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

Weight Chemical Formula InChI Key InChI IUPAC Name SMILES Mass Spec Kingdom Classes

Average: 365.404 Monoisotopic: 365.104541423 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/h3-6,911,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-,10-,11+,14-/m1/s1

(2S,5R,6R)-6-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]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

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

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, nose, and throat, the genitourinary tract, the skin and skin structure, and the lower respiratory tract due to susceptible (only b-lactamase-negative) strains of Streptococcus spp. (a- and b-hemolytic strains only), S. pneumoniae, Staphylococcus spp., H. influenzae, E. coli, P. mirabilis, or E. faecalis. Also for the treatment of acute, uncomplicated gonorrhea (ano-genital and urethral infections) due to N. gonorrhoeae (males and females). Amoxicillin is a moderate-spectrum antibiotic active against a wide range of Gram-positive, and a limited range of Gramnegative organisms. It is usually the drug of choice within the class because it is better absorbed, following oral administration, than other beta-lactam antibiotics. Amoxicillin is susceptible to degradation by -lactamase-producing bacteria, and so may be given with clavulanic acid to increase its susceptability. The incidence of -lactamase-producing resistant organisms, including E. coli, appears to be increasing. Amoxicillin is sometimes combined with clavulanic acid, a -lactamase inhibitor, to increase the spectrum of action against Gram-negative organisms, and to overcome bacterial antibiotic resistance mediated through -lactamase production. Amoxicillin binds to penicillin-binding protein 1A (PBP-1A) located inside the bacterial cell well. Penicillins acylate the penicillin-sensitive transpeptidase C-terminal domain by opening the lactam ring. This inactivation of the enzyme prevents the formation of a cross-link of two linear peptidoglycan strands, inhibiting the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that amoxicllin interferes with an autolysin inhibitor. Rapidly absorbed after oral administration. Not Available In blood serum, 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; its excretion can be delayed by concurrent administration of probenecid. 61.3 minutes Not Available

Toxicity

Affected organisms Pathways Manufacturers

Serious toxicity is unlikely following large doses of amoxicillin. Acute ingestion of large doses of amoxicillin may cause nausea, vomiting, diarrhea and abdominal pain. Acute oliguric renal failure and hematuria may occur following large doses. 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. American Antibiotics LLC Apotheca Inc. A-S Medication Solutions LLC Aurobindo Pharma Ltd. Blenheim Pharmacal

Packagers

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

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

UDL Laboratories Veratex Corp. West-Ward Pharmaceuticals Form

Dosage forms

Route Strength Capsule Oral Powder, for solution Oral Powder, for suspension Oral Suspension Oral Tablet Oral Unit description Cost Unit Amoxil 400 mg/5ml Suspension 100ml Bottle 19.99 USD bottle Amoxil 400 mg/5ml Suspension 75ml Bottle 17.99 USD bottle Amoxicillin 400 mg/5ml Suspension 100ml Bottle 16.99 USD bottle Amoxil 400 mg/5ml Suspension 50ml Bottle 15.99 USD bottle Amoxicillin 250 mg/5ml Suspension 150ml Bottle 14.0 USD bottle Amoxil 50 mg/ml Suspension 30ml Bottle 13.99 USD bottle Amoxil 250 mg/5ml Suspension 100ml Bottle 12.99 USD bottle Amoxil 250 mg/5ml Suspension 150ml Bottle 12.99 USD bottle Amoxil 200 mg/5ml Suspension 100ml Bottle 11.99 USD bottle Trimox 125 mg/5ml Suspension 100ml Bottle 11.99 USD bottle DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only. Country Patent Number Approved Expires (estimated) United States 6544555 2000-10-13 2020-10-13 Properties solid

Prices

Patents

State

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. Drawz SM, Bonomo RA: Three decades of beta-lactamase inhibitors. Clin Microbiol Rev. 2010 Jan;23(1):160201. Pubmed Resource KEGG Compound PubChem Compound PubChem Substance Link C06827 33613 46507578 Value 3430 mg/L 0 -6.1 [ADME Research, USCD] Value 9.58e-01 g/l 0.75 -2.3 -2.6 9.48 6 4 132.96 4 89.5 35.53 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

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.rxlist.com/cgi/generic/amox.htm Drugs.com http://www.drugs.com/amoxicillin.html Wikipedia http://en.wikipedia.org/wiki/Amoxicillin J01CA04

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Not Available show (49.6 KB) show (38.1 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

Food Interactions

Tetracycline Possible antagonism of action Take without regard to meals. Targets

1. 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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed 3. Okamoto T, Yoshiyama H, Nakazawa T, Park ID, Chang MW, Yanai H, Okita K, Shirai M: A change in PBP1 is involved in amoxicillin resistance of clinical isolates of Helicobacter pylori. J Antimicrob Chemother. 2002 Dec;50(6):849-56. Pubmed

Enzymes 1. Cytochrome P450 2C19 Actions: substrate Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil,

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