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Identification Name Accession Number Type Groups Description Amoxicillin DB01060 (APRD00248) small molecule approved A broad-spectrum

semisynthetic antibiotic similar to ampicillin except that its resistance to gastric acid permits higher serum levels with oral administration. Amoxicillin is commonly prescribed with clauvanic acid (a beta lactamase inhibitor) as it is susceptible to beta-lacatamase degradation. [PubChem]

Structure

Synonyms

Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure  Amoxicilina [INN-Spanish]  Amoxicillin anhydrous  Amoxicillin Trihydrate  Amoxicilline [INN-French]  Amoxicillinum [INN-Latin]  Amoxycillin  Amoxycillin Trihydrate  D-Amoxicillin  p-Hydroxyampicillin Amoxicilina [INN-Spanish] Amoxicillin anhydrous Amoxicillin Trihydrate Amoxicilline [INN-French]

Synonyms

Salts Brand names Amoxicillinum [INN-Latin] Amoxycillin Amoxycillin Trihydrate D-Amoxicillin p-Hydroxyampicillin Not Available Name Company Actimoxi Amoclen Amolin Amopen Amopenixin Amoxi Amoxi-Mast Amoxibiotic Amoxiden Amoxil Brand mixtures Categories Brand Name Ingredients Augmentin amoxicillin + clavulanic acid Co-amoxiclav amoxicillin + clavulanic acid Prevpac amoxicillin + clarithromycin + lansoprazole  Anti-Bacterial Agents  Penicillins 26787-78-0 CAS number .

104541423 C16H19N3O5S InChIKey=LSQZJLSUYDQPKJ-NJBDSQKTSA-N InChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6.404 Monoisotopic: 365.2.5R.17H2.911.Weight Chemical Formula InChI Key InChI IUPAC Name SMILES Mass Spec Kingdom Classes Average: 365.14.23.11+.0]heptane-2carboxylic acid CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)C3=CC=C(O)C=C3)C(=O)N2[C@H]1C(O)=O Plain Text Not Available Taxonomy Organic  Phenols and Derivatives  Penicillins  Phenethylamines               Substructures Hydroxy Compounds Acetates Phenols and Derivatives Amino Ketones Aliphatic and Aryl Amines Benzene and Derivatives Carboxylic Acids and Derivatives Beta Lactams Penicillins Thiazoles Phenethylamines Heterocyclic compounds Aromatic compounds Carboxamides and Derivatives .1-2H3.10-.18.3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.14-/m1/s1 Plain Text (2S.(H.21)(H.20H.24)/t9-.6R)-6-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3.

3 minutes Not Available . the genitourinary tract. E. following oral administration. Amoxicillin is sometimes combined with clavulanic acid. and throat. a β-lactamase inhibitor. and to overcome bacterial antibiotic resistance mediated through β-lactamase production. the skin and skin structure. faecalis. It is usually the drug of choice within the class because it is better absorbed. and so may be given with clavulanic acid to increase its susceptability. and the lower respiratory tract due to susceptible (only b-lactamase-negative) strains of Streptococcus spp. P.    Lactams Azetidines Thiazolidines Phenyl Esters Indication Pharmacodynamics Mechanism of action Absorption Volume of distribution Protein binding Metabolism Route of elimination Half life Clearance Pharmacology For the treatment of infections of the ear. gonorrhoeae (males and females). amoxicillin is approximately 20% protein-bound Hepatic metabolism accounts for less than 30% of the biotransformation of most penicillins Most of the amoxicillin is excreted unchanged in the urine. Amoxicillin is a moderate-spectrum antibiotic active against a wide range of Gram-positive.and b-hemolytic strains only). Penicillins acylate the penicillin-sensitive transpeptidase C-terminal domain by opening the lactam ring. The incidence of β-lactamase-producing resistant organisms. and a limited range of Gramnegative organisms. mirabilis. This inactivation of the enzyme prevents the formation of a cross-link of two linear peptidoglycan strands. or E. Not Available In blood serum. Staphylococcus spp. Amoxicillin is susceptible to degradation by β-lactamase-producing bacteria. coli. to increase the spectrum of action against Gram-negative organisms. S. 61. nose. (a. including E. coli. Also for the treatment of acute. Rapidly absorbed after oral administration. Amoxicillin binds to penicillin-binding protein 1A (PBP-1A) located inside the bacterial cell well. H. it is possible that amoxicllin interferes with an autolysin inhibitor. than other beta-lactam antibiotics. appears to be increasing. uncomplicated gonorrhea (ano-genital and urethral infections) due to N.. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins. influenzae. pneumoniae. inhibiting the third and last stage of bacterial cell wall synthesis. its excretion can be delayed by concurrent administration of probenecid.

 Enteric bacteria and other eubacteria Not Available                         Pharmacoeconomics American antibiotics llc Aurobindo pharma ltd Dava pharmaceuticals inc Hikma pharmaceuticals Laboratorios atral sarl Mylan pharmaceuticals inc Ranbaxy pharmaceuticals inc Sandoz inc Teva pharmaceuticals usa inc Glaxosmithkline Apothecon inc div bristol myers squibb Apothecon sub bristol myers squibb co Parke davis div warner lambert co Wyeth ayerst laboratories Wockhardt eu operations (swiss) ag Ranbaxy laboratories ltd Middlebrook pharmaceuticals inc Draximage inc Altura Pharmaceuticals Inc. Blenheim Pharmacal Packagers . Acute oliguric renal failure and hematuria may occur following large doses.Toxicity Affected organisms Pathways Manufacturers Serious toxicity is unlikely following large doses of amoxicillin. American Antibiotics LLC Apotheca Inc. A-S Medication Solutions LLC Aurobindo Pharma Ltd. vomiting. Acute ingestion of large doses of amoxicillin may cause nausea. diarrhea and abdominal pain.

Laboratorios Atral Sarl Lake Erie Medical and Surgical Supply Liberty Pharmaceuticals Major Pharmaceuticals Medpharm Inc. Harkins Co. Keltman Pharmaceuticals Inc. Inc. Golden State Medical Supply Inc.                                Bristol-Myers Squibb Co. International Ethical Labs Inc. Greenstone LLC H. DNA Pharmaceuticals E. Bryant Ranch Prepack C. Comprehensive Consultant Services Inc.O. Hikma Pharmaceuticals Innoviant Pharmacy Inc. Squibb and Sons LLC GlaxoSmithKline Inc. Truxton Inc.R.J. Darby Dental Supply Co. Cardinal Health Carlisle Laboratories Inc. Middlebrook Pharmaceuticals Mississippi State Dept Health . Dispensing Solutions Diversified Healthcare Services Inc. Inc. Medvantx Inc. Casa De Amigos Pharmacy Clonmel Healthcare Ltd. DAVA Pharmaceuticals Dept Health Central Pharmacy Direct Dispensing Inc.

Prescription Dispensing Service Inc. Prepackage Specialists Prepak Systems Inc.                                Murfreesboro Pharmaceutical Nursing Supply Novopharm Ltd. Redpharm Drug Reid Provident Laboratories Inc. Sandoz Signal Health Ltd. Qualitest Ranbaxy Laboratories Rebel Distributors Corp. Palmetto Pharmaceuticals Inc. Okasa Pvt Ltd. Tya Pharmaceuticals . Pharmedix Physicians Total Care Inc. Sandhills Packaging Inc. Southwood Pharmaceuticals St Mary's Medical Park Pharmacy Stat Rx Usa Stat Scripts LLC Talbert Medical Management Corp. Par Pharmaceuticals Patient First Corp. Putney Inc. Nucare Pharmaceuticals Inc. Poli Industria Chimica SPA Preferred Pharmaceuticals Inc. Teva Pharmaceutical Industries Ltd. PCA LLC PD-Rx Pharmaceuticals Inc.

99 USD bottle Amoxil 400 mg/5ml Suspension 75ml Bottle 17. Pricing information is supplied for informational purposes only.99 USD bottle Amoxicillin 400 mg/5ml Suspension 100ml Bottle 16.99 USD bottle Amoxil 250 mg/5ml Suspension 150ml Bottle 12.99 USD bottle DrugBank does not sell nor buy drugs. for suspension Oral Suspension Oral Tablet Oral Unit description Cost Unit Amoxil 400 mg/5ml Suspension 100ml Bottle 19.   UDL Laboratories Veratex Corp.99 USD bottle Amoxicillin 250 mg/5ml Suspension 150ml Bottle 14.99 USD bottle Amoxil 400 mg/5ml Suspension 50ml Bottle 15.0 USD bottle Amoxil 50 mg/ml Suspension 30ml Bottle 13. West-Ward Pharmaceuticals Form Dosage forms Route Strength Capsule Oral Powder. Country Patent Number Approved Expires (estimated) United States 6544555 2000-10-13 2020-10-13 Properties solid Prices Patents State .99 USD bottle Trimox 125 mg/5ml Suspension 100ml Bottle 11.99 USD bottle Amoxil 250 mg/5ml Suspension 100ml Bottle 12.99 USD bottle Amoxil 200 mg/5ml Suspension 100ml Bottle 11. for solution Oral Powder.

Clin Microbiol Rev. Bonomo RA: Three decades of beta-lactamase inhibitors.1 [ADME Research.5 35. Pubmed Resource KEGG Compound PubChem Compound PubChem Substance Link C06827 33613 46507578 Value 3430 mg/L 0 -6.58e-01 g/l 0.53 References Source PhysProp PhysProp BiGG Source ALOGPS ALOGPS ChemAxon Molconvert ALOGPS ChemAxon Molconvert ChemAxon Molconvert ChemAxon Molconvert ChemAxon Molconvert ChemAxon Molconvert ChemAxon Molconvert ChemAxon Molconvert Predicted Properties Synthesis Reference General Reference External Links .3 -2.Melting point Experimental Properties 194 oC Property water solubility logP Caco2 permeability Property water solubility logP logP logS pKa hydrogen acceptor count hydrogen donor count polar surface area rotatable bond count refractivity polarizability Not Available 1. 2010 Jan.23(1):160201.96 4 89. USCD] Value 9.6 9.75 -2. Drawz SM.48 6 4 132.

08 Not Available show (49.rxlist.html Wikipedia http://en.wikipedia.com/amoxicillin.ATC Codes AHFS Codes PDB Entries FDA label MSDS Drug Interactions ChemSpider 31006 ChEBI 2676 ChEMBL 2676 Therapeutic Targets Database DAP000443 PharmGKB PA448406 Drug Product Database 2262886 RxList http://www.1 KB) Interactions Drug Demeclocycline Doxycycline Ethinyl Estradiol Mestranol Methacycline Methotrexate Minocycline Oxytetracycline Rolitetracycline Interaction Possible antagonism of action Possible antagonism of action This anti-infectious agent could decrease the effect of the oral contraceptive This anti-infectious agent could decrease the effect of the oral contraceptive Possible antagonism of action The penicillin increases the effect and toxicity of methotrexate Possible antagonism of action Possible antagonism of action Possible antagonism of action .com http://www.6 KB) show (38.com/cgi/generic/amox.16.drugs.htm Drugs.org/wiki/Amoxicillin  J01CA04  08:12.

Okita K. .50(6):849-56. omeprazole.5(10):821-34. 2002 Dec. Al-Lazikani B. Targets 1. 2006 Oct. their targets and the nature and number of drug targets. Overington JP. Nat Rev Drug Discov. Pubmed 2. Nakazawa T. Pubmed 3. J Antimicrob Chemother.Food Interactions Tetracycline Possible antagonism of action  Take without regard to meals. Chang MW. Yoshiyama H. Sinning C. Yanai H. Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec. Shirai M: A change in PBP1 is involved in amoxicillin resistance of clinical isolates of Helicobacter pylori. proguanil. Meyer A: Drugs. Cytochrome P450 2C19 Actions: substrate Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin. Penicillin-binding proteins 1A/1B Pharmacological action: yes Actions: inhibitor Organism class: bacterial UniProt ID: Q8XJ01 Gene: pbpA Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 1. Imming P. Park ID.5(12):993-6. Okamoto T. Pubmed Enzymes 1.

Winnenburg R.certain barbiturates. Epub 2009 Nov 24. Guenther S. Nucleic Acids Res. Preissner S. Pubmed . Senger C. propranolol. 2010 Jan.38(Database issue):D237-43. diazepam. Kuzman D. Goldsobel G. Dunkel M. Kroll K. citalopram and imipramine UniProt ID: P33261 Gene: CYP2C19 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 1. Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Schroeder M.