Identification

Name
Azithromycin
Accession Number
DB00207  (APRD00397)
Type
Small Molecule
Groups
Approved
Description

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

Structure
Thumb
Synonyms
  • Azithromycine
  • Azithromycinum
  • Azitromicina
External IDs
CP 62993 / CP-62,993 / CP-62993 / XZ 405 / XZ 450 / XZ-450
Product Ingredients
IngredientUNIICASInChI Key
Azithromycin dihydrate5FD1131I7S117772-70-0SRMPHJKQVUDLQE-KUJJYQHYSA-N
Azithromycin monohydrateJTE4MNN1MD121470-24-4HQUPLSLYZHKKQT-WVVFQGGUSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act AzithromycinTablet600 mgOralActavis Pharma Company2005-11-02Not applicableCanada
Act AzithromycinTablet250 mgOralActavis Pharma Company2005-11-02Not applicableCanada
Ava-azithromycinPowder, for suspension100 mgOralAvanstra Inc2011-09-192014-08-21Canada
Ava-azithromycinPowder, for suspension200 mgOralAvanstra Inc2011-09-192014-08-21Canada
Ava-azithromycinTablet250 mgOralAvanstra Inc2011-09-192014-08-21Canada
AzaSITESolution1 %OphthalmicInsite Vision IncorporatedNot applicableNot applicableCanada
AzaSITESolution / drops10 mg/mLOphthalmicAkorn2014-05-14Not applicableUs
AzaSITESolution1 %OphthalmicInspire Pharmaceuticals, Inc.Not applicableNot applicableCanada
AzithromycinPowder, for suspension100 mgOralDominion PharmacalNot applicableNot applicableCanada
AzithromycinTablet250 mgOral4513347 Canada Inc.Not applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-azithromycinTablet250 mgOralApotex Corporation2005-11-02Not applicableCanada
Apo-azithromycin ZTablet250 mgOralApotex Corporation2014-03-06Not applicableCanada
AzithromycinTablet, film coated250 mg/1OralDispensing Solutions, Inc.2008-02-11Not applicableUs
AzithromycinTablet, film coated500 mg/1OralNucare Pharmaceuticals, Inc.2006-01-06Not applicableUs
AzithromycinTablet, film coated500 mg/1OralProficient Rx LP2005-11-14Not applicableUs
AzithromycinTablet, film coated250 mg/1OralAvera Mc Kennan Hospital2015-03-02Not applicableUs
AzithromycinTablet, film coated250 mg/1OralPd Rx Pharmaceuticals, Inc.2005-11-142017-10-26Us
AzithromycinInjection, powder, lyophilized, for solution100 mg/mLIntravenousPliva, Inc.2007-08-172016-10-13Us
AzithromycinTablet, film coated600 mg/1OralRemedy Repack2017-08-25Not applicableUs
AzithromycinFor suspension100 mg/5mLOralLupin Pharmaceuticals2017-09-27Not applicableUs
International/Other Brands
Azenil / Azibiot / Azifast / Azigram / Azimakrol / Azin / Azithrocin / Azitromax / Azitromin / Aztrin / Hemomycin / Misultina / Penalox / Sumamed / Vinzam / Zifin / Zitrocin / Zitrotek
Categories
UNII
J2KLZ20U1M
CAS number
83905-01-5
Weight
Average: 748.9845
Monoisotopic: 748.508525778
Chemical Formula
C38H72N2O12
InChI Key
MQTOSJVFKKJCRP-BICOPXKESA-N
InChI
InChI=1S/C38H72N2O12/c1-15-27-38(10,46)31(42)24(6)40(13)19-20(2)17-36(8,45)33(52-35-29(41)26(39(11)12)16-21(3)48-35)22(4)30(23(5)34(44)50-27)51-28-18-37(9,47-14)32(43)25(7)49-28/h20-33,35,41-43,45-46H,15-19H2,1-14H3/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
IUPAC Name
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
SMILES

Pharmacology

Indication

For 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
Pharmacodynamics

Azithromycin, 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 action

Azithromycin binds to the 50S subunit of the 70S bacterial ribosomes, and therefore inhibits RNA-dependent protein synthesis in bacterial cells.

TargetActionsOrganism
A23S rRNA
inhibitor
Enteric bacteria and other eubacteria
A50S ribosomal protein L4
inhibitor
Escherichia coli O157:H7
A50S ribosomal protein L22
inhibitor
Escherichia coli O157:H7
UProtein-arginine deiminase type-4Not AvailableHuman
Absorption

Bioavailability 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 binding

Serum 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 elimination

Biliary excretion of azithromycin, predominantly as unchanged drug, is a major route of elimination.

Half life

68 hours

Clearance
  • apparent plasma cl=630 mL/min [following single 500 mg oral and i.v. doses]
Toxicity

Potentially 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
PathwayCategory
Azithromycin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Azithromycin.Approved
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Azithromycin.Approved
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be increased when it is combined with Azithromycin.Approved
AcetyldigoxinThe serum concentration of Acetyldigoxin can be increased when it is combined with Azithromycin.Experimental
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
AlfuzosinAlfuzosin may increase the QTc-prolonging activities of 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
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
AnagrelideThe metabolism of Anagrelide can be decreased when combined with Azithromycin.Approved
AntipyrineThe metabolism of Antipyrine can be decreased when combined with Azithromycin.Approved
ApixabanThe metabolism of Apixaban can be decreased when 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, Investigational
AsenapineThe metabolism of Asenapine can be decreased when combined with Azithromycin.Approved
AtazanavirThe metabolism of Azithromycin can be decreased when combined with Atazanavir.Approved, Investigational
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 metabolism of Axitinib can be decreased when combined with Azithromycin.Approved, Investigational
AzelastineThe metabolism of Azelastine can be decreased when combined with Azithromycin.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine 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
BetaxololThe metabolism of Betaxolol can be decreased when combined with Azithromycin.Approved
BoceprevirThe metabolism of Azithromycin can be decreased when combined with Boceprevir.Approved, Withdrawn
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 risk or severity of adverse effects can be increased when Bromocriptine 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
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Azithromycin.Approved
CaffeineThe metabolism of Caffeine can be decreased when combined with Azithromycin.Approved
CarbamazepineThe metabolism of Azithromycin can be increased when combined with Carbamazepine.Approved, Investigational
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
CinacalcetThe metabolism of Cinacalcet can be decreased when combined with Azithromycin.Approved
CinnarizineThe metabolism of Cinnarizine can be decreased when combined with Azithromycin.Approved, Investigational
CiprofloxacinAzithromycin may increase the QTc-prolonging activities of Ciprofloxacin.Approved, Investigational
CisaprideThe metabolism of Cisapride can be decreased when combined with Azithromycin.Approved, Investigational, Withdrawn
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, Investigational, Vet Approved
ClevidipineThe metabolism of Clevidipine can be decreased when combined with Azithromycin.Approved
ClomipramineClomipramine may increase the QTc-prolonging activities of Azithromycin.Approved, Vet Approved
ClonidineThe metabolism of Clonidine can be decreased when combined with Azithromycin.Approved
ClopidogrelThe metabolism of Clopidogrel can be decreased when combined with Azithromycin.Approved, Nutraceutical
ClorindioneThe serum concentration of Clorindione can be increased when it is combined with Azithromycin.Experimental
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
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 estrogensThe metabolism of Conjugated estrogens can be decreased when 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
CymarinThe serum concentration of Cymarin can be increased when it is combined with Azithromycin.Experimental
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
DapagliflozinThe metabolism of Dapagliflozin can be decreased when 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 metabolism of Daunorubicin can be decreased when 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
DeutetrabenazineThe metabolism of Deutetrabenazine can be decreased when combined with Azithromycin.Approved, Investigational
DexfenfluramineThe metabolism of Dexfenfluramine can be decreased when combined with Azithromycin.Approved, Illicit, Investigational, Withdrawn
DiazepamThe metabolism of Diazepam can be decreased when 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
DigitoxinThe serum concentration of Digitoxin can be increased when it is combined with Azithromycin.Approved, Investigational
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Azithromycin.Approved
Digoxin Immune Fab (Ovine)The serum concentration of Digoxin Immune Fab (Ovine) can be increased when it is combined with Azithromycin.Approved
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Azithromycin.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Azithromycin.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Azithromycin.Experimental
DihydroergotamineThe metabolism of Azithromycin can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Azithromycin can be decreased when combined with Diltiazem.Approved
DinoprostoneThe metabolism of Dinoprostone can be decreased when combined with Azithromycin.Approved
DiphenadioneThe serum concentration of Diphenadione can be increased when it is combined with Azithromycin.Experimental
DiphenhydramineDiphenhydramine may increase the QTc-prolonging activities of Azithromycin.Approved
DisopyramideAzithromycin may increase the QTc-prolonging activities of Disopyramide.Approved
DofetilideAzithromycin may increase the QTc-prolonging activities of Dofetilide.Approved
DolasetronAzithromycin may increase the QTc-prolonging activities of Dolasetron.Approved
DomperidoneThe metabolism of Domperidone can be decreased when combined with Azithromycin.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
DronedaroneThe metabolism of Azithromycin can be decreased when combined with 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
EliglustatAzithromycin may increase the QTc-prolonging activities of Eliglustat.Approved
EltrombopagThe metabolism of Eltrombopag can be decreased when combined with Azithromycin.Approved
EnasidenibThe metabolism of Enasidenib can be decreased when combined with Azithromycin.Approved
EnzalutamideThe serum concentration of Azithromycin can be decreased when it is combined with Enzalutamide.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Azithromycin.Approved
ErgotamineThe metabolism of Ergotamine can be decreased when combined with Azithromycin.Approved
EribulinEribulin may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
ErlotinibThe metabolism of Erlotinib can be decreased when 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
EstradiolThe metabolism of Estradiol can be decreased when combined with Azithromycin.Approved, Investigational, Vet Approved
EstroneThe metabolism of Estrone can be decreased when 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
Ethyl biscoumacetateThe serum concentration of Ethyl biscoumacetate can be increased when it is combined with Azithromycin.Withdrawn
EtoposideThe metabolism of Etoposide can be decreased when combined with Azithromycin.Approved
EtoricoxibThe metabolism of Etoricoxib can be decreased when combined with Azithromycin.Approved, Investigational
EverolimusThe serum concentration of Everolimus 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
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
FluoxetineThe metabolism of Fluoxetine can be decreased when combined with Azithromycin.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
FluvastatinThe serum concentration of Fluvastatin 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
GemifloxacinAzithromycin may increase the QTc-prolonging activities of Gemifloxacin.Approved, Investigational
GenisteinThe metabolism of Genistein can be decreased when combined with Azithromycin.Investigational
GitoformateThe serum concentration of Gitoformate can be increased when it is combined with Azithromycin.Experimental
GoserelinGoserelin may increase the QTc-prolonging activities of Azithromycin.Approved
GranisetronAzithromycin may increase the QTc-prolonging activities of Granisetron.Approved, Investigational
GrepafloxacinThe metabolism of Grepafloxacin can be decreased when combined with Azithromycin.Investigational, Withdrawn
GuanabenzThe metabolism of Guanabenz can be decreased when combined with Azithromycin.Approved, Investigational
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
HydroxyzineHydroxyzine may increase the QTc-prolonging activities of Azithromycin.Approved
IbandronateIbandronate may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
IbutilideAzithromycin may increase the QTc-prolonging activities of Ibutilide.Approved
IcotinibThe metabolism of Icotinib can be decreased when combined with Azithromycin.Approved, Investigational
IdelalisibThe serum concentration of Azithromycin can be increased when it is combined with Idelalisib.Approved
IloperidoneThe metabolism of Iloperidone can be decreased when combined with Azithromycin.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
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
KetoconazoleThe metabolism of Azithromycin can be decreased when combined with Ketoconazole.Approved, Investigational
Lanatoside CThe serum concentration of Lanatoside C can be increased when it is combined with Azithromycin.Experimental
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
LenvatinibAzithromycin may increase the QTc-prolonging activities of Lenvatinib.Approved
LeuprolideLeuprolide may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
LevobupivacaineThe metabolism of Levobupivacaine can be decreased when combined with Azithromycin.Approved, Investigational
LevofloxacinAzithromycin may increase the QTc-prolonging activities of Levofloxacin.Approved, Investigational
LidocaineThe metabolism of Lidocaine can be decreased when combined with Azithromycin.Approved, Vet Approved
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Azithromycin.Approved, Investigational
LithiumLithium may increase the QTc-prolonging activities of Azithromycin.Approved
LomefloxacinThe metabolism of Lomefloxacin can be decreased when combined with Azithromycin.Approved, Investigational
LopinavirThe metabolism of Azithromycin can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Lorcaserin can be decreased when combined with Azithromycin.Approved
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
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Azithromycin.Illicit, Investigational, Withdrawn
MalathionThe metabolism of Malathion can be decreased when 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
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Azithromycin.Experimental
MethadoneAzithromycin may increase the QTc-prolonging activities of Methadone.Approved
MethotrimeprazineMethotrimeprazine may increase the QTc-prolonging activities of Azithromycin.Approved
MethoxyfluraneThe metabolism of Methoxyflurane can be decreased when combined with Azithromycin.Approved, Investigational, Vet Approved
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Azithromycin.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Azithromycin.Approved
MetildigoxinThe serum concentration of Metildigoxin can be increased when it is combined with Azithromycin.Experimental
MetoclopramideMetoclopramide may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
MetronidazoleMetronidazole may increase the QTc-prolonging activities of Azithromycin.Approved
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Azithromycin.Experimental
MexiletineThe metabolism of Mexiletine can be decreased when combined with Azithromycin.Approved
MianserinThe metabolism of Mianserin can be decreased when combined with Azithromycin.Approved, Investigational
MifepristoneThe serum concentration of Azithromycin can be increased when it is combined with Mifepristone.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
MoexiprilMoexipril may increase the QTc-prolonging activities of Azithromycin.Approved
MoxifloxacinAzithromycin may increase the QTc-prolonging activities of Moxifloxacin.Approved, Investigational
muraglitazarThe metabolism of muraglitazar can be decreased when combined with Azithromycin.Investigational
NabumetoneThe metabolism of Nabumetone can be decreased when combined with Azithromycin.Approved
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Azithromycin.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 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
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Azithromycin.Approved, Investigational
NicotineThe metabolism of Nicotine can be decreased when combined with Azithromycin.Approved
NifedipineThe metabolism of Nifedipine can be decreased when combined with Azithromycin.Approved
NilotinibThe metabolism of Azithromycin can be decreased when combined with 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
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
OleandrinThe serum concentration of Oleandrin can be increased when it is combined with Azithromycin.Experimental, Investigational
OlodaterolOlodaterol may increase the QTc-prolonging activities of 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
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
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Azithromycin.Approved, Investigational, Vet Approved, Withdrawn
PerphenazineThe metabolism of Perphenazine can be decreased when combined with Azithromycin.Approved
PeruvosideThe serum concentration of Peruvoside can be increased when it is combined with Azithromycin.Experimental
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, Investigational
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, Investigational
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, Investigational
PirfenidoneThe serum concentration of Pirfenidone can be increased when it is combined with Azithromycin.Approved, Investigational
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Azithromycin.Approved
PomalidomideThe metabolism of Pomalidomide can be decreased when 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
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 metabolism of Progesterone can be decreased when 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 metabolism of Propranolol can be decreased when combined with Azithromycin.Approved, Investigational
ProscillaridinThe serum concentration of Proscillaridin can be increased when it is combined with Azithromycin.Experimental
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 metabolism of Ranitidine can be decreased when 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
ResveratrolThe metabolism of Resveratrol can be decreased when combined with Azithromycin.Approved, Experimental, Investigational
RibociclibThe risk or severity of QTc prolongation can be increased when Ribociclib is combined with Azithromycin.Approved
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
RitonavirRitonavir may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
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
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
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Azithromycin.Approved
RotigotineThe metabolism of Rotigotine can be decreased when combined with Azithromycin.Approved
RucaparibThe metabolism of Rucaparib can be decreased when combined with Azithromycin.Approved, Investigational
SalbutamolSalbutamol may increase the QTc-prolonging activities of 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
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
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
St. John's WortThe serum concentration of Azithromycin can be decreased when it is combined with St. John's Wort.Investigational, 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.Investigational, 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
TelaprevirThe metabolism of Azithromycin can be decreased when combined with Telaprevir.Approved, Withdrawn
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
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
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Azithromycin.Experimental
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, Investigational
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
ThioridazineThe metabolism of Thioridazine can be decreased when combined with Azithromycin.Approved, Withdrawn
ThiothixeneThiothixene may increase the QTc-prolonging activities of Azithromycin.Approved
TiclopidineThe metabolism of Azithromycin can be decreased when combined with Ticlopidine.Approved
TioclomarolThe serum concentration of Tioclomarol can be increased when it is combined with Azithromycin.Experimental
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
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Azithromycin.Approved, Investigational
ToremifeneThe metabolism of Toremifene can be decreased when combined with Azithromycin.Approved, Investigational
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
UbidecarenoneThe serum concentration of Ubidecarenone can be increased when it is combined with Azithromycin.Approved, Experimental
UlipristalThe metabolism of Ulipristal can be decreased when combined with Azithromycin.Approved
VadimezanThe metabolism of Vadimezan can be decreased when combined with Azithromycin.Investigational
VandetanibAzithromycin may increase the QTc-prolonging activities of Vandetanib.Approved
VardenafilVardenafil may increase the QTc-prolonging activities of Azithromycin.Approved
VemurafenibAzithromycin may increase the QTc-prolonging activities of Vemurafenib.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
VincristineThe serum concentration of Vincristine can be increased when it is combined with Azithromycin.Approved, Investigational
VoriconazoleThe metabolism of Azithromycin can be decreased when combined with Voriconazole.Approved, Investigational
VorinostatVorinostat may increase the QTc-prolonging activities of Azithromycin.Approved, Investigational
VoxilaprevirThe metabolism of Voxilaprevir can be decreased when combined with Azithromycin.Approved
WarfarinThe metabolism of Warfarin can be decreased when combined with Azithromycin.Approved
ZileutonThe metabolism of Zileuton can be decreased when combined with Azithromycin.Approved, Investigational, Withdrawn
ZiprasidoneThe metabolism of Azithromycin can be decreased when combined with 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
Human Metabolome Database
HMDB14352
KEGG Compound
C06838
PubChem Compound
447043
PubChem Substance
46507743
ChemSpider
10482163
BindingDB
50373918
ChEBI
2955
ChEMBL
CHEMBL529
Therapeutic Targets Database
DNC001539
PharmGKB
PA448519
HET
ZIT
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Azithromycin
ATC Codes
J01FA10 — AzithromycinS01AA26 — AzithromycinJ01RA07 — Azithromycin, fluconazole and secnidazole
AHFS Codes
  • 52:04.04 — Antibacterials
  • 08:12.12.92 — Other Macrolides
PDB Entries
1m1k / 1nwy / 1yhq / 4v7y / 5igi / 5igv / 5uxc / 5uxd
FDA label
Download (76.3 KB)
MSDS
Download (73.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingTreatmentAcne Vulgaris1
0RecruitingTreatmentOsteomyelitis1
0RecruitingTreatmentRespiratory Syncytial Virus (RSV)1
1CompletedNot AvailableFasting1
1CompletedNot AvailableHealthy Volunteers7
1CompletedNot AvailableProphylaxis of Malaria1
1CompletedBasic ScienceInflammatory Reaction1
1CompletedBasic SciencePharmacokinetics1
1CompletedBasic SciencePrebiotics / Probiotics / Quorum Sensing / Sepsis1
1CompletedHealth Services ResearchPlasmodium Infections1
1CompletedTreatmentBacterial Infections / Human Immunodeficiency Virus (HIV) Infections2
1CompletedTreatmentBacterial Infections / Ureaplasma1
1CompletedTreatmentDrug Interactions1
1CompletedTreatmentEye Infections, Bacterial5
1CompletedTreatmentGonorrhoea1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Toxoplasmosis, Cerebral1
1CompletedTreatmentInfection NOS1
1Not Yet RecruitingPreventionHuman Immunodeficiency Virus (HIV) / Plasmodium Infections / Pregnant1
1RecruitingOtherPhysiological Response to Antibiotics1
1RecruitingPreventionAcute Chest Syndrome / Sickle Cell Disorders1
1RecruitingTreatmentConjunctivitis, Bacterial1
1, 2Not Yet RecruitingTreatmentEbola Virus Disease1
1, 2RecruitingNot AvailableSickle Cell Disorders1
1, 2TerminatedPreventionBacteria Infection / Respiratory Tract Infections (RTI)1
1, 2WithdrawnPreventionMalaria caused by Plasmodium falciparum1
1, 2WithdrawnTreatmentGraves Ophthalmopathy1
2Active Not RecruitingTreatmentChildhood Asthma With Acute Exacerbation1
2Active Not RecruitingTreatmentChronic Periodontitis1
2CompletedNot AvailableSinusitis1
2CompletedBasic SciencePharmacokinetics1
2CompletedPreventionChronic Lung Disease of Prematurity1
2CompletedTreatmentAcute Otitis Media1
2CompletedTreatmentBacterial Infections / Human Immunodeficiency Virus (HIV) Infections / Pneumonia, Pneumocystis Carinii1
2CompletedTreatmentChlamydia Trachomatis Infection1
2CompletedTreatmentChronic Periodontitis1
2CompletedTreatmentDisseminated Sclerosis1
2CompletedTreatmentEsophageal Motility Disorders1
2CompletedTreatmentFatty Liver / Insulin Resistance / Liver Dysfunction1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare2
2CompletedTreatmentMalaria caused by Plasmodium falciparum1
2CompletedTreatmentObliterative Bronchiolitis1
2CompletedTreatmentObsessive Compulsive Disorder (OCD) / PANS / Pediatric Autoimmune Neuropsychiatric Disorders Associated With Streptococcal Infections1
2CompletedTreatmentOnchocerciasis1
2CompletedTreatmentPlasmodium Falciparum Malaria1
2CompletedTreatmentPosterior Blepharitis1
2CompletedTreatmentRsv Bronchiolitis1
2CompletedTreatmentUncomplicated Falciparum Malaria1
2CompletedTreatmentUrethritis1
2CompletedTreatmentBacterial blepharitis3
2Not Yet RecruitingTreatmentTuberculosis, Pulmonary1
2RecruitingTreatmentAsthma Bronchial1
2RecruitingTreatmentChlamydial Infections1
2RecruitingTreatmentSarcoidosis; Antimycobacterial Therapy1
2RecruitingTreatmentUreaplasma Infections1
2TerminatedPreventionBronchiectasis / Chronic Bronchitis / Pulmonary Diseases1
2TerminatedPreventionChronic Obstructive Pulmonary Disease (COPD) / Tracheostomy care1
2TerminatedPreventionCryptogenic Organizing Pneumonia / Lung Diseases, Interstitial / Obliterative Bronchiolitis / Respiratory Tract Infections (RTI)1
2TerminatedPreventionPseudomonas Infections / Ventilator-Associated Pneumonia (VAP)1
2TerminatedTreatmentAsthma Bronchial / Chronic Obstructive Pulmonary Disease (COPD)1
2TerminatedTreatmentGastroparesis1
2TerminatedTreatmentMalaria caused by Plasmodium falciparum1
2TerminatedTreatmentPharyngitis / Tonsillitis1
2TerminatedTreatmentPosterior Blepharoconjunctivitis1
2TerminatedTreatmentBacterial blepharitis1
2Unknown StatusTreatmentAcne1
2Unknown StatusTreatmentCystic Fibrosis (CF)1
2Unknown StatusTreatmentPediatric Autoimmune Neuropsychiatric Disorders Associated With Streptococcal Infections1
2Unknown StatusTreatmentPlasmodium Infections1
2WithdrawnTreatmentMeibomian Gland Dysfunction (MGD)1
2, 3CompletedTreatmentMalaria caused by Plasmodium falciparum2
2, 3CompletedTreatmentPlasmodium Falciparum Malaria1
2, 3RecruitingScreeningLow Risk of Preterm Delivery1
2, 3RecruitingTreatmentRespiratory Syncytial Virus, Bronchiolitis1
2, 3TerminatedTreatmentLeishmaniasis, Cutaneous1
2, 3TerminatedTreatmentMalaria caused by Plasmodium falciparum1
2, 3WithdrawnTreatmentTrachoma1
3Active Not RecruitingPreventionMalignant Hematological Diseases1
3Active Not RecruitingTreatmentCystic Fibrosis (CF)1
3Active Not RecruitingTreatmentNon Cystic Fibrosis Bronchiectasis in Children1
3Active Not RecruitingTreatmentYaws1
3CompletedPreventionAnemias / Malaria in Pregnancy / Sexually Transmitted Infections (STIs)1
3CompletedPreventionCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Heart Diseases / Myocardial Infarction (MI)1
3CompletedPreventionNeonatal Infections1
3CompletedTreatmentAbdominal Pain (AP) / Diarrhea / Fevers / Vomiting1
3CompletedTreatmentAsthma Bronchial3
3CompletedTreatmentAsthma Bronchial / Wheezing1
3CompletedTreatmentBlepharoconjunctivitis1
3CompletedTreatmentChlamydial Infections1
3CompletedTreatmentCholera2
3CompletedTreatmentChronic Bronchitis1
3CompletedTreatmentChronic Bronchitis / Chronic Obstructive Pulmonary Disease (COPD) / Coughing1
3CompletedTreatmentCommunity Acquired Pneumonia (CAP)1
3CompletedTreatmentConjunctivitis, Bacterial3
3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare / Mycoses1
3CompletedTreatmentNeglected Tropical Disease / Treponema Infection / Yaws1
3CompletedTreatmentOtitis Media (OM)1
3CompletedTreatmentPelvic Inflammatory Disease (PID)1
3CompletedTreatmentPharyngitis / Tonsillitis1
3CompletedTreatmentPlasmodium Falciparum Infection1
3CompletedTreatmentPlasmodium Infections2
3CompletedTreatmentPneumonia2
3CompletedTreatmentReactive Arthritis / Reiter's Disease1
3CompletedTreatmentSyphilis1
3CompletedTreatmentTrachoma1
3CompletedTreatmentUncomplicated Urogenital Gonorrhea1
3CompletedTreatmentUrethritis1
3CompletedTreatmentYaws1
3CompletedTreatmentBacterial blepharitis2
3Not Yet RecruitingPreventionPlasmodium Infections / Respiratory Tract Infections (RTI)1
3Not Yet RecruitingTreatmentLung Infection / Mycobacterium avium complex infection1
3RecruitingPreventionBronchiectasis / Cystic Fibrosis (CF)1
3RecruitingTreatmentChronic Cough (CC)1
3RecruitingTreatmentChronic Lung Diseases / Human Immunodeficiency Virus (HIV) Infections1
3RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)3
3RecruitingTreatmentDiarrhea1
3RecruitingTreatmentPreterm Premature Rupture of Membranes (PPROM)1
3RecruitingTreatmentUndifferentiated Febrile Illness1
3TerminatedTreatmentAsymptomatic Parasitemia In Pregnancy1
3TerminatedTreatmentCervicitis / Vaginitis Bacterial1
3TerminatedTreatmentOtitis Media, Purulent / Otitis Media, Suppurative1
3Unknown StatusNot AvailableChronic Obstructive Pulmonary Disease (COPD)1
3Unknown StatusTreatmentBronchiectasis / Inflammatory Reaction1
3WithdrawnPreventionChronic Lung Disease of Prematurity1
3WithdrawnPreventionPreterm Premature Ruptured Membranes1
3WithdrawnTreatmentBlepharoconjunctivitis1
3WithdrawnTreatmentCommunity Acquired Pneumonia (CAP)1
4Active Not RecruitingTreatmentChild's Development1
4Active Not RecruitingTreatmentChronic Rhinosinusitis / High-risk Patients1
4Active Not RecruitingTreatmentImpetigo / Scabies / Yaws1
4CompletedNot AvailableHealthy Volunteers1
4CompletedNot AvailablePregnancy1
4CompletedNot AvailableRespiratory Tract Infections (RTI)1
4CompletedPreventionBronchiolitis Obliterans Syndrome (BOS) / Lymphocytic Bronchiolitis / Rejection, Transplant / Respiratory Tract Infections (RTI)1
4CompletedPreventionTrichiasis1
4CompletedSupportive CareBacterial Infections / Cataract Extraction / Eye Infections1
4CompletedSupportive CareBacterial Infections / Eye Infections2
4CompletedTreatmentAcute Otitis Media1
4CompletedTreatmentAsthma Bronchial3
4CompletedTreatmentBacterial Vaginosis (BV)1
4CompletedTreatmentBronchiectasis1
4CompletedTreatmentChlamydia Trachomatis / Human Immunodeficiency Virus (HIV) / Neisseria Gonorrhoeae Infection1
4CompletedTreatmentChlamydia Trachomatis / Trachoma1
4CompletedTreatmentChlamydial Infections / Trachoma1
4CompletedTreatmentCommunity Acquired Pneumonia (CAP)1
4CompletedTreatmentContact Lens Dry Eye1
4CompletedTreatmentCrohn's Disease (CD)1
4CompletedTreatmentCystic Fibrosis (CF)2
4CompletedTreatmentDiarrhea1
4CompletedTreatmentDisorders Related to Lung Transplantation1
4CompletedTreatmentDry Eye Syndrome (DES)1
4CompletedTreatmentGonorrhoea1
4CompletedTreatmentH-pylori / Indigestion / Peptic Ulcers1
4CompletedTreatmentLymphocytic Bronchi(Oli)Tis Post-lung Transplantation1
4CompletedTreatmentOveractive Bladder1
4CompletedTreatmentPneumonia1
4CompletedTreatmentSinusitis2
4CompletedTreatmentTonsillitis1
4CompletedTreatmentTrachoma1
4CompletedTreatmentBacterial blepharitis4
4Enrolling by InvitationTreatmentCystic Fibrosis (CF)1
4Not Yet RecruitingBasic ScienceMicrobial Colonization1
4Not Yet RecruitingDiagnosticHelminth Infection1
4Not Yet RecruitingPreventionFlu caused by Influenza1
4Not Yet RecruitingTreatmentDry Eye Syndromes / Meibomian Gland Dysfunction (MGD)1
4Not Yet RecruitingTreatmentTrachoma1
4RecruitingPreventionClinical Efficacy / Drug Kinetics / Infections, Plasmodia / Pregnancy1
4RecruitingPreventionTrachoma1
4RecruitingTreatmentAsthma Bronchial1
4RecruitingTreatmentChildhood Mortality3
4RecruitingTreatmentCo-Infection / Diarrhea / Malnutrition / Mortality / Plasmodium Infections / Pneumonia1
4RecruitingTreatmentCommunity Acquired Pneumonia (CAP)1
4RecruitingTreatmentCystic Fibrosis (CF)1
4TerminatedNot AvailableHealthy Volunteers1
4TerminatedDiagnosticMaxillary Sinusitis1
4TerminatedTreatmentAsthma Bronchial1
4TerminatedTreatmentChronic Bronchitis / Pneumonia / Respiratory Tract Infections (RTI)1
4TerminatedTreatmentPneumonia1
4Unknown StatusTreatmentBartonella Infections / Cat scratch disease1
4Unknown StatusTreatmentCervicitis / Chlamydia Trachomatis / Genital Mycoplasma Infection / Urethritis1
4Unknown StatusTreatmentLiver Cirrhosis1
4Unknown StatusTreatmentM. Abscessus / Mycobacterium avium complex infection1
4Unknown StatusTreatmentMycobacterium avium complex infection1
4Unknown StatusTreatmentPulmonary Disease, Chronic Obstructive1
4Unknown StatusTreatmentSalmonella Typhi Infection1
4Unknown StatusTreatmentBacterial blepharitis1
4WithdrawnNot AvailableLymphatic Filariasis / Trachoma1
4WithdrawnPreventionEndometritis1
4WithdrawnTreatmentChronic Bronchitis / Pneumonia, Bacterial1
4WithdrawnTreatmentTrachoma1
Not AvailableActive Not RecruitingNot AvailableBronchiectasis1
Not AvailableActive Not RecruitingOtherAnti-Bacterial Agents / Microbiota1
Not AvailableActive Not RecruitingPreventionChronic Lung Diseases1
Not AvailableActive Not RecruitingTreatmentAsthmatic Patients1
Not AvailableActive Not RecruitingTreatmentChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableCompletedNot AvailableChlamydial Infections1
Not AvailableCompletedNot AvailableCommunity Acquired Pneumonia (CAP) / Pelvic Inflammatory Disease (PID)1
Not AvailableCompletedNot AvailableCystic Fibrosis (CF)1
Not AvailableCompletedNot AvailableEndometritis1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedNot AvailableLegionella Pneumophila Infections / Legionnaires' Disease1
Not AvailableCompletedNot AvailablePulmonary Disease, Chronic Obstructive1
Not AvailableCompletedBasic ScienceBronchiectasis1
Not AvailableCompletedBasic SciencePregnancy1
Not AvailableCompletedDiagnosticPost-gastrointestinal bypass surgery1
Not AvailableCompletedPreventionAbscesses / Endometritis / Surgical Site Infections / Wound Infections1
Not AvailableCompletedPreventionChronic Obstructive Pulmonary Disease (COPD)1
Not AvailableCompletedPreventionFirst Trimester Abortion1
Not AvailableCompletedPreventionPlasmodium Infections1
Not AvailableCompletedPreventionPulmonary Disease, Chronic Obstructive1
Not AvailableCompletedPreventionSinusitis1
Not AvailableCompletedTreatmentBacterial Diseases / Parasitic Diseases1
Not AvailableCompletedTreatmentBronchiectasis1
Not AvailableCompletedTreatmentChronic Periodontitis / Periodontal Diseases1
Not AvailableCompletedTreatmentConjunctivitis caused by chlamydia1
Not AvailableCompletedTreatmentCryptosporidiosis infection / Human Immunodeficiency Virus (HIV) Infections2
Not AvailableCompletedTreatmentCystic Fibrosis (CF)1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare7
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare / Tuberculosis, Mycobacterium Infection1
Not AvailableCompletedTreatmentObliterative Bronchiolitis / Transplantation, Bone Marrow1
Not AvailableCompletedTreatmentPneumonia, Mycoplasma1
Not AvailableCompletedTreatmentSnoring / Strep Throat1
Not AvailableNot Yet RecruitingNot AvailableCommunity Acquired Pneumonia (CAP)1
Not AvailableNot Yet RecruitingNot AvailableNewborn; Infection1
Not AvailableRecruitingNot AvailableBronchiolitis Obliterans Syndrome (BOS)1
Not AvailableRecruitingTreatmentCoughing / Idiopathic Pulmonary Fibrosis (IPF)1
Not AvailableRecruitingTreatmentHaemolytic and Uremic Syndrome1
Not AvailableRecruitingTreatmentMalnutrition in Pregnancy / Nutrition Disorders / Pregnancy / Stunting1
Not AvailableTerminatedNot AvailableBacterial blepharitis1
Not AvailableTerminatedTreatmentAcute Watery Diarrhea / Dysentery/Febrile Diarrhea1
Not AvailableTerminatedTreatmentCryptosporidiosis infection / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableTerminatedTreatmentGraft Versus Host Disease (GVHD) / Obliterative Bronchiolitis1
Not AvailableTerminatedTreatmentRefractory Mycoplasma Pneumoniae Pneumonia1
Not AvailableUnknown StatusTreatmentAsthma Bronchial1
Not AvailableUnknown StatusTreatmentPneumonia1

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
TabletOral250 mg
TabletOral600 mg
SolutionOphthalmic1 %
Solution / dropsOphthalmic10 mg/mL
For suspensionOral100 mg/5mL
For suspensionOral200 mg/5mL
InjectionIntravenous500 mg/10mL
Injection, powder, lyophilized, for solutionIntravenous100 mg/mL
Injection, powder, lyophilized, for solutionIntravenous500 mg/1
Injection, powder, lyophilized, for solutionIntravenous500 mg/5mL
Powder, for solutionOral200 mg
Powder, for suspensionOral1 g/1
Powder, for suspensionOral100 mg/5mL
Powder, for suspensionOral1200 mg/30mL
Powder, for suspensionOral200 mg
Powder, for suspensionOral200 mg/5mL
Powder, for suspensionOral900 mg/22.5mL
TabletOral500 mg/1
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
Tablet, film coatedOral600 mg/1
Injection, powder, lyophilized, for solutionIntravenous500 mg/10mL
TabletOral250 mg/1
TabletOral600 mg/1
TabletOral500 mg
Powder, for suspensionOral100 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)
US5192535No1993-03-092010-03-09Us
CA2467611No2010-03-302024-05-18Canada
CA2148071No2000-10-172015-04-27Canada
US6984403No2004-02-142024-02-14Us
US7887844No2004-02-142024-02-14Us
US6268489No1998-07-312018-07-31Us
US6068859No1997-05-302017-05-30Us
US6159458No1997-11-042017-11-04Us
US6239113No1999-03-312019-03-31Us
US6569443No1999-03-312019-03-31Us
US6861411No1998-11-252018-11-25Us
US7056893No1999-03-312019-03-31Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)114 °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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004l-0309050000-5e1be028a242f0d384eb
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0f6t-0300030900-1a7ea512a0aa566e59ed
MS/MS Spectrum - , positiveLC-MS/MSsplash10-066r-4911100000-f759f24274aebce8e08c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-052f-3912280200-df9a72a4769570064ef9

Taxonomy

Description
This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Aminoglycosides
Alternative Parents
Macrolides and analogues / O-glycosyl compounds / Oxanes / Monosaccharides / Tertiary alcohols / Trialkylamines / Secondary alcohols / 1,2-aminoalcohols / Amino acids and derivatives / Carboxylic acid esters
show 11 more
Substituents
Aminoglycoside core / Macrolide / Glycosyl compound / O-glycosyl compound / Monosaccharide / Oxane / Tertiary alcohol / 1,2-aminoalcohol / Amino acid or derivatives / Carboxylic acid ester
show 22 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
macrolide antibiotic (CHEBI:2955)

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 diff...
Gene Name
rplD
Uniprot ID
P60725
Uniprot Name
50S ribosomal protein L4
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...
Gene Name
rplV
Uniprot ID
P61177
Uniprot Name
50S ribosomal protein L22
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...
Gene Name
PADI4
Uniprot ID
Q9UM07
Uniprot Name
Protein-arginine deiminase type-4
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. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
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]
Details
2. Cytochrome P450 3A4
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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 un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
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
Uniprot Name
Multidrug resistance protein 1
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]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:33