Ampicillin

Source: Wikipedia, the free encyclopedia.
Not to be confused with Amoxicillin.

Ampicillin
Skeletal formula of ampicillin
Ball-and-stick model of the zwitterionic form of ampicillin found in the crystal structure of the trihydrate[1][2]
Clinical data
Trade namesPrincipen, others[3]
Other namesAM/AMP[4]
AHFS/Drugs.comMonograph
MedlinePlusa685002
License data
Pregnancy
category
QJ51CA01 (WHO) J01CR50 (WHO) J01CA51 (WHO)
Legal status
Legal status
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
JSmol)
  • CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)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

urinary tract infections, meningitis, salmonellosis, and endocarditis.[7] It may also be used to prevent group B streptococcal infection in newborns.[7] It is used by mouth, by injection into a muscle, or intravenously.[7]

Common side effects include rash, nausea, and diarrhea.

kidney problems, the dose may need to be decreased.[7] Its use during pregnancy and breastfeeding appears to be generally safe.[7][8]

Ampicillin was discovered in 1958 and came into commercial use in 1961.

generic medication.[7]

Medical uses

Diseases

Ampicillin used to also be used to treat gonorrhea, but there are now too many strains resistant to penicillins.[7]

Bacteria

Ampicillin is used to treat infections by many

beta lactamase, an enzyme produced by bacteria to inactivate ampicillin and related antibiotics.[19][20] It is sometimes used in combination with other antibiotics that have different mechanisms of action, like vancomycin, linezolid, daptomycin, and tigecycline.[21][22]

Available forms

Ampicillin can be administered by

intravenous infusion.[7] 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.[7] For IV and IM injections, ampicillin is kept as a powder that must be reconstituted.[23]

IV injections must be given slowly, as rapid IV injections can lead to convulsive

seizures.[7][24]

Specific populations

Ampicillin is one of the most used drugs in pregnancy,[25] 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).[7][26] It is the drug of choice for treating Listeria monocytogenes in pregnant women, either alone or combined with an aminoglycoside.[7] Pregnancy increases the clearance of ampicillin by up to 50%, and a higher dose is thus needed to reach therapeutic levels.[25][27]

Ampicillin crosses the

plasma; this can lead to high concentrations of ampicillin in the newborn.[27]

While lactating mothers secrete some ampicillin into their breast milk, the amount is minimal.[7][25]

In newborns, ampicillin has a longer half-life and lower plasma protein binding.[28] The clearance by the kidneys is lower, as kidney function has not fully developed.[7]

Contraindications

Ampicillin is contraindicated in those with a

white blood cells.[13]

Ampicillin is not recommended in people with concurrent mononucleosis, as over 40% of patients develop a skin rash.[13]

Side effects

Ampicillin is comparatively less toxic than other antibiotics, and side effects are more likely in those who are sensitive to penicillins and those with a history of

itching, and blood dyscrasias. The gastrointestinal effects, such as hairy tongue, nausea, vomiting, diarrhea, and colitis, are more common with the oral form of penicillin.[13] Other conditions may develop up several weeks after treatment.[7]

Overdose

Ampicillin overdose can cause behavioral changes, confusion, blackouts, and convulsions, as well as neuromuscular hypersensitivity, electrolyte imbalance, and kidney failure.[13]

Interactions

Ampicillin reacts with

tetracyclines.[23] For example, tetracyclines inhibit protein synthesis in bacteria, reducing the target against which ampicillin acts.[31] If given at the same time as aminoglycosides, it can bind to it and inactivate it. When administered separately, aminoglycosides and ampicillin can potentiate each other instead.[7][32]

Ampicillin causes skin rashes more often when given with allopurinol.[13]

Both the live cholera vaccine and live typhoid vaccine can be made ineffective if given with ampicillin. Ampicillin is normally used to treat cholera and typhoid fever, lowering the immunological response that the body has to mount.[33][34][35]

Pharmacology

Mechanism of action

penicillin G
.

Ampicillin is in the

amino group. This amino group, present on both ampicillin and amoxicillin, helps these antibiotics pass through the pores of the outer membrane of gram-negative bacteria, such as Escherichia coli, Proteus mirabilis, Salmonella enterica, and Shigella.[19][36]

Ampicillin acts as an irreversible inhibitor of the enzyme

bacteriolytic.[7][37]

Pharmacokinetics

Ampicillin is well-absorbed from the

plasma proteins, ampicillin binds to only 15–20%.[7][28]

Ampicillin is distributed through most tissues, though it is concentrated in the liver and kidneys. It can also be found in the

glomerular filtration, and the rest is excreted in the feces and bile
.

esters that have been developed to increase bioavailability.[38]

History

Ampicillin has been used extensively to treat bacterial infections since 1961.

coliforms, and Proteus spp.[39]

Cost

Ampicillin is relatively inexpensive.

generic medication.[7]

Veterinary use

In veterinary medicine, ampicillin is used in cats, dogs, and farm animals to treat:[16]

Horses are generally not treated with oral ampicillin, as they have low bioavailability of beta-lactams.[17]

The half-life in animals is around that same of that in humans (just over an hour). Oral absorption is less than 50% in cats and dogs, and less than 4% in horses.[18]


See also

  • Amoxycillin
    (p-hydroxy metabolite of ampicillin)
  • Azlocillin and pirbenicillin (urea and amide made from ampicillin)
  • pro-drug
    of ampicillin)

References

  1. doi:10.5517/ccb0nkj
    . Retrieved 28 June 2022.
  2. doi:10.1107/S1600536806001371
    .
  3. ^ "Ampicillin - international drug names". Drugs.com. 30 November 2019. Archived from the original on 30 November 2019. Retrieved 26 January 2020.
  4. ^ "Antibiotic abbreviations list". Retrieved 22 June 2023.
  5. ^ a b "Ampicillin Use During Pregnancy". Drugs.com. 2 May 2019. Archived from the original on 22 August 2019. Retrieved 26 January 2020.
  6. FDA
    . Retrieved 22 October 2023.
  7. ^ 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 ab ac ad "Ampicillin". The American Society of Health-System Pharmacists. Archived from the original on 12 July 2015. Retrieved 1 August 2015.
  8. ^ "Ampicillin use while Breastfeeding". March 2015. Archived from the original on 23 September 2015. Retrieved 1 August 2015.
  9. ISBN 9783527607495. Archived
    from the original on 20 December 2016.
  10. ISBN 9783527326693. Archived
    from the original on 9 August 2016.
  11. hdl:10665/325771
    . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  12. ISBN 9789241515528
    .
  13. ^ a b c d e f g h i j k l "Ampicillin- ampicillin sodium injection, powder, for solution". DailyMed. 11 September 2019. Archived from the original on 22 February 2018. Retrieved 25 January 2020.
  14. ^ WebMD. "ampicillin (Rx)". Medscape. Archived from the original on 15 August 2017. Retrieved 22 August 2017.
  15. ISBN 978-0-07-174887-2
    .
  16. ^ a b "Ampicillin injection, powder, for suspension". DailyMed. 26 October 2017. Archived from the original on 22 February 2018. Retrieved 26 January 2020.
  17. ^
    ISBN 978-0-323-52438-4
    .
  18. ^
    ISBN 978-0-323-24485-5
    .
  19. ^
    ISBN 978-1-4511-1221-4
    .
  20. PMID 18154545
    .
  21. S2CID 25488987
    .
  22. ISBN 9780191503108. Archived
    from the original on 23 March 2017.
  23. ^
    ISBN 978-0-323-29170-5
    .
  24. ^ WebMD. "Ampicillin Intravenous: Uses, Side Effects, Interactions, Pictures, Warnings & Dosing". WebMD. Archived from the original on 23 February 2018. Retrieved 23 February 2018.
  25. ^
    ISBN 978-1-250-03720-6
    . ampicillin pregnancy.
  26. ^ Australian Government Department of Health Therapeutic Goods Administration (25 October 2017). "Prescribing medicines in pregnancy database". Therapeutic Goods Administration (TGA). Australian Government Department of Health. Archived from the original on 20 December 2016. Retrieved 23 February 2018. Note: scroll down to "Search by name" and type "ampicillin" into the search bar. Requires JavaScript to be enabled.
  27. ^
    ISBN 978-3-540-34406-3
    .
  28. ^
    ISBN 978-1-4918-0010-2
    .
  29. ^ "Drug interactions between ampicillin and anisindione". Drugs.com. Archived from the original on 23 February 2018. Retrieved 22 February 2018.
  30. ISBN 978-1-61779-213-7
    .
  31. ^ "Drug interactions between ampicillin and bismuth subcitrate potassium / metronidazole / tetracycline". Drugs.com. Archived from the original on 23 February 2018. Retrieved 22 February 2018.
  32. ^ "Drug interactions between amikacin and ampicillin". Drugs.com. Archived from the original on 23 February 2018. Retrieved 22 February 2018.
  33. ^ "Drug interactions between ampicillin and cholera vaccine, live". Drugs.com. Archived from the original on 23 February 2018. Retrieved 22 February 2018.
  34. ^ "Drug interactions between ampicillin and typhoid vaccine, live". Drugs.com. Archived from the original on 23 February 2018. Retrieved 22 February 2018.
  35. ^ Handa S (22 June 2017). "Cholera Medication". Medscape. Archived from the original on 23 February 2018. Retrieved 23 February 2018.
  36. PMID 19100346
    .
  37. ^
    ISBN 978-0-07-176939-6
    .
  38. ^
    ISBN 978-1-118-67507-6
    .
  39. ^
    PMID 13859205
    .
  40. ISBN 978-0-323-24466-4
    .
  41. ^ Erskine R. "Mastitis in Sows". Merck Veterinary Manual. Archived from the original on 4 July 2017. Retrieved 22 August 2017.

External links

  • "Ampicillin". Drug Information Portal. U.S. National Library of Medicine.
  • GB patent 902703, Frank Peter Doyle, John Herbert Charles Nayler, Harry Smith, "Penicillins", published 1962-08-09, assigned to Beecham Research Laboratories Ltd 
  • US patent 2985648, Frank Peter Doyle, John Herbert Charles Nayler, Harry Smith, "Alpha-aminobenzylpenicillins", published 1961-05-23, issued 1961-05-23 
  • US patent 3157640, David A Johnson & Glenn A Hardcastle Jr, "D-(-)-alpha-aminobenzylpenicillin trihydrate", published 1964-11-17, issued 1964-11-17, assigned to Bristol Myers Co 
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