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Amoxicillin

Catalog No. DB01060 Name DrugBank
CAS Number 26787-78-0 Website http://www.ualberta.ca/
M. F. C16H19N3O5S Telephone (780) 492-3111
M. W. 365.40416 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 931

SYNONYMS

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
IUPAC Traditional name
amoxicillin
Brand Name
Amoxil
Sawamox PM
Metafarma capsules
Amoxiden
Sumox
Lamoxy
Piramox
Polymox
Unicillin
Zimox
Amolin
Delacillin
Dispermox
Flemoxin
Hiconcil
Imacillin
Moxal
Pamoxicillin
Tolodina
Vetramox
AMPC
Amoxi
Amoxi-Mast
Amoxibiotic
Amoxivet
Anemolin
Aspenil
Biomox
Bristamox
Cemoxin
Efpenix
Histocillin
Ibiamox
Metifarma capsules
Moxacin
Ospamox
Robamox
Trimox
Utimox
Wymox
Actimoxi
Amoclen
Amopen
Amopenixin
Clamoxyl
Synonyms
Amoxycillin Trihydrate
AMC
D-Amoxicillin
Amoxicilina [INN-Spanish]
Amoxicillin anhydrous
Amoxicilline [INN-French]
Amoxicillinum [INN-Latin]
Amoxicillin Trihydrate
Amoxycillin
p-Hydroxyampicillin

DATABASE IDS

PubChem SID 46507578
CAS Number 26787-78-0
PubChem CID 33613

PROPERTIES

Hydrophobicity(logP) 0
Solubility 3430 mg/L

DETAILS

Description (English)
Item Information
Drug Groups approved
Description 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]
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).
Pharmacology 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.
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
Biotransformation Hepatic metabolism accounts for less than 30% of the biotransformation of most penicillins
Absorption Rapidly absorbed after oral administration.
Half Life 61.3 minutes
Protein Binding In blood serum, amoxicillin is approximately 20% protein-bound
Elimination Most of the amoxicillin is excreted unchanged in the urine; its excretion can be delayed by concurrent administration of probenecid.
References
Drawz SM, Bonomo RA: Three decades of beta-lactamase inhibitors. Clin Microbiol Rev. 2010 Jan;23(1):160-201. [Pubmed]
External Links
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REFERENCES

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