2016.1127349. PMID 26629598.
  19. ^ Torok, M. Estee; Moran, Ed; Cooke, Fiona. Oxford Handbook of Infectious Diseases and Microbiology. Oxford University Press. p. 721. ISBN 9780191503108. Archived from the original on 23 March 2017. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  20. ^ Wanamaker, Boyce P.; Massey, Kathy (2014). Applied Pharmacology for Veterinary Technicians - E-Book. Elsevier Health Sciences. p. 244. ISBN 978-0-323-29170-5. {{cite book}}: Invalid |ref=harv (help)
  21. ^ a b McAuley, David (25 July 2017). "AMPICILLIN  –  Intravenous (IV) Dilution". GlobalRPh. Retrieved 22 February 2018.
  22. ^ a b c Weiner, Carl P.; Rope, Kate (2013). The Complete Guide to Medications During Pregnancy and Breastfeeding: Everything You Need to Know to Make the Best Choices for You and Your Baby. St. Martin's Press. pp. 47–49. ISBN 978-1-250-03720-6. {{cite book}}: Invalid |ref=harv (help)
  23. ^ Administration, Australian Government Department of Health Therapeutic Goods (25 October 2017). "Prescribing medicines in pregnancy database". Therapeutic Goods Administration (TGA). Australian Government Department of Health. Retrieved 23 February 2018. Note: scroll down to "Seach by name" and type "ampicillin" into the search bar. Requires JavaScript to be enabled.
  24. ^ a b Rello, Jordi; Kollef, Martin H.; Díaz, Emilio; Rodríguez, Alejandro (2010). Infectious Diseases in Critical Care. Springer Science & Business Media. p. 172. ISBN 978-3-540-34406-3. {{cite book}}: Invalid |ref=harv (help)
  25. ^ Eghianruwa, Kingsley (2014). Essential Drug Data for Rational Therapy in Veterinary Practice. AuthorHouse. p. 26. ISBN 978-1-4918-0010-2. {{cite book}}: Invalid |ref=harv (help)
  26. ^ Delcour, Anne H. (May 2009). "Outer Membrane Permeability and Antibiotic Resistance". Biochimica et Biophysica Acta. 1794 (5): 808–816. doi:10.1016/j.bbapap.2008.11.005. ISSN 0006-3002. PMC 2696358. PMID 19100346.
  27. ^ 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.
  28. ^ a b Acred, P; Brown, D. M.; Turner, D. H.; Wilson, M. J. (April 1962). "Pharmacology and chemotherapy of ampicillin--a new broad-spectrum penicillin". Br J Pharmacol Chemother. 18 (2): 356–69. doi:10.1111/j.1476-5381.1962.tb01416.x. PMC 1482127. PMID 13859205.

External links

Retrieved from "https://en.wikipedia.org/w/index.php?title=Ampicillin&oldid=827146568"