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.
OverviewAI-generated
Ampicillin is a chemical compound with the formula C₁₆H₁₉N₃O₄S. Its IUPAC name is (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. The substance has a mass of 349.11 and a weight of 349.4. It possesses a charge of 0, an xlogp of -1.1, and a topological polar surface area of 138.
The molecule contains three hydrogen bond donors and six hydrogen bond acceptors. It is identified by the NCI Thesaurus ID C239. In scientific literature, ampicillin is the subject of 53,485 PubMed entries. Additionally, the compound is referenced by 399 other encyclopedia articles.
Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still 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
~11 min read
Encyclopedic overview
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.
Excerpted from Wikipedia’s “ampicillin” article, available under the CC BY-SA 4.0 licence.