File:Ampicillin_structure.svg · Wikimedia Commons · See Wikimedia Commons
ampicillin
Sign in to saveAlso known as ABPC, D-(−)-ampicillin, (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, AMP, AP, (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylethanoyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, D-(−)-6-(α-aminophenylacetamido)penicillanic acid, P-50
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. It may also be used to prevent group B streptococcal infection in newborns. It is used by mouth, by injection into a muscle, or intravenously.
Ampicillin is an antibiotic medication that works against bacterial infections and belongs to the penicillin family of drugs. It is used to treat or prevent a range of infections—including respiratory and urinary tract infections, meningitis, and others—and can be taken by mouth, injected into a muscle, or given intravenously.
AI-generated from the Wikipedia summary — may contain errors.
Chemical data
- Formula
- C16H19N3O4S
- Molecular weight
- 349.4 g/mol
- 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
- SMILES
- CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)C
- InChIKey
- AVKUERGKIZMTKX-NJBDSQKTSA-N
- XLogP
- -1.1
- Polar surface area
- 138 Ų
- H-bond donors
- 3
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
53,485 papers- Ampicillin.IARC monographs on the evaluation of carcinogenic risks to humans · 1990
- Sulbactam/ampicillin, a new beta-lactamase inhibitor/beta-lactam antibiotic combination.Drug intelligence & clinical pharmacy · 1988
- Ampicillin-sulbactam.Pediatric annals · 1993
- Sulbactam/ampicillin in paediatric infections.Drugs · 1988
- Ampicillin.Journal of the American Pharmaceutical Association · 1975
via PubMed
Wikidata facts
- Mass
- 349.11
Show 6 more facts
- chemical formula
- C₁₆H₁₉N₃O₄S
- Commons category
- Ampicillin
- canonical SMILES
- CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C
- isomeric SMILES
- CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)C
- World Health Organisation international non-proprietary name
- ampicillin
- NCI Thesaurus ID
- C239
Sources (8)
via Wikidata · CC0
~11 min read
Article
18 sectionsContents
- Medical uses
- Diseases
- Bacteria
- Available forms
- Specific populations
- Contraindications
- Side effects
- Overdose
- Interactions
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- History
- Society and culture
- Economics
- Veterinary use
- References
- External links
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. It may also be used to prevent group B streptococcal infection in newborns. It is used by mouth, by injection into a muscle, or intravenously.
Common side effects include rash, nausea, and diarrhea. It should not be used in people who are allergic to penicillin. Serious side effects may include Clostridioides difficile colitis or anaphylaxis. While usable in those with kidney problems, the dose may need to be decreased. Its use during pregnancy and breastfeeding appears to be generally safe.