      Document 0173
 DOCN  DRG0173
 UNIQUE IDENTIFIER        DRG-0074
 NAME OF SUBSTANCE        Ampicillin [USAN 1996]
 REGISTRY NUMBER          69-53-4
 RELATED REGISTRY NUMBER  69-52-3 (sodium)
 RELATED REGISTRY NUMBER  7177-48-2 (trihydrate)
 STANDARD CHEMICAL NAME   (2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-
                          3,3-dimethyl-7-oxo-4-thia-1-azabicyclo-
                          [3.2.0] heptane-2-carboxylic acid [USAN 1996]
 SYNONYMS                 6-[(Aminophenylacetyl)amino]-3,3-dimethyl-7-o-
                          xo-4-thia-1-azabicyclo[3.2.0]
                          heptane-2-carboxylic acid [Merck Index 1989]
 SYNONYMS                 6-[D(-)-alpha-aminophenylacetamido]penicillan-
                          ic acid [Merck Index 1989]
 SYNONYMS                 D(-)-alpha-aminobenzylpenicillin [Merck Index
                          1989]
 SYNONYMS                 Ampicillin A [Merck Index 1989]
 SYNONYMS                 Adobacillin [Merck Index 1989]
 SYNONYMS                 Alpen [Merck Index 1989]
 SYNONYMS                 Amblosin [Merck Index 1989]
 SYNONYMS                 Amfipen [Merck Index 1989]
 SYNONYMS                 Amipenix S [Merck Index 1989]
 SYNONYMS                 Ampi-Bol [Merck Index 1989]
 SYNONYMS                 Ampicin [Merck Index 1989]
 SYNONYMS                 Ampicina [Merck Index 1989]
 SYNONYMS                 Ampilar [Merck Index 1989]
 SYNONYMS                 Ampimed [Merck Index 1989]
 SYNONYMS                 Ampipenin [Merck Index 1989]
 SYNONYMS                 Ampi-Tablinen [Merck Index 1989]
 SYNONYMS                 Amplisom [Merck Index 1989]
 SYNONYMS                 Amplital [Merck Index 1989]
 SYNONYMS                 Ampy-Penyl [Merck Index 1989]
 SYNONYMS                 Austrapen [Merck Index 1989]
 SYNONYMS                 Binotal [Merck Index 1989]
 SYNONYMS                 Bonapicillin [Merck Index 1989]
 SYNONYMS                 Britacil [Merck Index 1989]
 SYNONYMS                 Copharcilin [Merck Index 1989]
 SYNONYMS                 Doktacillin [Merck Index 1989]
 SYNONYMS                 Grampenil [Merck Index 1989]
 SYNONYMS                 Guicitrina [Merck Index 1989]
 SYNONYMS                 Marisilan [Merck Index 1989]
 SYNONYMS                 Nuvapen [Merck Index 1989]
 SYNONYMS                 Pen-Bristol [Merck Index 1989]
 SYNONYMS                 Penbritin [Merck Index 1989]
 SYNONYMS                 Penbrock [Merck Index 1989]
 SYNONYMS                 Penicline [Merck Index 1989]
 SYNONYMS                 Penstabil [Merck Index 1989]
 SYNONYMS                 Pentrex [Merck Index 1989]
 SYNONYMS                 Pentrexyl [Merck Index 1989]
 SYNONYMS                 Polycillin [Merck Index 1989]
 SYNONYMS                 Ponecil [Merck Index 1989]
 SYNONYMS                 QI Damp [Merck Index 1989]
 SYNONYMS                 Rosampline [Merck Index 1989]
 SYNONYMS                 Synpenin [Merck Index 1989]
 SYNONYMS                 Tokiocillin [Merck Index 1989]
 SYNONYMS                 Totacillin [Merck Index 1989]
 SYNONYMS                 Totalciclina [Merck Index 1989]
 SYNONYMS                 Totapen [Merck Index 1989]
 SYNONYMS                 Ultrabion [Merck Index 1989]
 SYNONYMS                 Viccillin [Merck Index 1989]
 SYNONYMS                 Amcill [USAN 1996]
 SYNONYMS                 Omnipen [USAN 1996]
 SYNONYMS                 Principen [USAN 1996]
 SYNONYMS                 4-Thia-1-azabicyclo[3.2.0]
                          heptane-2-carboxylic acid,
                          6-[(aminophenylacetyl)amino]-3,3-
                          dimethyl-7-oxo-, [2S-[2 alpha, 5 alpha, 6
                          beta(S*)]]- [USAN 1996]
 PROTOCOL ID NUMBERS      FDA 019A
 SECONDARY SOURCE ID      AY-6108 [USAN 1996]
 SECONDARY SOURCE ID      BRL 1341 [USAN 1996]
 SECONDARY SOURCE ID      NSC-528986 [USAN 1996]
 SECONDARY SOURCE ID      P-50 [USAN 1996]
 PHARMACOLOGICAL ACTION   MODE OF ACTION: Ampicillin inhibits
                          mucopeptide synthesis in the bacterial cell
                          wall. Ampicillin, like other
                          aminopenicillins, binds to several enzymes in
                          the bacterial cytoplasmic membrane that are
                          involved in cell wall synthesis and cell
                          division causing lysis and cell death.
                          Ampicillin appears to produce abnormally
                          elongated or filamentous morphologic effects
                          in susceptible bacterial cell walls in
                          contrast to amoxicillin which appears to
                          cause rapid formation of spheroplasts and
                          lysis. It is possible that variations in
                          morphological response result in variations
                          in antibacterial spectra. Ampicillin has a
                          similar spectrum of activity to amoxicillin;
                          however, ampicillin is less active in vitro
                          on a weight basis against enterococci and
                          Salmonella but more active than amoxicillin
                          against Shigella and Enterobacter. In
                          general, ampicillin and other
                          aminopenicillins, are active in vitro against
                          most gram positive and gram negative aerobic
                          cocci, except penicillinase producing
                          strains, some gram positive aerobic and
                          anaerobic bacilli, and some spirochetes.
                          Ampicillin is inactive against Mycoplasma,
                          Rickettsia, fungi, and viruses. Between
                          30-55% of an oral dose is absorbed from the
                          GI tract in a fasting adult. Maximum serum
                          concentration is usually attained in about
                          two hours. Two hours after oral doses of 250
                          mg in fasting individuals average peak serum
                          levels of 1.8-2.9 mcg/ml are attained. A 500
                          mg oral dose results in average peak serum
                          levels of 3-6 mcg/ml. Absorption is decreased
                          by food in the gastrointestinal tract.
                          Following IM doses of ampicillin sodium peak
                          serum concentrations are generaly reached
                          more rapidly and are higher than those
                          following equivalent oral doses. Following IV
                          doses, single 2 g doses over 20 minutes in
                          healthy adults, serum levels averaged 47.6
                          mcg/ml within 30 minutes and 3.7 mcg/ml after
                          4 hours. Serum levels and half-life are
                          prolonged in patients with impaired renal
                          function. Biliary levels of ampicillin in
                          patients with normal biliary function may be
                          1-30 times greater than simultaneous serum
                          levels following a single oral dose. [AHFS
                          Drug Information 1995]
 DISEASES STUDIED/TREATED Bacterial infections [FDA 19A]
 CLASSIFICATION CODE      Antimicrobial [PDR 1995]
 OTHER MAJOR USES         Ampicillin is indicated in genitourinary
                          tract infections, including gonorrhea;
                          respiratory tract infections;
                          gastrointestinal tract infections caused by
                          Shigella, S. typhosa and other Salmonella, E.
                          coli, P. mirabilis and enterococci and in N.
                          meningitidis infections [PDR 1995]
 SUBSTANCE INTERACTIONS   Oral probenecid decreases the renal tubular
                          excretion of ampicillin resulting in
                          increased blood levels and/or increased
                          toxicity. Estrogen-containing oral
                          contraceptives may be less effective and
                          increased breakthrough bleeding may occur.
                          Allopurinol may increase the possibility of
                          skin rash, especially in hyperuricemic
                          patients. [AHFS Drug Information 1995] [PDR
                          1995]
 ADVERSE EFFECTS          Ampicillin adverse effects are similar to
                          those of other aminopenicillins, however,
                          diarrhea and rash have been reported more
                          frequently with ampicillin. As with other
                          penicillins it may be expected that untoward
                          reactions will be essentially limited to
                          sensitivity reactions. These are more likely
                          to occur in patients who have previously
                          demonstrated hypersensitivity to penicillins
                          and in subjects with a history of allergy,
                          asthma, hay fever or urticaria. The following
                          additional reactions have been reported with
                          ampicillin: gastrointestinal effects such as
                          glossitis, stomatitis, nausea and vomiting,
                          and pseudomembranous colitis; hepatoxicity,
                          hematologic reactions, e.g., anemia,
                          thrombocytopenic leukopenia and
                          agranulocytosis. [AHFS Drug Information 1995]
                          [PDR 1995]
 CONTRAINDICATIONS        Contraindicated if there is a history of
                          previous hypersensitivity to any of the
                          penicillins. Contraindicated in infections
                          caused by penicillinase-producing organisms.
                          [PDR 1995]
 CHEMICAL/PHYSICAL DATA   DRUG DESCRIPTION: A semisynthetic penicillin
                          derived from the basic penicillin nucleus,
                          6-amino-penicillanic acid [PDR 1995]
 CHEMICAL/PHYSICAL DATA   MOLECULAR FORMULA: C16H19N3O4S [USAN 1996]
 CHEMICAL/PHYSICAL DATA   MOLECULAR WEIGHT: 349.42 [USAN 1996]
 CHEMICAL/PHYSICAL DATA   PHYSICAL DESCRIPTION: White, practically
                          odorless crystalline powder (base and
                          trihydrate) [AHFS Drug Information 1995]
 CHEMICAL/PHYSICAL DATA   PHYSICAL COMMENT: Molecular formula (sodium
                          salt) C16H18N3NaO4S; molecular weight (sodium
                          salt) 371.39 [USAN 1996]
 CHEMICAL/PHYSICAL DATA   ELEMENTAL COMPOSITION: C55.00%, H5.48%,
                          N12.02%, O18.32%, S9.18% [Merck Index 1989]
 CHEMICAL/PHYSICAL DATA   SOLUBILITY: Slightly soluble in water (base
                          and trihydrate) [AHFS Drug Information 1995]
 CHEMICAL/PHYSICAL DATA   STABILITY: The stability of reconstituted
                          parenteral solutions is dependent on the
                          diluent used, the concentration of the
                          solution and the storage temperature [USP DI
                          1995]
 CHEMICAL/PHYSICAL DATA   STABILITY: Oral suspensions are stable for 7
                          days at room temperature and 14 days in the
                          refrigerator [USP DI 1995]
 SUBSTANCE DELIVERY DATA  DOSAGE FORM: Capsules, oral suspension, and
                          vials for injection containing 125 mg - 10 g
                          of base. [USP DI 1995]
 SUBSTANCE DELIVERY DATA  MODE OF DELIVERY: Oral; intramuscular or
                          intravenous injection. [USP DI 1995]
 SUBSTANCE DELIVERY DATA  STORAGE: Store all forms below 40 C (104 F),
                          preferably between 15 and 30 C (59 and 86 F).
                          Store in a tight container and protect from
                          freezing. [USP DI 1995]
 MANUFACTURERS            E. R. Squibb & Sons
 MANUFACTURERS            Eli Lilly
 MANUFACTURERS            Wyeth-Ayerst Research
 MANUFACTURERS            Warner-Lambert Parke-Davis
 MANUFACTURERS            Bristol-Myers
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 REFERENCES               Garcia-Tsao G, Panzini L, Yoselevitz M, West
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                          1992 Mar;102(3):1065-70.
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 ENTRY MONTH              8911
 LAST REVISION DATE       951031
 

SOURCE: National Library of Medicine, Bethesda, MD.  Distributed by AEGIS.
