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Namespace Prefixes

PrefixIRI
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n24http://linked.opendata.cz/resource/atc/
n8http://linked.opendata.cz/resource/drugbank/drug/DB00207/identifier/bindingdb/

Statements

Subject Item
n2:DB00207
rdf:type
n3:Drug
n3: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.
n3:dosage
n22:271B5BE8-363D-11E5-9242-09173F13E4C5 n22:271B5BE4-363D-11E5-9242-09173F13E4C5 n22:271B5BE5-363D-11E5-9242-09173F13E4C5 n22:271B5BE6-363D-11E5-9242-09173F13E4C5 n22:271B5BE7-363D-11E5-9242-09173F13E4C5 n22:271B5BE0-363D-11E5-9242-09173F13E4C5 n22:271B5BE1-363D-11E5-9242-09173F13E4C5 n22:271B5BE2-363D-11E5-9242-09173F13E4C5 n22:271B5BE3-363D-11E5-9242-09173F13E4C5 n22:271B5BDC-363D-11E5-9242-09173F13E4C5 n22:271B5BDD-363D-11E5-9242-09173F13E4C5 n22:271B5BDE-363D-11E5-9242-09173F13E4C5 n22:271B5BDF-363D-11E5-9242-09173F13E4C5 n22:271B5BD8-363D-11E5-9242-09173F13E4C5 n22:271B5BD9-363D-11E5-9242-09173F13E4C5 n22:271B5BDA-363D-11E5-9242-09173F13E4C5 n22:271B5BDB-363D-11E5-9242-09173F13E4C5 n22:271B5BD5-363D-11E5-9242-09173F13E4C5 n22:271B5BD6-363D-11E5-9242-09173F13E4C5 n22:271B5BD7-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# 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":http://www.ncbi.nlm.nih.gov/pubmed/17051490
n3:group
approved
n3:halfLife
68 hours
n3:indication
For the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms in the specific conditions: <i>H. influenzae</i>, <i>M. catarrhalis</i>, <i>S. pneumoniae</i>, <i>C. pneumoniae</i>, <i>M. pneumoniae</i>, <i>S. pyogenes</i>, <i>S. aureus</i>, <i>S. agal</i>
n3:manufacturer
n6:271B5BA1-363D-11E5-9242-09173F13E4C5 n6:271B5BA2-363D-11E5-9242-09173F13E4C5 n6:271B5B9F-363D-11E5-9242-09173F13E4C5 n6:271B5BA0-363D-11E5-9242-09173F13E4C5 n6:271B5BA5-363D-11E5-9242-09173F13E4C5 n6:271B5BA6-363D-11E5-9242-09173F13E4C5 n6:271B5BA3-363D-11E5-9242-09173F13E4C5 n6:271B5BA4-363D-11E5-9242-09173F13E4C5 n6:271B5B99-363D-11E5-9242-09173F13E4C5 n6:271B5B9A-363D-11E5-9242-09173F13E4C5 n6:271B5B97-363D-11E5-9242-09173F13E4C5 n6:271B5B98-363D-11E5-9242-09173F13E4C5 n6:271B5B9D-363D-11E5-9242-09173F13E4C5 n6:271B5B9E-363D-11E5-9242-09173F13E4C5 n6:271B5B9B-363D-11E5-9242-09173F13E4C5 n6:271B5B9C-363D-11E5-9242-09173F13E4C5 n6:271B5BA7-363D-11E5-9242-09173F13E4C5
owl:sameAs
n26:DB00207 n27:DB00207
dcterms:title
Azithromycin
adms:identifier
n8:50197040 n10:C06838 n12:2955 n13:DB00207 n14:PA448519 n15:0069-3060-30 n16:ZIT n29:Azithromycin
n3:mechanismOfAction
Azithromycin binds to the 50S subunit of the 70S bacterial ribosomes, and therefore inhibits RNA-dependent protein synthesis in bacterial cells.
n3:packager
n6:271B5B8D-363D-11E5-9242-09173F13E4C5 n6:271B5B8E-363D-11E5-9242-09173F13E4C5 n6:271B5B8B-363D-11E5-9242-09173F13E4C5 n6:271B5B8C-363D-11E5-9242-09173F13E4C5 n6:271B5B89-363D-11E5-9242-09173F13E4C5 n6:271B5B8A-363D-11E5-9242-09173F13E4C5 n6:271B5B87-363D-11E5-9242-09173F13E4C5 n6:271B5B88-363D-11E5-9242-09173F13E4C5 n6:271B5B95-363D-11E5-9242-09173F13E4C5 n6:271B5B96-363D-11E5-9242-09173F13E4C5 n6:271B5B93-363D-11E5-9242-09173F13E4C5 n6:271B5B94-363D-11E5-9242-09173F13E4C5 n6:271B5B91-363D-11E5-9242-09173F13E4C5 n6:271B5B92-363D-11E5-9242-09173F13E4C5 n6:271B5B8F-363D-11E5-9242-09173F13E4C5 n6:271B5B90-363D-11E5-9242-09173F13E4C5 n6:271B5B7D-363D-11E5-9242-09173F13E4C5 n6:271B5B7E-363D-11E5-9242-09173F13E4C5 n6:271B5B7B-363D-11E5-9242-09173F13E4C5 n6:271B5B7C-363D-11E5-9242-09173F13E4C5 n6:271B5B79-363D-11E5-9242-09173F13E4C5 n6:271B5B7A-363D-11E5-9242-09173F13E4C5 n6:271B5B77-363D-11E5-9242-09173F13E4C5 n6:271B5B78-363D-11E5-9242-09173F13E4C5 n6:271B5B85-363D-11E5-9242-09173F13E4C5 n6:271B5B86-363D-11E5-9242-09173F13E4C5 n6:271B5B83-363D-11E5-9242-09173F13E4C5 n6:271B5B84-363D-11E5-9242-09173F13E4C5 n6:271B5B81-363D-11E5-9242-09173F13E4C5 n6:271B5B82-363D-11E5-9242-09173F13E4C5 n6:271B5B7F-363D-11E5-9242-09173F13E4C5 n6:271B5B80-363D-11E5-9242-09173F13E4C5 n6:271B5B5E-363D-11E5-9242-09173F13E4C5 n6:271B5B6D-363D-11E5-9242-09173F13E4C5 n6:271B5B6E-363D-11E5-9242-09173F13E4C5 n6:271B5B6B-363D-11E5-9242-09173F13E4C5 n6:271B5B6C-363D-11E5-9242-09173F13E4C5 n6:271B5B69-363D-11E5-9242-09173F13E4C5 n6:271B5B6A-363D-11E5-9242-09173F13E4C5 n6:271B5B67-363D-11E5-9242-09173F13E4C5 n6:271B5B68-363D-11E5-9242-09173F13E4C5 n6:271B5B75-363D-11E5-9242-09173F13E4C5 n6:271B5B76-363D-11E5-9242-09173F13E4C5 n6:271B5B73-363D-11E5-9242-09173F13E4C5 n6:271B5B74-363D-11E5-9242-09173F13E4C5 n6:271B5B71-363D-11E5-9242-09173F13E4C5 n6:271B5B72-363D-11E5-9242-09173F13E4C5 n6:271B5B6F-363D-11E5-9242-09173F13E4C5 n6:271B5B70-363D-11E5-9242-09173F13E4C5 n6:271B5B65-363D-11E5-9242-09173F13E4C5 n6:271B5B66-363D-11E5-9242-09173F13E4C5 n6:271B5B63-363D-11E5-9242-09173F13E4C5 n6:271B5B64-363D-11E5-9242-09173F13E4C5 n6:271B5B61-363D-11E5-9242-09173F13E4C5 n6:271B5B62-363D-11E5-9242-09173F13E4C5 n6:271B5B5F-363D-11E5-9242-09173F13E4C5 n6:271B5B60-363D-11E5-9242-09173F13E4C5
n3:patent
n11:5192535 n11:2467611 n11:2148071 n11:6984403
n3:routeOfElimination
Biliary excretion of azithromycin, predominantly as unchanged drug, is a major route of elimination.
n3:synonym
(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)13-((2,6-Dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl)oxy)-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-((3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl)oxy)-1-oxa-6-azacyclopentadecan-15-one Azitromicina Azimakrol Azithromycine Azifast Hemomycin Zmax Zithromax Azigram Azenil Azitromin Azithromycinum
n3:toxicity
Potentially serious side effects of angioedema and cholestatic jaundice were reported
n3:volumeOfDistribution
* 31.1 L/kg
n23:hasAHFSCode
n28:08-12-12-92
n3:foodInteraction
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.
n3:proteinBinding
Serum protein binding is variable in the concentration range approximating human exposure, decreasing from 51% at 0.02 &micro;g/mL to 7% at 2 &micro;g/mL.
n3:salt
n3:synthesisReference
William Heggie, Zita Maria De Mouro Vaz Azevedo Mendes, "Process for the preparation of azithromycin." U.S. Patent US6013778, issued November, 1994.
n20:hasConcept
n21:M0027129
foaf:page
n18:azithromycin-drops.html n19:zithromax.htm
n3:IUPAC-Name
n4:271B5BED-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B5BF3-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B5BF2-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B5BEF-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B5BF0-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B5BF1-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B5C03-363D-11E5-9242-09173F13E4C5 n4:271B5BEB-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B5C05-363D-11E5-9242-09173F13E4C5 n4:271B5BEC-363D-11E5-9242-09173F13E4C5 n4:271B5BE9-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B5BEA-363D-11E5-9242-09173F13E4C5
n3:pKa
n4:271B5C06-363D-11E5-9242-09173F13E4C5
n23:hasATCCode
n24:S01AA26 n24:J01FA10
n3:H-Bond-Acceptor-Count
n4:271B5BF9-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B5BFA-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B5BF4-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B5BF5-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B5BF7-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B5BF6-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B5BF8-363D-11E5-9242-09173F13E4C5
n3: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.
n3:affectedOrganism
Streptococcus pyogenes Neisseria gonorrhoeae Legionella pneumophila Chlamydia trachomatis Corynebacterium diphtheriae Treponema pallidum Mycoplasma pneumoniae Bordetella pertussis Chlamydophila psittaci Enteric bacteria and other eubacteria Chlamydia pneumoniae
n3:casRegistryNumber
83905-01-5
n3:category
n3:clearance
* apparent plasma cl=630 mL/min [following single 500 mg oral and i.v. doses]
n3:containedIn
n9:271B5BCE-363D-11E5-9242-09173F13E4C5 n9:271B5BCF-363D-11E5-9242-09173F13E4C5 n9:271B5BCC-363D-11E5-9242-09173F13E4C5 n9:271B5BCD-363D-11E5-9242-09173F13E4C5 n9:271B5BCA-363D-11E5-9242-09173F13E4C5 n9:271B5BCB-363D-11E5-9242-09173F13E4C5 n9:271B5BC8-363D-11E5-9242-09173F13E4C5 n9:271B5BC9-363D-11E5-9242-09173F13E4C5 n9:271B5BD4-363D-11E5-9242-09173F13E4C5 n9:271B5BD2-363D-11E5-9242-09173F13E4C5 n9:271B5BD3-363D-11E5-9242-09173F13E4C5 n9:271B5BD0-363D-11E5-9242-09173F13E4C5 n9:271B5BD1-363D-11E5-9242-09173F13E4C5 n9:271B5BBE-363D-11E5-9242-09173F13E4C5 n9:271B5BBF-363D-11E5-9242-09173F13E4C5 n9:271B5BBC-363D-11E5-9242-09173F13E4C5 n9:271B5BBD-363D-11E5-9242-09173F13E4C5 n9:271B5BBA-363D-11E5-9242-09173F13E4C5 n9:271B5BBB-363D-11E5-9242-09173F13E4C5 n9:271B5BB8-363D-11E5-9242-09173F13E4C5 n9:271B5BB9-363D-11E5-9242-09173F13E4C5 n9:271B5BC6-363D-11E5-9242-09173F13E4C5 n9:271B5BC7-363D-11E5-9242-09173F13E4C5 n9:271B5BC4-363D-11E5-9242-09173F13E4C5 n9:271B5BC5-363D-11E5-9242-09173F13E4C5 n9:271B5BC2-363D-11E5-9242-09173F13E4C5 n9:271B5BC3-363D-11E5-9242-09173F13E4C5 n9:271B5BC0-363D-11E5-9242-09173F13E4C5 n9:271B5BC1-363D-11E5-9242-09173F13E4C5 n9:271B5BAE-363D-11E5-9242-09173F13E4C5 n9:271B5BAF-363D-11E5-9242-09173F13E4C5 n9:271B5BAC-363D-11E5-9242-09173F13E4C5 n9:271B5BAD-363D-11E5-9242-09173F13E4C5 n9:271B5BAA-363D-11E5-9242-09173F13E4C5 n9:271B5BAB-363D-11E5-9242-09173F13E4C5 n9:271B5BA8-363D-11E5-9242-09173F13E4C5 n9:271B5BA9-363D-11E5-9242-09173F13E4C5 n9:271B5BB6-363D-11E5-9242-09173F13E4C5 n9:271B5BB7-363D-11E5-9242-09173F13E4C5 n9:271B5BB4-363D-11E5-9242-09173F13E4C5 n9:271B5BB5-363D-11E5-9242-09173F13E4C5 n9:271B5BB2-363D-11E5-9242-09173F13E4C5 n9:271B5BB3-363D-11E5-9242-09173F13E4C5 n9:271B5BB0-363D-11E5-9242-09173F13E4C5 n9:271B5BB1-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B5BFF-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B5C01-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B5C02-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B5C04-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B5BFE-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B5BFD-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B5C00-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B5BEE-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B5BFB-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B5BFC-363D-11E5-9242-09173F13E4C5