Ampicillin

Ampicillin
Clinical data


Trade names	Principen, others
AHFS/Drugs.com	Monograph
MedlinePlus	a685002
License data	US FDA: Ampicillin
Pregnancy category	A (Au), B (U.S.)
Routes of administration	By mouth, intravenous
ATC code	J01CA01 (WHO) S01AA19 (WHO) QJ51CA01 (WHO)
Legal status
Legal status	UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability	40% (oral)
Protein binding	15 to 25%
Metabolism	12 to 50%
Biological half-life	approx 1 hour
Excretion	75 to 85% renal
Identifiers
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
CAS Number	69-53-4^Y
PubChem CID	6249
DrugBank	DB00415^Y
ChemSpider	6013^Y
UNII	7C782967RD
KEGG	D00204^Y
ChEBI	CHEBI:28971^Y
ChEMBL	CHEMBL174^Y
ECHA InfoCard	100.000.645
Chemical and physical data
Formula	C₁₆H₁₉N₃O₄S
Molar mass	349.41 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(O)[C@@H]2N3C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)N)[C@H]3SC2(C)C
InChI 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^Y Key:AVKUERGKIZMTKX-NJBDSQKTSA-N^Y

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. It may also be used to prevent in newborns. It is used by mouth, by injection into a muscle, or intravenously. Like all antibiotics, it is not useful for the treatment of viral infections.

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 Clostridium 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.

Ampicillin was discovered in 1958 and came into commercial use in 1961. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. 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. In the United States, it is available as a generic medication and 10 days of treatment cost about $13.

It is active against many Gram-positive and Gram-negative bacteria. Ampicillin was the first 'broad spectrum' penicillin with activity against Gram-positive bacteria including , , some isolates of Staphylococcus aureus (but not penicillin-resistant or methicillin-resistant strains), and some Enterococcus. Activity against Gram-negative bacteria includes Neisseria meningitidis, some Haemophilus influenzae, and some of the Enterobacteriaceae. 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.

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