Ampicillin
Systematic (IUPAC) name
7-(2-amino-2-phenyl-acetyl)amino-3,3 -dimethyl-6-oxo-2-thia-5-azabicyclo [3.2.0]heptane-4-carboxylic acid
Identifiers
CAS number	69-53-4
ATC code	J01CA01
PubChem	149171
DrugBank	APRD00320
Chemical data
Formula	C16H18N3O4S
Mol. weight	349.406 g/mol
Pharmacokinetic data
Bioavailability	40% (oral)
Protein binding	15 to 25%
Metabolism	?
Half life	approx 1 hour
Excretion	75 to 85% renal
Therapeutic considerations
Pregnancy cat.	A (Au), B (U.S.) Image File history File links Download high-resolution version (1100x645, 42 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Ampicillin ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules . ... DrugBank is a database available at the University of Alberta that provides information about thousands of products. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... This article is about the chemistry of hydrogen. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Atomic mass 15. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Atomic mass 32. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... BIC pen cap, about 1 gram. ... A mole (symbol: mol) is approximately 6. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Many drugs are bound to Blood plasma proteins. ... Overview of the citric acid cycle The citric acid cycle, one of the central metabolic pathways in aerobic organisms. ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... Kidneys viewed from behind with spine removed The kidneys are bean-shaped excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... Motto: None Anthem: Advance Australia Fair Royal anthem: God Save the Queen Capital Canberra Largest city Sydney Official languages English (de facto 1) Government Constitutional monarchy (federal)  - Queen Elizabeth II  - Governor-General Michael Jeffery  - Prime Minister John Howard Independence from the UK   - Constitution 1 January 1901   - Statute of Westminster 11... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...
Legal status
Routes	Oral, intravenous

Ampicillin is a beta-lactam antibiotic that has been used extensively to treat bacterial infections since 1961. It can sometimes result in allergic reactions that range in severity from a rash (e.g. patients with mononucleosis) to potentially lethal anaphylaxis. The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... β-lactam antibiotics are a broad class of antibiotics including penicillin derivatives, cephalosporins, monobactams, carbapenems and β-lactamase inhibitors; basically any antibiotic agent which contains a β-lactam nucleus in its molecular structure. ... Staphylococcus aureus - Antibiotics test plate. ... Phyla/Divisions Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Omnibacteria Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular, bacterium) are a major group of living organisms. ... An infection is the detrimental colonization of a host organism by a foreign species. ... }} In medicine, anaphylaxis is a severe and rapid multi-system allergic reaction. ...

Mechanism of action

Belonging to the penicillin group of beta-lactam antibiotics, ampicillin is able to penetrate Gram-positive and some Gram-negative bacteria. It inhibits the third and final stage of bacterial cell wall synthesis, which ultimately leads to cell lysis. Penicillin nucleus Penicillin (sometimes abbreviated PCN) refers to a group of β-lactam antibiotics used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms. ... Gram-positive bacteria are those that are stained dark blue or violet by gram staining, in contrast to gram-negative bacteria, which are not affected by the stain. ... Bacteria that are Gram-negative are not stained dark blue or violet by Gram staining, in contrast to Gram-positive bacteria. ... A cell wall is a fairly rigid layer surrounding a cell located outside of the plasma membrane (also known, in some cases, as the cell membrane) that provides additional support and protection. ... Lysis (Greek lusis from luein = to separate) refers to the death of a cell by bursting, often by viral or osmotic mechanisms that compromise the integrity of the cellular membrane. ...

Indications

Ampicillin is closely related to amoxicillin, another type of penicillin, and both are used to treat urinary tract infections, otitis media, uncomplicated community-acquired pneumonia, Haemophilus influenzae, salmonellosis and Listeria meningitis. It is used with flucloxacillin in the combination antibiotic co-fluampicil for empiric treatment of cellulitis; providing cover against Group A streptococcal infection whilst the flucloxacillin acts against the Staphylococcus aureus bacterium. Of concern is the number of bacteria that become resistant to Ampicillin necessitating combination therapy or use of other antibiotics. Amoxicillin (INN) or amoxycillin (former BAN) is a moderate-spectrum β-lactam antibiotic used to treat bacterial infections caused by susceptible microorganisms. ... A urinary tract infection is an infection of the urinary tract. ... Otitis media is an inflammation of the middle ear segment of the ear. ... Pneumonia is an illness of the lungs and respiratory system in which the alveoli (microscopic air-filled sacs of the lung responsible for absorbing oxygen from the atmosphere) become inflamed and flooded with fluid. ... Binomial name Haemophilus influenzae (Lehmann & Neumann 1896) Winslow 1917 Haemophilus influenzae, formerly called Pfeiffers bacillus or Bacillus influenzae, is a non-motile Gram-negative coccobacillus first described in 1892 by Dr. Richard Pfeiffer during an influenza pandemic. ... Salmonellosis is an infection with Salmonella bacteria. ... Listeriosis is an bacterial infection caused by a gram-positive, motile bacterium, Listeria monocytogenes. ... Meningitis is inflammation of the meninges, caused by microorganisms that have spread into the blood and into the cerebrospinal fluid (CSF). ... Flucloxacillin (INN) or floxacillin (USAN) is a narrow spectrum beta-lactam antibiotic. ... Co-fluampicil is the British Approved Name, for the combination of ampicillin and flucloxacillin β-lactam antibiotics (trade name Magnapen®). // Indication Ampicillin is a moderate spectrum penicillin antibiotic with good cover against Group A streptococcal infection whilst Flucloxacillin is a narrow spectrum antibiotic with cover against Staphylococcus aureus. ... Empirical is an adjective often used in conjunction with science, both the natural and social sciences, which means an observation or experiment based upon experience that is capable of being verified or disproved. ... The group A streptococcus bacterium (Streptococcus pyogenes, or GAS) is a form of Streptococcus bacteria responsible for most cases of streptococcal illness. ... Binomial name Staphylococcus aureus Rosenbach 1884 Staphylococcus aureus, the most common cause of staph infections, is a spherical bacterium, frequently living on the skin or in the nose of a healthy person, that can cause a range of illnesses from minor skin infections (such as pimples, boils, and cellulitis) and... Antibiotic resistance is the ability of a micro-organism to withstand the effects of an antibiotic. ... An antibiotic is a drug that kills or slows the growth of bacteria. ...

Use in research

Ampicillin is often used in molecular biology as a test for the uptake of genes (e.g., by plasmids) by bacteria (e.g., E. coli). A gene that is to be inserted into a bacterium is coupled to a gene coding for an ampicillin resistance (in E. coli, usually the bla gene, coding for β-lactamase). The treated bacteria are then grown on a medium containing ampicillin. Only the bacteria that successfully take up the desired genes become ampicillin resistant, and therefore contain the other desired gene as well. Molecular biology is the study of biology at a molecular level. ... For other meanings of this term, see gene (disambiguation). ... Figure 1: Schematic drawing of a bacterium with plasmids enclosed. ... Binomial name Escherichia coli T. Escherich, 1885 Escherichia coli (usually abbreviated to E. coli) is one of the main species of bacteria that live in the lower intestines of warm-blooded animals (including birds and mammals) and are necessary for the proper digestion of food. ... Beta-lactamase is a type of enzyme (EC 3. ...

External links

• Links to external chemical sources