Back Ampisillien Afrikaans أمبيسيلين Arabic Ampisillin Azerbaijani آمپیسیلین AZB এম্পিসিলিন Bengali/Bangla Ampicilin BS Ampicil·lina Catalan ئەمپیسیلین CKB Ampicilin Czech Ampicilin Welsh
 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 names | Principen, others[3] |
| Other names | AM/AMP[4] |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a685002 |
| License data |
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| Routes of administration | By mouth, intravenous, intramuscular |
| Drug class | Aminopenicillins |
| ATC code | |
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| Legal status | |
| Pharmacokinetic data | |
| Bioavailability | 62% ±17% (parenteral) < 30–55% (oral) |
| Protein binding | 15 to 25% |
| Metabolism | 12 to 50% |
| Metabolites | Penicilloic acid |
| Elimination half-life | Approx. 1 hour |
| Excretion | 75 to 85% kidney |
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| ChEMBL | |
| PDB ligand | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.000.645 |
| Chemical and physical data | |
| Formula | C16H19N3O4S |
| Molar mass | 349.41 g·mol−1 |
| 3D model (JSmol) | |
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Ampicillin is an antibiotic belonging to the aminopenicillin class of the penicillin family. The drug is used to prevent and treat several bacterial infections, such as respiratory tract infections, 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.[7] It should not be used in people who are allergic to penicillin.[7] Serious side effects may include Clostridioides difficile colitis or anaphylaxis.[7] While usable in those with 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.[9][10] It is on the World Health Organization's List of Essential Medicines.[11] The World Health Organization classifies ampicillin as critically important for human medicine.[12] It is available as a generic medication.[7]
- ^ Burley JC, Van De Streek J, Stephens PW (2006). "CSD Entry: AMPCIH01". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. doi:10.5517/ccb0nkj. Retrieved 28 June 2022.
- ^ Burley JC, van de Streek J, Stephens PW (2006). "Ampicillin trihydrate from synchrotron powder diffraction data". Acta Crystallographica Section E. 62 (2): o797–o799. Bibcode:2006AcCrE..62O.797B. doi:10.1107/S1600536806001371.
- ^ "Ampicillin - international drug names". Drugs.com. 30 November 2019. Archived from the original on 30 November 2019. Retrieved 26 January 2020.
- ^ "Antibiotic abbreviations list". Retrieved 22 June 2023.
- ^ "Ampicillin Use During Pregnancy". Drugs.com. 2 May 2019. Archived from the original on 22 August 2019. Retrieved 26 January 2020.
- ^ "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.
- ^ a b c d e f g h i j "Ampicillin". The American Society of Health-System Pharmacists. Archived from the original on 12 July 2015. Retrieved 1 August 2015.
- ^ "Ampicillin use while Breastfeeding". March 2015. Archived from the original on 23 September 2015. Retrieved 1 August 2015.
- ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 490. ISBN 9783527607495. Archived from the original on 20 December 2016.
- ^ Ravina E (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.
- ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
- ^ World Health Organization (2019). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 9789241515528.