Teknologi Sediaan Steril

1431753130778.
373
DrugBank:Azithromycin(DB00207)
Identification
Taxonomy
Pharmacology
ADMET
Pharmacoeconomics
Properties
Spectra
References
Interactions
2Comments
ShowDrugswithSimilarStructures
targets(3) enzymes(3) transporters(1) Biointeractions(8)(/drugs/DB00207/biointeractions)
Identification
Name
Azithromycin
AccessionNumber
DB00207(APRD00397)
Type
SmallMolecule
Groups
Approved
Description
Azithromycinisasemisyntheticmacrolideantibioticoftheazalideclass.Likeothermacrolideantibiotics,azithromycininhibitsbacterialprotein
synthesisbybindingtothe50Sribosomalsubunitofthebacterial70Sribosome.Bindinginhibitspeptidyltransferaseactivityandinterfereswith
aminoacidtranslocationduringtheprocessoftranslation.Itseffectsmaybebacteriostaticorbactericidaldependingoftheorganismandthedrug
concentration.Itslonghalflife,whichenablesoncedailydosingandshorteradministrationdurations,isapropertydistinctfromothermacrolides.
Structure
(http://moldb.wishartlab.com/molecules/DB00207/image.png)
MOL(/structures/structures/small_molecule_drugs/DB00207.mol) SDF(/structures/structures/small_molecule_drugs/DB00207.sdf)
PDB(/structures/structures/small_molecule_drugs/DB00207.pdb) SMILES(/structures/structures/small_molecule_drugs/DB00207.smiles)
InChI(/structures/structures/small_molecule_drugs/DB00207.inchi) ViewStructure(/structures/structures/small_molecule_drugs/DB00207)
Synonyms
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10
entries
Synonym
Language
Code
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)13((2,6Dideoxy3Cmethyl3OmethylalphaLribohexopyranosyl)oxy)2ethyl3,4,10
trihydroxy3,5,6,8,10,12,14heptamethyl11((3,4,6trideoxy3(dimethylamino)betaDxylohexopyranosyl)oxy)1oxa6
azacyclopentadecan15one
Not
Available
Not
Available
Azenil
Not
Available
Not
Available
Azifast
Not
Available
Not
Available
Azigram
Not
Available
Not
Available
Azimakrol
Not
Available
Not
Available
Azithromycine
French
INN
Azithromycinum
Latin
INN
Azitromicina
Spanish
Not
Available
Azitromin
Not
Available
Not
Available
Hemomycin
Not
Available
Not
Available
Previous
Showing1to10of12entries
Prescription
Products
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Next
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10
entries
Name
Dosage
Strength
Route
Labeller
Marketing
Start
Marketing
End
Azasite
solution/drops
10mg/mL
ophthalmic
Akorn,Inc.
20140514
NotAvailable
Azasite
solution
10mg/mL
ophthalmic
InspirePharmaceuticals,Inc.
20070716
NotAvailable
Azithromycin
injection,powder,lyophilized, 100mg/mL
forsolution
intravenous
BaxterHealthcareCorporation
19970101
NotAvailable
Azithromycin
tablet,filmcoated
500mg
oral
LakeErieMedicalDBAQualityCare
ProductsLLC
20020524
NotAvailable
Azithromycin
tablet,filmcoated
500mg
oral
REMEDYREPACKINC.
20130305
NotAvailable
http://www.drugbank.ca/drugs/DB00207
1/12
1431753130866.963
Azithromycin
tablet,filmcoated
600mg
oral
REMEDYREPACKINC.
20130305
NotAvailable
Azithromycin
tablet,filmcoated
250mg
oral
REMEDYREPACKINC.
20130924
NotAvailable
Azithromycin
powder,forsuspension
1g
oral
PhysiciansTotalCare,Inc.
20080908
NotAvailable
Azithromycin
tablet,filmcoated
250mg
oral
CardinalHealth
19960718
NotAvailable
Azithromycin
1g
oral
GreenstoneLLC
19990212
NotAvailable
Previous
Generic
Prescription
Products
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Search
10
entries
Name
Dosage
Strength
Route
Labeller
Marketing
Start
Marketing
End
Azithromycin
200
mg/5mL
oral
TevaPharmaceuticalsUSAInc
20101217
NotAvailable
Azithromycin
100
mg/5mL
oral
20101228
NotAvailable
Azithromycin
tablet,filmcoated
250mg
oral
20051116
NotAvailable
Azithromycin
tablet,filmcoated
600mg
oral
20051116
NotAvailable
Azithromycin
100
mg/5mL
oral
20080922
NotAvailable
Azithromycin
200
mg/5mL
oral
20080922
NotAvailable
Azithromycin
tablet,filmcoated
500mg
oral
20051116
NotAvailable
Azithromycin
tablet,filmcoated
600mg
oral
KAISERFOUNDATIONHOSPITALS
20090901
NotAvailable
Azithromycin
injection,powder,
lyophilized,forsolution
2mg/mL
intravenous Hospira,Inc.
20090626
NotAvailable
Azithromycin
injection,powder,
lyophilized,forsolution
100mg/mL
intravenous Hospira,Inc.
20090626
NotAvailable
Previous
OvertheCounter
Products
NotAvailable
International
Brands
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14
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10
entries
Name
Company
Azenil
NotAvailable
Azibiot
NotAvailable
Azin
NotAvailable
Azithrocin
NotAvailable
Azitromax
NotAvailable
Aztrin
NotAvailable
Hemomycin
NotAvailable
Misultina
NotAvailable
Penalox
NotAvailable
Sumamed
NotAvailable
Previous
Brandmixtures
Salts
NotAvailable
Name/CAS
Azithromycin
dihydrate
(/salts/DBSALT000882)
Structure
Properties
Not
applicable
DBSALT000882(/salts/DBSALT000882)
2/12
1431753130903.501
(http://moldb.wishartlab.com/molecules/DBSALT000882/image.png)
Categories
AntiBacterialAgents(/mesh/antibacterialagents)
Macrolides(/mesh/macrolides)
CASnumber
83905015
Weight
Average:748.9845
Monoisotopic:748.508525778
ChemicalFormula
C38H72N2O12
InChIKey
MQTOSJVFKKJCRPBICOPXKESAN
InChI
InChI=1S/C38H72N2O12/c1152738(10,46)31(42)24(6)40(13)1920(2)1736(8,45)33(523529(41)26(39(11)12)1621(3)48
35)22(4)30(23(5)34(44)5027)51281837(9,4714)32(43)25(7)4928/h2033,35,4143,4546H,1519H2,114H3/t20,21,22+,23,24,25+,26+,27
,28+,29,30+,31,32+,33,35+,36,37,38/m1/s1
IUPACName
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)11{[(2S,3R,4S,6R)4(dimethylamino)3hydroxy6methyloxan2yl]oxy}2ethyl3,4,10trihydroxy13
{[(2R,4R,5S,6S)5hydroxy4methoxy4,6dimethyloxan2yl]oxy}3,5,6,8,10,12,14heptamethyl1oxa6azacyclopentadecan15one
SMILES
CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]
([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O
Taxonomy
Description
Thiscompoundbelongstotheclassoforganiccompoundsknownasmacrolidesandanalogues.Theseareorganiccompoundscontaininga
lactoneringofatleasttwelvemembers.
Kingdom
Organiccompounds(http://classyfire.wishartlab.com/tax_nodes/C0000000)
SuperClass
Phenylpropanoidsandpolyketides(http://classyfire.wishartlab.com/tax_nodes/C0000261)
Class
Macrolidesandanalogues(http://classyfire.wishartlab.com/tax_nodes/C0000147)
SubClass
NotAvailable
DirectParent
Macrolidesandanalogues(http://classyfire.wishartlab.com/tax_nodes/C0000147)
AlternativeParents
Aminosugars(http://classyfire.wishartlab.com/tax_nodes/C0001148)
Oxanes(http://classyfire.wishartlab.com/tax_nodes/C0002012)
Monosaccharides(http://classyfire.wishartlab.com/tax_nodes/C0001540)
Tertiaryalcohols(http://classyfire.wishartlab.com/tax_nodes/C0001670)
Trialkylamines(http://classyfire.wishartlab.com/tax_nodes/C0002239)
Secondaryalcohols(http://classyfire.wishartlab.com/tax_nodes/C0001661)
Lactones(http://classyfire.wishartlab.com/tax_nodes/C0000050)
Carboxylicacidesters(http://classyfire.wishartlab.com/tax_nodes/C0001238)
1,2diols(http://classyfire.wishartlab.com/tax_nodes/C0002467)
1,2aminoalcohols(http://classyfire.wishartlab.com/tax_nodes/C0001897)
Oxacycliccompounds(http://classyfire.wishartlab.com/tax_nodes/C0004140)
Monocarboxylicacidsandderivatives(http://classyfire.wishartlab.com/tax_nodes/C0001137)
Dialkylethers(http://classyfire.wishartlab.com/tax_nodes/C0001167)
Azacycliccompounds(http://classyfire.wishartlab.com/tax_nodes/C0004139)
Acetals(http://classyfire.wishartlab.com/tax_nodes/C0001656)
Hydrocarbonderivatives(http://classyfire.wishartlab.com/tax_nodes/C0004150)
Carbonylcompounds(http://classyfire.wishartlab.com/tax_nodes/C0001831)
Substituents
Macrolide
Aminosugar
Desosamine
Aminosaccharide
Oxane
Monosaccharide
Saccharide
Tertiaryalcohol
Tertiaryaliphaticamine
Tertiaryamine
Secondaryalcohol
Polyol
Lactone
3/12
1431753130949.864
Carboxylicacidester
1,2diol
1,2aminoalcohol
Oxacycle
Azacycle
Organoheterocycliccompound
Monocarboxylicacidorderivatives
Ether
Dialkylether
Carboxylicacidderivative
Acetal
Hydrocarbonderivative
Organooxygencompound
Organonitrogencompound
Carbonylgroup
Amine
Alcohol
Aliphaticheteromonocycliccompound
Molecular
Framework
External
Descriptors
Aliphaticheteromonocycliccompounds
macrolideantibiotic(CHEBI:2955(http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2955))
Pharmacology
Indication
Forthetreatmentofpatientswithmildtomoderateinfectionscausedbysusceptiblestrainsofthedesignatedmicroorganismsinthespecific
conditions:H.influenzae,M.catarrhalis,S.pneumoniae,C.pneumoniae,M.pneumoniae,S.pyogenes,S.aureus,S.agal
Pharmacodynamics Azithromycin,asemisyntheticantibioticbelongingtothemacrolidesubgroupofazalides,isusedtotreatSTDsduetochlamydiaandgonorrhea,
communityacquiredpneumonia,pelvicinflammatorydisease,pediatricotitismediaandpharyngitis,andMycobacteriumaviumcomplex(MAC)in
patientswithadvancedHIVdisease.Similarinstructuretoerythromycin.azithromycinreacheshigherintracellularconcentrationsthan
erythromycin,increasingitsefficacyanddurationofaction.
Mechanismof
action
Azithromycinbindstothe50Ssubunitofthe70Sbacterialribosomes,andthereforeinhibitsRNAdependentproteinsynthesisinbacterialcells.
Absorption
Bioavailabilityis37%followingoraladministration.Absorptionisnotaffectedbyfood.Azithromycinisextensivelydistributedintissueswithtissue
concentrationsreachingupto50timesgreaterthanplasmaconcentrations.Drugbecomesconcentratedwithinmacrophagesand
polymorphonucleocytesgivingitgoodactivityagainstChlamydiatrachomatis.
Volumeof
distribution
31.1L/kg
Proteinbinding
Serumproteinbindingisvariableintheconcentrationrangeapproximatinghumanexposure,decreasingfrom51%at0.02g/mLto7%at2
g/mL.
Metabolism
Hepatic.Invitroandinvivostudiestoassessthemetabolismofazithromycinhavenotbeenperformed.
Routeof
elimination
Biliaryexcretionofazithromycin,predominantlyasunchangeddrug,isamajorrouteofelimination.
Halflife
68hours
Clearance
Toxicity
Affectedorganisms
Pathways
apparentplasmacl=630mL/min[followingsingle500mgoralandi.v.doses]
Potentiallyserioussideeffectsofangioedemaandcholestaticjaundicewerereported
Entericbacteriaandothereubacteria
Pathway
Category
AzithromycinActionPathway
Drugaction
SNPMediated
Effects
NotAvailable
SNPMediated
AdverseDrug
Reactions
NotAvailable
SMPDBID
SMP00247(http://smpdb.ca/view/SMP00247?highlight[compounds][]=DB00207&highlight[proteins][]=DB00207)
ADMET
PredictedADMET
features
Property
Value
Probability
HumanIntestinalAbsorption
0.5518
BloodBrainBarrier
0.9739
Caco2permeable
0.7578
4/12
1431753131115.435
Pglycoproteinsubstrate
Substrate
0.8765
PglycoproteininhibitorI
Inhibitor
0.8513
PglycoproteininhibitorII
Noninhibitor
0.8893
Renalorganiccationtransporter
Noninhibitor
0.8753
CYP4502C9substrate
Nonsubstrate
0.8373
CYP4502D6substrate
Nonsubstrate
0.9116
CYP4503A4substrate
Substrate
0.6403
CYP4501A2substrate
Noninhibitor
0.9295
CYP4502C9substrate
Noninhibitor
0.9021
CYP4502D6substrate
Noninhibitor
0.8904
CYP4502C19substrate
Noninhibitor
0.9023
CYP4503A4substrate
Noninhibitor
0.9533
CYP450inhibitorypromiscuity
LowCYPInhibitoryPromiscuity
0.9751
Amestest
NonAMEStoxic
0.9133
Carcinogenicity
Noncarcinogens
0.9397
Biodegradation
Notreadybiodegradable
0.9673
Ratacutetoxicity
2.5423LD50,mol/kg
Notapplicable
hERGinhibition(predictorI)
Weakinhibitor
0.9929
hERGinhibition(predictorII)
Noninhibitor
0.8555
Pharmacoeconomics
Manufacturers
Pfizerchemicalsdivpfizerinc
Pfizerglobalresearchdevelopment
Plivainc
Sandozinc
Tevapharmaceuticalsusa
Pfizercentralresearch
Apppharmaceuticalsllc
Glandpharmaltd
Hospirainc
Plivahrvatskadoo
Sagentstridesllc
Tevaparenteralmedicinesinc
Pfizerinc(http://www.pfizer.com/)
Inspirepharmaceuticalsinc
Mylanpharmaceuticalsinc
Tevapharmaceuticalsusainc
Wockhardtltd
Packagers
AdvancedPharmaceuticalServicesInc.
AidarexPharmacuticalsLLC(http://www.aidarex.com)
AmerisourceHealthServicesCorp.(http://www.amerisourcebergen.com)
ApothecaInc.
APPPharmaceuticals(http://www.apppharma.com)
AQPharmaceuticalsInc.(http://www.aqpharmaceuticals.com)
ASMedicationSolutionsLLC(http://orders.asmeds.com)
BaxterInternationalInc.(http://www.baxter.com)
CardinalHealth(http://www.cardinal.com)
CatalentPharmaSolutions(http://www.catalent.com)
ComprehensiveConsultantServicesInc.
DeptHealthCentralPharmacy
DirectDispensingInc.
DispensingSolutions(http://www.drxdispensing.com)
DiversifiedHealthcareServicesInc.(http://www.dhscorp.com)
EonLabs
GreenstoneLLC(http://www.greenstonellc.com)
H.J.HarkinsCo.Inc.(http://hjharkinscompanyinc.com)
HospiraInc.(http://www.hospira.com)
InnoviantPharmacyInc.(http://www.innoviantpharmacy.com)
InspirePharmaceuticals(http://www.inspirepharm.com)
KaiserFoundationHospital
LakeErieMedicalandSurgicalSupply
LibertyPharmaceuticals
5/12
1431753131173.804
MajorPharmaceuticals(http://www.majorpharmaceuticals.com)
MediscaInc.(http://www.medisca.com)
MurfreesboroPharmaceuticalNursingSupply(http://www.unitdosesupply.com)
Mylan(http://www.mylan.com)
NucarePharmaceuticalsInc.(http://www.nucarerx.com)
PalmettoPharmaceuticalsInc.(http://www.palmettopharm.com)
PatheonInc.(http://www.patheon.com)
PDRxPharmaceuticalsInc.(http://www.pdrx.com)
PfizerInc.(http://www.pfizer.com)
PharmaceuticalUtilizationManagementProgramVAInc.
PharmpakInc.(http://www.pharmpakinc.com)
PhysiciansTotalCareInc.(http://www.physicianstotalcare.com)
PlivaInc.(http://www.pliva.com)
PreferredPharmaceuticalsInc.(http://www.preferredpharmaceuticals.com)
PrepackageSpecialists
PrepakSystemsInc.(http://www.prepaksys.com)
PublicHealthDepartmentSeattleandKingCounty(http://www.kingcounty.gov/healthservices/health.aspx)
RebelDistributorsCorp.(http://www.rebelrx.com)
RedpharmDrug
RemedyRepack(http://www.remedyrepack.com)
SagentPharmaceuticals(http://www.sagentpharma.com)
Sandoz(http://www.sandoz.ca)
SicorPharmaceuticals
SouthwoodPharmaceuticals(http://www.southwoodhealthcare.com)
StatRxUsa(http://statrxusa.exporterus.com)
StatScriptsLLC(http://www.statscripts.com)
StridesArcolabLimited(http://www.stridesarco.com)
TevaPharmaceuticalIndustriesLtd.(http://www.tevapharm.com)
TyaPharmaceuticals
UDLLaboratories(http://www.udllabs.com)
USPharmaceuticalGroup
WarnerChilcottCo.Inc.(http://ir.wcrx.com)
WockhardtLtd.(http://www.wockhardtin.com)
Dosageforms
Show
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10
entries
Form
Route
Strength
Injection
intravenous
500mg/10mL
Injection,powder,lyophilized,forsolution
intravenous
100mg/mL
intravenous
2mg/mL
intravenous
500mg/5mL
Powderforsuspension
oral
100mg
Powderforsuspension
oral
200mg
Powder,forsuspension
oral
1g
oral
100mg/5mL
oral
1200mg/30mL
oral
2g/60mL
Previous
Prices
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10
entries
Unitdescription
Cost
Unit
ApoAzithromycin250mgTablet
3.11USD
tablet
Azasite1%eyedrops
42.85USD
ml
Azithromycin2.5gmbulkvial
75.6USD
each
Azithromycin200mg/5mlSuspension15mlBottle
34.25USD
bottle
Azithromycin250mgtablet
6.33USD
tablet
Azithromycin3500mgtabletDispPack
48.52USD
disp
15.87USD
tablet
6/12
1431753131233.812
Azithromycin6250mgtabletDispPack
48.52USD
disp
19.04USD
tablet
Azithromycini.v.500mgvial
11.09USD
each
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Next
Previous
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DrugBankdoesnotsellnorbuydrugs.Pricinginformationissuppliedforinformationalpurposesonly.
Patents
Show
Search
10
entries
Country
PatentNumber
Approved
Expires(estimated)
Canada
2148071
20001017
20150427
Canada
2467611
20100330
20240518
UnitedStates
5192535
19930309
20100309
UnitedStates
6984403
20040214
20240214
Properties
State
Experimental
Properties
Predicted
Properties
Solid
Property
Value
Source
meltingpoint
114C
PhysProp
watersolubility
slight
NotAvailable
logP
4.02
MCFARLAND,JWETAL.(1997)
pKa
8.74(at25C)
MCFARLAND,JWETAL.(1997)
Property
Value
Source
WaterSolubility
0.514mg/mL
ALOGPS(http://www.vcclab.org/lab/alogps/)
logP
3.03
logP
2.44
ChemAxon(http://www.chemaxon.com/products/calculatorplugins/propertypredictors/#logp_logd)
logS
3.2
pKa(StrongestAcidic)
12.43
ChemAxon(http://www.chemaxon.com/products/calculatorplugins/propertypredictors/#pka)
pKa(StrongestBasic)
9.57
PhysiologicalCharge
HydrogenAcceptorCount
13
ChemAxon(http://www.chemaxon.com/products/calculatorplugins/propertycalculations/#h_bond)
HydrogenDonorCount
PolarSurfaceArea
180.08
RotatableBondCount
ChemAxon(http://www.chemaxon.com/products/calculatorplugins/propertycalculations/#h_bond)
2
ChemAxon(http://www.chemaxon.com/products/calculatorplugins/propertycalculations/#topolgical_surface)
ChemAxon(http://www.chemaxon.com/products/calculatorplugins/propertycalculations/#topology_analysis)
Refractivity
194.11m mol
Polarizability
83.113
ChemAxon(http://www.chemaxon.com/products/calculatorplugins/propertycalculations/#refractivity)
ChemAxon(http://www.chemaxon.com/products/calculatorplugins/molecularmodelling/#polarization)
NumberofRings
ChemAxon(http://www.chemaxon.com/products/calculatorplugins/propertycalculations/#topology_analysis)
Bioavailability
RuleofFive
Yes
GhoseFilter
Yes
Veber'sRule
Yes
MDDRlikeRule
Yes
Spectra
MassSpec(NIST)
NotAvailable
Spectra
NotAvailable
References
Synthesis
Reference
WilliamHeggie,ZitaMariaDeMouroVazAzevedoMendes,Processforthepreparationofazithromycin.U.S.PatentUS6013778,issued
November,1994.
7/12
1431753131264.765
US6013778(https://www.google.com/?tbm=pts#q=6013778&tbm=pts)
GeneralReference
ExternalLinks
ATCCodes
1. NoedlH,KrudsoodS,ChalermratanaK,SilachamroonU,LeowattanaW,TangpukdeeN,LooareesuwanS,MillerRS,FukudaM,Jongsakul
K,SriwichaiS,RowanJ,BhattacharyyaH,OhrtC,KnirschC:Azithromycincombinationtherapywithartesunateorquinineforthetreatment
ofuncomplicatedPlasmodiumfalciparummalariainadults:arandomized,phase2clinicaltrialinThailand.ClinInfectDis.2006Nov
1543(10):126471.Epub2006Oct12.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/17051490)
Resource
Link
KEGGCompound
C06838(http://www.genome.jp/dbgetbin/www_bget?cpd:C06838)
BindingDB
50197040(http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50197040)
ChEBI
2955(http://www.ebi.ac.uk/chebi/searchId.do?chebiId=2955)
ChEMBL
CHEMBL529(http://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL529)
TherapeuticTargetsDatabase
DNC001539(http://bidd.nus.edu.sg/group/cjttd/ZFTTDDRUG.asp?ID=DNC001539)
PharmGKB
PA448519(http://www.pharmgkb.org/drug/PA448519)
HET
ZIT(http://www.ebi.ac.uk/msdsrv/chempdb/cgibin/cgi.pl?FUNCTION=getByCode&CODE=ZIT)
RxList
http://www.rxlist.com/cgi/generic/zithromax.htm(http://www.rxlist.com/cgi/generic/zithromax.htm)
Drugs.com
http://www.drugs.com/cdi/azithromycindrops.html(http://www.drugs.com/cdi/azithromycindrops.html)
Wikipedia
Azithromycin(http://en.wikipedia.org/wiki/Azithromycin)
J01FA10
JANTIINFECTIVESFORSYSTEMICUSE(/atc/J#J)
J01ANTIBACTERIALSFORSYSTEMICUSE(/atc/J01#J01)
J01FMACROLIDES,LINCOSAMIDESANDSTREPTOGRAMINS(/atc/J01F#J01F)
J01FAMacrolides(/atc/J01FA#J01FA)
S01AA26
SSENSORYORGANS(/atc/S#S)
S01OPHTHALMOLOGICALS(/atc/S01#S01)
S01AANTIINFECTIVES(/atc/S01A#S01A)
S01AAAntibiotics(/atc/S01AA#S01AA)
AHFSCodes
08:12.12.92
PDBEntries
NotAvailable
FDAlabel
Download(/system/fda_labels/DB00207.pdf?1265922797)(76.3KB)
MSDS
Download(/system/msds/DB00207.pdf?1265922737)(73.9KB)
Interactions
DrugInteractions
Drug
Acenocoumarol
(/drugs/DB01418)
Azithromycinmayincreasetheanticoagulanteffectofacenocoumarolbyincreasingitsserumconcentration.
Anisindione(/drugs/DB01125)
Azithromycinmayincreasetheanticoagulanteffectofanisindionebyincreasingitsserumconcentration.
Artemether(/drugs/DB06697)
AdditiveQTcprolongationmayoccur.Concomitanttherapyshouldbeavoided.
Cyclosporine
(/drugs/DB00091)
Themacrolide,azithromycin,mayincreasetheeffectofcyclosporine.
Dicoumarol(/drugs/DB00266)
Azithromycinmayincreasetheanticoagulanteffectofdicumarolbyincreasingitsserumconcentration.
Disopyramide
(/drugs/DB00280)
Themacrolide,azithromycin,mayincreasetheeffectofdisopyramide.
Lovastatin(/drugs/DB00227)
Themacrolideantibiotic,azithromycin,mayincreasetheserumconcentrationoflovastatinbydecreasingitsmetabolism.
Monitorforchangesinthetherapeuticandadverseeffectsoflovastatinifazithromycinisinitiated,discontinuedordose
changed.
Lumefantrine
(/drugs/DB06708)
AdditiveQTcprolongationmayoccur.Concomitanttherapyshouldbeavoided.
Vismodegib(/drugs/DB08828) Pglycoproteininhibitorsmayincreasethechanceofadversedrugreactions.
FoodInteractions
Vorinostat(/drugs/DB02546)
AdditiveQTcprolongationmayoccur.ConsideralternatetherapyormonitorforQTcprolongationasthiscanleadtoTorsade
dePointes(TdP).
Warfarin(/drugs/DB00682)
Azithromycinmayincreasetheanticoagulanteffectofwarfarinbyincreasingitsserumconcentration.
Ziprasidone(/drugs/DB00246)
AdditiveQTcprolongingeffectsmayincreasetheriskofseverearrhythmias.Concomitanttherapyiscontraindicated.
Zuclopenthixol
(/drugs/DB01624)
AdditiveQTcprolongationmayoccur.ConsideralternatetherapyorusecautionandmonitorforQTcprolongationasthiscan
leadtoTorsadedePointes(TdP).
DonottakeAluminumormagnesiumantacidsorsupplementswhileonthismedication.
8/12
1431753131298.898
Takeonemptystomach:1hourbeforeor2hoursaftermeals.
Targets
1.23SrRNA(/biodb/bio_entities/BE0004800)
Kind:nucleotide
Organism:Entericbacteriaandothereubacteria
Pharmacologicalaction:
yes
Actions: inhibitor
Components
Name
UniProtID
Details
References:
1. NgLK,MartinI,LiuG,BrydenL:Mutationin23SrRNAassociatedwithmacrolideresistanceinNeisseriagonorrhoeae.AntimicrobAgentsChemother.2002Sep46(9):30205.
Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/12183262)
2. JalavaJ,VaaraM,HuovinenP:Mutationattheposition2058ofthe23SrRNAasacauseofmacrolideresistanceinStreptococcuspyogenes.AnnClinMicrobiolAntimicrob.
2004May63:5.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/15128458)
3. PereyreS,RenaudinH,CharronA,BebearC,BebearCM:Emergenceofa23SrRNAmutationinMycoplasmahominisassociatedwithalossoftheintrinsicresistanceto
erythromycinandazithromycin.JAntimicrobChemother.2006Apr57(4):7536.Epub2006Feb7.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/16464889)
2.50SribosomalproteinL4(/biodb/bio_entities/BE0002465)
Kind:protein
Organism:EscherichiacoliO157:H7
yes
Actions: inhibitor
Components
Name
UniProtID
50SribosomalproteinL4
P60725(http://www.uniprot.org/uniprot/P60725)
Details
Details(/biodb/polypeptides/P60725)
References:
1. HallingSM,JensenAE:Intrinsicandselectedresistancetoantibioticsbindingtheribosome:analysesofBrucella23Srrn,L4,L22,EFTu1,EFTu2,effluxandphylogenetic
implications.BMCMicrobiol.2006Oct26:84.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/17014718)
2. TuD,BlahaG,MoorePB,SteitzTA:StructuresofMLSBKantibioticsboundtomutatedlargeribosomalsubunitsprovideastructuralexplanationforresistance.Cell.2005Apr
22121(2):25770.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/15851032)
3. SchlunzenF,HarmsJM,FranceschiF,HansenHA,BartelsH,ZarivachR,YonathA:Structuralbasisfortheantibioticactivityofketolidesandazalides.Structure.2003
Mar11(3):32938.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/12623020)
4. PetropoulosAD,KouvelaEC,StarostaAL,WilsonDN,DinosGP,KalpaxisDL:TimeresolvedbindingofazithromycintoEscherichiacoliribosomes.JMolBiol.2009Jan
30385(4):117992.Epub2008Nov27.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/19071138)
5. ChampneyWS,MillerM:Inhibitionof50SribosomalsubunitassemblyinHaemophilusinfluenzaecellsbyazithromycinanderythromycin.CurrMicrobiol.2002Jun44(6):418
24.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/12000992)
3.50SribosomalproteinL22(/biodb/bio_entities/BE0002464)
Kind:protein
Organism:EscherichiacoliO157:H7
yes
Actions: inhibitor
Components
Name
UniProtID
50SribosomalproteinL22
Details
References:
1. HallingSM,JensenAE:Intrinsicandselectedresistancetoantibioticsbindingtheribosome:analysesofBrucella23Srrn,L4,L22,EFTu1,EFTu2,effluxandphylogenetic
implications.BMCMicrobiol.2006Oct26:84.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/17014718)
9/12
1431753131328.023
2. TuD,BlahaG,MoorePB,SteitzTA:StructuresofMLSBKantibioticsboundtomutatedlargeribosomalsubunitsprovideastructuralexplanationforresistance.Cell.2005Apr
22121(2):25770.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/15851032)
3. SchlunzenF,HarmsJM,FranceschiF,HansenHA,BartelsH,ZarivachR,YonathA:Structuralbasisfortheantibioticactivityofketolidesandazalides.Structure.2003
Mar11(3):32938.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/12623020)
4. PetropoulosAD,KouvelaEC,StarostaAL,WilsonDN,DinosGP,KalpaxisDL:TimeresolvedbindingofazithromycintoEscherichiacoliribosomes.JMolBiol.2009Jan
30385(4):117992.Epub2008Nov27.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/19071138)
5. ChampneyWS,MillerM:Inhibitionof50SribosomalsubunitassemblyinHaemophilusinfluenzaecellsbyazithromycinanderythromycin.CurrMicrobiol.2002Jun44(6):418
24.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/12000992)
Enzymes
1.CytochromeP4502A6(/biodb/bio_entities/BE0003336)
Kind:protein
Organism:Human
unknown
Actions: inhibitor
Components
Name
UniProtID
CytochromeP4502A6
Details
References:
1. PreissnerS,KrollK,DunkelM,SengerC,GoldsobelG,KuzmanD,GuentherS,WinnenburgR,SchroederM,PreissnerR:SuperCYP:acomprehensivedatabaseon
CytochromeP450enzymesincludingatoolforanalysisofCYPdruginteractions.NucleicAcidsRes.2010Jan38(Databaseissue):D23743.Epub2009Nov24.Pubmed
(http://www.ncbi.nlm.nih.gov/pubmed/19934256)
Kind:protein
Organism:Human
unknown
Actions: substrate inhibitor
Components
Name
UniProtID
CytochromeP4503A4
Details
References:
1. PreissnerS,KrollK,DunkelM,SengerC,GoldsobelG,KuzmanD,GuentherS,WinnenburgR,SchroederM,PreissnerR:SuperCYP:acomprehensivedatabaseon
CytochromeP450enzymesincludingatoolforanalysisofCYPdruginteractions.NucleicAcidsRes.2010Jan38(Databaseissue):D23743.Epub2009Nov24.Pubmed
(http://www.ncbi.nlm.nih.gov/pubmed/19934256)
Kind:protein
Organism:Human
unknown
Actions: inhibitor
Components
Name
UniProtID
CytochromeP4501A2
Details
References:
1. Lexicomp
10/12
1431753131353.312
Transporters
1.Multidrugresistanceprotein1(/biodb/bio_entities/BE0001032)
Kind:protein
Organism:Human
unknown
Actions: inhibitor
Components
Name
UniProtID
Details
Multidrugresistanceprotein1
References:
1. WangE,LewK,BareckiM,CascianoCN,ClementRP,JohnsonWW:QuantitativedistinctionsofactivesitemolecularrecognitionbyPglycoproteinandcytochromeP4503A4.
ChemResToxicol.2001Dec14(12):1596603.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/11743742)
2. AsakuraE,NakayamaH,SugieM,ZhaoYL,NadaiM,KitaichiK,ShimizuA,MiyoshiM,TakagiK,TakagiK,HasegawaT:Azithromycinreversesanticancerdrugresistanceand
modifieshepatobiliaryexcretionofdoxorubicininrats.EurJPharmacol.2004Jan26484(23):3339.Pubmed(http://www.ncbi.nlm.nih.gov/pubmed/14744620)
Comments
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Jointhediscussion
Bmorale2 3yearsago
IthinktheSpanishversionofthisshouldbetranslatedto"Azitromicina"notasitshowsas"Aritromicina".
Reply Share
CraigKnox
Mod >Bmorale2 3yearsago
Hi,thanksforthetip,lookslikeitwasaspellingerror.I'vecorrectedit.
1
Reply Share
WHAT'STHIS?
ALSOONDRUGBANK
Abiraterone(DB05812)
Denosumab(DB06643)
4comments2yearsago
1comment2yearsago
AdamMaciejewskiHiPangPangGunThanksforyourquestion.
GlennPilkingtonTsequencesyouhavelistedaredifferenttothe
Currently,wedon'thavethisfeature,butpleaselookatourcurrent
'pharmacoeconomics'sectionforinformationregardingprices,
manufacturers,packagers,anddosages.Thankyou,Adam
patent(WO2013181575A2)sequencesandtheheavychainsequence
isforahIgG1nothIgG2.
LYM2(DB05788)
FTY720(DB05286)
2commentsayearago
2commentsayearago
AdamMaciejewskiHiNieLun,thankyouforlettingusknowaboutthis.
AdamMaciejewskiHelloDanielHimmelstein,thankyouforpointing
IhavecreatedabiotechentryforLYM2,andhavemergedthetwo
drugs.PleaseseeDB09025.Thankyou!
thisout.Indeed,FTY720isthesamedrugasthelaterapproved
Fingolimod.IwillmergethetwoentriesintoDB08868.Ifyouhaveany
furtherquestionsorcomments,pleasedon'thesitateto
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DrugcreatedonJune13,200507:24/UpdatedonSeptember16,201317:08
(http://www.cihrirsc.gc.ca)
(http://www.metabolomicscentre.ca)
11/12
1431753133823.464
(http://www.aihealthsolutions.ca)
(http://genomealberta.ca)
(http://genomebc.ca)
(http://genomecanada.ca)
ThisprojectissupportedbytheCanadianInstitutesofHealthResearch(http://www.cihrirsc.gc.ca)(award#111062),AlbertaInnovatesHealthSolutions
(http://www.aihealthsolutions.ca),andbyTheMetabolomicsInnovationCentre(TMIC)(http://www.metabolomicscentre.ca/),anationallyfundedresearchandcore
facilitythatsupportsawiderangeofcuttingedgemetabolomicstudies.TMICisfundedbyGenomeAlberta(http://www.genomealberta.ca),GenomeBritishColumbia
(http://www.genomebc.ca/),andGenomeCanada(http://www.genomecanada.ca),anotforprofitorganizationthatisleadingCanada'snationalgenomicsstrategywith
$900millioninfundingfromthefederalgovernment.
DrugBankVersion4.2ContactUs(http://drugbank/w/contact)
12/12

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1431753130778.

targets(3) enzymes(3) transporters(1) Biointeractions(8)(/drugs/DB00207/biointeractions)

Actions: substrate inhibitor

Mod >Bmorale2 3yearsago

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