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Identification
NameAzithromycin
Accession NumberDB00207  (APRD00397)
TypeSmall Molecule
GroupsApproved
DescriptionAzithromycin 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-azithromycinTablet250 mgOralAvanstra Inc2011-09-192014-08-21Canada
Ava-azithromycinPowder, for suspension100 mgOralAvanstra Inc2011-09-192014-08-21Canada
Ava-azithromycinPowder, for suspension200 mgOralAvanstra Inc2011-09-192014-08-21Canada
AzasiteSolution / drops10 mg/mLOphthalmicAkorn, Inc.2014-05-14Not applicableUs
AzasiteSolution1 %OphthalmicInsite Vision IncorporatedNot applicableNot applicableCanada
AzasiteSolution1 %OphthalmicInspire Pharmaceuticals IncNot applicableNot applicableCanada
AzithromycinTablet, film coated600 mg/1OralREMEDYREPACK INC.2013-03-05Not applicableUs
AzithromycinInjection, powder, lyophilized, for solution100 mg/mLIntravenousBaxter Healthcare Corporation1997-01-01Not applicableUs
AzithromycinPowder, for suspension1200 mg/30mLOralGreenstone LLC1995-10-19Not applicableUs
AzithromycinTablet, film coated600 mg/1OralGreenstone LLC1996-06-12Not applicableUs
AzithromycinPowder, for suspension100 mgOralPharmascience Inc2006-04-19Not applicableCanada
AzithromycinPowder, for suspension1 g/1OralPhysicians Total Care, Inc.2008-09-08Not applicableUs
AzithromycinTablet600 mgOralSanis Health Inc2010-02-012014-08-01Canada
AzithromycinPowder, for suspension1 g/1OralDispensing Solutions, Inc.1999-02-12Not applicableUs
AzithromycinTablet250 mgOral4513347 Canada Inc.Not applicableNot applicableCanada
AzithromycinPowder, for suspension1 g/1OralGreenstone LLC1999-02-12Not applicableUs
AzithromycinPowder, for suspension1 g/1OralPreferred Pharmaceuticals, Inc.1999-02-12Not applicableUs
AzithromycinTablet, film coated250 mg/1OralCentral Texas Community Health Centers1996-07-18Not applicableUs
AzithromycinTablet, film coated250 mg/1OralDepartment Of State Health Services, Pharmacy Branch1996-07-18Not applicableUs
AzithromycinPowder, for suspension100 mgOralDominion PharmacalNot applicableNot applicableCanada
AzithromycinPowder, for suspension100 mg/5mLOralGreenstone LLC1995-10-19Not applicableUs
AzithromycinTablet250 mgOralCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
AzithromycinTablet, film coated250 mg/1OralREMEDYREPACK INC.2013-09-24Not applicableUs
AzithromycinPowder, for suspension200 mgOralPharmascience Inc2006-04-19Not applicableCanada
AzithromycinTablet, film coated250 mg/1OralCardinal Health1996-07-18Not applicableUs
AzithromycinTablet250 mgOralSivem Pharmaceuticals Ulc2015-07-22Not applicableCanada
AzithromycinTablet600 mgOral4513347 Canada Inc.Not applicableNot applicableCanada
AzithromycinTablet, film coated250 mg/1OralGreenstone LLC1996-07-18Not applicableUs
AzithromycinTablet, film coated250 mg/1OralPreferred Pharmaceuticals, Inc.1996-07-18Not applicableUs
AzithromycinPowder, for suspension900 mg/22.5mLOralDepartment Of State Health Services, Pharmacy Branch1995-10-19Not applicableUs
AzithromycinTablet250 mgOralSanis Health Inc2010-02-01Not applicableCanada
AzithromycinPowder, for suspension1200 mg/30mLOralA S Medication Solutions1995-10-19Not applicableUs
AzithromycinPowder, for solution200 mgOralDominion PharmacalNot applicableNot applicableCanada
AzithromycinPowder, for suspension200 mg/5mLOralGreenstone LLC1995-10-19Not applicableUs
AzithromycinTablet600 mgOralCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
AzithromycinTablet, film coated500 mg/1OralREMEDYREPACK INC.2013-03-05Not applicableUs
AzithromycinTablet, film coated500 mg/1OralGreenstone LLC2002-05-24Not applicableUs
AzithromycinTablet, film coated500 mg/1OralPd Rx Pharmaceuticals, Inc.2002-05-24Not applicableUs
AzithromycinTablet, film coated500 mg/1OralLake Erie Medical DBA Quality Care Products LLC2002-05-24Not applicableUs
AzithromycinTablet, film coated250 mg/1OralCentral Texas Community Health Centers1996-07-18Not applicableUs
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 mgIntravenousHospira Healthcare CorporationNot applicableNot applicableCanada
Azithromycin for Injection, USPPowder, for solution500 mgIntravenousHospira Healthcare Corporation2011-12-29Not applicableCanada
Azithromycin for Injection, USPPowder, for solution500 mgIntravenousMylan Pharmaceuticals Ulc2013-05-13Not applicableCanada
Dom-azithromycinTablet250 mgOralDominion Pharmacal2008-04-16Not applicableCanada
Dom-azithromycinPowder, for suspension100 mgOralDominion PharmacalNot applicableNot applicableCanada
Dom-azithromycinTablet600 mgOralDominion Pharmacal2008-04-16Not applicableCanada
Dom-azithromycinPowder, for suspension200 mgOralDominion PharmacalNot applicableNot 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
Gd-azithromycinTablet250 mgOralGenmed A Division Of Pfizer Canada Inc2010-11-11Not applicableCanada
Ipg-azithromycinTablet250 mgOralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Ipg-azithromycinTablet600 mgOralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Jamp-azithromycinTablet600 mgOralJamp Pharma CorporationNot applicableNot applicableCanada
Jamp-azithromycinTablet250 mgOralJamp Pharma Corporation2016-09-29Not applicableCanada
Mar-azithromycinTablet250 mgOralMarcan Pharmaceuticals Inc2016-10-12Not applicableCanada
Mar-azithromycinTablet600 mgOralMarcan Pharmaceuticals IncNot 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-azithromycinTablet250 mgOralPharmel Inc2007-07-27Not applicableCanada
PHL-azithromycinTablet600 mgOralPharmel IncNot applicableNot applicableCanada
PHL-azithromycinPowder, for suspension100 mgOralPharmel Inc2006-08-17Not applicableCanada
PMS-azithromycinPowder, for suspension100 mgOralPharmascience Inc2014-03-19Not applicableCanada
PMS-azithromycinTablet250 mgOralPharmascience Inc2006-01-04Not applicableCanada
PMS-azithromycinTablet600 mgOralPharmascience Inc2006-01-04Not applicableCanada
PMS-azithromycinPowder, for suspension200 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 AzithromycinTablet250 mgOralLaboratoire Riva Inc2006-03-16Not applicableCanada
Riva AzithromycinTablet600 mgOralLaboratoire Riva Inc2006-03-162013-07-31Canada
Sandoz AzithromycinTablet250 mgOralSandoz Canada Incorporated2005-11-11Not applicableCanada
Sandoz AzithromycinPowder, for suspension100 mgOralSandoz Canada Incorporated2009-09-08Not applicableCanada
Sandoz AzithromycinPowder, for suspension200 mgOralSandoz Canada Incorporated2009-09-08Not applicableCanada
Sandoz AzithromycinTablet500 mgOralSandoz Canada IncorporatedNot applicableNot applicableCanada
ZithromaxTablet, film coated250 mg/1OralPd Rx Pharmaceuticals, Inc.1996-07-18Not applicableUs
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 coated500 mg/1OralREMEDYREPACK INC.2013-09-19Not applicableUs
ZithromaxTablet, film coated250 mg/1OralREMEDYREPACK INC.2013-03-12Not applicableUs
ZithromaxTablet, film coated600 mg/1OralPfizer Laboratories Div Pfizer Inc1996-06-12Not applicableUs
ZithromaxPowder, for suspension200 mg/5mLOralPfizer Laboratories Div Pfizer Inc1995-10-19Not applicableUs
ZithromaxPowder, for suspension1 g/1OralPfizer Laboratories Div Pfizer Inc1994-09-28Not applicableUs
ZithromaxTablet, film coated250 mg/1OralA S Medication Solutions1996-07-18Not applicableUs
ZithromaxPowder, for suspension100 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/1OralPfizer Laboratories Div Pfizer Inc1996-07-18Not applicableUs
ZithromaxTablet, film coated250 mg/1OralCardinal Health1996-07-18Not applicableUs
ZithromaxPowder, for suspension200 mg/5mLOralPfizer Laboratories Div Pfizer Inc1995-10-19Not applicableUs
ZithromaxTablet, film coated250 mg/1OralREMEDYREPACK INC.2013-04-04Not applicableUs
ZithromaxTablet, film coated250 mg/1OralA S Medication Solutions1996-07-18Not applicableUs
ZithromaxTablet, film coated500 mg/1OralPfizer Laboratories Div Pfizer Inc2002-05-24Not 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 SRGranule, 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/1OralPd Rx Pharmaceuticals, Inc.2008-02-11Not applicableUs
AzithromycinTablet, film coated600 mg/1OralWockhardt Limited2008-02-11Not applicableUs
AzithromycinTablet, film coated250 mg/1OralProficient Rx LP2008-02-11Not applicableUs
AzithromycinTablet, film coated250 mg/1OralTeva Pharmaceuticals Usa, Inc.2006-01-06Not applicableUs
AzithromycinInjection500 mg/10mLIntravenousApotex Corp.2010-04-25Not applicableUs
AzithromycinTablet, film coated600 mg/1OralTeva Pharmaceuticals Usa, Inc.2005-12-01Not applicableUs
AzithromycinInjection, powder, lyophilized, for solution500 mg/5mLIntravenousSagent Pharmaceuticals2009-05-01Not applicableUs
AzithromycinTablet500 mg/1OralREMEDYREPACK INC.2011-04-12Not applicableUs
AzithromycinPowder, for suspension200 mg/5mLOralDepartment Of State Health Services, Pharmacy Branch2010-12-17Not applicableUs
AzithromycinTablet, film coated600 mg/1OralPhysicians Total Care, Inc.2012-04-26Not applicableUs
AzithromycinTablet, film coated500 mg/1OralWockhardt USA LLC.2008-02-11Not applicableUs
AzithromycinTablet, film coated500 mg/1OralProficient Rx LP2006-01-06Not applicableUs
AzithromycinTablet, film coated500 mg/1OralTeva Pharmaceuticals USA Inc2005-11-16Not applicableUs
AzithromycinTablet, film coated500 mg/1OralClinical Solutions Wholesale2005-11-16Not applicableUs
AzithromycinPowder, for suspension200 mg/5mLOralPhysicians Total Care, Inc.2006-08-03Not applicableUs
AzithromycinPowder, for suspension100 mg/5mLOralA S Medication Solutions2008-09-22Not applicableUs
AzithromycinTablet, film coated500 mg/1OralA S Medication Solutions2005-11-16Not applicableUs
AzithromycinPowder, for suspension100 mg/5mLOralTeva Pharmaceuticals USA Inc2008-09-22Not applicableUs
AzithromycinInjection, powder, lyophilized, for solution500 mg/1IntravenousAuro Medics Pharma Llc2015-06-19Not applicableUs
AzithromycinTablet, film coated500 mg/1OralDIRECT RX2015-01-01Not applicableUs
AzithromycinTablet, film coated250 mg/1OralPd Rx Pharmaceuticals, Inc.2005-11-14Not applicableUs
AzithromycinTablet, film coated250 mg/1OralPhysicians Total Care, Inc.2005-11-16Not applicableUs
AzithromycinTablet, film coated250 mg/1OralUnit Dose Services2008-02-11Not applicableUs
AzithromycinTablet, film coated500 mg/1OralVivimed Labs Limited2008-02-11Not applicableUs
AzithromycinPowder, for suspension200 mg/5mLOralTeva Pharmaceuticals Usa, Inc.2010-12-17Not applicableUs
AzithromycinTablet, film coated250 mg/1OralPreferred Pharmaceuticals Inc.2015-10-19Not applicableUs
AzithromycinTablet, film coated500 mg/1OralDispensing Solutions Inc.2008-05-30Not applicableUs
AzithromycinTablet, film coated250 mg/1OralMed Vantx, Inc.2011-10-24Not applicableUs
AzithromycinTablet, film coated250 mg/1OralMajor Pharmaceuticals2009-06-10Not applicableUs
AzithromycinTablet, film coated250 mg/1OralAvera Mc Kennan Hospital2015-03-02Not applicableUs
AzithromycinTablet, film coated500 mg/1OralREMEDYREPACK INC.2015-04-23Not applicableUs
AzithromycinInjection, powder, lyophilized, for solution500 mg/5mLIntravenousCardinal Health2006-03-20Not applicableUs
AzithromycinTablet, film coated250 mg/1OralA S Medication Solutions2005-11-16Not applicableUs
AzithromycinTablet, film coated250 mg/1OralCardinal Health2005-11-14Not applicableUs
AzithromycinPowder, for suspension100 mg/5mLOralRebel Distributors Corp.2008-06-24Not applicableUs
AzithromycinTablet, film coated250 mg/1OralAidarex Pharmaceuticals LLC2008-02-11Not applicableUs
AzithromycinTablet, film coated500 mg/1OralPd Rx Pharmaceuticals, Inc.2008-02-11Not applicableUs
AzithromycinTablet, film coated250 mg/1OralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-12-21Not applicableUs
AzithromycinTablet, film coated500 mg/1OralWockhardt Limited2008-02-11Not applicableUs
AzithromycinTablet, film coated250 mg/1OralPreferred Pharmaceuticals, Inc.2008-02-11Not applicableUs
AzithromycinTablet, film coated250 mg/1OralAmerican Health Packaging2015-01-152016-06-30Us
AzithromycinTablet, film coated500 mg/1OralTeva Pharmaceuticals Usa, Inc.2006-01-06Not applicableUs
AzithromycinTablet, film coated500 mg/1OralREMEDYREPACK INC.2015-01-06Not applicableUs
AzithromycinTablet, film coated250 mg/1OralUnit Dose Services2005-11-14Not applicableUs
AzithromycinTablet500 mg/1OralLake Erie Medical DBA Quality Care Products LLC2010-11-09Not applicableUs
AzithromycinTablet500 mg/1OralREMEDYREPACK INC.2012-01-12Not applicableUs
AzithromycinTablet, film coated500 mg/1OralSTAT Rx USA LLC2008-02-11Not applicableUs
AzithromycinTablet, film coated500 mg/1OralDispensing Solutions, Inc.2008-02-11Not applicableUs
AzithromycinTablet, film coated250 mg/1OralDispensing Solutions, Inc.2008-02-11Not applicableUs
AzithromycinTablet, film coated250 mg/1OralSandoz Inc2005-11-14Not applicableUs
AzithromycinTablet, film coated600 mg/1OralREMEDYREPACK INC.2015-02-09Not applicableUs
AzithromycinPowder, for suspension200 mg/5mLOralA S Medication Solutions2008-09-22Not applicableUs
AzithromycinTablet, film coated250 mg/1OralRed Pharm Drug, Inc.2005-11-16Not applicableUs
AzithromycinPowder, for suspension200 mg/5mLOralTeva Pharmaceuticals USA Inc2008-09-22Not applicableUs
AzithromycinTablet, film coated500 mg/1OralProficient Rx LP2008-02-11Not applicableUs
AzithromycinPowder, for suspension100 mg/5mLOralTeva Pharmaceuticals Usa, Inc.2010-12-28Not applicableUs
AzithromycinTablet, film coated500 mg/1OralPreferred Pharmaceuticals Inc.2015-10-27Not applicableUs
AzithromycinPowder, for suspension200 mg/5mLOralClinical Solutions Wholesale2010-12-17Not applicableUs
AzithromycinTablet, film coated250 mg/1OralProficient Rx LP2006-01-06Not applicableUs
AzithromycinTablet, film coated500 mg/1OralCambridge Therapeutics Technologies, Llc2005-11-14Not applicableUs
AzithromycinTablet, film coated250 mg/1OralPd Rx Pharmaceuticals, Inc.2005-11-16Not applicableUs
AzithromycinTablet, film coated250 mg/1OralPhysicians Total Care, Inc.2005-11-23Not applicableUs
AzithromycinTablet, film coated250 mg/1OralREMEDYREPACK INC.2013-10-30Not applicableUs
AzithromycinTablet, film coated500 mg/1OralAidarex Pharmaceuticals LLC2008-02-11Not applicableUs
AzithromycinTablet, film coated250 mg/1OralPd Rx Pharmaceuticals, Inc.2008-02-11Not applicableUs
AzithromycinTablet, film coated250 mg/1OralAmerican Health Packaging2010-08-092015-12-29Us
AzithromycinTablet, film coated250 mg/1OralMed Vantx, Inc.2005-11-16Not applicableUs
AzithromycinTablet, film coated250 mg/1OralREMEDYREPACK INC.2013-05-23Not applicableUs
AzithromycinInjection, powder, lyophilized, for solution500 mg/5mLIntravenousSun Pharmaceutical Industries Limited2013-04-03Not applicableUs
AzithromycinInjection, powder, lyophilized, for solution100 mg/mLIntravenousCardinal Health2009-12-10Not applicableUs
AzithromycinPowder, for suspension100 mg/5mLOralA S Medication Solutions2010-12-28Not applicableUs
AzithromycinPowder, for suspension200 mg/5mLOralRebel Distributors Corp.2008-06-24Not applicableUs
AzithromycinTablet, film coated250 mg/1OralUnit Dose Services2011-10-24Not applicableUs
AzithromycinTablet, film coated250 mg/1OralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2005-11-14Not applicableUs
AzithromycinTablet, film coated250 mg/1OralAidarex Pharmaceuticals LLC2005-11-14Not applicableUs
AzithromycinTablet, film coated250 mg/1OralAv Pak2011-05-20Not applicableUs
AzithromycinTablet, film coated250 mg/1OralVivimed Labs Limited2008-02-11Not applicableUs
AzithromycinTablet, film coated500 mg/1OralPreferred Pharmaceuticals, Inc.2008-02-11Not applicableUs
AzithromycinTablet, film coated500 mg/1OralAmerican Health Packaging2015-01-152016-10-31Us
AzithromycinTablet, film coated250 mg/1OralREMEDYREPACK INC.2012-12-28Not applicableUs
AzithromycinTablet, film coated500 mg/1OralProficient Rx LP2005-11-14Not applicableUs
AzithromycinTablet, film coated600 mg/1OralA S Medication Solutions2005-11-16Not applicableUs
AzithromycinTablet, film coated500 mg/1OralPreferred Pharmaceuticals, Inc.2006-01-06Not applicableUs
AzithromycinTablet, film coated600 mg/1OralKAISER FOUNDATION HOSPITALS2009-09-01Not applicableUs
AzithromycinInjection, powder, lyophilized, for solution100 mg/mLIntravenousPliva Inc.2007-08-172016-10-13Us
AzithromycinTablet, film coated250 mg/1OralRebel Distributors Corp.2008-02-11Not applicableUs
AzithromycinTablet, film coated250 mg/1OralCardinal Health2008-04-02Not applicableUs
AzithromycinTablet, film coated250 mg/1OralAmerican Health Packaging2013-07-19Not applicableUs
AzithromycinInjection, powder, lyophilized, for solution500 mg/5mLIntravenousFresenius Kabi USA, LLC2006-03-20Not applicableUs
AzithromycinTablet, film coated600 mg/1OralSandoz Inc2005-11-14Not applicableUs
AzithromycinPowder, for suspension100 mg/5mLOralPreferred Pharmaceuticals, Inc.2012-01-10Not applicableUs
AzithromycinTablet, film coated250 mg/1OralREMEDYREPACK INC.2015-02-13Not applicableUs
AzithromycinPowder, for suspension200 mg/5mLOralA S Medication Solutions2010-12-17Not applicableUs
AzithromycinTablet, film coated500 mg/1OralPhysicians Total Care, Inc.2007-08-10Not applicableUs
AzithromycinTablet, film coated500 mg/1OralREMEDYREPACK INC.2014-02-20Not applicableUs
AzithromycinTablet, film coated250 mg/1OralWockhardt USA LLC.2008-02-11Not applicableUs
AzithromycinTablet, film coated250 mg/1OralTeva Pharmaceuticals USA Inc2005-11-16Not applicableUs
AzithromycinPowder, for suspension100 mg/5mLOralPreferred Pharmaceuticals, Inc.2011-03-10Not applicableUs
AzithromycinTablet, film coated250 mg/1OralClinical Solutions Wholesale2008-02-11Not applicableUs
AzithromycinTablet, film coated250 mg/1OralDepartment Of State Health Services, Pharmacy Branch2005-11-16Not applicableUs
AzithromycinTablet, film coated250 mg/1OralA S Medication Solutions2005-11-14Not applicableUs
AzithromycinPowder, for suspension200 mg/5mLOralProficient Rx LP2010-12-17Not applicableUs
AzithromycinTablet, film coated250 mg/1OralUnit Dose Services2005-11-14Not applicableUs
AzithromycinTablet, film coated250 mg/1OralAphena Pharma Solutions Tennessee, Llc2005-11-14Not applicableUs
AzithromycinTablet, film coated250 mg/1OralREMEDYREPACK INC.2013-05-23Not applicableUs
AzithromycinTablet, film coated250 mg/1OralRx Change Co.2014-11-13Not applicableUs
AzithromycinTablet, film coated250 mg/1OralWockhardt Limited2008-02-11Not applicableUs
AzithromycinTablet, film coated600 mg/1OralAmerican Health Packaging2012-07-022015-12-29Us
AzithromycinPowder, for suspension200 mg/5mLOralMed Vantx, Inc.2008-09-22Not applicableUs
AzithromycinTablet, film coated500 mg/1OralPd Rx Pharmaceuticals, Inc.2005-11-14Not applicableUs
AzithromycinTablet, film coated250 mg/1OralA S Medication Solutions2005-11-16Not applicableUs
AzithromycinPowder, for suspension200 mg/5mLOralA S Medication Solutions2010-12-172016-11-08Us
AzithromycinTablet, film coated250 mg/1OralLake Erie Medical DBA Quality Care Products LLC2008-02-11Not applicableUs
AzithromycinTablet500 mg/1OralREMEDYREPACK INC.2011-11-152016-11-02Us
AzithromycinPowder, for suspension200 mg/5mLOralDIRECT RX2014-01-01Not applicableUs
AzithromycinTablet, film coated500 mg/1OralA S Medication Solutions2005-11-16Not applicableUs
AzithromycinTablet, film coated500 mg/1OralPhysicians Total Care, Inc.1995-08-15Not applicableUs
AzithromycinTablet, film coated500 mg/1OralAv Pak2011-05-20Not applicableUs
AzithromycinTablet, film coated600 mg/1OralVivimed Labs Limited2008-02-11Not applicableUs
AzithromycinPowder, for suspension200 mg/5mLOralREMEDYREPACK INC.2016-04-13Not applicableUs
AzithromycinTablet, film coated600 mg/1OralAmerican Health Packaging2015-01-15Not applicableUs
AzithromycinTablet, film coated250 mg/1OralREMEDYREPACK INC.2012-10-08Not applicableUs
AzithromycinTablet, film coated500 mg/1OralPd Rx Pharmaceuticals, Inc.2005-11-14Not applicableUs
AzithromycinTablet, film coated250 mg/1OralREMEDYREPACK INC.2015-04-16Not applicableUs
AzithromycinInjection, powder, lyophilized, for solution100 mg/mLIntravenousCardinal Health2011-01-31Not applicableUs
AzithromycinPowder, for suspension200 mg/5mLOralA S Medication Solutions2010-12-17Not applicableUs
AzithromycinTablet, film coated250 mg/1OralPreferred Pharmaceuticals, Inc.2015-04-16Not applicableUs
AzithromycinInjection, powder, lyophilized, for solution2 mg/mLIntravenousHospira, Inc.2009-06-26Not applicableUs
AzithromycinTablet, film coated500 mg/1OralRebel Distributors Corp.2008-02-11Not applicableUs
AzithromycinTablet, film coated250 mg/1OralCardinal Health2011-05-20Not applicableUs
AzithromycinTablet, film coated500 mg/1OralAmerican Health Packaging2013-07-19Not applicableUs
AzithromycinTablet, film coated250 mg/1OralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2013-12-02Not applicableUs
AzithromycinTablet, film coated500 mg/1OralSandoz Inc2005-11-14Not applicableUs
AzithromycinPowder, for suspension200 mg/5mLOralPreferred Pharmaceuticals, Inc.2012-01-10Not applicableUs
AzithromycinPowder, for suspension100 mg/5mLOralPhysicians Total Care, Inc.2006-08-01Not applicableUs
AzithromycinTablet, film coated250 mg/1OralH.J. Harkins Company, Inc.2008-02-11Not applicableUs
AzithromycinTablet, film coated600 mg/1OralWockhardt USA LLC.2008-02-11Not applicableUs
AzithromycinTablet, film coated600 mg/1OralTeva Pharmaceuticals USA Inc2005-11-16Not applicableUs
AzithromycinPowder, for suspension200 mg/5mLOralPreferred Pharmaceuticals, Inc.2011-03-10Not applicableUs
AzithromycinTablet, film coated600 mg/1OralClinical Solutions Wholesale2005-11-16Not applicableUs
AzithromycinPowder, for suspension100 mg/5mLOralDepartment Of State Health Services, Pharmacy Branch2010-12-28Not applicableUs
AzithromycinTablet, film coated500 mg/1OralA S Medication Solutions2006-01-06Not applicableUs
AzithromycinTablet, film coated250 mg/1OralProficient Rx LP2005-11-14Not applicableUs
AzithromycinTablet, film coated250 mg/1OralA S Medication Solutions2006-01-06Not applicableUs
AzithromycinTablet, film coated250 mg/1OralA S Medication Solutions2006-01-06Not applicableUs
AzithromycinTablet, film coated250 mg/1OralMedsource Pharmaceuticals2006-01-06Not applicableUs
Azithromycin DihydrateTablet, film coated250 mg/1OralREMEDYREPACK INC.2013-10-15Not 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/1OralPreferred Pharmaceuticals, Inc.2014-02-06Not applicableUs
Azithromycin DihydrateTablet, film coated500 mg/1OralAv Pak2016-11-16Not applicableUs
Azithromycin DihydrateTablet, film coated500 mg/1OralAv Pak2014-03-26Not applicableUs
Azithromycin DihydrateTablet, film coated500 mg/1OralREMEDYREPACK INC.2013-12-04Not 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/1OralPreferred Pharmaceuticals, Inc.2014-02-06Not applicableUs
Azithromycin DihydrateTablet, film coated250 mg/1OralCardinal Health2014-03-26Not applicableUs
Azithromycin DihydrateTablet, film coated250 mg/1OralA S Medication Solutions2011-07-18Not applicableUs
Azithromycin DihydrateTablet, film coated250 mg/1OralAmerican Health Packaging2014-02-172015-10-31Us
Azithromycin DihydrateTablet, film coated500 mg/1OralA S Medication Solutions2011-07-18Not applicableUs
Azithromycin DihydrateTablet, film coated250 mg/1OralCardinal Health2014-02-17Not applicableUs
Azithromycin DihydrateTablet, film coated250 mg/1OralMajor Pharmaceuticals2011-07-18Not applicableUs
Azithromycin DihydrateTablet, film coated600 mg/1OralApotex Corp.2011-07-132016-11-22Us
Azithromycin DihydrateTablet, film coated250 mg/1OralAv Pak2016-11-16Not applicableUs
Azithromycin DihydrateTablet, film coated500 mg/1OralPd Rx Pharmaceuticals, Inc.2011-07-18Not applicableUs
Azithromycin DihydrateTablet, film coated250 mg/1OralDIRECT RX2014-01-01Not applicableUs
Azithromycin DihydrateTablet, film coated250 mg/1OralAv Pak2014-03-26Not applicableUs
Azithromycin MonohydrateTablet250 mg/1OralLupin Pharmaceuticals, Inc.2015-07-22Not applicableUs
Azithromycin MonohydrateTablet500 mg/1OralA S Medication Solutions2015-07-22Not applicableUs
Azithromycin MonohydrateTablet500 mg/1OralLUPIN LIMITED2015-07-22Not applicableUs
Azithromycin MonohydrateTablet500 mg/1OralPd Rx Pharmaceuticals, Inc.2015-07-22Not applicableUs
Azithromycin MonohydrateTablet500 mg/1OralLupin Pharmaceuticals, Inc.2015-07-22Not applicableUs
Azithromycin MonohydrateTablet600 mg/1OralLUPIN LIMITED2015-07-22Not applicableUs
Azithromycin MonohydrateTablet500 mg/1OralPd Rx Pharmaceuticals, Inc.2015-07-22Not applicableUs
Azithromycin MonohydrateTablet600 mg/1OralLupin Pharmaceuticals, Inc.2015-07-22Not applicableUs
Azithromycin MonohydrateTablet, film coated250 mg/1OralDIRECT RX2014-01-01Not applicableUs
Azithromycin MonohydrateTablet250 mg/1OralPd Rx Pharmaceuticals, Inc.2015-07-22Not applicableUs
Azithromycin MonohydrateTablet500 mg/1OralA S Medication Solutions2015-07-22Not applicableUs
Azithromycin MonohydrateInjection, powder, lyophilized, for solution500 mg/10mLIntravenousGland Pharma Limited2009-11-09Not applicableUs
Azithromycin MonohydrateTablet250 mg/1OralLUPIN LIMITED2015-07-22Not applicableUs
ZithromaxTablet, film coated250 mg/1OralDIRECT RX2016-03-02Not applicableUs
ZithromaxTablet500 mg/1OralDIRECT RX2016-05-27Not 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
117772-70-0
Thumb
  • InChI Key: SRMPHJKQVUDLQE-KUJJYQHYSA-N
  • Monoisotopic Mass: 784.529655135
  • Average Mass: 785.026
DBSALT000882
Azithromycin monohydrate
121470-24-4
Thumb
  • InChI Key: HQUPLSLYZHKKQT-WVVFQGGUSA-N
  • Monoisotopic Mass: 766.519090451
  • Average Mass: 767.011
DBSALT001208
Categories
UNIIJ2KLZ20U1M
CAS number83905-01-5
WeightAverage: 748.9845
Monoisotopic: 748.508525778
Chemical FormulaC38H72N2O12
InChI KeyMQTOSJVFKKJCRP-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
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
Structured Indications
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
23S rRNANucleotideyes
inhibitor
Enteric bacteria and other eubacterianot applicabledetails
50S ribosomal protein L4Proteinyes
inhibitor
Escherichia coli O157:H7P60725 details
50S ribosomal protein L22Proteinyes
inhibitor
Escherichia coli O157:H7P61177 details
Protein-arginine deiminase type-4ProteinunknownNot AvailableHumanQ9UM07 details
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
Interactions
Drug Interactions
DrugInteractionDrug group
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Azithromycin.Approved
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Azithromycin.Approved
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Azithromycin.Approved
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be increased when it is combined with Azithromycin.Approved
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Azithromycin.Approved, Vet Approved
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Azithromycin.Approved
AgomelatineThe serum concentration of Agomelatine can be increased when it is combined with Azithromycin.Approved, Investigational
AlbendazoleThe metabolism of Albendazole can be decreased when combined with Azithromycin.Approved, Vet Approved
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Azithromycin.Experimental
AlfuzosinAlfuzosin may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Azithromycin.Approved, Investigational
AlmotriptanThe metabolism of Almotriptan can be decreased when combined with Azithromycin.Approved, Investigational
AlosetronThe metabolism of Alosetron can be decreased when combined with Azithromycin.Approved, Withdrawn
AmantadineAmantadine may increase the QTc-prolonging activities of Azithromycin.Approved
AmbrisentanThe serum concentration of Ambrisentan can be increased when it is combined with Azithromycin.Approved, Investigational
AminophenazoneThe metabolism of Aminophenazone can be decreased when combined with Azithromycin.Approved, Withdrawn
AminophyllineThe metabolism of Aminophylline can be decreased when combined with Azithromycin.Approved
AmiodaroneAzithromycin may increase the QTc-prolonging activities of Amiodarone.Approved, Investigational
AmitriptylineAmitriptyline may increase the QTc-prolonging activities of Azithromycin.Approved
AmoxapineAmoxapine may increase the QTc-prolonging activities of Azithromycin.Approved
AnagrelideAzithromycin may increase the QTc-prolonging activities of Anagrelide.Approved
AntipyrineThe metabolism of Antipyrine can be decreased when combined with Azithromycin.Approved
AnvirzelThe serum concentration of Anvirzel can be increased when it is combined with Azithromycin.Investigational
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Azithromycin.Approved
ApomorphineApomorphine may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
AprepitantThe serum concentration of Azithromycin can be increased when it is combined with Aprepitant.Approved, Investigational
ArformoterolArformoterol may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
AripiprazoleAripiprazole may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
Arsenic trioxideAzithromycin may increase the QTc-prolonging activities of Arsenic trioxide.Approved, Investigational
ArtemetherAzithromycin may increase the QTc-prolonging activities of Artemether.Approved
ArtesunateThe serum concentration of the active metabolites of Artesunate can be reduced when Artesunate is used in combination with Azithromycin resulting in a loss in efficacy.Approved
ASA404The metabolism of ASA404 can be decreased when combined with Azithromycin.Investigational
AsenapineAzithromycin may increase the QTc-prolonging activities of Asenapine.Approved
AtazanavirThe metabolism of Azithromycin can be decreased when combined with Atazanavir.Approved, Investigational
AtenololThe serum concentration of Atenolol can be increased when it is combined with Azithromycin.Approved
AtomoxetineAtomoxetine may increase the QTc-prolonging activities of Azithromycin.Approved
AtorvastatinAzithromycin may increase the myopathic rhabdomyolysis activities of Atorvastatin.Approved
AV650The metabolism of AV650 can be decreased when combined with Azithromycin.Approved, Investigational
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Azithromycin.Approved, Investigational
AzelastineThe metabolism of Azelastine can be decreased when combined with Azithromycin.Approved
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Azithromycin.Investigational
BedaquilineAzithromycin may increase the QTc-prolonging activities of Bedaquiline.Approved
BendamustineThe metabolism of Bendamustine can be decreased when combined with Azithromycin.Approved, Investigational
Benzyl alcoholThe metabolism of Benzyl alcohol can be decreased when combined with Azithromycin.Approved
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Azithromycin.Approved, Vet Approved
BetaxololThe metabolism of Betaxolol can be decreased when combined with Azithromycin.Approved
BexaroteneThe serum concentration of Azithromycin can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe metabolism of Azithromycin can be decreased when combined with Boceprevir.Approved
BortezomibBortezomib may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
BosentanThe serum concentration of Azithromycin can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Azithromycin.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Azithromycin.Approved
BromazepamThe metabolism of Bromazepam can be decreased when combined with Azithromycin.Approved, Illicit
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Azithromycin.Approved, Investigational
BupivacaineThe metabolism of Bupivacaine can be decreased when combined with Azithromycin.Approved, Investigational
BupropionThe metabolism of Bupropion can be decreased when combined with Azithromycin.Approved
BuserelinBuserelin may increase the QTc-prolonging activities of Azithromycin.Approved
CabazitaxelThe serum concentration of Cabazitaxel can be increased when it is combined with Azithromycin.Approved
CaffeineThe serum concentration of Caffeine can be increased when it is combined with Azithromycin.Approved
CamptothecinThe serum concentration of Camptothecin can be increased when it is combined with Azithromycin.Experimental
CanagliflozinThe serum concentration of Canagliflozin can be increased when it is combined with Azithromycin.Approved
CarbamazepineThe metabolism of Azithromycin can be increased when combined with Carbamazepine.Approved, Investigational
CarfilzomibThe serum concentration of Carfilzomib can be increased when it is combined with Azithromycin.Approved
CarmustineThe metabolism of Carmustine can be decreased when combined with Azithromycin.Approved
CarvedilolThe metabolism of Carvedilol can be decreased when combined with Azithromycin.Approved, Investigational
CeritinibThe serum concentration of Azithromycin can be increased when it is combined with Ceritinib.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Azithromycin.Withdrawn
ChloroquineAzithromycin may increase the QTc-prolonging activities of Chloroquine.Approved, Vet Approved
ChlorpromazineAzithromycin may increase the QTc-prolonging activities of Chlorpromazine.Approved, Vet Approved
ChlorzoxazoneThe metabolism of Chlorzoxazone can be decreased when combined with Azithromycin.Approved
CilostazolThe metabolism of Cilostazol can be decreased when combined with Azithromycin.Approved
CimetidineThe serum concentration of Cimetidine can be increased when it is combined with Azithromycin.Approved
CinacalcetThe metabolism of Cinacalcet can be decreased when combined with Azithromycin.Approved
CinnarizineThe metabolism of Cinnarizine can be decreased when combined with Azithromycin.Approved
CiprofloxacinAzithromycin may increase the QTc-prolonging activities of Ciprofloxacin.Approved, Investigational
CisaprideAzithromycin may increase the QTc-prolonging activities of Cisapride.Approved, Investigational, Withdrawn
CisplatinThe serum concentration of Cisplatin can be increased when it is combined with Azithromycin.Approved
CitalopramAzithromycin may increase the QTc-prolonging activities of Citalopram.Approved
ClarithromycinAzithromycin may increase the QTc-prolonging activities of Clarithromycin.Approved
ClemastineThe metabolism of Azithromycin can be decreased when combined with Clemastine.Approved
ClenbuterolThe metabolism of Clenbuterol can be decreased when combined with Azithromycin.Approved, Vet Approved
ClevidipineThe metabolism of Clevidipine can be decreased when combined with Azithromycin.Approved
ClobazamThe serum concentration of Clobazam can be increased when it is combined with Azithromycin.Approved, Illicit
ClomifeneThe serum concentration of Clomifene can be increased when it is combined with Azithromycin.Approved, Investigational
ClomipramineClomipramine may increase the QTc-prolonging activities of Azithromycin.Approved, Vet Approved
ClonidineThe serum concentration of Clonidine can be increased when it is combined with Azithromycin.Approved
ClopidogrelThe serum concentration of Clopidogrel can be increased when it is combined with Azithromycin.Approved, Nutraceutical
ClotrimazoleThe metabolism of Azithromycin can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineAzithromycin may increase the QTc-prolonging activities of Clozapine.Approved
CobicistatThe metabolism of Azithromycin can be decreased when combined with Cobicistat.Approved
CobimetinibThe serum concentration of Cobimetinib can be increased when it is combined with Azithromycin.Approved
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Azithromycin.Approved
ConivaptanThe serum concentration of Azithromycin can be increased when it is combined with Conivaptan.Approved, Investigational
Conjugated Equine EstrogensThe serum concentration of Conjugated Equine Estrogens can be increased when it is combined with Azithromycin.Approved
CrizotinibAzithromycin may increase the QTc-prolonging activities of Crizotinib.Approved
CyclobenzaprineThe metabolism of Cyclobenzaprine can be decreased when combined with Azithromycin.Approved
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Azithromycin.Approved, Investigational, Vet Approved
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Azithromycin.Approved
DabrafenibThe serum concentration of Azithromycin can be decreased when it is combined with Dabrafenib.Approved
DacarbazineThe metabolism of Dacarbazine can be decreased when combined with Azithromycin.Approved, Investigational
DactinomycinThe serum concentration of Dactinomycin can be increased when it is combined with Azithromycin.Approved
DapagliflozinThe serum concentration of Dapagliflozin can be increased when it is combined with Azithromycin.Approved
DarunavirThe metabolism of Azithromycin can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Azithromycin can be increased when it is combined with Dasatinib.Approved, Investigational
DaunorubicinThe serum concentration of Daunorubicin can be increased when it is combined with Azithromycin.Approved
DebrisoquinThe serum concentration of Debrisoquin can be increased when it is combined with Azithromycin.Approved
DeferasiroxThe serum concentration of Azithromycin can be decreased when it is combined with Deferasirox.Approved, Investigational
DegarelixDegarelix may increase the QTc-prolonging activities of Azithromycin.Approved
DelavirdineThe metabolism of Azithromycin can be decreased when combined with Delavirdine.Approved
DesfluraneDesflurane may increase the QTc-prolonging activities of Azithromycin.Approved
DesipramineDesipramine may increase the QTc-prolonging activities of Azithromycin.Approved
DeslanosideThe serum concentration of Deslanoside can be increased when it is combined with Azithromycin.Approved
DexamethasoneThe serum concentration of Azithromycin can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DexfenfluramineThe metabolism of Dexfenfluramine can be decreased when combined with Azithromycin.Approved, Illicit, Withdrawn
DiazepamThe serum concentration of Diazepam can be increased when it is combined with Azithromycin.Approved, Illicit, Vet Approved
DiclofenacThe metabolism of Diclofenac can be decreased when combined with Azithromycin.Approved, Vet Approved
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Azithromycin.Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be increased when it is combined with Azithromycin.Approved
DigitoxinThe serum concentration of Digitoxin can be increased when it is combined with Azithromycin.Approved
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Azithromycin.Approved
DihydroergotamineThe metabolism of Azithromycin can be decreased when combined with Dihydroergotamine.Approved
DihydrotestosteroneThe serum concentration of Dihydrotestosterone can be increased when it is combined with Azithromycin.Illicit
DiltiazemThe metabolism of Azithromycin can be decreased when combined with Diltiazem.Approved
DinoprostoneThe metabolism of Dinoprostone can be decreased when combined with Azithromycin.Approved
DiphenhydramineDiphenhydramine may increase the QTc-prolonging activities of Azithromycin.Approved
DipyridamoleThe serum concentration of Dipyridamole can be increased when it is combined with Azithromycin.Approved
DisopyramideAzithromycin may increase the QTc-prolonging activities of Disopyramide.Approved
DocetaxelThe serum concentration of Docetaxel can be increased when it is combined with Azithromycin.Approved, Investigational
DofetilideAzithromycin may increase the QTc-prolonging activities of Dofetilide.Approved
DolasetronAzithromycin may increase the QTc-prolonging activities of Dolasetron.Approved
DomperidoneAzithromycin may increase the QTc-prolonging activities of Domperidone.Approved, Investigational, Vet Approved
DoxepinDoxepin may increase the QTc-prolonging activities of Azithromycin.Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Azithromycin.Approved, Investigational
DoxycyclineThe metabolism of Azithromycin can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneAzithromycin may increase the QTc-prolonging activities of Dronedarone.Approved
DroperidolAzithromycin may increase the QTc-prolonging activities of Droperidol.Approved, Vet Approved
DuloxetineThe metabolism of Duloxetine can be decreased when combined with Azithromycin.Approved
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Azithromycin.Approved
EfavirenzThe serum concentration of Azithromycin can be decreased when it is combined with Efavirenz.Approved, Investigational
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Azithromycin.Approved, Investigational
EliglustatAzithromycin may increase the QTc-prolonging activities of Eliglustat.Approved
EltrombopagThe metabolism of Eltrombopag can be decreased when combined with Azithromycin.Approved
EnzalutamideThe serum concentration of Azithromycin can be decreased when it is combined with Enzalutamide.Approved
EpinastineThe serum concentration of Epinastine can be increased when it is combined with Azithromycin.Approved, Investigational
ErgotamineThe metabolism of Ergotamine can be decreased when combined with Azithromycin.Approved
EribulinEribulin may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Azithromycin.Approved, Investigational
ErythromycinErythromycin may increase the QTc-prolonging activities of Azithromycin.Approved, Vet Approved
EscitalopramAzithromycin may increase the QTc-prolonging activities of Escitalopram.Approved, Investigational
Eslicarbazepine acetateThe serum concentration of Azithromycin can be decreased when it is combined with Eslicarbazepine acetate.Approved
EstradiolThe serum concentration of Estradiol can be increased when it is combined with Azithromycin.Approved, Investigational, Vet Approved
EstriolThe serum concentration of Estriol can be increased when it is combined with Azithromycin.Approved, Vet Approved
EstroneThe serum concentration of Estrone can be increased when it is combined with Azithromycin.Approved
Estrone sulfateThe metabolism of Estrone sulfate can be decreased when combined with Azithromycin.Approved
EthanolThe metabolism of Ethanol can be decreased when combined with Azithromycin.Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Azithromycin.Approved
Ethyl biscoumacetateThe serum concentration of Ethyl biscoumacetate can be increased when it is combined with Azithromycin.Withdrawn
EtoposideThe serum concentration of Etoposide can be increased when it is combined with Azithromycin.Approved
EtoricoxibThe metabolism of Etoricoxib can be decreased when combined with Azithromycin.Approved, Investigational
EtravirineThe serum concentration of Azithromycin can be decreased when it is combined with Etravirine.Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Azithromycin.Approved
EzetimibeThe serum concentration of Ezetimibe can be increased when it is combined with Azithromycin.Approved
EzogabineEzogabine may increase the QTc-prolonging activities of Azithromycin.Approved
FamotidineFamotidine may increase the QTc-prolonging activities of Azithromycin.Approved
FelbamateFelbamate may increase the QTc-prolonging activities of Azithromycin.Approved
FesoterodineThe serum concentration of Fesoterodine can be increased when it is combined with Azithromycin.Approved
FexofenadineThe serum concentration of Fexofenadine can be increased when it is combined with Azithromycin.Approved
FidaxomicinThe serum concentration of Fidaxomicin can be increased when it is combined with Azithromycin.Approved
FingolimodFingolimod may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
FlecainideAzithromycin may increase the QTc-prolonging activities of Flecainide.Approved, Withdrawn
FluconazoleFluconazole may increase the QTc-prolonging activities of Azithromycin.Approved
FluindioneThe serum concentration of Fluindione can be increased when it is combined with Azithromycin.Investigational
FlunarizineThe metabolism of Flunarizine can be decreased when combined with Azithromycin.Approved
FlunitrazepamThe metabolism of Flunitrazepam can be decreased when combined with Azithromycin.Approved, Illicit
FluorouracilThe metabolism of Fluorouracil can be decreased when combined with Azithromycin.Approved
FluoxetineAzithromycin may increase the QTc-prolonging activities of Fluoxetine.Approved, Vet Approved
FlupentixolAzithromycin may increase the QTc-prolonging activities of Flupentixol.Approved, Withdrawn
FlutamideThe metabolism of Flutamide can be decreased when combined with Azithromycin.Approved
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Azithromycin.Approved
FluvoxamineThe metabolism of Azithromycin can be decreased when combined with Fluvoxamine.Approved, Investigational
FormoterolFormoterol may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
FosamprenavirThe metabolism of Azithromycin can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Azithromycin can be increased when it is combined with Fosaprepitant.Approved
FoscarnetFoscarnet may increase the QTc-prolonging activities of Azithromycin.Approved
FosphenytoinThe metabolism of Azithromycin can be increased when combined with Fosphenytoin.Approved
FrovatriptanThe metabolism of Frovatriptan can be decreased when combined with Azithromycin.Approved, Investigational
Fusidic AcidThe serum concentration of Azithromycin can be increased when it is combined with Fusidic Acid.Approved
Gadobenic acidAzithromycin may increase the QTc-prolonging activities of Gadobenic acid.Approved
GalantamineGalantamine may increase the QTc-prolonging activities of Azithromycin.Approved
GefitinibThe serum concentration of Gefitinib can be increased when it is combined with Azithromycin.Approved, Investigational
GemcitabineThe serum concentration of Gemcitabine can be increased when it is combined with Azithromycin.Approved
GemifloxacinAzithromycin may increase the QTc-prolonging activities of Gemifloxacin.Approved, Investigational
GenisteinThe metabolism of Genistein can be decreased when combined with Azithromycin.Investigational
GoserelinGoserelin may increase the QTc-prolonging activities of Azithromycin.Approved
GranisetronAzithromycin may increase the QTc-prolonging activities of Granisetron.Approved, Investigational
GrazoprevirThe serum concentration of Grazoprevir can be increased when it is combined with Azithromycin.Approved
GrepafloxacinThe serum concentration of Grepafloxacin can be increased when it is combined with Azithromycin.Withdrawn
GuanabenzThe metabolism of Guanabenz can be decreased when combined with Azithromycin.Approved
HaloperidolAzithromycin may increase the QTc-prolonging activities of Haloperidol.Approved
HesperetinThe metabolism of Hesperetin can be decreased when combined with Azithromycin.Approved
HexobarbitalThe metabolism of Hexobarbital can be decreased when combined with Azithromycin.Approved
HistrelinHistrelin may increase the QTc-prolonging activities of Azithromycin.Approved
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Azithromycin.Approved, Vet Approved
HydroxyzineHydroxyzine may increase the QTc-prolonging activities of Azithromycin.Approved
IbandronateIbandronate may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
IbuprofenThe serum concentration of Ibuprofen can be increased when it is combined with Azithromycin.Approved
IbutilideAzithromycin may increase the QTc-prolonging activities of Ibutilide.Approved
IdelalisibThe serum concentration of Azithromycin can be increased when it is combined with Idelalisib.Approved
IloperidoneAzithromycin may increase the QTc-prolonging activities of Iloperidone.Approved
ImatinibThe metabolism of Azithromycin can be decreased when combined with Imatinib.Approved
ImipramineImipramine may increase the QTc-prolonging activities of Azithromycin.Approved
ImiquimodThe metabolism of Imiquimod can be decreased when combined with Azithromycin.Approved, Investigational
IndacaterolIndacaterol may increase the QTc-prolonging activities of Azithromycin.Approved
IndapamideIndapamide may increase the QTc-prolonging activities of Azithromycin.Approved
IndinavirThe metabolism of Azithromycin can be decreased when combined with Indinavir.Approved
IndomethacinThe serum concentration of Indomethacin can be increased when it is combined with Azithromycin.Approved, Investigational
IrinotecanThe serum concentration of Irinotecan can be increased when it is combined with Azithromycin.Approved, Investigational
IsavuconazoniumThe metabolism of Azithromycin can be decreased when combined with Isavuconazonium.Approved, Investigational
IsofluraneIsoflurane may increase the QTc-prolonging activities of Azithromycin.Approved, Vet Approved
IsradipineIsradipine may increase the QTc-prolonging activities of Azithromycin.Approved
ItraconazoleThe metabolism of Azithromycin can be decreased when combined with Itraconazole.Approved, Investigational
IvabradineIvabradine may increase the QTc-prolonging activities of Azithromycin.Approved
IvacaftorThe serum concentration of Azithromycin can be increased when it is combined with Ivacaftor.Approved
IvermectinThe serum concentration of Ivermectin can be increased when it is combined with Azithromycin.Approved, Vet Approved
IxazomibThe metabolism of Ixazomib can be decreased when combined with Azithromycin.Approved
KetazolamThe serum concentration of Ketazolam can be increased when it is combined with Azithromycin.Approved
KetoconazoleThe metabolism of Azithromycin can be decreased when combined with Ketoconazole.Approved, Investigational
LamivudineThe serum concentration of Lamivudine can be increased when it is combined with Azithromycin.Approved, Investigational
LamotrigineThe serum concentration of Lamotrigine can be increased when it is combined with Azithromycin.Approved, Investigational
LansoprazoleThe serum concentration of Lansoprazole can be increased when it is combined with Azithromycin.Approved, Investigational
LapatinibLapatinib may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Azithromycin.Approved
LeflunomideThe metabolism of Leflunomide can be decreased when combined with Azithromycin.Approved, Investigational
LenalidomideThe serum concentration of Lenalidomide can be increased when it is combined with Azithromycin.Approved
LenvatinibAzithromycin may increase the QTc-prolonging activities of Lenvatinib.Approved
LeuprolideLeuprolide may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
LevetiracetamThe serum concentration of Levetiracetam can be increased when it is combined with Azithromycin.Approved, Investigational
LevobupivacaineThe metabolism of Levobupivacaine can be decreased when combined with Azithromycin.Approved
LevofloxacinAzithromycin may increase the QTc-prolonging activities of Levofloxacin.Approved, Investigational
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Azithromycin.Approved
LidocaineThe metabolism of Lidocaine can be decreased when combined with Azithromycin.Approved, Vet Approved
LinagliptinThe serum concentration of Linagliptin can be increased when it is combined with Azithromycin.Approved
LithiumLithium may increase the QTc-prolonging activities of Azithromycin.Approved
LomefloxacinThe metabolism of Lomefloxacin can be decreased when combined with Azithromycin.Approved
LoperamideThe serum concentration of Loperamide can be increased when it is combined with Azithromycin.Approved
LopinavirAzithromycin may increase the QTc-prolonging activities of Lopinavir.Approved
LorcaserinThe metabolism of Lorcaserin can be decreased when combined with Azithromycin.Approved
LosartanThe serum concentration of Losartan can be increased when it is combined with Azithromycin.Approved
LovastatinThe metabolism of Azithromycin can be decreased when combined with Lovastatin.Approved, Investigational
LovastatinAzithromycin may increase the myopathic rhabdomyolysis activities of Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Azithromycin can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Azithromycin can be increased when combined with Lumacaftor.Approved
LumefantrineAzithromycin may increase the QTc-prolonging activities of Lumefantrine.Approved
LumiracoxibThe metabolism of Lumiracoxib can be decreased when combined with Azithromycin.Approved, Investigational
MalathionThe metabolism of Malathion can be decreased when combined with Azithromycin.Approved, Investigational
MannitolThe serum concentration of Mannitol can be increased when it is combined with Azithromycin.Approved, Investigational
MaprotilineMaprotiline may increase the QTc-prolonging activities of Azithromycin.Approved
MefloquineMefloquine may increase the QTc-prolonging activities of Azithromycin.Approved
MelatoninThe metabolism of Melatonin can be decreased when combined with Azithromycin.Approved, Nutraceutical, Vet Approved
MenadioneThe metabolism of Menadione can be decreased when combined with Azithromycin.Approved, Nutraceutical
MephenytoinThe metabolism of Mephenytoin can be decreased when combined with Azithromycin.Investigational, Withdrawn
MethadoneAzithromycin may increase the QTc-prolonging activities of Methadone.Approved
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Azithromycin.Approved
MethotrimeprazineMethotrimeprazine may increase the QTc-prolonging activities of Azithromycin.Approved
MethoxyfluraneThe metabolism of Methoxyflurane can be decreased when combined with Azithromycin.Approved, Vet Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Azithromycin.Approved, Vet Approved
MetoclopramideMetoclopramide may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Azithromycin.Approved, Investigational
MetronidazoleMetronidazole may increase the QTc-prolonging activities of Azithromycin.Approved
MexiletineThe metabolism of Mexiletine can be decreased when combined with Azithromycin.Approved
MianserinThe metabolism of Mianserin can be decreased when combined with Azithromycin.Approved
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Azithromycin.Approved, Illicit
MifepristoneMifepristone may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
MirabegronMirabegron may increase the QTc-prolonging activities of Azithromycin.Approved
MirtazapineMirtazapine may increase the QTc-prolonging activities of Azithromycin.Approved
MitotaneThe serum concentration of Azithromycin can be decreased when it is combined with Mitotane.Approved
MitoxantroneThe serum concentration of Mitoxantrone can be increased when it is combined with Azithromycin.Approved, Investigational
ModafinilThe serum concentration of Azithromycin can be decreased when it is combined with Modafinil.Approved, Investigational
MoexiprilMoexipril may increase the QTc-prolonging activities of Azithromycin.Approved
MorphineThe serum concentration of Morphine can be increased when it is combined with Azithromycin.Approved, Investigational
MoxifloxacinAzithromycin may increase the QTc-prolonging activities of Moxifloxacin.Approved, Investigational
muraglitazarThe metabolism of muraglitazar can be decreased when combined with Azithromycin.Investigational
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Azithromycin.Approved, Investigational
NabumetoneThe metabolism of Nabumetone can be decreased when combined with Azithromycin.Approved
NadololThe serum concentration of Nadolol can be increased when it is combined with Azithromycin.Approved
NafcillinThe serum concentration of Azithromycin can be decreased when it is combined with Nafcillin.Approved
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Azithromycin.Approved
NaloxoneThe serum concentration of Naloxone can be increased when it is combined with Azithromycin.Approved, Vet Approved
NaproxenThe metabolism of Naproxen can be decreased when combined with Azithromycin.Approved, Vet Approved
NefazodoneThe metabolism of Azithromycin can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Azithromycin can be decreased when combined with Nelfinavir.Approved
NelfinavirThe serum concentration of Azithromycin can be increased when it is combined with Nelfinavir.Approved
NetupitantThe serum concentration of Azithromycin can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Azithromycin can be increased when combined with Nevirapine.Approved
NicardipineNicardipine may increase the QTc-prolonging activities of Azithromycin.Approved
NicotineThe metabolism of Nicotine can be decreased when combined with Azithromycin.Approved
NifedipineThe serum concentration of Nifedipine can be increased when it is combined with Azithromycin.Approved
NilotinibAzithromycin may increase the QTc-prolonging activities of Nilotinib.Approved, Investigational
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Azithromycin.Approved
Nitric OxideThe metabolism of Nitric Oxide can be decreased when combined with Azithromycin.Approved
NizatidineThe serum concentration of Nizatidine can be increased when it is combined with Azithromycin.Approved
NorfloxacinNorfloxacin may increase the QTc-prolonging activities of Azithromycin.Approved
NortriptylineNortriptyline may increase the QTc-prolonging activities of Azithromycin.Approved
OctreotideOctreotide may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
OfloxacinAzithromycin may increase the QTc-prolonging activities of Ofloxacin.Approved
OlanzapineOlanzapine may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
OlaparibThe metabolism of Azithromycin can be decreased when combined with Olaparib.Approved
OlodaterolOlodaterol may increase the QTc-prolonging activities of Azithromycin.Approved
OmbitasvirThe serum concentration of Ombitasvir can be increased when it is combined with Azithromycin.Approved
OmeprazoleThe metabolism of Omeprazole can be decreased when combined with Azithromycin.Approved, Investigational, Vet Approved
OndansetronAzithromycin may increase the QTc-prolonging activities of Ondansetron.Approved
OsimertinibThe serum concentration of Azithromycin can be increased when it is combined with Osimertinib.Approved
OuabainThe serum concentration of Ouabain can be increased when it is combined with Azithromycin.Approved
OxaliplatinThe metabolism of Oxaliplatin can be decreased when combined with Azithromycin.Approved, Investigational
OxtriphyllineThe metabolism of Oxtriphylline can be decreased when combined with Azithromycin.Approved
OxytocinOxytocin may increase the QTc-prolonging activities of Azithromycin.Approved, Vet Approved
PaclitaxelThe serum concentration of Paclitaxel can be increased when it is combined with Azithromycin.Approved, Vet Approved
PalbociclibThe serum concentration of Azithromycin can be increased when it is combined with Palbociclib.Approved
PaliperidoneAzithromycin may increase the QTc-prolonging activities of Paliperidone.Approved
PalonosetronThe metabolism of Palonosetron can be decreased when combined with Azithromycin.Approved, Investigational
PanobinostatAzithromycin may increase the QTc-prolonging activities of Panobinostat.Approved, Investigational
PantoprazoleThe metabolism of Pantoprazole can be decreased when combined with Azithromycin.Approved
ParoxetineParoxetine may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
PasireotidePasireotide may increase the QTc-prolonging activities of Azithromycin.Approved
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Azithromycin.Approved
PentamidineAzithromycin may increase the QTc-prolonging activities of Pentamidine.Approved
PentobarbitalThe metabolism of Azithromycin can be increased when combined with Pentobarbital.Approved, Vet Approved
PentoxifyllineThe metabolism of Pentoxifylline can be decreased when combined with Azithromycin.Approved, Investigational
PerflutrenAzithromycin may increase the QTc-prolonging activities of Perflutren.Approved
PerphenazineThe metabolism of Perphenazine can be decreased when combined with Azithromycin.Approved
PhenacetinThe metabolism of Phenacetin can be decreased when combined with Azithromycin.Withdrawn
PhenindioneThe serum concentration of Phenindione can be increased when it is combined with Azithromycin.Approved
PhenobarbitalThe metabolism of Azithromycin can be increased when combined with Phenobarbital.Approved
PhenprocoumonThe serum concentration of Phenprocoumon can be increased when it is combined with Azithromycin.Approved
PhenytoinThe metabolism of Azithromycin 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 Azithromycin.Approved
PimozideAzithromycin may increase the QTc-prolonging activities of Pimozide.Approved
PipotiazineThe metabolism of Pipotiazine can be decreased when combined with Azithromycin.Approved
PirfenidoneThe serum concentration of Pirfenidone can be increased when it is combined with Azithromycin.Investigational
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Azithromycin.Approved
PomalidomideThe serum concentration of Pomalidomide can be increased when it is combined with Azithromycin.Approved
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Azithromycin.Approved
PosaconazoleThe metabolism of Azithromycin can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Azithromycin.Approved
PraziquantelThe metabolism of Praziquantel can be decreased when combined with Azithromycin.Approved, Vet Approved
PrazosinThe serum concentration of Prazosin can be increased when it is combined with Azithromycin.Approved
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Azithromycin.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Azithromycin.Approved, Vet Approved
PrimaquineAzithromycin may increase the QTc-prolonging activities of Primaquine.Approved
PrimidoneThe metabolism of Azithromycin can be increased when combined with Primidone.Approved, Vet Approved
ProcainamideAzithromycin may increase the QTc-prolonging activities of Procainamide.Approved
ProgesteroneThe serum concentration of Progesterone can be increased when it is combined with Azithromycin.Approved, Vet Approved
ProguanilThe metabolism of Proguanil can be decreased when combined with Azithromycin.Approved
PromazineAzithromycin may increase the QTc-prolonging activities of Promazine.Approved, Vet Approved
PromethazinePromethazine may increase the QTc-prolonging activities of Azithromycin.Approved
PropafenoneAzithromycin may increase the QTc-prolonging activities of Propafenone.Approved
PropofolPropofol may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational, Vet Approved
PropranololThe serum concentration of Propranolol can be increased when it is combined with Azithromycin.Approved, Investigational
ProtriptylineProtriptyline may increase the QTc-prolonging activities of Azithromycin.Approved
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Azithromycin.Approved
PyrazinamideThe metabolism of Pyrazinamide can be decreased when combined with Azithromycin.Approved
QuetiapineAzithromycin may increase the QTc-prolonging activities of Quetiapine.Approved
QuinidineAzithromycin may increase the QTc-prolonging activities of Quinidine.Approved
QuinineThe serum concentration of Quinine can be increased when it is combined with Azithromycin.Approved
RamelteonThe metabolism of Ramelteon can be decreased when combined with Azithromycin.Approved, Investigational
RanitidineThe serum concentration of Ranitidine can be increased when it is combined with Azithromycin.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Azithromycin.Approved, Investigational
RasagilineThe metabolism of Rasagiline can be decreased when combined with Azithromycin.Approved
ReserpineThe serum concentration of Reserpine can be increased when it is combined with Azithromycin.Approved
ResveratrolThe metabolism of Resveratrol can be decreased when combined with Azithromycin.Experimental, Investigational
RifabutinThe metabolism of Azithromycin can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Azithromycin can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Azithromycin can be increased when combined with Rifapentine.Approved
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Azithromycin.Approved, Investigational
RilpivirineThe serum concentration of Rilpivirine can be increased when it is combined with Azithromycin.Approved
RiluzoleThe metabolism of Riluzole can be decreased when combined with Azithromycin.Approved, Investigational
RisperidoneRisperidone may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
RitonavirThe metabolism of Azithromycin can be decreased when combined with Ritonavir.Approved, Investigational
RivaroxabanThe serum concentration of Rivaroxaban can be increased when it is combined with Azithromycin.Approved
RizatriptanThe metabolism of Rizatriptan can be decreased when combined with Azithromycin.Approved
RofecoxibThe metabolism of Rofecoxib can be decreased when combined with Azithromycin.Investigational, Withdrawn
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Azithromycin.Approved, Investigational
RopiniroleThe metabolism of Ropinirole can be decreased when combined with Azithromycin.Approved, Investigational
RopivacaineThe metabolism of Ropivacaine can be decreased when combined with Azithromycin.Approved
RotigotineThe metabolism of Rotigotine can be decreased when combined with Azithromycin.Approved
SalbutamolSalbutamol may increase the QTc-prolonging activities of Azithromycin.Approved, Vet Approved
Salicylic acidThe serum concentration of Salicylic acid can be increased when it is combined with Azithromycin.Approved, Vet Approved
SalmeterolSalmeterol may increase the QTc-prolonging activities of Azithromycin.Approved
SaquinavirAzithromycin may increase the QTc-prolonging activities of Saquinavir.Approved, Investigational
SelegilineThe metabolism of Selegiline can be decreased when combined with Azithromycin.Approved, Investigational, Vet Approved
SelexipagThe serum concentration of Selexipag can be increased when it is combined with Azithromycin.Approved
SertralineSertraline may increase the QTc-prolonging activities of Azithromycin.Approved
SevofluraneSevoflurane may increase the QTc-prolonging activities of Azithromycin.Approved, Vet Approved
SildenafilThe metabolism of Azithromycin can be decreased when combined with Sildenafil.Approved, Investigational
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Azithromycin.Approved
SiltuximabThe serum concentration of Azithromycin can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Azithromycin can be increased when it is combined with Simeprevir.Approved
SimvastatinAzithromycin may increase the myopathic rhabdomyolysis activities of Simvastatin.Approved
SitagliptinThe serum concentration of Sitagliptin can be increased when it is combined with Azithromycin.Approved, Investigational
SofosbuvirThe serum concentration of Sofosbuvir can be increased when it is combined with Azithromycin.Approved
SolifenacinSolifenacin may increase the QTc-prolonging activities of Azithromycin.Approved
SorafenibSorafenib may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
SotalolAzithromycin may increase the QTc-prolonging activities of Sotalol.Approved
SparfloxacinThe serum concentration of Sparfloxacin can be increased when it is combined with Azithromycin.Approved
SphingosineThe serum concentration of Sphingosine can be increased when it is combined with Azithromycin.Experimental
St. John's WortThe serum concentration of Azithromycin can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Azithromycin can be increased when it is combined with Stiripentol.Approved
SulfamethoxazoleSulfamethoxazole may increase the QTc-prolonging activities of Azithromycin.Approved
SulfisoxazoleAzithromycin may increase the QTc-prolonging activities of Sulfisoxazole.Approved, Vet Approved
SunitinibSunitinib may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
TacrineThe metabolism of Tacrine can be decreased when combined with Azithromycin.Withdrawn
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Azithromycin.Approved, Investigational
TamoxifenTamoxifen may increase the QTc-prolonging activities of Azithromycin.Approved
Taurocholic AcidThe serum concentration of Taurocholic Acid can be increased when it is combined with Azithromycin.Experimental
Technetium Tc-99m sestamibiThe serum concentration of Technetium Tc-99m sestamibi can be increased when it is combined with Azithromycin.Approved
TelaprevirThe metabolism of Azithromycin can be decreased when combined with Telaprevir.Approved
TelavancinAzithromycin may increase the QTc-prolonging activities of Telavancin.Approved
TelithromycinAzithromycin may increase the QTc-prolonging activities of Telithromycin.Approved
TemafloxacinThe metabolism of Temafloxacin can be decreased when combined with Azithromycin.Withdrawn
TemsirolimusThe serum concentration of Temsirolimus can be increased when it is combined with Azithromycin.Approved
TerbinafineThe metabolism of Terbinafine can be decreased when combined with Azithromycin.Approved, Investigational, Vet Approved
TerbutalineTerbutaline may increase the QTc-prolonging activities of Azithromycin.Approved
TerfenadineAzithromycin may increase the QTc-prolonging activities of Terfenadine.Withdrawn
TetrabenazineAzithromycin may increase the QTc-prolonging activities of Tetrabenazine.Approved
ThalidomideThe metabolism of Thalidomide can be decreased when combined with Azithromycin.Approved, Investigational, Withdrawn
TheobromineThe metabolism of Theobromine can be decreased when combined with Azithromycin.Approved
TheophyllineThe metabolism of Theophylline can be decreased when combined with Azithromycin.Approved
ThiabendazoleThe metabolism of Thiabendazole can be decreased when combined with Azithromycin.Approved, Vet Approved
ThioridazineAzithromycin may increase the QTc-prolonging activities of Thioridazine.Approved
ThiothixeneThiothixene may increase the QTc-prolonging activities of Azithromycin.Approved
TicagrelorThe serum concentration of Ticagrelor can be increased when it is combined with Azithromycin.Approved
TiclopidineThe metabolism of Azithromycin can be decreased when combined with Ticlopidine.Approved
TimololThe serum concentration of Timolol can be increased when it is combined with Azithromycin.Approved
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Azithromycin.Approved
TocilizumabThe serum concentration of Azithromycin can be decreased when it is combined with Tocilizumab.Approved
TolterodineTolterodine may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Azithromycin.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Azithromycin.Approved, Investigational
ToremifeneAzithromycin may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
Trastuzumab emtansineThe serum concentration of Trastuzumab emtansine can be increased when it is combined with Azithromycin.Approved
TrazodoneTrazodone may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
TreprostinilTreprostinil may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
TriamtereneThe metabolism of Triamterene can be decreased when combined with Azithromycin.Approved
TrifluoperazineThe metabolism of Trifluoperazine can be decreased when combined with Azithromycin.Approved
TrimethoprimTrimethoprim may increase the QTc-prolonging activities of Azithromycin.Approved, Vet Approved
TrimipramineTrimipramine may increase the QTc-prolonging activities of Azithromycin.Approved
TriptorelinTriptorelin may increase the QTc-prolonging activities of Azithromycin.Approved, Vet Approved
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Azithromycin.Approved
UmeclidiniumThe serum concentration of Umeclidinium can be increased when it is combined with Azithromycin.Approved
VandetanibAzithromycin may increase the QTc-prolonging activities of Vandetanib.Approved
VardenafilVardenafil may increase the QTc-prolonging activities of Azithromycin.Approved
VecuroniumThe serum concentration of Vecuronium can be increased when it is combined with Azithromycin.Approved
VemurafenibAzithromycin may increase the QTc-prolonging activities of Vemurafenib.Approved
VenetoclaxThe serum concentration of Venetoclax can be increased when it is combined with Azithromycin.Approved
VenlafaxineVenlafaxine may increase the QTc-prolonging activities of Azithromycin.Approved
VerapamilThe metabolism of Azithromycin can be decreased when combined with Verapamil.Approved
VilanterolVilanterol may increase the QTc-prolonging activities of Azithromycin.Approved
VinblastineThe serum concentration of Vinblastine can be increased when it is combined with Azithromycin.Approved
VincristineThe serum concentration of Vincristine can be increased when it is combined with Azithromycin.Approved, Investigational
VismodegibThe serum concentration of Vismodegib can be increased when it is combined with Azithromycin.Approved
VoriconazoleThe metabolism of Azithromycin can be decreased when combined with Voriconazole.Approved, Investigational
VorinostatVorinostat may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
WarfarinThe metabolism of Warfarin can be decreased when combined with Azithromycin.Approved
ZidovudineThe serum concentration of Zidovudine can be increased when it is combined with Azithromycin.Approved
ZileutonThe metabolism of Zileuton can be decreased when combined with Azithromycin.Approved, Investigational, Withdrawn
ZiprasidoneAzithromycin may increase the QTc-prolonging activities of Ziprasidone.Approved
ZolmitriptanThe metabolism of Zolmitriptan can be decreased when combined with Azithromycin.Approved, Investigational
ZolpidemThe metabolism of Zolpidem can be decreased when combined with Azithromycin.Approved
ZuclopenthixolAzithromycin may increase the QTc-prolonging activities of Zuclopenthixol.Approved, Investigational
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.
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 CodesJ01FA10S01AA26J01RA07
AHFS Codes
  • 08:12.12.92
PDB EntriesNot Available
FDA labelDownload (76.3 KB)
MSDSDownload (73.9 KB)
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
Injection, powder, lyophilized, for solutionIntravenous500 mg/5mL
Powder, for suspensionOral1 g/1
Powder, for suspensionOral100 mg/5mL
Powder, for suspensionOral1200 mg/30mL
Powder, for suspensionOral200 mg/5mL
Powder, for suspensionOral200 mg
Powder, for suspensionOral900 mg/22.5mL
TabletOral500 mg/1
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral600 mg/1
Tablet, film coatedOral500 mg/1
Injection, powder, lyophilized, for solutionIntravenous500 mg/10mL
TabletOral250 mg/1
TabletOral600 mg/1
TabletOral500 mg
Powder, for suspensionOral100 mg
Powder, for solutionOral200 mg
TabletOral250 mg
TabletOral600 mg
CapsuleOral250 mg
Powder, for solutionIntravenous500 mg
Powder, for suspensionOral2 g/60mL
Granule, 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
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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

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 ]

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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on December 08, 2016 11:46