Ampicillin - wikipedia Ampicillin Not to be confused with Amoxicillin. Ampicillin Clinical data Trade names Principen, others AHFS / Drugs.com Monograph MedlinePlus a685002 License data US DailyMed : 0642ef5e - 7eff - 4117 - a0df - 4bd15d7b7d63 US FDA : Ampicillin Pregnancy category AU : A US : B ( No risk in non-human studies ) Routes of administration By mouth, intravenous, or intramuscular Drug class penicillin ATC code J01CA01 ( WHO ) S01AA19 ( WHO ) QJ51CA01 ( WHO ) Legal status Legal status AU : S4 ( Prescription only ) UK : POM ( Prescription only ) US : ℞ - only 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 % 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 PubChem CID 6249 DrugBank DB00415 ChemSpider 6013 UNII 7C782967RD KEGG D00204 ChEBI CHEBI : 28971 ChEMBL CHEMBL174 ECHA InfoCard 100.000. 645 Chemical and physical data Formula Molar mass 349.41 g / mol 3D model ( JSmol ) 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 Key : AVKUERGKIZMTKX - NJBDSQKTSA - N ( verify ) 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 group B streptococcal infection 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. Contents 1 Medical uses 1.1 Diseases 1.2 Bacteria 1.3 Available forms 1.4 Specific populations 2 Contraindications 3 Side effects 3.1 Overdose 4 Interactions 5 Pharmacology 5.1 Mechanism of action 5.2 Pharmacokinetics 6 History 7 Cost 8 Veterinary use 9 See also 10 References 11 External links Medical Uses Diseases Bacterial meningitis ; an aminoglycoside can be added to increase efficacy against Gram - negative meningitis bacteria Endocarditis by enterococcal strains ( off - label use ) ; often given with an aminoglycoside Gastrointestinal infections caused by contaminated water or food ( for example, by Salmonella ) Genito - urinary tract infections Healthcare - associated infections that are related to infections from using urinary catheters and that are unresponsive to other medications and unresponsive to other medications Otitis media ( middle ear infection ) Prophylaxis ( i.e. to prevent infection ) in those who previously had rheumatic heart disease or are undergoing dental procedures, vaginal hysterectomies, or C - sections. It is also used in pregnant woman who are carriers of group B streptococci to prevent early - onset neonatal infections. Respiratory infections, including bronchitis, pharyngitis Sinusitis Sepsis Whooping cough, to prevent and treat secondary infections Ampicillin used to also be used to treat gonorrhea, but there are now too many strains resistant to penicillins. Bacteria Ampicillin is used to treat infections by many Gram - positive and Gram - negative bacteria. It was the first `` broad spectrum '' penicillin with activity against Gram - positive bacteria, including Streptococcus pneumoniae, Streptococcus pyogenes, some isolates of Staphylococcus aureus ( but not penicillin - resistant or methicillin - resistant strains ), Trueperella, and some Enterococcus. It is one of the few antibiotics that works against multidrug resistant Enterococcus faecalis and E. faecium. Activity against Gram - negative bacteria includes Neisseria meningitidis, some Haemophilus influenzae, and some of the Enterobacteriaceae ( though most Enterobacteriaceae and Pseudomonas are resistant ). 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. It is sometimes used in combination with other antibiotics that have different mechanisms of action, like vancomycin, linezolid, daptomycin, and tigecycline. Available forms Ampicillin can be administered by mouth, an intramuscular injection ( shot ) or by intravenous infusion. The oral form, available as capsules or oral suspensions, is not given as an initial treatment for severe infections, but rather as a follow - up to an IM or IV injection. For IV and IM injections, ampicillin is kept as a powder that must be reconstituted. IV injections must be given slowly, as rapid IV injections can lead to convulsive seizures. Specific populations Ampicillin is one of the most commonly used drugs in pregnancy, and has been found to be generally harmless both by the Food and Drug Administration in the U.S. ( which classified it as category B) and the Therapeutic Goods Administration in Australia ( which classified it as category A ). It is the drug of choice for treating Listeria monocytogenes in pregnant women, either alone or combined with an aminoglycoside. Pregnancy increases the clearance of ampicillin by up to 50 %, and a higher dose is thus needed to reach therapeutic levels. Ampicillin crosses the placenta and remains in the amniotic fluid at 50 -- 100 % of the concentration in maternal plasma ; this can lead to high concentrations of ampicillin in the newborn. While lactating mothers secrete some ampicillin into their breast milk, the amount is minimal. In newborns, ampicillin has a longer half - life and lower plasma protein binding. The clearance by the kidneys is lower, as kidney function has not fully developed. Contraindications Ampicillin is contraindicated in those with a hypersensitivity to penicillins, as they can cause fatal anaphylactic reactions. Hypersensitivity reactions can include frequent skin rashes and hives, exfoliative dermatitis, erythema multiforme, and a temporary decrease in both red and white blood cells. Ampicillin is not recommended in people with concurrent mononucleosis, as over 40 % of patients develop a skin rash. Side effects Ampicillin is comparatively less toxic than other antibiotics, and side effects are more likely in those who are sensitive to penicillins and those with a history of asthma or allergies. In very rare cases, it causes severe side effects such as angioedema, anaphylaxis, and C. difficile infection ( that can range from mild diarrhea to serious pseudomembranous colitis ). Some develop black `` furry '' tongue. Serious adverse effects also include seizures and serum sickness. The most common side effects, experienced by about 10 % of users are diarrhea and rash. Less common side effects can be nausea, vomiting, itching, and blood dyscrasias. The gastrointestinal effects, such as hairy tongue, nausea, vomiting, diarrhea, and colitis, are more common with the oral form of penicillin. Other conditions may develop up several weeks after treatment. Overdose Ampicillin overdose can cause behavioral changes, confusion, blackouts, and convulsions, as well as neuromuscular hypersensitivity, electrolyte imbalance, and renal failure. Interactions Ampicillin reacts with probenecid and methotrexate to decrease renal excretion. Large doses of ampicillin can increase the risk of bleeding with concurrent use of warfarin and other oral anticoagulants, possibly by inhibiting platelet aggregation. Ampicillin has been said to make oral contraceptives less effective, but this has been disputed. It can be made less effective by other antibiotic, such as chloramphenicol, erythromycin, cephalosporins, and tetracyclines. For example, tetracyclines inhibit protein synthesis in bacteria, reducing the target against which ampicillin acts. If given at the same time as aminoglycosides, it can bind to it and inactivate it. When administered separately, aminoglycosides and ampicillin can potentiate each other instead. Ampicillin causes skin rashes more often when given with allopurinol. Both the liver cholera vaccine and live typhoid vaccine can be made ineffective if given with ampicillin. Ampicillin is normally used to treat cholera and typhoid fever, lowering the immunological response that the body has to mount. Pharmacology Mechanism of action The amino group ( highlighted in magenta ) is present on ampicillin but not penicillin G. Ampicillin is in the penicillin group of beta - lactam antibiotics and is part of the aminopenicillin family. It is roughly equivalent to amoxicillin in terms of activity. Ampicillin is able to penetrate Gram - positive and some Gram - negative bacteria. It differs from penicillin G, or benzylpenicillin, only by the presence of an amino group. That amino group, present on both ampicillin and amoxicillin, helps them enter the pores of the outer membrane of Gram - negative bacteria, such as E. coli, Proteus mirabilis, Salmonella enterica, and Shigella ). Ampicillin acts as an irreversible inhibitor of the enzyme transpeptidase, which is needed by bacteria to make the cell wall. It inhibits the third and final stage of bacterial cell wall synthesis in binary fission, which ultimately leads to cell lysis ; therefore, ampicillin is usually bacteriolytic. Pharmacokinetics Ampicillin is well - absorbed from the GI tract ( though food reduces its absorption ), and reaches peak concentrations in one to two hours. The bioavailability is around 62 % for parenteral routes. Unlike other penicillins, which usually have bind 60 -- 90 % to plasma proteins, ampicillin binds to only 15 -- 20 %. Ampicillin is distributed through most tissues, though it is concentrated in the liver and kidneys. It can also be found in the cerebrospinal fluid when the meninges become inflamed ( such as, for example, meningitis ). Some ampicillin is metabolized by hydrolyzing the beta - lactam ring to penicilloic acid, though most of it is excreted unchanged. In the kidneys, it is filtered out mostly by tubular secretion ; some also undergoes glomerular filtration, and the rest is excreted in the feces and bile. Hetacillin and pivampicillin are ampicillin esters that have been developed to increase bioavailability. History Ampicillin has been used extensively to treat bacterial infections since 1961. Until the introduction of ampicillin by the British company Beecham, penicillin therapies had only been effective against Gram - positive organisms such as staphylococci and streptococci. Ampicillin ( originally branded as `` Penbritin :) also demonstrated activity against Gram - negative organisms such as H. influenzae, coliforms, and Proteus spp. Cost As of 2014, ampicillin 's wholesale cost is between US $0.13 and 1.20 for a vial of the intravenous solution. In the United States, it is available as a generic medication : 10 days of treatment cost about $13. Veterinary use In veterinary medicine, ampicillin is used in cats, dogs, and farm animals to treat : Anal gland infections Cutaneous infections, such as abscesses, cellulitis, and pustular dermatitis E. coli and Salmonella infections in cattle, sheep, and goats ( oral form ). Ampicillin use for this purpose had declined as bacterial resistance has increased. Mastitis in sows Mixed aerobic -- anaerobic infections, such as from cat bites Multidrug - resistant Enterococcus faecalis and E. faecium Prophylactic use in poultry against Salmonella and sepsis from E. coli or Staphylococcus aureus Respiratory tract infections, including tonsilitis, bovine respiratory disease, shipping fever, bronchopneumonia, and calf and bovine pneumonia Urinary tract infections in dogs Horses are generally not treated with ampicillin, as they have low bioavailability of beta - lactams. The half - life in animals is around that same of that in humans ( just over an hour ). Oral absorption is less than 50 % in cats and dogs, and less than 4 % in horses. See also Amoxycillin ( p - hydroxy metabolite of ampicillin ) Pivampicillin ( special pro-drug of ampicillin ) Azlocillin and pirbenicillin ( urea and amide made from ampicillin ) References Jump up ^ Drugs.com International trade names for Ampicillin Archived 16 February 2016 at the Wayback Machine. Retrieved 14 January 2015 ^ Jump up to : `` Ampicillin ''. The American Society of Health - System Pharmacists. Archived from the original on 12 July 2015. Retrieved 1 August 2015. Jump up ^ `` Ampicillin use while Breastfeeding ''. March 2015. Archived from the original on 23 September 2015. Retrieved 1 August 2015. Jump up ^ Fischer, Janos ; Ganellin, C. Robin ( 2006 ). Analogue - based Drug Discovery. John Wiley & Sons. p. 490. ISBN 9783527607495. Archived from the original on 20 December 2016. Jump up ^ Ravina, Enrique ( 2011 ). The evolution of drug discovery : from traditional medicines to modern drugs ( 1 ed. ). Weinheim : Wiley - VCH. p. 262. ISBN 9783527326693. 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The Complete Guide to Medications During Pregnancy and Breastfeeding : Everything You Need to Know to Make the Best Choices for You and Your Baby. St. Martin 's Press. pp. 47 -- 49. ISBN 978 - 1 - 250 - 03720 - 6. Jump up ^ Administration, Australian Government Department of Health Therapeutic Goods ( 25 October 2017 ). `` Prescribing medicines in pregnancy database ''. Therapeutic Goods Administration ( TGA ). Australian Government Department of Health. Retrieved 23 February 2018. Note : scroll down to `` Seach by name '' and type `` ampicillin '' into the search bar. Requires JavaScript to be enabled. ^ Jump up to : Rello, Jordi ; Kollef, Martin H. ; Díaz, Emilio ; Rodríguez, Alejandro ( 2010 ). Infectious Diseases in Critical Care. Springer Science & Business Media. p. 172. ISBN 978 - 3 - 540 - 34406 - 3. ^ Jump up to : Eghianruwa, Kingsley ( 2014 ). Essential Drug Data for Rational Therapy in Veterinary Practice. AuthorHouse. p. 26. ISBN 978 - 1 - 4918 - 0010 - 2. 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External links Ampicillin bound to proteins in the PDB Antibiotics active on the cell wall and envelope ( J01C - J01D ) Intracellular Inhibit peptidoglycan subunit synthesis and transport : NAM synthesis inhibition ( Fosfomycin ) DADAL / AR inhibitors ( Cycloserine ) bactoprenol inhibitors ( Bacitracin ) Glycopeptide Inhibit PG chain elongation : Vancomycin ( Oritavancin Telavancin ) Teicoplanin ( Dalbavancin ) Ramoplanin β - lactams / ( inhibit PBP cross-links ) Penicillins ( Penams ) Narrow spectrum β - lactamase sensitive ( 1st generation ) Benzylpenicillin ( G ) Benzathine benzylpenicillin Procaine benzylpenicillin Phenoxymethylpenicillin ( V ) Propicillin Pheneticillin Azidocillin Clometocillin Penamecillin β - lactamase resistant ( 2nd generation ) Cloxacillin ( Dicloxacillin Flucloxacillin ) Oxacillin Nafcillin Methicillin Extended spectrum Aminopenicillins ( 3rd generation ) Amoxicillin Ampicillin ( Pivampicillin Hetacillin Bacampicillin Metampicillin Talampicillin ) Epicillin Carboxypenicillins ( 4th generation ) Ticarcillin Carbenicillin / Carindacillin Temocillin Ureidopenicillins ( 4th generation ) Piperacillin Azlocillin Mezlocillin Other Mecillinam ( Pivmecillinam ) Sulbenicillin Penems Faropenem Ritipenem Carbapenems Ertapenem Antipseudomonal ( Doripenem Imipenem Meropenem ) Biapenem Panipenem Cephalosporins / Cephamycins ( Cephems ) 1st generation Cefazolin Cefalexin Cefadroxil Cefapirin Cefazedone Cefazaflur Cefradine Cefroxadine Ceftezole Cefaloglycin Cefacetrile Cefalonium Cefaloridine Cefalotin Cefatrizine 2nd generation Cefaclor Cefotetan Cephamycin ( Cefoxitin Cefprozil Cefuroxime Cefuroxime axetil Cefamandole Cefminox Cefonicid Ceforanide Cefotiam Cefbuperazone Cefuzonam Cefmetazole ) Carbacephem ( Loracarbef ) 3rd generation Cefixime Ceftriaxone Antipseudomonal ( Ceftazidime Cefoperazone ) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefotaxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefetamet Cefodizime Cefpimizole Cefsulodin Cefteram Ceftiolene Oxacephem ( Flomoxef Latamoxef ) 4th generation Cefepime Cefozopran Cefpirome Cefquinome 5th generation Ceftaroline fosamil Ceftolozane Ceftobiprole Veterinary Ceftiofur Cefquinome Cefovecin Monobactams Aztreonam Tigemonam Carumonam Nocardicin A β - lactamase inhibitors Penam ( Sulbactam Tazobactam ) Clavam ( Clavulanic acid ) Avibactam Vaborbactam Combinations Amoxicillin / clavulanic acid Imipenem / cilastatin Ampicillin / flucloxacillin Ampicillin / sulbactam ( Sultamicillin ) Ceftazidime / avibactam Piperacillin / tazobactam Ceftolozane / tazobactam cefoperazone / sulbactam Meropenem / vaborbactam Other polymyxins / detergent Colistin Polymyxin B depolarizing Daptomycin Hydrolyze NAM - NAG lysozyme Tyrothricin Gramicidin Tyrocidine Isoniazid Teixobactin WHO - EM Withdrawn from market Clinical trials : Phase III Never to phase III Pharmacy and pharmacology portal Medicine portal Retrieved from `` https://en.wikipedia.org/w/index.php?title=Ampicillin&oldid=840210616 '' Categories : Penicillins Enantiopure drugs World Health Organization essential medicines Phenyl compounds Hidden categories : Webarchive template wayback links Use dmy dates from July 2012 Template : drugs.com link with non-standard subpage ECHA InfoCard ID from Wikidata Drugboxes which contain changes to watched fields Articles containing potentially dated statements from 2014 All articles containing potentially dated statements RTT Talk Contents About Wikipedia Afrikaans تۆرکجه বাংলা Bosanski Català Čeština Cymraeg Dansk Deutsch Español Euskara فارسی Français Hrvatski Bahasa Indonesia Italiano עברית Қазақша Kreyòl ayisyen Lingála Magyar Македонски 日本 語 ଓଡ଼ିଆ Polski Português Română Русский Slovenčina کوردی Српски / srpski Srpskohrvatski / српскохрватски Suomi Svenska ไทย Türkçe Українська Tiếng Việt 中文 31 more Edit links This page was last edited on 8 May 2018, at 12 : 31. 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Question: which cellular component in the bacterial cell is targeted by ampicillin
Answer: inhibits the third and final stage of bacterial cell wall synthesis in binary fission