IdentificationName AmoxicillinAccession Number DB01060 (APRD00248) Type small moleculeGroups approvedDescription 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

Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure

Synonyms Amoxicilina [INN-Spanish] Amoxicillin anhydrous Amoxicillin Trihydrate Amoxicilline [INN-French] Amoxicillinum [INN-Latin] Amoxycillin Amoxycillin Trihydrate D-Amoxicillin p-Hydroxyampicillin

Synonyms Amoxicilina [INN-Spanish]Amoxicillin anhydrousAmoxicillin TrihydrateAmoxicilline [INN-French]

Amoxicillinum [INN-Latin]AmoxycillinAmoxycillin TrihydrateD-Amoxicillinp-Hydroxyampicillin

Salts Not AvailableBrand names Name Company

ActimoxiAmoclenAmolinAmopenAmopenixinAmoxiAmoxi-MastAmoxibioticAmoxidenAmoxil

Brand mixtures Brand Name IngredientsAugmentin amoxicillin + clavulanic acidCo-amoxiclav amoxicillin + clavulanic acidPrevpac amoxicillin + clarithromycin + lansoprazole

Categories Anti-Bacterial Agents Penicillins

CAS number 26787-78-0Weight Average: 365.404

Monoisotopic: 365.104541423 Chemical Formula C16H19N3O5S

InChI Key InChIKey=LSQZJLSUYDQPKJ-NJBDSQKTSA-NInChI 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/h3-6,9-

11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-,10-,11+,14-/m1/s1Plain Text

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

SMILES 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)=OPlain Text

Mass Spec Not Available Taxonomy

Kingdom OrganicClasses 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

PharmacologyIndication 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).

Pharmacodynamics Amoxicillin is a moderate-spectrum antibiotic active against a wide range of Gram-positive, and a limited range of Gram-negative 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 β-lactamase-producing bacteria, and so may be given with clavulanic acid to increase its susceptability. The incidence of β-lactamase-producing resistant organisms, including E. coli, appears to be increasing. Amoxicillin is sometimes combined with clavulanic acid, a β-lactamase inhibitor, to increase the spectrum of action against Gram-negative organisms, and to overcome bacterial antibiotic resistance mediated through β-lactamase production.

Mechanism of action

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.

Absorption Rapidly absorbed after oral administration.Volume of distribution

Not Available

Protein binding In blood serum, amoxicillin is approximately 20% protein-boundMetabolism Hepatic metabolism accounts for less than 30% of the biotransformation of most penicillinsRoute of elimination

Most of the amoxicillin is excreted unchanged in the urine; its excretion can be delayed by concurrent administration of probenecid.

Half life 61.3 minutesClearance Not AvailableToxicity 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.

Affected organisms Enteric bacteria and other eubacteria

Pathways Not AvailablePharmacoeconomics

Manufacturers 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

Packagers Altura Pharmaceuticals Inc. American Antibiotics LLC Apotheca Inc. A-S Medication Solutions LLC Aurobindo Pharma Ltd. Blenheim Pharmacal 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

Dosage forms Form Route StrengthCapsule OralPowder, for solution OralPowder, for suspension OralSuspension OralTablet Oral

Prices Unit description Cost UnitAmoxil 400 mg/5ml Suspension 100ml Bottle 19.99 USD bottleAmoxil 400 mg/5ml Suspension 75ml Bottle 17.99 USD bottleAmoxicillin 400 mg/5ml Suspension 100ml Bottle 16.99 USD bottleAmoxil 400 mg/5ml Suspension 50ml Bottle 15.99 USD bottleAmoxicillin 250 mg/5ml Suspension 150ml Bottle 14.0 USD bottleAmoxil 50 mg/ml Suspension 30ml Bottle 13.99 USD bottleAmoxil 250 mg/5ml Suspension 100ml Bottle 12.99 USD bottleAmoxil 250 mg/5ml Suspension 150ml Bottle 12.99 USD bottleAmoxil 200 mg/5ml Suspension 100ml Bottle 11.99 USD bottleTrimox 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.

Patents Country Patent Number Approved Expires (estimated)United States 6544555 2000-10-13 2020-10-13

PropertiesState solidMelting point 194 oCExperimental Properties

Property Value Sourcewater solubility 3430 mg/L PhysProp

logP 0 PhysPropCaco2 permeability -6.1 [ADME Research, USCD] BiGG

Predicted Properties

Property Value Sourcewater solubility 9.58e-01 g/l ALOGPSlogP 0.75 ALOGPSlogP -2.3 ChemAxon MolconvertlogS -2.6 ALOGPSpKa 9.48 ChemAxon Molconverthydrogen acceptor count 6 ChemAxon Molconverthydrogen donor count 4 ChemAxon Molconvertpolar surface area 132.96 ChemAxon Molconvertrotatable bond count 4 ChemAxon Molconvertrefractivity 89.5 ChemAxon Molconvertpolarizability 35.53 ChemAxon Molconvert

ReferencesSynthesis Reference

Not Available

General Reference 1. Drawz SM, Bonomo RA: Three decades of beta-lactamase inhibitors. Clin Microbiol Rev. 2010 Jan;23(1):160-201. Pubmed

External Links Resource LinkKEGG Compound C06827 PubChem Compound 33613 PubChem Substance 46507578 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

ATC Codes J01CA04

AHFS Codes 08:12.16.08

PDB Entries Not AvailableFDA label show (49.6 KB) MSDS show (38.1 KB)

InteractionsDrug Interactions Drug Interaction

Demeclocycline Possible antagonism of actionDoxycycline Possible antagonism of actionEthinyl Estradiol This anti-infectious agent could decrease the effect of the oral contraceptiveMestranol This anti-infectious agent could decrease the effect of the oral contraceptiveMethacycline Possible antagonism of actionMethotrexate The penicillin increases the effect and toxicity of methotrexateMinocycline Possible antagonism of actionOxytetracycline Possible antagonism of actionRolitetracycline Possible antagonism of actionTetracycline Possible antagonism of action

Food Interactions Take without regard to meals.

Targets1. Penicillin-binding proteins 1A/1B

Pharmacological action: yesActions: inhibitor

Organism class: bacterialUniProt ID: Q8XJ01 Gene: pbpAProtein Sequence: FASTAGene Sequence: FASTASNPs: 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. Pubmed2. 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. Pubmed3. 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

Enzymes1. 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: FASTAGene Sequence: FASTASNPs: 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