      Document 0172
 DOCN  DRG0172
 UNIQUE IDENTIFIER        DRG-0075
 NAME OF SUBSTANCE        Amoxicillin [USAN 1996]
 REGISTRY NUMBER          26787-78-0
 RELATED REGISTRY NUMBER  61336-70-7
 STANDARD CHEMICAL NAME   [2S-[2 alpha, 5 alpha, 6
                          beta(S*)]]-6-[[Amino(4-
                          hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-
                          oxo-4-thia-1-azabicyclo
                          [3.2.0]heptane-2-carboxylic acid [Merck Index
                          1989]
 SYNONYMS                 Amoclen [CHEMLINE]
 SYNONYMS                 Amopen [CHEMLINE]
 SYNONYMS                 Amoxicillin Trihydrate [CHEMLINE]
 SYNONYMS                 Amoxicilline [CHEMLINE]
 SYNONYMS                 Amoxil (Trihydrate) [USAN 1996]
 SYNONYMS                 Amoxycillin [CHEMLINE]
 SYNONYMS                 Cemoxin [CHEMLINE]
 SYNONYMS                 Clamoxyl (Trihydrate) [Merck Index 1989]
 SYNONYMS                 Histocillin [CHEMLINE]
 SYNONYMS                 Imacillin [CHEMLINE]
 SYNONYMS                 p-Hydroxyampicillin [CHEMLINE]
 SYNONYMS                 Larotid [USAN 1996]
 SYNONYMS                 Polymox [USAN 1996]
 SYNONYMS                 Trimox (Trihydrate) [USAN 1996]
 SYNONYMS                 Sawacillin (Trihydrate) [Merck Index 1989]
 SYNONYMS                 Utimox [USAN 1996]
 SYNONYMS                 Wymox (Trihydrate) [USAN 1996]
 SYNONYMS                 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxyli-
                          c acid,
                          6-(2-amino-2-(p-hydroxyphenyl)acetamido)-3,3--
                          dimethyl-7-oxo, D-(8CI) [CHEMLINE]
 SYNONYMS                 6-(D-(-)-p-Hydroxy-alpha-aminobenzyl)penicill-
                          in [CHEMLINE]
 SYNONYMS                 6-(p-Hydroxy-alpha-aminophenylacetamido)penci-
                          llanic acid [CHEMLINE]
 SYNONYMS                 6-[D(-)-alpha-amino-p-hydroxyphenylacetamido]-
                          penicillanic acid [Merck Index 1989]
 SYNONYMS                 (-)-6-[2-amino-2-(p-hydroxyphenyl)acetamido]--
                          3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]-
                          heptane-2-carboxylic acid
 SYNONYMS                 alpha-amino-p-hydroxybenzyl penicillin [Merck
                          Index 1989]
 SYNONYMS                 6-(p-hydroxy-alpha-aminophenylacetamido)penic-
                          illanic acid [Merck Index 1989]
 SYNONYMS                 p-hydroxyampicillin [Merck Index 1989]
 SYNONYMS                 AMPC [Merck Index 1989]
 SYNONYMS                 Alfamox [Merck Index 1989]
 SYNONYMS                 Almodan [Merck Index 1989]
 SYNONYMS                 Amocilline [Merck Index 1989]
 SYNONYMS                 Amolin [Merck Index 1989]
 SYNONYMS                 Amopenixin [Merck Index 1989]
 SYNONYMS                 Amoxi [Merck Index 1989]
 SYNONYMS                 Amoxipen [Merck Index 1989]
 SYNONYMS                 Anemolin [Merck Index 1989]
 SYNONYMS                 Aspenil [Merck Index 1989]
 SYNONYMS                 Betamox [Merck Index 1989]
 SYNONYMS                 Bristamox [Merck Index 1989]
 SYNONYMS                 Cabermox [Merck Index 1989]
 SYNONYMS                 Cuxacillin [Merck Index 1989]
 SYNONYMS                 Delacillin [Merck Index 1989]
 SYNONYMS                 Efpenix [Merck Index 1989]
 SYNONYMS                 Grinsil [Merck Index 1989]
 SYNONYMS                 Ibiamox [Merck Index 1989]
 SYNONYMS                 Ospamox [Merck Index 1989]
 SYNONYMS                 Optium [Merck Index 1989]
 SYNONYMS                 Piramox [Merck Index 1989]
 SYNONYMS                 Simoxil [Merck Index 1989]
 SYNONYMS                 Sumox [Merck Index 1989]
 SYNONYMS                 Agram (Trihydrate) [Merck Index 1989]
 SYNONYMS                 Amodex (Trihydrate) [Merck Index 1989]
 SYNONYMS                 Amoxibiotic (Trihydrate) [Merck Index 1989]
 SYNONYMS                 Amoxidal (Trihydrate) [Merck Index 1989]
 SYNONYMS                 Amoxidin (Trihydrate) [Merck Index 1989]
 SYNONYMS                 Amoxillat (Trihydrate) [Merck Index 1989]
 SYNONYMS                 Amoxi-Wolff (Trihydrate) [Merck Index 1989]
 PROTOCOL ID NUMBERS      FDA 019A
 PROTOCOL ID NUMBERS      FDA 243A
 SECONDARY SOURCE ID      BLP 1410 [CHEMLINE]
 SECONDARY SOURCE ID      BRL 2333 [USAN 1996]
 SECONDARY SOURCE ID      HSDB 3204 [CHEMLINE]
 SECONDARY SOURCE ID      AX 250 (Trihydrate) [Merck Index 1989]
 PHARMACOLOGICAL ACTION   MODE OF ACTION: Aminopenicillins, including
                          amoxicillin, have a mechanism of action
                          similar to that of other penicillins, i.e.,
                          the antibacterial activity of these drugs
                          results from the inhibition of mucopeptide
                          synthesis in the bacterial cell wall.
                          Amoxicillin appears to cause rapid formation
                          of spheroplasts and lysis in susceptible
                          bacteria. This drug is stable in the presence
                          of gastric acid and may be given without
                          regard to meals. It is rapidly absorbed after
                          oral administration and diffuses rapidly into
                          most body tissues and fluids (with the
                          exception of brain and spinal fluid, except
                          when meninges are inflamed). Its half-life is
                          61.3 minutes. It is mostly excreted unchanged
                          in the urine, with approximately 60% of the
                          oral dose excreted within 6-8 hours. It is
                          not highly protein-bound (approximately 20%
                          is protein-bound in blood serum, compared to
                          60% for penicillin G). Oral doses of 250 mg
                          and 500 mg capsules result in average peak
                          blood levels 1-2 hours after dosing of
                          3.5-5.0 mcg/ml and 5.5-7.5 mcg/ml,
                          respectively. Oral doses of amoxicillin
                          suspension of 125 mg/5 ml and 250 mg/5 ml
                          result in average peak blood levels 1-2 hours
                          after dosing of 1.5-3.0 mcg/ml and 3.5-5.0
                          mcg/ml, respectively. Amoxicillin chewable
                          tablets of 125 mg and 250 mg result in
                          average peak blood levels similar to those
                          obtained with corresponding doses of
                          amoxicillin oral suspensions. The drug is
                          detected in serum up to 8 hours after oral
                          dosing. [PDR 1995]
 DISEASES STUDIED/TREATED Bacterial infections [FDA 19A]
 CLASSIFICATION CODE      Antimicrobial [PDR 1993]
 OTHER MAJOR USES         Infections of the ear, nose, throat,
                          genitourinary tract, skin, and soft tissues
                          due to susceptible strains of gram-negative
                          and gram-positive bacteria [PDR 1995]
 SUBSTANCE INTERACTIONS   The effectiveness of estrogen containing oral
                          contraceptives may be reduced by amoxicillin.
                          In patients with hyperuricemia, concomitant
                          allopurinal may increase the incidence of
                          rash. Urinary excretion of this drug can be
                          delayed by concurrent administration of
                          probenecid. [AHFS Drug Information 1995] [USP
                          DI 1995]
 ADVERSE EFFECTS          Hypersensitivity, especially in subjects who
                          have previously demonstrated a penicillin
                          hypersensitivity, and in those with a history
                          of allergy, asthma, hay fever or urticaria,
                          has been reported. Mild to severe
                          pseudomembranous colitis, usually due to
                          Clostridum difficile, has also occurred. May
                          cause nausea, vomiting, diarrhea,
                          erythematous maculopapular rashes and
                          urticaria, anemia, thrombocytopenia,
                          thrombocytopenic purpura, eosinophilia,
                          leukopenia, agranulocytosis, moderate rise in
                          serum glutamic oxaloacetic transaminase
                          (SGOT). [PDR 1995]
 CONTRAINDICATIONS        Contraindicated in patients with history of
                          allergic reaction to any of the penicillins.
                          Because a high percentage of patients with
                          infectious mononucleosis have developed a
                          rash during aminopenicillin therapy,
                          amoxicillin probably should not be used in
                          these patients. [AHFS Drug Information 1995]
 CHEMICAL/PHYSICAL DATA   DRUG DESCRIPTION: Semisynthetic penicillin,
                          an analog of ampicillin [PDR 1995]
 CHEMICAL/PHYSICAL DATA   MOLECULAR FORMULA: C16H19N3O5S (Parent drug)
                          [Merck Index 1989]
 CHEMICAL/PHYSICAL DATA   MOLECULAR WEIGHT: 365.41 (Parent drug) [Merck
                          Index 1989]
 CHEMICAL/PHYSICAL DATA   ELEMENTAL COMPOSITION: C52.59%, H5.24%,
                          N11.50%, O21.89%, S8.77% [Merck Index 1989]
 CHEMICAL/PHYSICAL DATA   SOLUBILITY (mg/ml of trihydrate): Water 4.0;
                          methanol 7.5; absolute ethanol 3.4
                          (trihydrate insoluble in hexane, benzene,
                          ethyl acetate, and acetonitrile) [Merck Index
                          1989]
 CHEMICAL/PHYSICAL DATA   PHYSICAL COMMENT: Molecular formula
                          (Trihydrate: C16H19N3O5S.3H2O); Molecular
                          weight: (Trihydrate: 419.45) [USAN 1996]
 CHEMICAL/PHYSICAL DATA   PHYSICAL DESCRIPTION: White, practically
                          odorless, crystalline powder (trihydrate)
                          [AHFS Drug Information 1995]
 SUBSTANCE DELIVERY DATA  DOSAGE FORM: Capsules, suspension, chewable
                          tablets, or pediatric drops. [USP DI 1995]
 SUBSTANCE DELIVERY DATA  MODE OF DELIVERY: Oral (trihydrate). [USP DI
                          1995]
 SUBSTANCE DELIVERY DATA  STORAGE: Store in tightly closed container,
                          preferably under refrigeration. Unused
                          portions of reconstituted suspensions must be
                          discarded after 14 days. [PDR 1993] [USP DI
                          1995]
 SUBSTANCE DELIVERY DATA  STORAGE: Store capsules and unreconstituted
                          powders between 15-30 C. [PDR 1993] [USP DI
                          1995]
 MANUFACTURERS            Beecham Laboratories
 MANUFACTURERS            E. R. Squibb & Sons
 MANUFACTURERS            Wyeth-Ayerst Resource
 MANUFACTURERS            Bristol-Myers
 MANUFACTURERS            Warner-Lambert Parke-Davis
 REFERENCES               Ciaffi L, Franzetti F, Gervasoni C,
                          Romaniello A, Maillard M, Moro M, Ruggieri A,
                          Cernuschi M, Lazzarin A. Azithromycin versus
                          amoxicillin/clavulanate in community acquired
                          pneumonias of HIV-patients. Int Conf AIDS.
                          1994 Aug 7-12;10(2):135 (abstract no.
                          PB0554).
 REFERENCES               Paparello SF, Davis CE, Malone JL. Cutaneous
                          reactions to amoxicillin-clavulanate among
                          Haitians [letter]. AIDS. 1994 Feb;8(2):276-7.
 REFERENCES               Rolfs R, Gold M, Hackett K, Augenbraun M,
                          Brady W, Larsen S. Treatment of early
                          syphilis in HIV-infected and HIV-uninfected
                          patients--preliminary report of the syphilis
                          & HIV study group. Int Conf AIDS. 1993 Jun
                          6-11;9(1):391 (abstract no. PO-B11-1534).
 REFERENCES               Maini M, French P, Prince M, Bingham JS.
                          Urethritis due to Neisseria meningitidis in a
                          London genitourinary medicine clinic
                          population. Int J STD AIDS. 1992 Nov-Dec
                          ;3(6):423-5.
 REFERENCES               Drancourt M, Bonnet E, Gallais H, Peloux Y,
                          Raoult D. Rhodococcus equi infection in
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                          Mar;24(2):123-31.
 REFERENCES               Principi N, Marchisio P, Tornaghi R, Onorato
                          J, Massironi E, Picco P. Acute otitis media
                          in human immunodeficiency virus-infected
                          children. Pediatrics. 1991 Sep;88(3):566-71.
 REFERENCES               Hay PE, Taylor-Robinson D, Waldron S,
                          Goldmeier D. Amoxycillin, syphilis, and HIV
                          infection [letter; comment]. Lancet. 1990 Feb
                          24;335(8687):474-5.
 REFERENCES               Battegay M, Opravil M, Wuthrich B, Luthy R.
                          Rash with amoxycillin-clavulanate therapy in
                          HIV-infected patients [letter] [see
                          comments]. Lancet. 1989 Nov 4;2(8671):1100.
 REFERENCES               Phillip H, Harris JR, Goldmeier D.
                          Retreatment of syphilis in HIV positive
                          patients. Int Conf AIDS. 1989 Jun 4-9;5:361
                          (abstract no. W.B.P.58)
 REFERENCES               Hay P, Kitchen V, Harris JR, Goldmeier D.
                          Failure of benzathine penicillin to eradicate
                          syphilis in HIV positive patients. Int Conf
                          AIDS. 1989 Jun 4-9;5:361 (abstracts no.
                          W.B.P.59).
 ENTRY MONTH              8911
 LAST REVISION DATE       951128
 

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