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Identification
NameAzithromycin
Accession NumberDB00207  (APRD00397)
TypeSmall Molecule
GroupsApproved
Description

Azithromycin is a semi-synthetic macrolide antibiotic of the azalide class. Like other macrolide antibiotics, azithromycin inhibits bacterial protein synthesis by binding to the 50S ribosomal subunit of the bacterial 70S ribosome. Binding inhibits peptidyl transferase activity and interferes with amino acid translocation during the process of translation. Its effects may be bacteriostatic or bactericidal depending of the organism and the drug concentration. Its long half life, which enables once daily dosing and shorter administration durations, is a property distinct from other macrolides.

Structure
Thumb
Synonyms
Azithromycine
Azithromycinum
Azitromicina
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Azithromycintablet600 mgoralActavis Pharma Company2005-11-02Not applicableCanada
Act Azithromycintablet250 mgoralActavis Pharma Company2005-11-02Not applicableCanada
Ava-azithromycinpowder for suspension100 mgoralAvanstra Inc2011-09-192014-08-21Canada
Ava-azithromycintablet250 mgoralAvanstra Inc2011-09-192014-08-21Canada
Ava-azithromycinpowder for suspension200 mgoralAvanstra Inc2011-09-192014-08-21Canada
Azasitesolution1 %ophthalmicInsite Vision IncorporatedNot applicableNot applicableCanada
Azasitesolution/ drops10 mg/mLophthalmicAkorn, Inc.2014-05-14Not applicableUs
Azasitesolution1 %ophthalmicInspire Pharmaceuticals IncNot applicableNot applicableCanada
Azithromycintablet, film coated250 mg/1oralCardinal Health1996-07-18Not applicableUs
Azithromycinpowder, for suspension1 g/1oralPhysicians Total Care, Inc.2008-09-08Not applicableUs
Azithromycintablet250 mgoral4513347 Canada Inc.Not applicableNot applicableCanada
Azithromycintablet, film coated250 mg/1oralCentral Texas Community Health Centers1996-07-18Not applicableUs
Azithromycintablet600 mgoral4513347 Canada Inc.Not applicableNot applicableCanada
Azithromycinpowder, for suspension200 mg/5mLoralGreenstone LLC1995-10-19Not applicableUs
Azithromycintablet, film coated600 mg/1oralREMEDYREPACK INC.2013-03-05Not applicableUs
Azithromycintablet, film coated500 mg/1oralREMEDYREPACK INC.2013-03-05Not applicableUs
Azithromycintablet250 mgoralSivem Pharmaceuticals Ulc2015-07-22Not applicableCanada
Azithromycintablet250 mgoralSanis Health Inc2010-02-01Not applicableCanada
Azithromycinpowder, for suspension100 mg/5mLoralGreenstone LLC1995-10-19Not applicableUs
Azithromycinpowder for suspension200 mgoralPharmascience Inc2006-04-19Not applicableCanada
Azithromycintablet, film coated250 mg/1oralREMEDYREPACK INC.2013-09-24Not applicableUs
Azithromycinpowder for solution200 mgoralDominion PharmacalNot applicableNot applicableCanada
Azithromycintablet, film coated600 mg/1oralGreenstone LLC1996-06-12Not applicableUs
Azithromycinpowder for suspension100 mgoralPharmascience Inc2006-04-19Not applicableCanada
Azithromycintablet, film coated500 mg/1oralPd Rx Pharmaceuticals, Inc.2002-05-24Not applicableUs
Azithromycintablet600 mgoralSanis Health Inc2010-02-012014-08-01Canada
Azithromycinpowder for suspension100 mgoralDominion PharmacalNot applicableNot applicableCanada
Azithromycintablet, film coated500 mg/1oralGreenstone LLC2002-05-24Not applicableUs
Azithromycintablet, film coated500 mg/1oralLake Erie Medical DBA Quality Care Products LLC2002-05-24Not applicableUs
Azithromycintablet, film coated250 mg/1oralPreferred Pharmaceuticals, Inc.1996-07-18Not applicableUs
Azithromycintablet, film coated250 mg/1oralGreenstone LLC1996-07-18Not applicableUs
Azithromycinpowder, for suspension900 mg/22.5mLoralDepartment Of State Health Services, Pharmacy Branch1995-10-19Not applicableUs
Azithromycinpowder, for suspension1 g/1oralPreferred Pharmaceuticals, Inc.1999-02-12Not applicableUs
Azithromycinpowder, for suspension1 g/1oralGreenstone LLC1999-02-12Not applicableUs
Azithromycinpowder, for suspension1 g/1oralDispensing Solutions, Inc.1999-02-12Not applicableUs
Azithromycininjection, powder, lyophilized, for solution100 mg/mLintravenousBaxter Healthcare Corporation1997-01-01Not applicableUs
Azithromycintablet, film coated250 mg/1oralDepartment Of State Health Services, Pharmacy Branch1996-07-18Not applicableUs
Azithromycintablet600 mgoralCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
Azithromycinpowder, for suspension1200 mg/30mLoralGreenstone LLC1995-10-19Not applicableUs
Azithromycintablet250 mgoralCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
Azithromycinpowder, for suspension900 mg/22.5mLoralGreenstone LLC1995-10-19Not applicableUs
Azithromycin for Injectionpowder for solution500 mgintravenousSterimax Inc2011-10-04Not applicableCanada
Azithromycin for Injectionpowder for solution500 mgintravenousTeva Canada Limited2009-10-14Not applicableCanada
Azithromycin for Injection, USPpowder for solution500 mgintravenousMylan Pharmaceuticals Ulc2013-05-13Not applicableCanada
Azithromycin for Injection, USPpowder for solution500 mgintravenousHospira Healthcare Corporation2011-12-29Not applicableCanada
Azithromycin for Injection, USPpowder for solution500 mgintravenousHospira Healthcare CorporationNot applicableNot applicableCanada
Dom-azithromycintablet600 mgoralDominion Pharmacal2008-04-16Not applicableCanada
Dom-azithromycinpowder for suspension200 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-azithromycintablet250 mgoralDominion Pharmacal2008-04-16Not applicableCanada
Dom-azithromycinpowder for suspension100 mgoralDominion PharmacalNot applicableNot applicableCanada
Gd-azithromycintablet250 mgoralGenmed A Division Of Pfizer Canada Inc2010-11-11Not applicableCanada
Gd-azithromycinpowder for suspension100 mgoralGenmed A Division Of Pfizer Canada Inc2013-11-04Not applicableCanada
Gd-azithromycinpowder for suspension200 mgoralGenmed A Division Of Pfizer Canada Inc2013-11-04Not applicableCanada
Ipg-azithromycintablet250 mgoralInternational Pharmaceutical Generics LtdNot applicableNot applicableCanada
Ipg-azithromycintablet600 mgoralInternational Pharmaceutical Generics LtdNot applicableNot applicableCanada
Jamp-azithromycintablet600 mgoralJamp Pharma CorporationNot applicableNot applicableCanada
Jamp-azithromycintablet250 mgoralJamp Pharma CorporationNot applicableNot applicableCanada
Mylan-azithromycintablet250 mgoralMylan Pharmaceuticals Ulc2006-05-04Not applicableCanada
Mylan-azithromycin for Injectionpowder for solution500 mgintravenousMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Novo-azithromycintablet250 mgoralTeva Canada Limited2005-12-01Not applicableCanada
Novo-azithromycin Pediatricpowder for suspension200 mgoralTeva Canada Limited2008-12-24Not applicableCanada
Novo-azithromycin Pediatricpowder for suspension100 mgoralTeva Canada Limited2008-12-24Not applicableCanada
PHL-azithromycinpowder for suspension200 mgoralPharmel Inc2006-08-17Not applicableCanada
PHL-azithromycinpowder for suspension100 mgoralPharmel Inc2006-08-17Not applicableCanada
PHL-azithromycintablet250 mgoralPharmel Inc2007-07-27Not applicableCanada
PHL-azithromycintablet600 mgoralPharmel IncNot applicableNot applicableCanada
PMS-azithromycintablet600 mgoralPharmascience Inc2006-01-04Not applicableCanada
PMS-azithromycintablet250 mgoralPharmascience Inc2006-01-04Not applicableCanada
PMS-azithromycinpowder for suspension200 mgoralPharmascience Inc2014-03-19Not applicableCanada
PMS-azithromycinpowder for suspension100 mgoralPharmascience Inc2014-03-19Not applicableCanada
Pro-azithromycinetablet250 mgoralPro Doc Limitee2008-10-27Not applicableCanada
Ratio Azithromycintablet250 mgoralRatiopharm Inc Division Of Teva Canada Limited2006-02-082014-09-19Canada
Riva Azithromycintablet600 mgoralLaboratoire Riva Inc2006-03-162013-07-31Canada
Riva Azithromycintablet250 mgoralLaboratoire Riva Inc2006-03-16Not applicableCanada
Sandoz Azithromycinpowder for suspension200 mgoralSandoz Canada Incorporated2009-09-08Not applicableCanada
Sandoz Azithromycintablet250 mgoralSandoz Canada Incorporated2005-11-11Not applicableCanada
Sandoz Azithromycinpowder for suspension100 mgoralSandoz Canada Incorporated2009-09-08Not applicableCanada
Sandoz Azithromycintablet500 mgoralSandoz Canada IncorporatedNot applicableNot applicableCanada
Zithromaxpowder, for suspension200 mg/5mLoralPfizer Laboratories Div Pfizer Inc1995-10-19Not applicableUs
Zithromaxinjection, powder, lyophilized, for solution500 mg/5mLintravenousPfizer Laboratories Div Pfizer Inc1997-01-30Not applicableUs
Zithromaxtablet, film coated250 mg/1oralREMEDYREPACK INC.2013-04-04Not applicableUs
Zithromaxpowder, for suspension200 mg/5mLoralPfizer Laboratories Div Pfizer Inc1995-10-19Not applicableUs
Zithromaxtablet, film coated500 mg/1oralREMEDYREPACK INC.2013-09-19Not applicableUs
Zithromaxpowder, for suspension200 mg/5mLoralPfizer Laboratories Div Pfizer Inc1995-10-19Not applicableUs
Zithromaxtablet, film coated250 mg/1oralREMEDYREPACK INC.2013-03-12Not applicableUs
Zithromaxtablet, film coated250 mg/1oralA S Medication Solutions1996-07-18Not applicableUs
Zithromaxpowder, for suspension100 mg/5mLoralPfizer Laboratories Div Pfizer Inc1995-10-19Not applicableUs
Zithromaxtablet, film coated600 mg/1oralPfizer Laboratories Div Pfizer Inc1996-06-12Not applicableUs
Zithromaxtablet, film coated500 mg/1oralPfizer Laboratories Div Pfizer Inc2002-05-24Not applicableUs
Zithromaxtablet, film coated250 mg/1oralPd Rx Pharmaceuticals, Inc.1996-07-18Not applicableUs
Zithromaxtablet, film coated250 mg/1oralPfizer Laboratories Div Pfizer Inc1996-07-18Not applicableUs
Zithromaxtablet, film coated250 mg/1oralCardinal Health1996-07-18Not applicableUs
Zithromaxinjection, powder, lyophilized, for solution500 mg/5mLintravenousPfizer Laboratories Div Pfizer Inc1997-01-30Not applicableUs
Zithromaxpowder, for suspension1 g/1oralPfizer Laboratories Div Pfizer Inc1994-09-28Not applicableUs
Zithromax - Pws Orl 100mg/5mlpowder for suspension100 mgoralPfizer Canada Inc1996-09-26Not applicableCanada
Zithromax - Pws Orl 200mg/5mlpowder for solution200 mgoralPfizer Canada Inc1996-09-26Not applicableCanada
Zithromax - Tab 250mgtablet250 mgoralPfizer Canada Inc1999-03-23Not applicableCanada
Zithromax 600mgtablet600 mgoralPfizer Canada Inc1997-07-21Not applicableCanada
Zithromax Cap 250mgcapsule250 mgoralPfizer Canada Inc1994-12-312000-07-26Canada
Zithromax for Intravenous Injectionpowder for solution500 mgintravenousPfizer Canada Inc1999-08-27Not applicableCanada
Zmaxpowder, for suspension2 g/60mLoralRebel Distributors Corp1995-06-10Not applicableUs
Zmaxpowder, for suspension2 g/60mLoralPfizer Laboratories Div Pfizer Inc1995-06-10Not applicableUs
Zmax SRgranules for suspension,extended release2 goralPfizer Canada Inc2010-09-222015-07-31Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-azithromycintablet250 mgoralApotex Inc2005-11-02Not applicableCanada
Apo-azithromycin Ztablet250 mgoralApotex Inc2014-03-06Not applicableCanada
Azithromycintablet, film coated250 mg/1oralREMEDYREPACK INC.2013-05-23Not applicableUs
Azithromycintablet500 mg/1oralREMEDYREPACK INC.2012-01-12Not applicableUs
Azithromycintablet, film coated250 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2005-11-14Not applicableUs
Azithromycintablet500 mg/1oralLake Erie Medical DBA Quality Care Products LLC2010-11-09Not applicableUs
Azithromycininjection, powder, lyophilized, for solution2 mg/mLintravenousHospira, Inc.2009-06-26Not applicableUs
Azithromycinpowder, for suspension200 mg/5mLoralTeva Pharmaceuticals USA Inc2010-12-17Not applicableUs
Azithromycintablet, film coated600 mg/1oralVivimed Labs Limited2008-02-11Not applicableUs
Azithromycintablet, film coated250 mg/1oralCardinal Health2011-05-20Not applicableUs
Azithromycinpowder, for suspension200 mg/5mLoralClinical Solutions Wholesale2010-12-17Not applicableUs
Azithromycintablet, film coated250 mg/1oralUnit Dose Services2008-02-11Not applicableUs
Azithromycinpowder, for suspension200 mg/5mLoralPhysicians Total Care, Inc.2006-08-03Not applicableUs
Azithromycintablet, film coated500 mg/1oralDispensing Solutions Inc.2008-05-30Not applicableUs
Azithromycintablet, film coated500 mg/1oralVivimed Labs Limited2008-02-11Not applicableUs
Azithromycintablet, film coated250 mg/1oralProficient Rx LP2006-01-06Not applicableUs
Azithromycintablet, film coated250 mg/1oralREMEDYREPACK INC.2015-02-13Not applicableUs
Azithromycintablet, film coated600 mg/1oralClinical Solutions Wholesale2005-11-16Not applicableUs
Azithromycinpowder, for suspension200 mg/5mLoralMed Vantx, Inc.2008-09-22Not applicableUs
Azithromycinpowder, for suspension200 mg/5mLoralProficient Rx LP2010-12-17Not applicableUs
Azithromycinpowder, for suspension200 mg/5mLoralPreferred Pharmaceuticals, Inc.2012-01-10Not applicableUs
Azithromycintablet, film coated500 mg/1oralAv Pak2011-05-20Not applicableUs
Azithromycintablet, film coated250 mg/1oralPreferred Pharmaceuticals Inc.2015-10-19Not applicableUs
Azithromycintablet, film coated500 mg/1oralRebel Distributors Corp.2008-02-11Not applicableUs
Azithromycintablet, film coated600 mg/1oralKAISER FOUNDATION HOSPITALS2009-09-01Not applicableUs
Azithromycintablet, film coated250 mg/1oralVivimed Labs Limited2008-02-11Not applicableUs
Azithromycintablet, film coated250 mg/1oralCardinal Health2008-04-02Not applicableUs
Azithromycininjection, powder, lyophilized, for solution100 mg/mLintravenousCardinal Health2009-12-10Not applicableUs
Azithromycinpowder, for suspension100 mg/5mLoralPhysicians Total Care, Inc.2006-08-01Not applicableUs
Azithromycintablet, film coated500 mg/1oralAmerican Health Packaging2013-07-19Not applicableUs
Azithromycininjection, powder, lyophilized, for solution500 mg/5mLintravenousSun Pharmaceutical Industries Limited2013-04-03Not applicableUs
Azithromycintablet, film coated600 mg/1oralREMEDYREPACK INC.2015-02-16Not applicableUs
Azithromycintablet, film coated250 mg/1oralMed Vantx, Inc.2005-11-16Not applicableUs
Azithromycintablet, film coated500 mg/1oralProficient Rx LP2005-11-14Not applicableUs
Azithromycinpowder, for suspension100 mg/5mLoralPreferred Pharmaceuticals, Inc.2012-01-10Not applicableUs
Azithromycintablet, film coated250 mg/1oralAv Pak2011-05-20Not applicableUs
Azithromycintablet, film coated250 mg/1oralRebel Distributors Corp.2008-02-11Not applicableUs
Azithromycintablet, film coated250 mg/1oralREMEDYREPACK INC.2012-12-28Not applicableUs
Azithromycintablet500 mg/1oralREMEDYREPACK INC.2011-04-12Not applicableUs
Azithromycininjection, powder, lyophilized, for solution500 mg/5mLintravenousSagent Pharmaceuticals2009-05-01Not applicableUs
Azithromycintablet, film coated250 mg/1oralClinical Solutions Wholesale2008-02-11Not applicableUs
Azithromycintablet, film coated500 mg/1oralDispensing Solutions, Inc.2008-02-11Not applicableUs
Azithromycininjection, powder, lyophilized, for solution500 mg/5mLintravenousCardinal Health2006-03-20Not applicableUs
Azithromycinpowder, for suspension200 mg/5mLoralREMEDYREPACK INC.2016-04-13Not applicableUs
Azithromycintablet, film coated500 mg/1oralPhysicians Total Care, Inc.2007-08-10Not applicableUs
Azithromycintablet, film coated250 mg/1oralAmerican Health Packaging2013-07-19Not applicableUs
Azithromycintablet, film coated500 mg/1oralDIRECT RX2015-01-01Not applicableUs
Azithromycintablet, film coated500 mg/1oralREMEDYREPACK INC.2015-01-06Not applicableUs
Azithromycintablet, film coated250 mg/1oralMed Vantx, Inc.2011-10-24Not applicableUs
Azithromycintablet, film coated250 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-12-21Not applicableUs
Azithromycintablet, film coated500 mg/1oralSTAT Rx USA LLC2008-02-11Not applicableUs
Azithromycintablet, film coated250 mg/1oralUnit Dose Services2011-10-24Not applicableUs
Azithromycintablet, film coated250 mg/1oralMedsource Pharmaceuticals2006-01-06Not applicableUs
Azithromycintablet500 mg/1oralREMEDYREPACK INC.2011-11-15Not applicableUs
Azithromycintablet, film coated500 mg/1oralTeva Pharmaceuticals USA Inc2005-11-16Not applicableUs
Azithromycintablet, film coated500 mg/1oralWockhardt Limited2008-02-11Not applicableUs
Azithromycintablet, film coated600 mg/1oralPhysicians Total Care, Inc.2012-04-26Not applicableUs
Azithromycininjection, powder, lyophilized, for solution100 mg/mLintravenousCardinal Health2011-01-31Not applicableUs
Azithromycintablet, film coated500 mg/1oralPreferred Pharmaceuticals, Inc.2008-02-11Not applicableUs
Azithromycintablet, film coated250 mg/1oralPhysicians Total Care, Inc.2005-11-23Not applicableUs
Azithromycintablet, film coated250 mg/1oralDispensing Solutions, Inc.2008-02-11Not applicableUs
Azithromycinpowder, for suspension200 mg/5mLoralDIRECT RX2014-01-01Not applicableUs
Azithromycininjection500 mg/10mLintravenousApotex Corp.2010-04-25Not applicableUs
Azithromycintablet, film coated600 mg/1oralAmerican Health Packaging2015-01-15Not applicableUs
Azithromycintablet, film coated250 mg/1oralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2013-12-02Not applicableUs
Azithromycintablet, film coated250 mg/1oralPd Rx Pharmaceuticals, Inc.2008-02-11Not applicableUs
Azithromycintablet, film coated250 mg/1oralMajor Pharmaceuticals2009-06-10Not applicableUs
Azithromycintablet, film coated250 mg/1oralAphena Pharma Solutions Tennessee, Llc2005-11-14Not applicableUs
Azithromycinpowder, for suspension200 mg/5mLoralRebel Distributors Corp.2008-06-24Not applicableUs
Azithromycinpowder, for suspension200 mg/5mLoralTeva Pharmaceuticals USA Inc2008-09-22Not applicableUs
Azithromycintablet, film coated250 mg/1oralPreferred Pharmaceuticals, Inc.2008-02-11Not applicableUs
Azithromycintablet, film coated250 mg/1oralPhysicians Total Care, Inc.2005-11-16Not applicableUs
Azithromycintablet, film coated500 mg/1oralWockhardt USA LLC.2008-02-11Not applicableUs
Azithromycintablet, film coated500 mg/1oralAmerican Health Packaging2015-01-15Not applicableUs
Azithromycininjection, powder, lyophilized, for solution500 mg/5mLintravenousFresenius Kabi USA, LLC2006-03-20Not applicableUs
Azithromycintablet, film coated250 mg/1oralA S Medication Solutions2005-11-16Not applicableUs
Azithromycintablet, film coated500 mg/1oralPreferred Pharmaceuticals, Inc.2006-01-06Not applicableUs
Azithromycintablet, film coated250 mg/1oralRx Change Co.2014-11-13Not applicableUs
Azithromycinpowder, for suspension200 mg/5mLoralDepartment Of State Health Services, Pharmacy Branch2010-12-17Not applicableUs
Azithromycintablet, film coated250 mg/1oralPd Rx Pharmaceuticals, Inc.2005-11-16Not applicableUs
Azithromycinpowder, for suspension100 mg/5mLoralRebel Distributors Corp.2008-06-24Not applicableUs
Azithromycinpowder, for suspension100 mg/5mLoralTeva Pharmaceuticals USA Inc2008-09-22Not applicableUs
Azithromycintablet, film coated600 mg/1oralWockhardt Limited2008-02-11Not applicableUs
Azithromycintablet, film coated250 mg/1oralH.J. Harkins Company, Inc.2008-02-11Not applicableUs
Azithromycintablet, film coated250 mg/1oralAmerican Health Packaging2015-01-15Not applicableUs
Azithromycinpowder, for suspension200 mg/5mLoralPreferred Pharmaceuticals, Inc.2011-03-10Not applicableUs
Azithromycintablet, film coated500 mg/1oralAidarex Pharmaceuticals LLC2008-02-11Not applicableUs
Azithromycinpowder, for suspension100 mg/5mLoralDepartment Of State Health Services, Pharmacy Branch2010-12-28Not applicableUs
Azithromycininjection, powder, lyophilized, for solution100 mg/mLintravenousPliva Inc.2007-08-17Not applicableUs
Azithromycintablet, film coated500 mg/1oralPd Rx Pharmaceuticals, Inc.2005-11-14Not applicableUs
Azithromycintablet, film coated500 mg/1oralSandoz Inc2005-11-14Not applicableUs
Azithromycintablet, film coated600 mg/1oralTeva Pharmaceuticals USA Inc2005-11-16Not applicableUs
Azithromycintablet, film coated250 mg/1oralWockhardt Limited2008-02-11Not applicableUs
Azithromycintablet, film coated500 mg/1oralREMEDYREPACK INC.2014-02-20Not applicableUs
Azithromycintablet, film coated250 mg/1oralProficient Rx LP2008-02-11Not applicableUs
Azithromycintablet, film coated500 mg/1oralPhysicians Total Care, Inc.1995-08-15Not applicableUs
Azithromycintablet, film coated600 mg/1oralWockhardt USA LLC.2008-02-11Not applicableUs
Azithromycintablet, film coated500 mg/1oralProficient Rx LP2006-01-06Not applicableUs
Azithromycintablet, film coated250 mg/1oralAvera Mc Kennan Hospital2015-03-02Not applicableUs
Azithromycinpowder, for suspension100 mg/5mLoralPreferred Pharmaceuticals, Inc.2011-03-10Not applicableUs
Azithromycintablet, film coated250 mg/1oralAidarex Pharmaceuticals LLC2008-02-11Not applicableUs
Azithromycintablet, film coated250 mg/1oralDepartment Of State Health Services, Pharmacy Branch2005-11-16Not applicableUs
Azithromycintablet, film coated500 mg/1oralPliva, Inc.2006-01-06Not applicableUs
Azithromycintablet, film coated250 mg/1oralPd Rx Pharmaceuticals, Inc.2005-11-14Not applicableUs
Azithromycintablet, film coated600 mg/1oralSandoz Inc2005-11-14Not applicableUs
Azithromycintablet, film coated250 mg/1oralTeva Pharmaceuticals USA Inc2005-11-16Not applicableUs
Azithromycintablet, film coated250 mg/1oralPd Rx Pharmaceuticals, Inc.2008-02-11Not applicableUs
Azithromycintablet, film coated250 mg/1oralREMEDYREPACK INC.2013-10-30Not applicableUs
Azithromycintablet, film coated250 mg/1oralCardinal Health2005-11-14Not applicableUs
Azithromycintablet, film coated600 mg/1oralAmerican Health Packaging2012-07-022015-12-29Us
Azithromycintablet, film coated250 mg/1oralAidarex Pharmaceuticals LLC2005-11-14Not applicableUs
Azithromycintablet, film coated250 mg/1oralWockhardt USA LLC.2008-02-11Not applicableUs
Azithromycintablet, film coated500 mg/1oralREMEDYREPACK INC.2015-05-21Not applicableUs
Azithromycintablet, film coated250 mg/1oralREMEDYREPACK INC.2013-05-23Not applicableUs
Azithromycintablet, film coated250 mg/1oralPliva, Inc.2006-01-06Not applicableUs
Azithromycintablet, film coated250 mg/1oralSandoz Inc2005-11-14Not applicableUs
Azithromycinpowder, for suspension100 mg/5mLoralTeva Pharmaceuticals USA Inc2010-12-28Not applicableUs
Azithromycintablet, film coated500 mg/1oralPd Rx Pharmaceuticals, Inc.2008-02-11Not applicableUs
Azithromycintablet, film coated250 mg/1oralREMEDYREPACK INC.2013-05-06Not applicableUs
Azithromycininjection, powder, lyophilized, for solution500 mg/1intravenousAuro Medics Pharma Llc2015-06-19Not applicableUs
Azithromycintablet, film coated250 mg/1oralAmerican Health Packaging2010-08-092015-12-29Us
Azithromycintablet, film coated500 mg/1oralProficient Rx LP2008-02-11Not applicableUs
Azithromycintablet, film coated250 mg/1oralREMEDYREPACK INC.2015-04-16Not applicableUs
Azithromycintablet, film coated500 mg/1oralClinical Solutions Wholesale2005-11-16Not applicableUs
Azithromycintablet, film coated250 mg/1oralProficient Rx LP2005-11-14Not applicableUs
Azithromycintablet, film coated250 mg/1oralPreferred Pharmaceuticals, Inc.2015-04-16Not applicableUs
Azithromycintablet, film coated500 mg/1oralPreferred Pharmaceuticals Inc.2015-10-27Not applicableUs
Azithromycin Dihydratetablet, film coated250 mg/1oralREMEDYREPACK INC.2013-10-15Not applicableUs
Azithromycin Dihydratetablet, film coated250 mg/1oralPreferred Pharmaceuticals, Inc.2014-02-06Not applicableUs
Azithromycin Dihydratetablet, film coated500 mg/1oralPreferred Pharmaceuticals, Inc.2014-02-06Not applicableUs
Azithromycin Dihydratetablet, film coated500 mg/1oralAv Pak2014-03-26Not applicableUs
Azithromycin Dihydratetablet, film coated250 mg/1oralCardinal Health2014-02-17Not applicableUs
Azithromycin Dihydratetablet, film coated250 1/1oralDIRECT RX2014-01-01Not applicableUs
Azithromycin Dihydratetablet, film coated600 mg/1oralApotex Corp.2011-07-13Not applicableUs
Azithromycin Dihydratetablet, film coated250 mg/1oralAv Pak2014-03-26Not applicableUs
Azithromycin Dihydratetablet, film coated500 mg/1oralApotex Corp.2011-07-18Not applicableUs
Azithromycin Dihydratetablet, film coated250 mg/1oralProficient Rx LP2011-07-18Not applicableUs
Azithromycin Dihydratetablet, film coated250 mg/1oralAmerican Health Packaging2014-02-172015-10-31Us
Azithromycin Dihydratetablet, film coated250 mg/1oralCardinal Health2014-03-26Not applicableUs
Azithromycin Dihydratetablet, film coated500 mg/1oralAmerican Health Packaging2014-02-17Not applicableUs
Azithromycin Dihydratetablet, film coated250 mg/1oralApotex Corp.2011-07-18Not applicableUs
Azithromycin Dihydratetablet, film coated500 mg/1oralPd Rx Pharmaceuticals, Inc.2011-07-18Not applicableUs
Azithromycin Dihydratetablet, film coated500 mg/1oralREMEDYREPACK INC.2013-12-04Not applicableUs
Azithromycin Monohydratetablet600 mg/1oralLupin Pharmaceuticals, Inc.2015-07-22Not applicableUs
Azithromycin Monohydratetablet250 mg/1oralLUPIN LIMITED2015-07-22Not applicableUs
Azithromycin Monohydratetablet500 mg/1oralLUPIN LIMITED2015-07-22Not applicableUs
Azithromycin Monohydratetablet500 mg/1oralLupin Pharmaceuticals, Inc.2015-07-22Not applicableUs
Azithromycin Monohydratetablet250 mg/1oralLupin Pharmaceuticals, Inc.2015-07-22Not applicableUs
Azithromycin Monohydratetablet, film coated250 mg/1oralDIRECT RX2014-01-01Not applicableUs
Azithromycin Monohydratetablet600 mg/1oralLUPIN LIMITED2015-07-22Not applicableUs
Azithromycin Monohydrateinjection, powder, lyophilized, for solution500 mg/10mLintravenousGland Pharma Limited2009-11-09Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AzenilNot Available
AzibiotNot Available
AzifastNot Available
AzigramNot Available
AzimakrolNot Available
AzinNot Available
AzithrocinNot Available
AzitromaxNot Available
AzitrominNot Available
AztrinNot Available
HemomycinNot Available
MisultinaNot Available
PenaloxNot Available
SumamedNot Available
VinzamNot Available
ZifinNot Available
ZitrocinNot Available
ZitrotekNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Azithromycin dihydrate
ThumbNot applicableDBSALT000882
Azithromycin monohydrate
ThumbNot applicableDBSALT001208
Categories
UNIIJ2KLZ20U1M
CAS number83905-01-5
WeightAverage: 748.9845
Monoisotopic: 748.508525778
Chemical FormulaC38H72N2O12
InChI KeyInChIKey=MQTOSJVFKKJCRP-BICOPXKESA-N
InChI
InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
IUPAC Name
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
SMILES
CC[[email protected]]1OC(=O)[[email protected]](C)[C@@H](O[[email protected]]2C[C@@](C)(OC)[C@@H](O)[[email protected]](C)O2)[[email protected]](C)[C@@H](O[C@@H]2O[[email protected]](C)C[C@@H]([[email protected]]2O)N(C)C)[C@](C)(O)C[C@@H](C)CN(C)[[email protected]](C)[C@@H](O)[C@]1(C)O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
Substituents
  • Macrolide
  • Amino sugar
  • Desosamine
  • Amino saccharide
  • Oxane
  • Monosaccharide
  • Saccharide
  • Tertiary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Polyol
  • Lactone
  • Carboxylic acid ester
  • 1,2-diol
  • 1,2-aminoalcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms in the specific conditions: H. influenzae, M. catarrhalis, S. pneumoniae, C. pneumoniae, M. pneumoniae, S. pyogenes, S. aureus, S. agal
PharmacodynamicsAzithromycin, a semisynthetic antibiotic belonging to the macrolide subgroup of azalides, is used to treat STDs due to chlamydia and gonorrhea, community-acquired pneumonia, pelvic inflammatory disease, pediatric otitis media and pharyngitis, and Mycobacterium avium complex (MAC) in patients with advanced HIV disease. Similar in structure to erythromycin. azithromycin reaches higher intracellular concentrations than erythromycin, increasing its efficacy and duration of action.
Mechanism of actionAzithromycin binds to the 50S subunit of the 70S bacterial ribosomes, and therefore inhibits RNA-dependent protein synthesis in bacterial cells.
Related Articles
AbsorptionBioavailability is 37% following oral administration. Absorption is not affected by food. Azithromycin is extensively distributed in tissues with tissue concentrations reaching up to 50 times greater than plasma concentrations. Drug becomes concentrated within macrophages and polymorphonucleocytes giving it good activity against Chlamydia trachomatis.
Volume of distribution
  • 31.1 L/kg
Protein bindingSerum protein binding is variable in the concentration range approximating human exposure, decreasing from 51% at 0.02 µg/mL to 7% at 2 µg/mL.
Metabolism

Hepatic. In vitro and in vivo studies to assess the metabolism of azithromycin have not been performed.

Route of eliminationBiliary excretion of azithromycin, predominantly as unchanged drug, is a major route of elimination.
Half life68 hours
Clearance
  • apparent plasma cl=630 mL/min [following single 500 mg oral and i.v. doses]
ToxicityPotentially serious side effects of angioedema and cholestatic jaundice were reported
Affected organisms
  • Enteric bacteria and other eubacteria
  • Corynebacterium diphtheriae
  • Treponema pallidum
  • Streptococcus pyogenes
  • Chlamydia pneumoniae
  • Chlamydia trachomatis
  • Chlamydophila psittaci
  • Mycoplasma pneumoniae
  • Neisseria gonorrhoeae
  • Legionella pneumophila
  • Bordetella pertussis
Pathways
PathwayCategorySMPDB ID
Azithromycin Action PathwayDrug actionSMP00247
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5518
Blood Brain Barrier-0.9739
Caco-2 permeable-0.7578
P-glycoprotein substrateSubstrate0.8765
P-glycoprotein inhibitor IInhibitor0.8513
P-glycoprotein inhibitor IINon-inhibitor0.8893
Renal organic cation transporterNon-inhibitor0.8753
CYP450 2C9 substrateNon-substrate0.8373
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6403
CYP450 1A2 substrateNon-inhibitor0.9295
CYP450 2C9 inhibitorNon-inhibitor0.9021
CYP450 2D6 inhibitorNon-inhibitor0.8904
CYP450 2C19 inhibitorNon-inhibitor0.9023
CYP450 3A4 inhibitorNon-inhibitor0.9533
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9751
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9397
BiodegradationNot ready biodegradable0.9673
Rat acute toxicity2.5423 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9929
hERG inhibition (predictor II)Non-inhibitor0.8555
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Pfizer chemicals div pfizer inc
  • Pfizer global research development
  • Pliva inc
  • Sandoz inc
  • Teva pharmaceuticals usa
  • Pfizer central research
  • App pharmaceuticals llc
  • Gland pharma ltd
  • Hospira inc
  • Pliva hrvatska doo
  • Sagent strides llc
  • Teva parenteral medicines inc
  • Pfizer inc
  • Inspire pharmaceuticals inc
  • Mylan pharmaceuticals inc
  • Teva pharmaceuticals usa inc
  • Wockhardt ltd
Packagers
Dosage forms
FormRouteStrength
Solutionophthalmic1 %
Solution/ dropsophthalmic10 mg/mL
Injectionintravenous500 mg/10mL
Injection, powder, lyophilized, for solutionintravenous100 mg/mL
Injection, powder, lyophilized, for solutionintravenous2 mg/mL
Injection, powder, lyophilized, for solutionintravenous500 mg/1
Powder for suspensionoral200 mg
Powder, for suspensionoral1200 mg/30mL
Powder, for suspensionoral900 mg/22.5mL
Tabletoral500 mg/1
Tablet, film coatedoral250 1/1
Injection, powder, lyophilized, for solutionintravenous500 mg/10mL
Tabletoral250 mg/1
Tabletoral600 mg/1
Tabletoral500 mg
Injection, powder, lyophilized, for solutionintravenous500 mg/5mL
Powder, for suspensionoral1 g/1
Powder, for suspensionoral100 mg/5mL
Powder, for suspensionoral200 mg/5mL
Tablet, film coatedoral250 mg/1
Tablet, film coatedoral500 mg/1
Tablet, film coatedoral600 mg/1
Powder for suspensionoral100 mg
Powder for solutionoral200 mg
Tabletoral250 mg
Tabletoral600 mg
Capsuleoral250 mg
Powder for solutionintravenous500 mg
Powder, for suspensionoral2 g/60mL
Granules for suspension,extended releaseoral2 g
Prices
Unit descriptionCostUnit
Zithromax 3 1 gm Packets Box118.26USD box
Azithromycin 2.5 gm bulk vial75.6USD each
Zmax adult-ped 2 g/60 ml susp70.39USD each
Zithromax Tri-Pak 3 500 mg tablet Disp Pack69.67USD disp
Zithromax Z-Pak 6 250 mg tablet Disp Pack68.62USD disp
Zmax 2 g/60 ml susp sr67.04USD each
Zmax pediatric 2 g/60 ml susp67.04USD each
Zithromax 200 mg/5ml Suspension 30ml Bottle52.0USD bottle
Zithromax 100 mg/5ml Suspension 15ml Bottle51.6USD bottle
Zithromax 200 mg/5ml Suspension 15ml Bottle50.46USD bottle
Zithromax 200 mg/5ml Suspension 22.5ml Bottle50.46USD bottle
Azithromycin 3 500 mg tablet Disp Pack48.52USD disp
Azithromycin 6 250 mg tablet Disp Pack48.52USD disp
Azasite 1% eye drops42.85USD ml
Zithromax i.v. 500 mg vial34.39USD vial
Azithromycin 200 mg/5ml Suspension 15ml Bottle34.25USD bottle
Zithromax 600 mg tablet27.22USD tablet
Zithromax 500 mg tablet22.68USD tablet
Zithromax tri-pak 500 mg tablet22.24USD tablet
Azithromycin 600 mg tablet19.04USD tablet
Azithromycin 500 mg tablet15.87USD tablet
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
Zithromax 250 mg z-pak tablet11.12USD tablet
Azithromycin i.v. 500 mg vial11.09USD each
Azithromycin powder10.89USD g
Zithromax 250 mg tablet9.41USD tablet
Azithromycin 250 mg tablet6.33USD tablet
Apo-Azithromycin 250 mg Tablet3.11USD tablet
Co Azithromycin 250 mg Tablet3.11USD tablet
Mylan-Azithromycin 250 mg Tablet3.11USD tablet
Novo-Azithromycin 250 mg Tablet3.11USD tablet
Phl-Azithromycin 250 mg Tablet3.11USD tablet
Pms-Azithromycin 250 mg Tablet3.11USD tablet
Ratio-Azithromycin 250 mg Tablet3.11USD tablet
Sandoz Azithromycin 250 mg Tablet3.11USD tablet
Zithromax 40 mg/ml Suspension1.7USD ml
Zithromax 20 mg/ml Suspension1.2USD ml
Novo-Azithromycin 40 mg/ml Suspension0.95USD ml
Pms-Azithromycin 40 mg/ml Suspension0.95USD ml
Sandoz Azithromycin 40 mg/ml Suspension0.95USD ml
Novo-Azithromycin 20 mg/ml Suspension0.67USD ml
Pms-Azithromycin 20 mg/ml Suspension0.67USD ml
Sandoz Azithromycin 20 mg/ml Suspension0.67USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2148071 No2000-10-172015-04-27Canada
CA2467611 No2010-03-302024-05-18Canada
US5192535 No1993-03-092010-03-09Us
US6068859 No1997-05-302017-05-30Us
US6159458 No1997-11-042017-11-04Us
US6239113 No1999-03-312019-03-31Us
US6268489 No1998-07-312018-07-31Us
US6569443 No1999-03-312019-03-31Us
US6861411 No1998-11-252018-11-25Us
US6984403 No2004-02-142024-02-14Us
US7056893 No1999-03-312019-03-31Us
US7887844 No2004-02-142024-02-14Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point114 °CPhysProp
water solubilityslightNot Available
logP4.02MCFARLAND,JW ET AL. (1997)
pKa8.74 (at 25 °C)MCFARLAND,JW ET AL. (1997)
Predicted Properties
PropertyValueSource
Water Solubility0.514 mg/mLALOGPS
logP3.03ALOGPS
logP2.44ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)12.43ChemAxon
pKa (Strongest Basic)9.57ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area180.08 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity194.11 m3·mol-1ChemAxon
Polarizability83.11 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

William Heggie, Zita Maria De Mouro Vaz Azevedo Mendes, “Process for the preparation of azithromycin.” U.S. Patent US6013778, issued November, 1994.

US6013778
General References
  1. Noedl H, Krudsood S, Chalermratana K, Silachamroon U, Leowattana W, Tangpukdee N, Looareesuwan S, Miller RS, Fukuda M, Jongsakul K, Sriwichai S, Rowan J, Bhattacharyya H, Ohrt C, Knirsch C: Azithromycin combination therapy with artesunate or quinine for the treatment of uncomplicated Plasmodium falciparum malaria in adults: a randomized, phase 2 clinical trial in Thailand. Clin Infect Dis. 2006 Nov 15;43(10):1264-71. Epub 2006 Oct 12. [PubMed:17051490 ]
External Links
ATC CodesJ01FA10J01RA07S01AA26
AHFS Codes
  • 08:12.12.92
PDB EntriesNot Available
FDA labelDownload (76.3 KB)
MSDSDownload (73.9 KB)
Interactions
Drug Interactions
Drug
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Azithromycin.
AmiodaroneAzithromycin may increase the QTc-prolonging activities of Amiodarone.
AtorvastatinAzithromycin may increase the myopathic rhabdomyolysis activities of Atorvastatin.
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Azithromycin.
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Azithromycin.
CitalopramAzithromycin may increase the QTc-prolonging activities of Citalopram.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Azithromycin.
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Azithromycin.
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Azithromycin.
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Azithromycin.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Azithromycin.
DofetilideAzithromycin may increase the QTc-prolonging activities of Dofetilide.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Azithromycin.
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Azithromycin.
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Azithromycin.
GoserelinGoserelin may increase the QTc-prolonging activities of Azithromycin.
IvabradineIvabradine may increase the QTc-prolonging activities of Azithromycin.
IvermectinThe serum concentration of Ivermectin can be increased when it is combined with Azithromycin.
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Azithromycin.
LeuprolideLeuprolide may increase the QTc-prolonging activities of Azithromycin.
LovastatinAzithromycin may increase the myopathic rhabdomyolysis activities of Lovastatin.
MifepristoneMifepristone may increase the QTc-prolonging activities of Azithromycin.
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Azithromycin.
NelfinavirThe serum concentration of Azithromycin can be increased when it is combined with Nelfinavir.
OctreotideOctreotide may increase the QTc-prolonging activities of Azithromycin.
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Azithromycin.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Azithromycin.
PimozideAzithromycin may increase the QTc-prolonging activities of Pimozide.
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Azithromycin.
QuinineThe serum concentration of Quinine can be increased when it is combined with Azithromycin.
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Azithromycin.
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Azithromycin.
RilpivirineThe serum concentration of Rilpivirine can be increased when it is combined with Azithromycin.
SaquinavirThe serum concentration of Saquinavir can be increased when it is combined with Azithromycin.
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Azithromycin.
SimvastatinAzithromycin may increase the myopathic rhabdomyolysis activities of Simvastatin.
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Azithromycin.
TerfenadineAzithromycin may increase the QTc-prolonging activities of Terfenadine.
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Azithromycin.
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Azithromycin.
VerapamilThe serum concentration of Verapamil can be increased when it is combined with Azithromycin.
VincristineThe serum concentration of Vincristine can be increased when it is combined with Azithromycin.
Food Interactions
  • Do not take Aluminum or magnesium antacids or supplements while on this medication.
  • Take on empty stomach: 1 hour before or 2 hours after meals.

Targets

1. 23S rRNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
yes
Actions
inhibitor
References
  1. Ng LK, Martin I, Liu G, Bryden L: Mutation in 23S rRNA associated with macrolide resistance in Neisseria gonorrhoeae. Antimicrob Agents Chemother. 2002 Sep;46(9):3020-5. [PubMed:12183262 ]
  2. Jalava J, Vaara M, Huovinen P: Mutation at the position 2058 of the 23S rRNA as a cause of macrolide resistance in Streptococcus pyogenes. Ann Clin Microbiol Antimicrob. 2004 May 6;3:5. [PubMed:15128458 ]
  3. Pereyre S, Renaudin H, Charron A, Bebear C, Bebear CM: Emergence of a 23S rRNA mutation in Mycoplasma hominis associated with a loss of the intrinsic resistance to erythromycin and azithromycin. J Antimicrob Chemother. 2006 Apr;57(4):753-6. Epub 2006 Feb 7. [PubMed:16464889 ]
Kind
Protein
Organism
Escherichia coli O157:H7
Pharmacological action
yes
Actions
inhibitor
General Function:
Structural constituent of ribosome
Specific Function:
One of the primary rRNA binding proteins, this protein initially binds near the 5'-end of the 23S rRNA. It is important during the early stages of 50S assembly. It makes multiple contacts with different domains of the 23S rRNA in the assembled 50S subunit and ribosome.Protein L4 is a both a transcriptional repressor and a translational repressor protein. It regulates transcription of the S10 op...
Gene Name:
rplD
Uniprot ID:
P60725
Molecular Weight:
22086.36 Da
References
  1. Halling SM, Jensen AE: Intrinsic and selected resistance to antibiotics binding the ribosome: analyses of Brucella 23S rrn, L4, L22, EF-Tu1, EF-Tu2, efflux and phylogenetic implications. BMC Microbiol. 2006 Oct 2;6:84. [PubMed:17014718 ]
  2. Tu D, Blaha G, Moore PB, Steitz TA: Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance. Cell. 2005 Apr 22;121(2):257-70. [PubMed:15851032 ]
  3. Schlunzen F, Harms JM, Franceschi F, Hansen HA, Bartels H, Zarivach R, Yonath A: Structural basis for the antibiotic activity of ketolides and azalides. Structure. 2003 Mar;11(3):329-38. [PubMed:12623020 ]
  4. Petropoulos AD, Kouvela EC, Starosta AL, Wilson DN, Dinos GP, Kalpaxis DL: Time-resolved binding of azithromycin to Escherichia coli ribosomes. J Mol Biol. 2009 Jan 30;385(4):1179-92. doi: 10.1016/j.jmb.2008.11.042. Epub 2008 Nov 27. [PubMed:19071138 ]
  5. Champney WS, Miller M: Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin. Curr Microbiol. 2002 Jun;44(6):418-24. [PubMed:12000992 ]
Kind
Protein
Organism
Escherichia coli O157:H7
Pharmacological action
yes
Actions
inhibitor
General Function:
Structural constituent of ribosome
Specific Function:
This protein binds specifically to 23S rRNA; its binding is stimulated by other ribosomal proteins, e.g. L4, L17, and L20. It is important during the early stages of 50S assembly. It makes multiple contacts with different domains of the 23S rRNA in the assembled 50S subunit and ribosome (By similarity).The globular domain of the protein is located near the polypeptide exit tunnel on the outside...
Gene Name:
rplV
Uniprot ID:
P61177
Molecular Weight:
12226.165 Da
References
  1. Halling SM, Jensen AE: Intrinsic and selected resistance to antibiotics binding the ribosome: analyses of Brucella 23S rrn, L4, L22, EF-Tu1, EF-Tu2, efflux and phylogenetic implications. BMC Microbiol. 2006 Oct 2;6:84. [PubMed:17014718 ]
  2. Tu D, Blaha G, Moore PB, Steitz TA: Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance. Cell. 2005 Apr 22;121(2):257-70. [PubMed:15851032 ]
  3. Schlunzen F, Harms JM, Franceschi F, Hansen HA, Bartels H, Zarivach R, Yonath A: Structural basis for the antibiotic activity of ketolides and azalides. Structure. 2003 Mar;11(3):329-38. [PubMed:12623020 ]
  4. Petropoulos AD, Kouvela EC, Starosta AL, Wilson DN, Dinos GP, Kalpaxis DL: Time-resolved binding of azithromycin to Escherichia coli ribosomes. J Mol Biol. 2009 Jan 30;385(4):1179-92. doi: 10.1016/j.jmb.2008.11.042. Epub 2008 Nov 27. [PubMed:19071138 ]
  5. Champney WS, Miller M: Inhibition of 50S ribosomal subunit assembly in Haemophilus influenzae cells by azithromycin and erythromycin. Curr Microbiol. 2002 Jun;44(6):418-24. [PubMed:12000992 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein-arginine deiminase activity
Specific Function:
Catalyzes the citrullination/deimination of arginine residues of proteins such as histones, thereby playing a key role in histone code and regulation of stem cell maintenance. Citrullinates histone H1 at 'Arg-54' (to form H1R54ci), histone H3 at 'Arg-2', 'Arg-8', 'Arg-17' and/or 'Arg-26' (to form H3R2ci, H3R8ci, H3R17ci, H3R26ci, respectively) and histone H4 at 'Arg-3' (to form H4R3ci). Acts as...
Gene Name:
PADI4
Uniprot ID:
Q9UM07
Molecular Weight:
74078.65 Da
References
  1. Knuckley B, Luo Y, Thompson PR: Profiling Protein Arginine Deiminase 4 (PAD4): a novel screen to identify PAD4 inhibitors. Bioorg Med Chem. 2008 Jan 15;16(2):739-45. Epub 2007 Oct 13. [PubMed:17964793 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Bosnar M, Kragol G, Kostrun S, Vujasinovic I, Bosnjak B, Bencetic Mihaljevic V, Marusic Istuk Z, Kapic S, Hrvacic B, Brajsa K, Tavcar B, Jelic D, Glojnaric I, Verbanac D, Culic O, Padovan J, Alihodzic S, Erakovic Haber V, Spaventi R: N'-substituted-2'-O,3'-N-carbonimidoyl bridged macrolides: novel anti-inflammatory macrolides without antimicrobial activity. J Med Chem. 2012 Jul 12;55(13):6111-23. doi: 10.1021/jm300356u. Epub 2012 Jun 25. [PubMed:22697905 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular Weight:
56501.005 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Wang E, Lew K, Barecki M, Casciano CN, Clement RP, Johnson WW: Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4. Chem Res Toxicol. 2001 Dec;14(12):1596-603. [PubMed:11743742 ]
  2. Asakura E, Nakayama H, Sugie M, Zhao YL, Nadai M, Kitaichi K, Shimizu A, Miyoshi M, Takagi K, Takagi K, Hasegawa T: Azithromycin reverses anticancer drug resistance and modifies hepatobiliary excretion of doxorubicin in rats. Eur J Pharmacol. 2004 Jan 26;484(2-3):333-9. [PubMed:14744620 ]
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Drug created on June 13, 2005 07:24 / Updated on June 29, 2016 01:52