Actimoxi;Amoclen;Amolin;Amopen;Amopenixin;Amoxi;Amoxi-Mast;Amoxibiotic;Amoxiden;Amoxil;Amoxivet;AMPC;Anemolin;Aspenil;Biomox;Bristamox;Cemoxin;Clamoxyl;Delacillin;Dispermox;Efpenix;Flemoxin;Hiconcil;Histocillin;Ibiamox;Imacillin;Lamoxy;Metafarma capsules;Metifarma capsules;Moxacin;Moxal;Ospamox;Pamoxicillin;Piramox;Polymox;Robamox;Sawamox PM;Sumox;Tolodina;Trimox;Unicillin;Utimox;Vetramox;Wymox;Zimox;

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

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]

• American antibiotics llc
• Apothecon inc div bristol myers squibb
• Apothecon sub bristol myers squibb co
• Aurobindo pharma ltd
• Dava pharmaceuticals inc
• Draximage inc
• Glaxosmithkline
• Hikma pharmaceuticals
• Laboratorios atral sarl
• Middlebrook pharmaceuticals inc
• Mylan pharmaceuticals inc
• Parke davis div warner lambert co
• Ranbaxy laboratories ltd
• Ranbaxy pharmaceuticals inc
• Sandoz inc
• Teva pharmaceuticals usa inc
• Wockhardt eu operations (swiss) ag
• Wyeth ayerst laboratories

• 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

Synthesis Reference	Not Available
General Reference	Drawz SM, Bonomo RA: Three decades of beta-lactamase inhibitors. Clin Microbiol Rev. 2010 Jan;23(1):160-201. Pubmed

Type	small molecule

Classes

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

antibacterials 抗细菌;

Indication	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-bound
Metabolism	Hepatic metabolism accounts for less than 30% of the biotransformation of most penicillins
Route 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 minutes
Clearance	Not Available
Toxicity	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 Available

Properties
State	solid
Experimental Properties	Property Value Source melting point 194 °C Not Available water solubility 3430 mg/L Not Available logP 0.87 SANGSTER (1994) Caco2 permeability -6.1 ADME Research, USCD
Predicted Properties	Property Value Source water solubility 9.58e-01 g/l ALOGPS logP 0.75 ALOGPS logP -2.3 ChemAxon logS -2.6 ALOGPS pKa (strongest acidic) 3.23 ChemAxon pKa (strongest basic) 7.43 ChemAxon physiological charge 0 ChemAxon hydrogen acceptor count 6 ChemAxon hydrogen donor count 4 ChemAxon polar surface area 132.96 ChemAxon rotatable bond count 4 ChemAxon refractivity 89.5 ChemAxon polarizability 35.53 ChemAxon

Drug	Interaction
Demeclocycline	Possible antagonism of action
Doxycycline	Possible antagonism of action
Ethinyl Estradiol	This anti-infectious agent could decrease the effect of the oral contraceptive
Mestranol	This anti-infectious agent could decrease the effect of the oral contraceptive
Methacycline	Possible antagonism of action
Methotrexate	The penicillin increases the effect and toxicity of methotrexate
Minocycline	Possible antagonism of action
Oxytetracycline	Possible antagonism of action
Rolitetracycline	Possible antagonism of action
Tetracycline	Possible antagonism of action

• Take without regard to meals.