Identification

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
Thumb
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
IngredientUNIICASInChI Key
Amoxicillin sodium544Y3D6MYH34642-77-8BYHDFCISJXIVBV-YWUHCJSESA-M
Amoxycillin trihydrate804826J2HU61336-70-7MQXQVCLAUDMCEF-CWLIKTDRSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Amox 250 Cap 250mgCapsule250 mgOralJaapharm Canada Inc.1991-12-31Not applicableCanada
Amox 500 Cap 500mgCapsule500 mgOralJaapharm Canada Inc.1991-12-31Not applicableCanada
Amox S 125 Sus 125mg/5mlSuspension125 mgOralJaapharm Canada Inc.1991-12-31Not applicableCanada
Amox S 250 Sus 250mg/5mlSuspension250 mgOralJaapharm Canada Inc.1991-12-31Not applicableCanada
AmoxicillinGranule, for suspension250 mgOralSanis Health Inc2010-09-27Not applicableCanada
AmoxicillinCapsule250 mgOralSanis Health Inc2010-08-28Not applicableCanada
AmoxicillinTablet, film coated875 mg/1OralDr Reddy's Laboratories1978-07-10Not applicableUs
AmoxicillinPowder, for suspension400 mg/5mLOralClinical Solutions Wholsesale1999-04-152017-06-23Us
AmoxicillinPowder, for suspension200 mg/5mLOralClinical Solutions Wholsesale1999-04-152017-06-23Us
AmoxicillinGranule, for suspension250 mgOralSanis Health Inc2010-11-02Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AmoxicillanCapsule500 mg/1OralNorthwind Pharmaceuticals2014-06-01Not applicableUs67253 0141 50 nlmimage10 e215711b
AmoxicillanTablet500 mg/1OralNorthwind Pharmaceuticals2014-07-18Not applicableUs
AmoxicillinPowder, for suspension250 mg/5mLOralPhysicians Total Care, Inc.2009-01-22Not applicableUs
AmoxicillinCapsule500 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2011-12-15Not applicableUs
AmoxicillinPowder, for suspension250 mg/5mLOralHikma Pharmaceutical2006-06-19Not applicableUs
AmoxicillinPowder, for suspension250 mg/5mLOralPreferreed Pharmaceuticals Inc.2011-06-15Not applicableUs
AmoxicillinCapsule500 mg/1OralA S Medication Solutions2014-08-012017-06-20Us
AmoxicillinPowder, for suspension250 mg/5mLOralProficient Rx LP2006-06-19Not applicableUs
AmoxicillinCapsule500 mg/1OralRed Pharm Drug, Inc.2016-02-01Not applicableUs
AmoxicillinTablet, film coated875 mg/1OralDirectrx2016-12-01Not applicableUs
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
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Amoxi-clavAmoxicillin (875 mg) + Clavulanate potassium (125 mg)TabletOralPro Doc Limitee2009-10-08Not applicableCanada
Amoxi-clavAmoxicillin (500 mg) + Clavulanate potassium (125 mg)TabletOralPro Doc Limitee2009-10-08Not applicableCanada
Amoxicillan and clavulanate potassiumAmoxicillin (500 mg/1) + Clavulanate potassium (125 mg/1)Tablet, film coatedOralNorthwind Pharmaceuticals2014-07-18Not applicableUs
Amoxicillin and Clavulanate PotassiumAmoxicillin (875 mg/1) + Clavulanate potassium (125 mg/1)Tablet, film coatedOralProficient Rx LP2002-11-21Not applicableUs
Amoxicillin and Clavulanate PotassiumAmoxicillin (200 mg/5mL) + Clavulanate potassium (28.5 mg/5mL)Powder, for suspensionOralPreferreed Pharmaceuticals Inc.2016-02-11Not applicableUs
Amoxicillin and Clavulanate PotassiumAmoxicillin (875 mg/1) + Clavulanate potassium (125 mg/1)Tablet, film coatedOralMed Vantx, Inc.2011-11-16Not applicableUs
Amoxicillin and Clavulanate PotassiumAmoxicillin (875 mg/1) + Clavulanate potassium (125 mg/1)Tablet, film coatedOralMylan Pharmaceuticals2016-06-022018-04-30Us
Amoxicillin and Clavulanate PotassiumAmoxicillin (875 mg/1) + Clavulanate potassium (125 mg/1)Tablet, film coatedOralBlenheim Pharmacal, Inc.2015-10-06Not applicableUs
Amoxicillin and Clavulanate PotassiumAmoxicillin (500 mg/1) + Clavulanate potassium (125 mg/1)Tablet, film coatedOralAidarex Pharmaceuticals LLC2002-10-31Not applicableUs
Amoxicillin and Clavulanate PotassiumAmoxicillin (1000 mg/1) + Clavulanate (62.5 mg/1)Tablet, multilayer, extended releaseOralSandoz2010-04-21Not applicableUs00781 1943 39 nlmimage10 870443c2
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
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.

TargetActionsOrganism
APenicillin-binding protein 1A
inhibitor
Clostridium 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
DrugInteractionDrug group
AbirateroneThe metabolism of Amoxicillin can be decreased when combined with Abiraterone.Approved
AcenocoumarolAmoxicillin may increase the anticoagulant activities of Acenocoumarol.Approved
AclarubicinThe serum concentration of Aclarubicin can be decreased when it is combined with Amoxicillin.Investigational
AllopurinolThe risk of a hypersensitivity reaction to Amoxicillin is increased when it is combined with Allopurinol.Approved
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Amoxicillin.Approved, Vet Approved
AmrubicinThe serum concentration of Amrubicin can be decreased when it is combined with Amoxicillin.Approved, Investigational
annamycinThe serum concentration of annamycin can be decreased when it is combined with Amoxicillin.Investigational
ApramycinThe serum concentration of Apramycin can be decreased when it is combined with Amoxicillin.Experimental, Vet Approved
ArbekacinThe serum concentration of Arbekacin can be decreased when it is combined with Amoxicillin.Approved
ArmodafinilThe metabolism of Amoxicillin can be decreased when combined with Armodafinil.Approved, Investigational
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Amoxicillin.Investigational
BekanamycinThe serum concentration of Bekanamycin can be decreased when it is combined with Amoxicillin.Experimental
BortezomibThe metabolism of Amoxicillin can be decreased when combined with Bortezomib.Approved, Investigational
CarbamazepineThe metabolism of Amoxicillin can be increased when combined with Carbamazepine.Approved, Investigational
ChloramphenicolThe metabolism of Amoxicillin can be decreased when combined with Chloramphenicol.Approved, Vet Approved
ChlortetracyclineThe therapeutic efficacy of Amoxicillin can be decreased when used in combination with Chlortetracycline.Approved, Vet Approved
CholecalciferolThe metabolism of Amoxicillin can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Amoxicillin can be decreased when combined with Cimetidine.Approved
CitalopramThe metabolism of Amoxicillin can be decreased when combined with Citalopram.Approved
ClorindioneAmoxicillin may increase the anticoagulant activities of Clorindione.Experimental
ClotrimazoleThe metabolism of Amoxicillin can be decreased when combined with Clotrimazole.Approved, Vet Approved
DabrafenibThe serum concentration of Amoxicillin can be decreased when it is combined with Dabrafenib.Approved
DaunorubicinThe serum concentration of Daunorubicin can be decreased when it is combined with Amoxicillin.Approved
DelavirdineThe metabolism of Amoxicillin can be decreased when combined with Delavirdine.Approved
DemeclocyclineThe therapeutic efficacy of Amoxicillin can be decreased when used in combination with Demeclocycline.Approved
DibekacinThe serum concentration of Dibekacin can be decreased when it is combined with Amoxicillin.Experimental
DicoumarolAmoxicillin may increase the anticoagulant activities of Dicoumarol.Approved
DihydrostreptomycinThe serum concentration of Dihydrostreptomycin can be decreased when it is combined with Amoxicillin.Vet Approved
DiphenadioneAmoxicillin may increase the anticoagulant activities of Diphenadione.Experimental
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Amoxicillin.Approved, Investigational
DoxycyclineThe therapeutic efficacy of Amoxicillin can be decreased when used in combination with Doxycycline.Approved, Investigational, Vet Approved
EfavirenzThe metabolism of Amoxicillin can be decreased when combined with Efavirenz.Approved, Investigational
EpirubicinThe serum concentration of Epirubicin can be decreased when it is combined with Amoxicillin.Approved
Eslicarbazepine acetateThe metabolism of Amoxicillin can be decreased when combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Amoxicillin can be decreased when combined with Esomeprazole.Approved, Investigational
Ethyl biscoumacetateAmoxicillin may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtravirineThe metabolism of Amoxicillin can be decreased when combined with Etravirine.Approved
FluconazoleThe metabolism of Amoxicillin can be decreased when combined with Fluconazole.Approved
FluindioneAmoxicillin may increase the anticoagulant activities of Fluindione.Investigational
FluoxetineThe metabolism of Amoxicillin can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvoxamineThe metabolism of Amoxicillin can be decreased when combined with Fluvoxamine.Approved, Investigational
FosphenytoinThe metabolism of Amoxicillin can be increased when combined with Fosphenytoin.Approved
FramycetinThe serum concentration of Framycetin can be decreased when it is combined with Amoxicillin.Approved
GemfibrozilThe metabolism of Amoxicillin can be decreased when combined with Gemfibrozil.Approved
GeneticinThe serum concentration of Geneticin can be decreased when it is combined with Amoxicillin.Experimental
GentamicinThe serum concentration of Gentamicin can be decreased when it is combined with Amoxicillin.Approved, Vet Approved
GENTAMICIN C1AThe serum concentration of GENTAMICIN C1A can be decreased when it is combined with Amoxicillin.Experimental
GPX-150The serum concentration of GPX-150 can be decreased when it is combined with Amoxicillin.Investigational
Hygromycin BThe serum concentration of Hygromycin B can be decreased when it is combined with Amoxicillin.Vet Approved
IdarubicinThe serum concentration of Idarubicin can be decreased when it is combined with Amoxicillin.Approved
IndinavirThe metabolism of Amoxicillin can be decreased when combined with Indinavir.Approved
INNO-206The serum concentration of INNO-206 can be decreased when it is combined with Amoxicillin.Investigational
IsepamicinThe serum concentration of Isepamicin can be decreased when it is combined with Amoxicillin.Experimental
IsoniazidThe metabolism of Amoxicillin can be decreased when combined with Isoniazid.Approved
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Amoxicillin.Approved, Vet Approved
KetoconazoleThe metabolism of Amoxicillin can be decreased when combined with Ketoconazole.Approved, Investigational
LobeglitazoneThe metabolism of Amoxicillin can be decreased when combined with Lobeglitazone.Approved
LopinavirThe metabolism of Amoxicillin can be increased when combined with Lopinavir.Approved
LuliconazoleThe serum concentration of Amoxicillin can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Amoxicillin can be decreased when it is combined with Lumacaftor.Approved
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Amoxicillin.Approved
MetrizamideThe serum concentration of Metrizamide can be decreased when it is combined with Amoxicillin.Approved
MicronomicinThe serum concentration of Micronomicin can be decreased when it is combined with Amoxicillin.Experimental
MinocyclineThe therapeutic efficacy of Amoxicillin can be decreased when used in combination with Minocycline.Approved, Investigational
MoclobemideThe metabolism of Amoxicillin can be decreased when combined with Moclobemide.Approved
ModafinilThe metabolism of Amoxicillin can be decreased when combined with Modafinil.Approved, Investigational
Mycophenolic acidThe 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
NeamineThe serum concentration of Neamine can be decreased when it is combined with Amoxicillin.Experimental
NelfinavirThe metabolism of Amoxicillin can be decreased when combined with Nelfinavir.Approved
NeomycinThe serum concentration of Neomycin can be decreased when it is combined with Amoxicillin.Approved, Vet Approved
NetilmicinThe serum concentration of Netilmicin can be decreased when it is combined with Amoxicillin.Approved
NicardipineThe metabolism of Amoxicillin can be decreased when combined with Nicardipine.Approved
OmeprazoleThe metabolism of Amoxicillin can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
PantoprazoleThe metabolism of Amoxicillin can be decreased when combined with Pantoprazole.Approved
ParomomycinThe serum concentration of Paromomycin can be decreased when it is combined with Amoxicillin.Approved, Investigational
PhenindioneAmoxicillin may increase the anticoagulant activities of Phenindione.Approved
PhenprocoumonAmoxicillin may increase the anticoagulant activities of Phenprocoumon.Approved
PhenytoinThe metabolism of Amoxicillin can be increased when combined with Phenytoin.Approved, Vet Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Amoxicillin.Approved
PirarubicinThe serum concentration of Pirarubicin can be decreased when it is combined with Amoxicillin.Investigational
PlazomicinThe serum concentration of Plazomicin can be decreased when it is combined with Amoxicillin.Investigational
PlicamycinThe serum concentration of Plicamycin can be decreased when it is combined with Amoxicillin.Approved, Withdrawn
ProbenecidThe serum concentration of Amoxicillin can be increased when it is combined with Probenecid.Approved
PuromycinThe serum concentration of Puromycin can be decreased when it is combined with Amoxicillin.Experimental
RibostamycinThe serum concentration of Ribostamycin can be decreased when it is combined with Amoxicillin.Approved
RifampicinThe metabolism of Amoxicillin can be increased when combined with Rifampicin.Approved
SabarubicinThe serum concentration of Sabarubicin can be decreased when it is combined with Amoxicillin.Investigational
SertralineThe metabolism of Amoxicillin can be decreased when combined with Sertraline.Approved
SisomicinThe serum concentration of Sisomicin can be decreased when it is combined with Amoxicillin.Investigational
SP1049CThe serum concentration of SP1049C can be decreased when it is combined with Amoxicillin.Investigational
SpectinomycinThe serum concentration of Spectinomycin can be decreased when it is combined with Amoxicillin.Approved, Vet Approved
StiripentolThe metabolism of Amoxicillin can be decreased when combined with Stiripentol.Approved
StreptomycinThe serum concentration of Streptomycin can be decreased when it is combined with Amoxicillin.Approved, Vet Approved
StreptozocinThe serum concentration of Streptozocin can be decreased when it is combined with Amoxicillin.Approved
TiclopidineThe metabolism of Amoxicillin can be decreased when combined with Ticlopidine.Approved
TioclomarolAmoxicillin may increase the anticoagulant activities of Tioclomarol.Experimental
TobramycinThe serum concentration of Tobramycin can be decreased when it is combined with Amoxicillin.Approved, Investigational
TopiramateThe metabolism of Amoxicillin can be decreased when combined with Topiramate.Approved
TranylcypromineThe metabolism of Amoxicillin can be decreased when combined with Tranylcypromine.Approved
ValrubicinThe serum concentration of Valrubicin can be decreased when it is combined with Amoxicillin.Approved
VoriconazoleThe metabolism of Amoxicillin can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinAmoxicillin may increase the anticoagulant activities of Warfarin.Approved
Zoptarelin doxorubicinThe serum concentration of Zoptarelin doxorubicin can be decreased when it is combined with Amoxicillin.Investigational
ZorubicinThe serum concentration of Zorubicin can be decreased when it is combined with Amoxicillin.Experimental
ZucapsaicinThe 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
  1. 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 penicillinsA02BD10 — Lansoprazole, amoxicillin and levofloxacinA02BD01 — Omeprazole, amoxicillin and metronidazoleA02BD05 — Omeprazole, amoxicillin and clarithromycinJ01CA04 — AmoxicillinA02BD06 — Esomeprazole, amoxicillin and clarithromycinA02BD03 — Lansoprazole, amoxicillin and metronidazoleA02BD07 — Lansoprazole, amoxicillin and clarithromycinA02BD11 — Pantoprazole, amoxicillin, clarithromycin and metronidazoleA02BD04 — Pantoprazole, amoxicillin and clarithromycinJ01CR02 — Amoxicillin and enzyme inhibitor
AHFS Codes
  • 08:12.16.08 — Aminopenicillins
FDA label
Download (49.6 KB)
MSDS
Download (38.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentImpacted Third Molar Tooth1
0RecruitingTreatmentOsteomyelitis1
1Active Not RecruitingTreatmentAnaplastic Astrocytoma (AA) / Astrocytic Tumors / Glioblastoma Multiforme / Neoplasms, Brain1
1CompletedNot AvailableHealthy Volunteers3
1CompletedNot AvailableInfections, Bacterial1
1CompletedBasic ScienceDrug Interactions / Pharmacodynamics / Pharmacokinetics1
1CompletedBasic ScienceObesity, Morbid1
1CompletedBasic ScienceUpper gastrointestinal motility disorders1
1CompletedSupportive CareHealthy Volunteers1
1CompletedTreatmentAcute Bacterial Sinusitis (ABS) / Respiratory Tract Infections (RTI)1
1CompletedTreatmentDental Implants1
1CompletedTreatmentDrug Interaction Potentiation1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentHelicobacter Pylori1
1CompletedTreatmentStreptococcal Sore Throat1
1CompletedTreatmentTuberculosis1
1RecruitingOtherPhysiological Response to Antibiotics1
1, 2CompletedPreventionMolar, Third / Postoperative Complications1
1, 2CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
1, 2CompletedTreatmentCentral Serous Chorioretinopathy (CSC)1
1, 2CompletedTreatmentOral Helicobacter Pylori1
1, 2CompletedTreatmentPneumonia2
1, 2RecruitingTreatmentBMI >30 kg/m21
2CompletedTreatmentAcute Rhinosinusitis1
2CompletedTreatmentChlamydia Trachomatis Infection in Pregnancy1
2CompletedTreatmentFatty Liver / Insulin Resistance / Liver Dysfunction1
2CompletedTreatmentFunctional Dyspepsia1
2CompletedTreatmentGram-Negative Bacterial Infections / Helicobacter Infections / Indigestion1
2CompletedTreatmentMalignant Lymphomas2
2CompletedTreatmentPeriodontal Diseases / Periodontitis1
2CompletedTreatmentPneumonia, Bacterial1
2Not Yet RecruitingTreatmentVaginitis gardnerella1
2RecruitingTreatmentAppendiceal Neoplasms / Pseudomyxoma Peritonei1
2RecruitingTreatmentCommunity Acquired Pneumonia (CAP)1
2RecruitingTreatmentGastric Diffuse Large B-cell Lymphoma1
2RecruitingTreatmentTuberculosis1
2RecruitingTreatmentTuberculosis, Pulmonary1
2TerminatedTreatmentAcute Otitis Media1
2, 3CompletedPreventionBiting / Infection NOS / Wound site1
2, 3CompletedTreatmentAggressive Periodontitis1
2, 3CompletedTreatmentAggressive Periodontitis, Generalized1
2, 3CompletedTreatmentHelicobacter Pylori [H. Pylori] as the Cause of Diseases1
2, 3Not Yet RecruitingTreatmentSymptomatic Periapical Periodontitis1
2, 3RecruitingTreatmentCommunity Acquired Pneumonia (CAP)1
2, 3Unknown StatusTreatmentDuodenal Ulcer / Gastric Ulcer (GU) / Gastritis / Helicobacter Infections1
3Active Not RecruitingOtherAcute Otitis Media1
3CompletedDiagnosticHistory of IgE Dependent Reaction to a Penicillin Product1
3CompletedPreventionAcute Appendicitis / Perforated Gastroduodenal Ulcer / Small intestinal obstruction1
3CompletedPreventionHealthy Volunteers1
3CompletedPreventionPrecancerous Gastric Lesions1
3CompletedTreatmentAcute Bacterial Sinusitis (ABS)1
3CompletedTreatmentAcute Lithiasic Cholecystitis Grade I or II / Preoperative Amoxicillin Clavulanic Acid for at Most 5 Days / Required Cholecystectomy / Symptoms Lasting for Less Than 5 Days1
3CompletedTreatmentAcute Otitis Media1
3CompletedTreatmentAcute Rhinosinusitis1
3CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)3
3CompletedTreatmentChildhood Pneumonia1
3CompletedTreatmentDrug Resistant Malaria Due to Plasmodium Falciparum1
3CompletedTreatmentH. Pylori Infection1
3CompletedTreatmentHelicobacter Infections1
3CompletedTreatmentInfection NOS / Neonatal Sepsis / Sepsis1
3CompletedTreatmentInfectious Diseases1
3CompletedTreatmentIntraabdominal Infections1
3CompletedTreatmentNon-Severe Pneumonia With Wheeze1
3CompletedTreatmentOtitis Media (OM)1
3CompletedTreatmentPeriodontitis1
3CompletedTreatmentPneumonia2
3CompletedTreatmentSinusitis1
3CompletedTreatmentTonsillitis2
3RecruitingTreatmentAlcoholic Hepatitis (AH) / Severe alcoholic liver disease1
3RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Indigestion1
3RecruitingTreatmentEnterobacteriaceae Infections1
3RecruitingTreatmentH. Pylori Infection1
3RecruitingTreatmentInfective Endocarditis1
3RecruitingTreatmentLow Back Pain (LBP) / Modic Changes Type I or II Seen on MRI1
3RecruitingTreatmentPreterm Premature Rupture of Membranes (PPROM)1
3TerminatedTreatmentAbdominal Abscess / Abdominal Pain (AP) / Abscess, Intra-Abdominal / Acute Abdomen / Appendicitis / Ileus / Infection NOS / Intestinal Perforations / Peritonitis / Rupture1
3TerminatedTreatmentCancers / Fevers / Neutropenias1
3TerminatedTreatmentCommunity-Acquired Infections / Hospital Acquired Infections / Pneumonia, Bacterial / Ventilator-Associated Pneumonia (VAP)1
3TerminatedTreatmentComplicated Urinary Tract Infections or Pyelonephritis1
3Unknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Chronic Gastritis1
3Unknown StatusTreatmentDuodenal Ulcer / Gastric Ulcer (GU) / Gastritis / Helicobacter Infections1
3Unknown StatusTreatmentHelicobacter Infections / Motor Fluctuations / Parkinson's Disease (PD)1
3Unknown StatusTreatmentMalignant Lymphomas / Non-Hodgkin's Lymphoma (NHL)1
4Active Not RecruitingTreatmentChild's Development1
4Active Not RecruitingTreatmentChronic Periodontitis1
4Active Not RecruitingTreatmentHelicobacter Pylori Gastrointestinal Tract Infection1
4Active Not RecruitingTreatmentPneumonia2
4CompletedNot AvailableHealthy Volunteers2
4CompletedNot AvailableHelicobacter Infections1
4CompletedBasic ScienceBioequivalence of Amoxicillin1
4CompletedPreventionFevers / Pneumonia1
4CompletedPreventionOtitis Media (OM)1
4CompletedSupportive CareAggressive Periodontitis / Generalized Aggressive Periodontitis1
4CompletedTreatmentAcute Appendicitis / Lower Abdominal Pain / Right Iliac Fossa Pain1
4CompletedTreatmentAcute Bacterial Sinusitis (ABS)1
4CompletedTreatmentAcute Otitis Media2
4CompletedTreatmentAcute Respiratory Infections / Acute Rhinosinusitis1
4CompletedTreatmentAutoimmune Diseases / Obsessive Compulsive Disorder (OCD) / Psychiatric Disorder NOS / Streptococcal Infections / Tic Disorders1
4CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)3
4CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Chronic Idiopathic Thrombocytopenic Purpura1
4CompletedTreatmentBorreliosis / Early Lyme Disease / Erythema Chronicum Migrans / Lyme Disease1
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4CompletedTreatmentChronic Periodontitis / Smoking1
4CompletedTreatmentCommunity Acquired Pneumonia (CAP)2
4CompletedTreatmentCure Rate of Helicobacter Pylori Infection1
4CompletedTreatmentDental Implants / Tooth Socket1
4CompletedTreatmentFocal Infection, Dental1
4CompletedTreatmentFunctional Dyspepsia / Helicobacter Pylori / Peptic Ulcers1
4CompletedTreatmentFunctional Dyspepsia / Peptic Ulcers1
4CompletedTreatmentFunctional Dyspepsia / Scarred Peptic Ulcer1
4CompletedTreatmentGastritis / Indigestion / Peptic Ulcers2
4CompletedTreatmentHelicobacter Infection1
4CompletedTreatmentHelicobacter Infections3
4CompletedTreatmentHelicobacter Pylori Treatment Failure1
4CompletedTreatmentIndigestion / Peptic Ulcers1
4CompletedTreatmentInfection NOS2
4CompletedTreatmentOut-Of-Hospital Cardiac Arrest1
4CompletedTreatmentPeptic Ulcers1
4CompletedTreatmentPeri-Implantitis1
4CompletedTreatmentPeriodontitis1
4CompletedTreatmentPneumonia1
4CompletedTreatmentPneumonia Ventilator Associated1
4CompletedTreatmentSinusitis3
4CompletedTreatmentTonsillitis1
4Enrolling by InvitationTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4Not Yet RecruitingBasic ScienceMicrobial Colonization1
4Not Yet RecruitingTreatmentAntimicrobial Susceptibility Testing / Triple Therapy1
4Not Yet RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4Not Yet RecruitingTreatmentGastroesophageal Reflux Disease1
4Not Yet RecruitingTreatmentHelicobacter Pylori Gastrointestinal Tract Infection1
4RecruitingNot AvailableAcute Otitis Media1
4RecruitingNot AvailableCleft Palates1
4RecruitingPreventionBacteremia / Endocarditis1
4RecruitingTreatmentAntimicrobial Susceptibility Testing / Bacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4RecruitingTreatmentAppendicitis1
4RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)7
4RecruitingTreatmentCommunity Acquired Pneumonia (CAP)1
4RecruitingTreatmentGroup A Streptococcal Pharyngitis1
4RecruitingTreatmentPneumonia3
4RecruitingTreatmentSinusitis1
4RecruitingTreatmentSnake Bites1
4TerminatedPreventionPerineal Wound Infection1
4TerminatedTreatmentCommunity Acquired Pneumonia (CAP)1
4TerminatedTreatmentErysipelas1
4TerminatedTreatmentFast Breathing in Young Infants1
4TerminatedTreatmentInfections, Bacterial / Sinusitis1
4TerminatedTreatmentObstructive Sleep Apnea Syndrome (OSAS)1
4TerminatedTreatmentOdontogenic Infection1
4TerminatedTreatmentPharyngotonsillitis1
4Unknown StatusTreatmentAmputation Wound / Wound Infections1
4Unknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)2
4Unknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Functional Dyspepsia1
4Unknown StatusTreatmentEradication Rate for Helicobacter1
4Unknown StatusTreatmentEradication Rates of the Two Regimens1
4Unknown StatusTreatmentGastritis, Gastric Ulcer, and Duodenal Ulcer1
4Unknown StatusTreatmentHelicobacter Pylori1
4Unknown StatusTreatmentLiver Cirrhosis1
4WithdrawnTreatmentCoronary artery thrombosis / Positive Helicobacter Pylori Serology / Supra-aortic Artery Thrombosis1
Not AvailableActive Not RecruitingTreatmentFunctional Gastrointestinal Disorders1
Not AvailableCompletedNot AvailableChronic Periodontitis1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailableOtitis Maedia1
Not AvailableCompletedBasic ScienceHuman Gut Microbiota1
Not AvailableCompletedBasic ScienceHypercholesterolaemia1
Not AvailableCompletedHealth Services ResearchPlasmodium Infections / Pneumonia1
Not AvailableCompletedPreventionBacteremia1
Not AvailableCompletedPreventionSurgical Site Infections1
Not AvailableCompletedSupportive CareGlomerulonephritis / Glomerulonephritis membranous / Glomerulonephritis minimal lesion1
Not AvailableCompletedTreatmentAcute Appendicitis1
Not AvailableCompletedTreatmentAcute Respiratory Infections / Pneumonia1
Not AvailableCompletedTreatmentAppendicitis1
Not AvailableCompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)6
Not AvailableCompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Functional Dyspepsia1
Not AvailableCompletedTreatmentGastric MALT Lymphoma1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Salmonella Infections1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Sinusitis1
Not AvailableCompletedTreatmentKerosene Pneumonitis1
Not AvailableCompletedTreatmentKwashiorkor / Marasmus2
Not AvailableCompletedTreatmentPerforated Appendicitis1
Not AvailableCompletedTreatmentPharyngitis / Streptococcal Infections1
Not AvailableCompletedTreatmentPlasmodium Infections / Pneumonia1
Not AvailableCompletedTreatmentPneumonia1
Not AvailableCompletedTreatmentSepsis1
Not AvailableCompletedTreatmentSevere Acute Malnutrition1
Not AvailableCompletedTreatmentSevere Pneumonia1
Not AvailableCompletedTreatmentSinusitis1
Not AvailableCompletedTreatmentSnoring / Strep Throat1
Not AvailableCompletedTreatmentTreatment of Helicobacter Pylori1
Not AvailableCompletedTreatmentUrinary Tract Infections (UTIs)1
Not AvailableEnrolling by InvitationTreatmentHelicobacter Infection1
Not AvailableEnrolling by InvitationTreatmentPartially Edentulous Jaw1
Not AvailableNot Yet RecruitingNot AvailableNewborn; Infection1
Not AvailableNot Yet RecruitingTreatmentSevere Acute Malnutrition1
Not AvailableRecruitingNot AvailableImpacted Third Molar Tooth1
Not AvailableRecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)5
Not AvailableRecruitingTreatmentHelicobacter Infection1
Not AvailableRecruitingTreatmentPneumonia / Tachypnoea1
Not AvailableRecruitingTreatmentSinusitis1
Not AvailableRecruitingTreatmentTic Disorders1
Not AvailableTerminatedTreatmentUlcerative Colitis (UC)1
Not AvailableUnknown StatusBasic ScienceBMI >30 kg/m2 / Insulin Resistance1
Not AvailableUnknown StatusTreatmentAcute Upper Respiratory Tract Infections1
Not AvailableUnknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
TabletOral500 mg/1
CapsuleOral250 mg/1
CapsuleOral500 mg/1
For suspensionOral125 mg/5mL
For suspensionOral25 mg/mL
For suspensionOral50 mg/mL
Powder, for suspensionOral125 mg/5mL
Powder, for suspensionOral200 mg/5mL
Powder, for suspensionOral250 mg/5mL
Powder, for suspensionOral400 mg/5mL
Powder, for suspensionOral600 mg/5mL
TabletOral250 mg/1
TabletOral875 mg/1
Tablet, chewableOral125 mg/1
Tablet, chewableOral250 mg/1
Tablet, coatedOral875 mg/1
Tablet, film coatedOral500 mg/1
Tablet, film coatedOral875 mg/1
Powder, for suspensionOral
SuspensionOral
Tablet, chewableOral
Tablet, film coatedOral
Tablet, multilayer, extended releaseOral
Tablet, film coated, extended releaseOral775 mg/1
TabletOral
SuspensionOral25 mg
SuspensionOral50 mg
TabletOral125 mg
TabletOral250 mg
Powder, for solutionOral50 mg
Powder, for solutionOral125 mg
Powder, for solutionOral250 mg
Tablet, film coated, extended releaseOral
Capsule; capsule, extended release; kit; tabletOral
Kit
CapsuleOral250 mg
CapsuleOral500 mg
Granule, for suspensionOral125 mg
Granule, for suspensionOral25 mg
Granule, for suspensionOral250 mg
Granule, for suspensionOral50 mg
Tablet, chewableOral125 mg
Tablet, chewableOral250 mg
SuspensionOral125 mg
SuspensionOral250 mg
Powder, for solutionOral
Powder, for suspensionOral125 mg
Powder, for suspensionOral250 mg
Prices
Unit descriptionCostUnit
Amoxil 400 mg/5ml Suspension 100ml Bottle19.99USD bottle
Amoxil 400 mg/5ml Suspension 75ml Bottle17.99USD bottle
Amoxicillin 400 mg/5ml Suspension 100ml Bottle16.99USD bottle
Amoxil 400 mg/5ml Suspension 50ml Bottle15.99USD bottle
Amoxicillin 250 mg/5ml Suspension 150ml Bottle14.0USD bottle
Amoxil 50 mg/ml Suspension 30ml Bottle13.99USD bottle
Amoxil 250 mg/5ml Suspension 100ml Bottle12.99USD bottle
Amoxil 250 mg/5ml Suspension 150ml Bottle12.99USD bottle
Amoxil 200 mg/5ml Suspension 100ml Bottle11.99USD bottle
Trimox 125 mg/5ml Suspension 100ml Bottle11.99USD bottle
Trimox 125 mg/5ml Suspension 150ml Bottle11.99USD bottle
Trimox 250 mg/5ml Suspension 80ml Bottle11.99USD bottle
Amoxil 875 mg tablet1.13USD tablet
Amoxil 400 mg Chew Tabs1.05USD tab
Amoxicillin 875 mg tablet0.89USD tablet
Amoxil 500 mg tablet0.77USD tablet
Novamoxin 250 mg Chewable Tablet0.64USD tablet
Amoxicillin 125 mg Chew Tabs0.57USD tab
Amoxil 500 mg capsule0.53USD capsule
Amoxicillin 500 mg tablet0.5USD tablet
Amoxicillin 250 mg Chew Tabs0.47USD tab
Amoxicillin 500 mg capsule0.47USD capsule
Novamoxin 125 mg Chewable Tablet0.44USD tablet
Apo-Amoxi 500 mg Capsule0.36USD capsule
Mylan-Amoxillin 500 mg Capsule0.36USD capsule
Novamoxin 500 mg Capsule0.36USD capsule
Nu-Amoxi 500 mg Capsule0.36USD capsule
Pms-Amoxicillin 500 mg Capsule0.36USD capsule
Amoxicillin 250 mg capsule0.25USD capsule
Apo-Amoxi 250 mg Capsule0.18USD capsule
Mylan-Amoxillin 250 mg Capsule0.18USD capsule
Novamoxin 250 mg Capsule0.18USD capsule
Nu-Amoxi 250 mg Capsule0.18USD capsule
Pms-Amoxicillin 250 mg Capsule0.18USD capsule
Apo-Amoxi 50 mg/ml Suspension0.06USD ml
Novamoxin 50 mg/ml Suspension0.06USD ml
Novamoxin Sugar-Reduced 50 mg/ml Suspension0.06USD ml
Nu-Amoxi 50 mg/ml Suspension0.06USD ml
Pms-Amoxicillin 50 mg/ml Suspension0.06USD ml
Apo-Amoxi 25 mg/ml Suspension0.04USD ml
Novamoxin 25 mg/ml Suspension0.04USD ml
Novamoxin Sugar-Reduced 25 mg/ml Suspension0.04USD ml
Nu-Amoxi 25 mg/ml Suspension0.04USD ml
Pms-Amoxicillin 25 mg/ml Suspension0.04USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6544555No2000-10-132020-10-13Us
US6669948No2000-10-132020-10-13Us
US6723341No2000-10-132020-10-13Us
US8299052No2007-05-072027-05-07Us
US8778924No2006-12-082026-12-08Us
US8357394No2006-12-082026-12-08Us
US6878386No2000-04-042020-04-04Us
US7217430No2000-04-042020-04-04Us
US7250176No2000-04-042020-04-04Us
US6783773No2000-04-042020-04-04Us
US6746692No2000-04-042020-04-04Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)194 °CNot Available
water solubility3430 mg/LNot Available
logP0.87SANGSTER (1994)
Caco2 permeability-6.1ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.958 mg/mLALOGPS
logP0.75ALOGPS
logP-2.3ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.23ChemAxon
pKa (Strongest Basic)7.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.96 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity89.5 m3·mol-1ChemAxon
Polarizability35.53 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9008
Blood Brain Barrier-0.9967
Caco-2 permeable-0.8722
P-glycoprotein substrateSubstrate0.5741
P-glycoprotein inhibitor INon-inhibitor0.9665
P-glycoprotein inhibitor IINon-inhibitor0.9968
Renal organic cation transporterNon-inhibitor0.9636
CYP450 2C9 substrateNon-substrate0.843
CYP450 2D6 substrateNon-substrate0.8446
CYP450 3A4 substrateNon-substrate0.5478
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.915
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9767
Ames testNon AMES toxic0.9099
CarcinogenicityNon-carcinogens0.5439
BiodegradationNot ready biodegradable0.9606
Rat acute toxicity1.7036 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9996
hERG inhibition (predictor II)Non-inhibitor0.8761
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00di-0190000000-febb22de5b7f210e4a46
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-056u-4960000000-f3c347843d63d99418c5
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0036-8900000000-eca01f197da058161684
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-007o-9800000000-cec182c5a522a2979385
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00ec-9700000000-dc767a962e9f2608b083
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00dl-9600000000-b831842a45369bb2b48c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-06r2-0589000000-9c90c12d4fbef3a04a14
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0910000000-e26fa392674b2a230233
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-1900000000-9e60140bfff56767dbec
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-1900000000-f3065ce1009dda06cf72
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03e9-2900000000-5516c0723837b4149a68
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-06s9-5900000000-cd377b53cefaa4b23c6f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03xs-0859000000-8225987d1a20c14acc00

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
  1. 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]
  2. 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]
  3. 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
  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. 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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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
  1. 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]
  2. 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]
  3. 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
  1. 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