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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Amoxicillin
- Accession Number
- DB01060 (APRD00248)
- Type
- Small Molecule
- Groups
- Approved, Vet 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.
- Structure
Structure for DB01060 (Amoxicillin)
- Synonyms
- (2S,5R,6R)-6-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- 6-(p-hydroxy-α-aminophenylacetamido)penicillanic acid
- Amox
- Amoxicilina
- Amoxicillin (anhydrous)
- Amoxicillin anhydrous
- Amoxicilline
- Amoxicillinum
- Amoxycillin
- AX
- p-Hydroxyampicillin
- α-amino-p-hydroxybenzylpenicillin
- External IDs
- NSC-277174
- Product Ingredients
Ingredient UNII CAS InChI Key Amoxicillin sodium 544Y3D6MYH 34642-77-8 BYHDFCISJXIVBV-YWUHCJSESA-M Amoxycillin trihydrate 804826J2HU 61336-70-7 MQXQVCLAUDMCEF-CWLIKTDRSA-N - Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Amox 250 Cap 250mg Capsule 250 mg Oral Jaapharm Canada Inc. 1991-12-31 Not applicable Canada 
Amox 500 Cap 500mg Capsule 500 mg Oral Jaapharm Canada Inc. 1991-12-31 Not applicable Canada Amox S 125 Sus 125mg/5ml Suspension 125 mg Oral Jaapharm Canada Inc. 1991-12-31 Not applicable Canada Amox S 250 Sus 250mg/5ml Suspension 250 mg Oral Jaapharm Canada Inc. 1991-12-31 Not applicable Canada Amoxicillin Granule, for suspension 250 mg Oral Sanis Health Inc 2010-09-27 Not applicable Canada Amoxicillin Capsule 250 mg Oral Sanis Health Inc 2010-08-28 Not applicable Canada Amoxicillin Tablet, film coated 875 mg/1 Oral Dr Reddy's Laboratories 1978-07-10 Not applicable US 
Amoxicillin Powder, for suspension 400 mg/5mL Oral Clinical Solutions Wholsesale 1999-04-15 2017-06-23 US Amoxicillin Powder, for suspension 200 mg/5mL Oral Clinical Solutions Wholsesale 1999-04-15 2017-06-23 US Amoxicillin Granule, for suspension 250 mg Oral Sanis Health Inc 2010-11-02 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Amoxicillan Capsule 500 mg/1 Oral Northwind Pharmaceuticals 2014-06-01 Not applicable US 
Amoxicillan Tablet 500 mg/1 Oral Northwind Pharmaceuticals 2014-07-18 Not applicable US Amoxicillin Powder, for suspension 250 mg/5mL Oral Physicians Total Care, Inc. 2009-01-22 Not applicable US Amoxicillin Capsule 500 mg/1 Oral Lake Erie Medical Dba Quality Care Produts Llc 2011-12-15 Not applicable US Amoxicillin Powder, for suspension 250 mg/5mL Oral Hikma Pharmaceutical 2006-06-19 Not applicable US Amoxicillin Powder, for suspension 250 mg/5mL Oral Preferreed Pharmaceuticals Inc. 2011-06-15 Not applicable US Amoxicillin Capsule 500 mg/1 Oral A S Medication Solutions 2014-08-01 2017-06-20 US Amoxicillin Powder, for suspension 250 mg/5mL Oral Proficient Rx LP 2006-06-19 Not applicable US Amoxicillin Capsule 500 mg/1 Oral Red Pharm Drug, Inc. 2016-02-01 Not applicable US Amoxicillin Tablet, film coated 875 mg/1 Oral Directrx 2016-12-01 Not applicable US - International/Other Brands
- Actimoxi / Amoclen / Amolin / Amopen / Amopenixin / Amoxibiotic / Amoxil (GlaxoSmithKline) / AMPC / Apo-Amoxi / Clamoxyl / Dispermox / Efpenix / Flemoxin / Hiconcil / Ibiamox / Imacillin / Larotid (Roche) / Moxacin / Moxal / Ospamox / Pamoxicillin / Polymox / Trimox / Wymox
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Amoxi-clav Amoxicillin (875 mg) + Clavulanate potassium (125 mg) Tablet Oral Pro Doc Limitee 2009-10-08 Not applicable Canada Amoxi-clav Amoxicillin (500 mg) + Clavulanate potassium (125 mg) Tablet Oral Pro Doc Limitee 2009-10-08 Not applicable Canada Amoxicillan and clavulanate potassium Amoxicillin (500 mg/1) + Clavulanate potassium (125 mg/1) Tablet, film coated Oral Northwind Pharmaceuticals 2014-07-18 Not applicable US Amoxicillin and Clavulanate Potassium Amoxicillin (875 mg/1) + Clavulanate potassium (125 mg/1) Tablet, film coated Oral Proficient Rx LP 2002-11-21 Not applicable US Amoxicillin and Clavulanate Potassium Amoxicillin (200 mg/5mL) + Clavulanate potassium (28.5 mg/5mL) Powder, for suspension Oral Preferreed Pharmaceuticals Inc. 2016-02-11 Not applicable US Amoxicillin and Clavulanate Potassium Amoxicillin (875 mg/1) + Clavulanate potassium (125 mg/1) Tablet, film coated Oral Med Vantx, Inc. 2011-11-16 Not applicable US Amoxicillin and Clavulanate Potassium Amoxicillin (875 mg/1) + Clavulanate potassium (125 mg/1) Tablet, film coated Oral Mylan Pharmaceuticals 2016-06-02 2018-04-30 US Amoxicillin and Clavulanate Potassium Amoxicillin (875 mg/1) + Clavulanate potassium (125 mg/1) Tablet, film coated Oral Blenheim Pharmacal, Inc. 2015-10-06 Not applicable US Amoxicillin and Clavulanate Potassium Amoxicillin (500 mg/1) + Clavulanate potassium (125 mg/1) Tablet, film coated Oral Aidarex Pharmaceuticals LLC 2002-10-31 Not applicable US Amoxicillin and Clavulanate Potassium Amoxicillin (1000 mg/1) + Clavulanate (62.5 mg/1) Tablet, multilayer, extended release Oral Sandoz 2010-04-21 Not applicable US 
- Categories
- UNII
- 9EM05410Q9
- CAS number
- 26787-78-0
- Weight
- Average: 365.404
Monoisotopic: 365.104541423 - Chemical Formula
- C16H19N3O5S
- InChI Key
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N
- InChI
- 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/s1
- 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
- [H][[email protected]]12SC(C)(C)[[email protected]@H](N1C(=O)[[email protected]]2NC(=O)[[email protected]](N)C1=CC=C(O)C=C1)C(O)=O
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 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).
- Structured Indications
- Acute maxillary sinusitis caused by M. catarrhalis
- Bronchiectasis
- Community Acquired Pneumonia (CAP)
- Duodenal ulcer caused by helicobacter pylori
- Erysipeloid
- Infective Endocarditis
- Lower Respiratory Tract Infection (LRTI)
- Lyme Neuroborreliosis
- Otitis media bacterial
- Sinusitis
- Skin and Subcutaneous Tissue Bacterial Infections
- Streptococcal Pharyngitis
- Streptococcal tonsillitis
- Urinary Tract Infections (UTIs)
- Acute Gonorrhea
- Uncomplicated Gonorrhea
- 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.
Target Actions Organism APenicillin-binding protein 1A inhibitorClostridium perfringens (strain 13 / Type A) - 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
- Gram negative and gram positive bacteria
- Streptococcus pyogenes
- Streptococcus pneumoniae
- Borrelia burgdorferi
- Chlamydia pneumoniae
- Salmonella typhi
- Chlamydia psittaci
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction Drug group Abiraterone The metabolism of Amoxicillin can be decreased when combined with Abiraterone. Approved Acenocoumarol Amoxicillin may increase the anticoagulant activities of Acenocoumarol. Approved Aclarubicin The serum concentration of Aclarubicin can be decreased when it is combined with Amoxicillin. Investigational Allopurinol The risk of a hypersensitivity reaction to Amoxicillin is increased when it is combined with Allopurinol. Approved Amikacin The serum concentration of Amikacin can be decreased when it is combined with Amoxicillin. Approved, Vet Approved Amrubicin The serum concentration of Amrubicin can be decreased when it is combined with Amoxicillin. Approved, Investigational annamycin The serum concentration of annamycin can be decreased when it is combined with Amoxicillin. Investigational Apramycin The serum concentration of Apramycin can be decreased when it is combined with Amoxicillin. Experimental, Vet Approved Arbekacin The serum concentration of Arbekacin can be decreased when it is combined with Amoxicillin. Approved Armodafinil The metabolism of Amoxicillin can be decreased when combined with Armodafinil. Approved, Investigational BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Amoxicillin. Investigational Bekanamycin The serum concentration of Bekanamycin can be decreased when it is combined with Amoxicillin. Experimental Bortezomib The metabolism of Amoxicillin can be decreased when combined with Bortezomib. Approved, Investigational Carbamazepine The metabolism of Amoxicillin can be increased when combined with Carbamazepine. Approved, Investigational Chloramphenicol The metabolism of Amoxicillin can be decreased when combined with Chloramphenicol. Approved, Vet Approved Chlortetracycline The therapeutic efficacy of Amoxicillin can be decreased when used in combination with Chlortetracycline. Approved, Vet Approved Cholecalciferol The metabolism of Amoxicillin can be decreased when combined with Cholecalciferol. Approved, Nutraceutical Cimetidine The metabolism of Amoxicillin can be decreased when combined with Cimetidine. Approved Citalopram The metabolism of Amoxicillin can be decreased when combined with Citalopram. Approved Clorindione Amoxicillin may increase the anticoagulant activities of Clorindione. Experimental Clotrimazole The metabolism of Amoxicillin can be decreased when combined with Clotrimazole. Approved, Vet Approved Dabrafenib The serum concentration of Amoxicillin can be decreased when it is combined with Dabrafenib. Approved Daunorubicin The serum concentration of Daunorubicin can be decreased when it is combined with Amoxicillin. Approved Delavirdine The metabolism of Amoxicillin can be decreased when combined with Delavirdine. Approved Demeclocycline The therapeutic efficacy of Amoxicillin can be decreased when used in combination with Demeclocycline. Approved Dibekacin The serum concentration of Dibekacin can be decreased when it is combined with Amoxicillin. Experimental Dicoumarol Amoxicillin may increase the anticoagulant activities of Dicoumarol. Approved Dihydrostreptomycin The serum concentration of Dihydrostreptomycin can be decreased when it is combined with Amoxicillin. Vet Approved Diphenadione Amoxicillin may increase the anticoagulant activities of Diphenadione. Experimental Doxorubicin The serum concentration of Doxorubicin can be decreased when it is combined with Amoxicillin. Approved, Investigational Doxycycline The therapeutic efficacy of Amoxicillin can be decreased when used in combination with Doxycycline. Approved, Investigational, Vet Approved Efavirenz The metabolism of Amoxicillin can be decreased when combined with Efavirenz. Approved, Investigational Epirubicin The serum concentration of Epirubicin can be decreased when it is combined with Amoxicillin. Approved Eslicarbazepine acetate The metabolism of Amoxicillin can be decreased when combined with Eslicarbazepine acetate. Approved Esomeprazole The metabolism of Amoxicillin can be decreased when combined with Esomeprazole. Approved, Investigational Ethyl biscoumacetate Amoxicillin may increase the anticoagulant activities of Ethyl biscoumacetate. Withdrawn Etravirine The metabolism of Amoxicillin can be decreased when combined with Etravirine. Approved Fluconazole The metabolism of Amoxicillin can be decreased when combined with Fluconazole. Approved Fluindione Amoxicillin may increase the anticoagulant activities of Fluindione. Investigational Fluoxetine The metabolism of Amoxicillin can be decreased when combined with Fluoxetine. Approved, Vet Approved Fluvoxamine The metabolism of Amoxicillin can be decreased when combined with Fluvoxamine. Approved, Investigational Fosphenytoin The metabolism of Amoxicillin can be increased when combined with Fosphenytoin. Approved Framycetin The serum concentration of Framycetin can be decreased when it is combined with Amoxicillin. Approved Gemfibrozil The metabolism of Amoxicillin can be decreased when combined with Gemfibrozil. Approved Geneticin The serum concentration of Geneticin can be decreased when it is combined with Amoxicillin. Experimental Gentamicin The serum concentration of Gentamicin can be decreased when it is combined with Amoxicillin. Approved, Vet Approved GENTAMICIN C1A The serum concentration of GENTAMICIN C1A can be decreased when it is combined with Amoxicillin. Experimental GPX-150 The serum concentration of GPX-150 can be decreased when it is combined with Amoxicillin. Investigational Hygromycin B The serum concentration of Hygromycin B can be decreased when it is combined with Amoxicillin. Vet Approved Idarubicin The serum concentration of Idarubicin can be decreased when it is combined with Amoxicillin. Approved Indinavir The metabolism of Amoxicillin can be decreased when combined with Indinavir. Approved INNO-206 The serum concentration of INNO-206 can be decreased when it is combined with Amoxicillin. Investigational Isepamicin The serum concentration of Isepamicin can be decreased when it is combined with Amoxicillin. Experimental Isoniazid The metabolism of Amoxicillin can be decreased when combined with Isoniazid. Approved Kanamycin The serum concentration of Kanamycin can be decreased when it is combined with Amoxicillin. Approved, Vet Approved Ketoconazole The metabolism of Amoxicillin can be decreased when combined with Ketoconazole. Approved, Investigational Lobeglitazone The metabolism of Amoxicillin can be decreased when combined with Lobeglitazone. Approved Lopinavir The metabolism of Amoxicillin can be increased when combined with Lopinavir. Approved Luliconazole The serum concentration of Amoxicillin can be increased when it is combined with Luliconazole. Approved Lumacaftor The serum concentration of Amoxicillin can be decreased when it is combined with Lumacaftor. Approved Methotrexate The serum concentration of Methotrexate can be increased when it is combined with Amoxicillin. Approved Metrizamide The serum concentration of Metrizamide can be decreased when it is combined with Amoxicillin. Approved Micronomicin The serum concentration of Micronomicin can be decreased when it is combined with Amoxicillin. Experimental Minocycline The therapeutic efficacy of Amoxicillin can be decreased when used in combination with Minocycline. Approved, Investigational Moclobemide The metabolism of Amoxicillin can be decreased when combined with Moclobemide. Approved Modafinil The metabolism of Amoxicillin can be decreased when combined with Modafinil. Approved, Investigational Mycophenolic acid The serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Amoxicillin resulting in a loss in efficacy. Approved Neamine The serum concentration of Neamine can be decreased when it is combined with Amoxicillin. Experimental Nelfinavir The metabolism of Amoxicillin can be decreased when combined with Nelfinavir. Approved Neomycin The serum concentration of Neomycin can be decreased when it is combined with Amoxicillin. Approved, Vet Approved Netilmicin The serum concentration of Netilmicin can be decreased when it is combined with Amoxicillin. Approved Nicardipine The metabolism of Amoxicillin can be decreased when combined with Nicardipine. Approved Omeprazole The metabolism of Amoxicillin can be decreased when combined with Omeprazole. Approved, Investigational, Vet Approved Pantoprazole The metabolism of Amoxicillin can be decreased when combined with Pantoprazole. Approved Paromomycin The serum concentration of Paromomycin can be decreased when it is combined with Amoxicillin. Approved, Investigational Phenindione Amoxicillin may increase the anticoagulant activities of Phenindione. Approved Phenprocoumon Amoxicillin may increase the anticoagulant activities of Phenprocoumon. Approved Phenytoin The metabolism of Amoxicillin can be increased when combined with Phenytoin. Approved, Vet Approved Picosulfuric acid The therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Amoxicillin. Approved Pirarubicin The serum concentration of Pirarubicin can be decreased when it is combined with Amoxicillin. Investigational Plazomicin The serum concentration of Plazomicin can be decreased when it is combined with Amoxicillin. Investigational Plicamycin The serum concentration of Plicamycin can be decreased when it is combined with Amoxicillin. Approved, Withdrawn Probenecid The serum concentration of Amoxicillin can be increased when it is combined with Probenecid. Approved Puromycin The serum concentration of Puromycin can be decreased when it is combined with Amoxicillin. Experimental Ribostamycin The serum concentration of Ribostamycin can be decreased when it is combined with Amoxicillin. Approved Rifampicin The metabolism of Amoxicillin can be increased when combined with Rifampicin. Approved Sabarubicin The serum concentration of Sabarubicin can be decreased when it is combined with Amoxicillin. Investigational Sertraline The metabolism of Amoxicillin can be decreased when combined with Sertraline. Approved Sisomicin The serum concentration of Sisomicin can be decreased when it is combined with Amoxicillin. Investigational SP1049C The serum concentration of SP1049C can be decreased when it is combined with Amoxicillin. Investigational Spectinomycin The serum concentration of Spectinomycin can be decreased when it is combined with Amoxicillin. Approved, Vet Approved Stiripentol The metabolism of Amoxicillin can be decreased when combined with Stiripentol. Approved Streptomycin The serum concentration of Streptomycin can be decreased when it is combined with Amoxicillin. Approved, Vet Approved Streptozocin The serum concentration of Streptozocin can be decreased when it is combined with Amoxicillin. Approved Ticlopidine The metabolism of Amoxicillin can be decreased when combined with Ticlopidine. Approved Tioclomarol Amoxicillin may increase the anticoagulant activities of Tioclomarol. Experimental Tobramycin The serum concentration of Tobramycin can be decreased when it is combined with Amoxicillin. Approved, Investigational Topiramate The metabolism of Amoxicillin can be decreased when combined with Topiramate. Approved Tranylcypromine The metabolism of Amoxicillin can be decreased when combined with Tranylcypromine. Approved Valrubicin The serum concentration of Valrubicin can be decreased when it is combined with Amoxicillin. Approved Voriconazole The metabolism of Amoxicillin can be decreased when combined with Voriconazole. Approved, Investigational Warfarin Amoxicillin may increase the anticoagulant activities of Warfarin. Approved Zoptarelin doxorubicin The serum concentration of Zoptarelin doxorubicin can be decreased when it is combined with Amoxicillin. Investigational Zorubicin The serum concentration of Zorubicin can be decreased when it is combined with Amoxicillin. Experimental Zucapsaicin The metabolism of Amoxicillin can be decreased when combined with Zucapsaicin. Approved - Food Interactions
- Take without regard to meals.
References
- Synthesis Reference
Joan Cabre, Jose Diago, Asuncion Esteve, Johannes Ludescher, "Production of a crystalline salt of amoxicillin." U.S. Patent US6103897, issued April, 1971.
US6103897- General References
- Drawz SM, Bonomo RA: Three decades of beta-lactamase inhibitors. Clin Microbiol Rev. 2010 Jan;23(1):160-201. doi: 10.1128/CMR.00037-09. [PubMed:20065329]
- External Links
- Human Metabolome Database
- HMDB15193
- KEGG Drug
- D07452
- KEGG Compound
- C06827
- PubChem Compound
- 33613
- PubChem Substance
- 46507578
- ChemSpider
- 31006
- BindingDB
- 50350464
- ChEBI
- 2676
- ChEMBL
- CHEMBL1082
- Therapeutic Targets Database
- DAP000443
- PharmGKB
- PA448406
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Amoxicillin
- ATC Codes
- J01CR50 — Combinations of penicillins
- J01CR — Combinations of penicillins, incl. beta-lactamase inhibitors
- J01C — BETA-LACTAM ANTIBACTERIALS, PENICILLINS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- J01CA — Penicillins with extended spectrum
- J01C — BETA-LACTAM ANTIBACTERIALS, PENICILLINS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- A02BD — Combinations for eradication of Helicobacter pylori
- A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
- A02 — DRUGS FOR ACID RELATED DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- AHFS Codes
- 08:12.16.08 — Aminopenicillins
- FDA label
- Download (49.6 KB)
- MSDS
- Download (38.1 KB)
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- 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 Strength Tablet Oral 500 mg/1 Capsule Oral 250 mg/1 Capsule Oral 500 mg/1 For suspension Oral 125 mg/5mL For suspension Oral 25 mg/mL For suspension Oral 50 mg/mL Powder, for suspension Oral 125 mg/5mL Powder, for suspension Oral 200 mg/5mL Powder, for suspension Oral 250 mg/5mL Powder, for suspension Oral 400 mg/5mL Powder, for suspension Oral 600 mg/5mL Tablet Oral 250 mg/1 Tablet Oral 875 mg/1 Tablet, chewable Oral 125 mg/1 Tablet, chewable Oral 250 mg/1 Tablet, coated Oral 875 mg/1 Tablet, film coated Oral 500 mg/1 Tablet, film coated Oral 875 mg/1 Powder, for suspension Oral Suspension Oral Tablet, chewable Oral Tablet, film coated Oral Tablet, multilayer, extended release Oral Tablet, film coated, extended release Oral 775 mg/1 Tablet Oral Suspension Oral 25 mg Suspension Oral 50 mg Tablet Oral 125 mg Tablet Oral 250 mg Powder, for solution Oral 50 mg Powder, for solution Oral 125 mg Powder, for solution Oral 250 mg Tablet, film coated, extended release Oral Capsule; capsule, extended release; kit; tablet Oral Kit Capsule Oral 250 mg Capsule Oral 500 mg Granule, for suspension Oral 125 mg Granule, for suspension Oral 25 mg Granule, for suspension Oral 250 mg Granule, for suspension Oral 50 mg Tablet, chewable Oral 125 mg Tablet, chewable Oral 250 mg Suspension Oral 125 mg Suspension Oral 250 mg Powder, for solution Oral Powder, for suspension Oral 125 mg Powder, for suspension Oral 250 mg - Prices
Unit description Cost Unit Amoxil 400 mg/5ml Suspension 100ml Bottle 19.99USD bottle Amoxil 400 mg/5ml Suspension 75ml Bottle 17.99USD bottle Amoxicillin 400 mg/5ml Suspension 100ml Bottle 16.99USD bottle Amoxil 400 mg/5ml Suspension 50ml Bottle 15.99USD bottle Amoxicillin 250 mg/5ml Suspension 150ml Bottle 14.0USD bottle Amoxil 50 mg/ml Suspension 30ml Bottle 13.99USD bottle Amoxil 250 mg/5ml Suspension 100ml Bottle 12.99USD bottle Amoxil 250 mg/5ml Suspension 150ml Bottle 12.99USD bottle Amoxil 200 mg/5ml Suspension 100ml Bottle 11.99USD bottle Trimox 125 mg/5ml Suspension 100ml Bottle 11.99USD bottle Trimox 125 mg/5ml Suspension 150ml Bottle 11.99USD bottle Trimox 250 mg/5ml Suspension 80ml Bottle 11.99USD bottle Amoxil 875 mg tablet 1.13USD tablet Amoxil 400 mg Chew Tabs 1.05USD tab Amoxicillin 875 mg tablet 0.89USD tablet Amoxil 500 mg tablet 0.77USD tablet Novamoxin 250 mg Chewable Tablet 0.64USD tablet Amoxicillin 125 mg Chew Tabs 0.57USD tab Amoxil 500 mg capsule 0.53USD capsule Amoxicillin 500 mg tablet 0.5USD tablet Amoxicillin 250 mg Chew Tabs 0.47USD tab Amoxicillin 500 mg capsule 0.47USD capsule Novamoxin 125 mg Chewable Tablet 0.44USD tablet Apo-Amoxi 500 mg Capsule 0.36USD capsule Mylan-Amoxillin 500 mg Capsule 0.36USD capsule Novamoxin 500 mg Capsule 0.36USD capsule Nu-Amoxi 500 mg Capsule 0.36USD capsule Pms-Amoxicillin 500 mg Capsule 0.36USD capsule Amoxicillin 250 mg capsule 0.25USD capsule Apo-Amoxi 250 mg Capsule 0.18USD capsule Mylan-Amoxillin 250 mg Capsule 0.18USD capsule Novamoxin 250 mg Capsule 0.18USD capsule Nu-Amoxi 250 mg Capsule 0.18USD capsule Pms-Amoxicillin 250 mg Capsule 0.18USD capsule Apo-Amoxi 50 mg/ml Suspension 0.06USD ml Novamoxin 50 mg/ml Suspension 0.06USD ml Novamoxin Sugar-Reduced 50 mg/ml Suspension 0.06USD ml Nu-Amoxi 50 mg/ml Suspension 0.06USD ml Pms-Amoxicillin 50 mg/ml Suspension 0.06USD ml Apo-Amoxi 25 mg/ml Suspension 0.04USD ml Novamoxin 25 mg/ml Suspension 0.04USD ml Novamoxin Sugar-Reduced 25 mg/ml Suspension 0.04USD ml Nu-Amoxi 25 mg/ml Suspension 0.04USD ml Pms-Amoxicillin 25 mg/ml Suspension 0.04USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) US6544555 No 2000-10-13 2020-10-13 US US6669948 No 2000-10-13 2020-10-13 US US6723341 No 2000-10-13 2020-10-13 US US8299052 No 2007-05-07 2027-05-07 US US8778924 No 2006-12-08 2026-12-08 US US8357394 No 2006-12-08 2026-12-08 US US6878386 No 2000-04-04 2020-04-04 US US7217430 No 2000-04-04 2020-04-04 US US7250176 No 2000-04-04 2020-04-04 US US6783773 No 2000-04-04 2020-04-04 US US6746692 No 2000-04-04 2020-04-04 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 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 0.958 mg/mL 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 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 89.5 m3·mol-1 ChemAxon Polarizability 35.53 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption - 0.9008 Blood Brain Barrier - 0.9967 Caco-2 permeable - 0.8722 P-glycoprotein substrate Substrate 0.5741 P-glycoprotein inhibitor I Non-inhibitor 0.9665 P-glycoprotein inhibitor II Non-inhibitor 0.9968 Renal organic cation transporter Non-inhibitor 0.9636 CYP450 2C9 substrate Non-substrate 0.843 CYP450 2D6 substrate Non-substrate 0.8446 CYP450 3A4 substrate Non-substrate 0.5478 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.915 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9767 Ames test Non AMES toxic 0.9099 Carcinogenicity Non-carcinogens 0.5439 Biodegradation Not ready biodegradable 0.9606 Rat acute toxicity 1.7036 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9996 hERG inhibition (predictor II) Non-inhibitor 0.8761
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactams
- Sub Class
- Beta lactams
- Direct Parent
- Penicillins
- Alternative Parents
- N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Phenylacetamides / 1-hydroxy-2-unsubstituted benzenoids / Aralkylamines / Thiazolidines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Amino acids / Azetidines show 10 more
- Substituents
- Penicillin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / Phenylacetamide / Phenol / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Benzenoid / Monocyclic benzene moiety show 26 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- penicillin (CHEBI:2676)
Targets
- Kind
- Protein
- Organism
- Clostridium perfringens (strain 13 / Type A)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Transferase activity, transferring glycosyl groups
- Specific Function
- Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
- Gene Name
- pbpA
- Uniprot ID
- Q8XJ01
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 75176.35 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- 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:17016423]
- 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:12461003]
Enzymes
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- 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 im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Transporters
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Proton-dependent oligopeptide secondary active transmembrane transporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
- Gene Name
- SLC15A1
- Uniprot ID
- P46059
- Uniprot Name
- Solute carrier family 15 member 1
- Molecular Weight
- 78805.265 Da
References
- Wenzel U, Gebert I, Weintraut H, Weber WM, Clauss W, Daniel H: Transport characteristics of differently charged cephalosporin antibiotics in oocytes expressing the cloned intestinal peptide transporter PepT1 and in human intestinal Caco-2 cells. J Pharmacol Exp Ther. 1996 May;277(2):831-9. [PubMed:8627565]
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297]
- Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833]
- Sala-Rabanal M, Loo DD, Hirayama BA, Turk E, Wright EM: Molecular interactions between dipeptides, drugs and the human intestinal H+ -oligopeptide cotransporter hPEPT1. J Physiol. 2006 Jul 1;574(Pt 1):149-66. Epub 2006 Apr 20. [PubMed:16627568]
- Li M, Anderson GD, Phillips BR, Kong W, Shen DD, Wang J: Interactions of amoxicillin and cefaclor with human renal organic anion and peptide transporters. Drug Metab Dispos. 2006 Apr;34(4):547-55. Epub 2006 Jan 24. [PubMed:16434549]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Peptide:proton symporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
- Gene Name
- SLC15A2
- Uniprot ID
- Q16348
- Uniprot Name
- Solute carrier family 15 member 2
- Molecular Weight
- 81782.77 Da
References
- Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833]
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297]
- Li M, Anderson GD, Phillips BR, Kong W, Shen DD, Wang J: Interactions of amoxicillin and cefaclor with human renal organic anion and peptide transporters. Drug Metab Dispos. 2006 Apr;34(4):547-55. Epub 2006 Jan 24. [PubMed:16434549]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577]
Drug created on June 13, 2005 07:24 / Updated on October 23, 2017 14:13