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QuickView for amoxicillin (compound)


PubChem
Name: Amoxicillin
PubChem Compound ID: 20847
Description: A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.
Molecular formula: C17H26Cl3N3O
Molecular weight: 394.766 g/mol
Synonyms:
CLAMOXYQUIN DIHYDROCHLORIDE; Clamoxyl (TN); 8-Quinolinol, 5-chloro-7-(((3-(diethylamino)propyl)amino)methyl)-, dihydrochloride; 5-Chloro-7-(((3-(diethylamino)propyl)amino)methyl)-8-quinolinol dihydrochloride; Clamoxyquin hydrochloride (USAN); CN-17,900-2B; Clamoxyquin hydrochloride; Clamoxyquin hydrochloride [USAN]; D03529; CI 433.
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DrugBank
Identification
Name: Amoxicillin
Name (isomeric): DB01060
Drug Type: small molecule
Description: A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.
Synonyms:
Amoxycillin Trihydrate; Amoxicillin Trihydrate; Amoxicillin anhydrous; Amoxycillin; Amoxicilina [INN-Spanish]; p-Hydroxyampicillin; AMC; Amoxicillinum [INN-Latin]; D-Amoxicillin; Amoxicilline [INN-French]
Brand: Amoxil, Imacillin, Unicillin, Ospamox, Bristamox, Efpenix, Wymox, Amoxi-Mast, Actimoxi, Ibiamox, Vetramox, Moxacin, Dispermox, Utimox, Amoxivet, Cemoxin, Delacillin, Amopenixin, Anemolin, Trimox, Metafarma capsules, Aspenil, Flemoxin, Robamox, Polymox, Amopen, Pamoxicillin, Amoxibiotic, Piramox, Biomox, Amoclen, Lamoxy, Sawamox PM, Sumox, Hiconcil, Zimox, AMPC, Clamoxyl, Tolodina, Moxal, Amoxiden, Amoxi, Amolin, Histocillin, Metifarma capsules
Brand name mixture: Co-amoxiclav(amoxicillin + clavulanic acid), Prevpac(amoxicillin + clarithromycin + lansoprazole), Augmentin(amoxicillin + clavulanic acid)
Category: Anti-Bacterial Agents, Penicillins
CAS number: 26787-78-0
Pharmacology
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 <i>Streptococcus</i> spp. (a- and b-hemolytic strains only), <i>S. pneumoniae</i>, <i>Staphylococcus</i> spp., <i>H. influenzae</i>, <i>E. coli</i>, <i>P. mirabilis</i>, or <i>E. faecalis</i>. Also for the treatment of acute, uncomplicated gonorrhea (ano-genital and urethral infections) due to <i>N. gonorrhoeae</i> (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-...
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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 ...
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Absorption: Rapidly absorbed after oral administration.
Protein binding: In blood serum, amoxicillin is approximately 20% protein-bound
Biotransformation: 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
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
Interactions
Food interaction:
Take without regard to meals.
Drug interaction:
OxytetracyclinePossible antagonism of action
Ethinyl EstradiolThis anti-infectious agent could decrease the effect of the oral contraceptive
MethacyclinePossible antagonism of action
DoxycyclinePossible antagonism of action
DemeclocyclinePossible antagonism of action
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