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Namespace Prefixes

PrefixIRI
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n21http://linked.opendata.cz/resource/drugbank/drug/DB01211/identifier/wikipedia/

Statements

Subject Item
n2:DB01211
rdf:type
n3:Drug
n3:description
Clarithromycin, a semisynthetic macrolide antibiotic derived from erythromycin, inhibits bacterial protein synthesis by binding to the bacterial 50S ribosomal subunit. Binding inhibits peptidyl transferase activity and interferes with amino acid translocation during the translation and protein assembly process. Clarithromycin may be bacteriostatic or bactericidal depending on the organism and drug concentration.
n3:dosage
n4:271B56D0-363D-11E5-9242-09173F13E4C5 n4:271B56D5-363D-11E5-9242-09173F13E4C5 n4:271B56D6-363D-11E5-9242-09173F13E4C5 n4:271B56D7-363D-11E5-9242-09173F13E4C5 n4:271B56D8-363D-11E5-9242-09173F13E4C5 n4:271B56D1-363D-11E5-9242-09173F13E4C5 n4:271B56D2-363D-11E5-9242-09173F13E4C5 n4:271B56D3-363D-11E5-9242-09173F13E4C5 n4:271B56D4-363D-11E5-9242-09173F13E4C5 n4:271B56D9-363D-11E5-9242-09173F13E4C5 n4:271B56DA-363D-11E5-9242-09173F13E4C5 n4:271B56DB-363D-11E5-9242-09173F13E4C5 n4:271B56CE-363D-11E5-9242-09173F13E4C5 n4:271B56CF-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Malhotra-Kumar S, Lammens C, Coenen S, Van Herck K, Goossens H: Effect of azithromycin and clarithromycin therapy on pharyngeal carriage of macrolide-resistant streptococci in healthy volunteers: a randomised, double-blind, placebo-controlled study. Lancet. 2007 Feb 10;369(9560):482-90. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17292768 # Zuckerman JM, Qamar F, Bono BR: Macrolides, ketolides, and glycylcyclines: azithromycin, clarithromycin, telithromycin, tigecycline. Infect Dis Clin North Am. 2009 Dec;23(4):997-1026, ix-x. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19909895 # Piscitelli SC, Danziger LH, Rodvold KA: Clarithromycin and azithromycin: new macrolide antibiotics. Clin Pharm. 1992 Feb;11(2):137-52. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/1312921 # Peters DH, Clissold SP: Clarithromycin. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic potential. Drugs. 1992 Jul;44(1):117-64. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/1379907 # Clarithromycin. Tuberculosis (Edinb). 2008 Mar;88(2):92-5. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18486039 # Stephenson GA, Stowell JG, Toma PH, Pfeiffer RR, Byrn SR: Solid-state investigations of erythromycin A dihydrate: structure, NMR spectroscopy, and hygroscopicity. J Pharm Sci. 1997 Nov;86(11):1239-44. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/9383733
n3:group
approved
n3:halfLife
3-4 hours
n3:indication
An alternative medication for the treatment of acute otitis media caused by <i>H. influenzae, M. catarrhalis, or S. pneumoniae</i> in patients with a history of type I penicillin hypersensitivity. Also for the treatment of pharyngitis and tonsillitis caused by susceptible <i>Streptococcus pyogenes</i>, as well as respiratory tract infections including acute maxillary sinusitis, acute bacterial exacerbations of chronic bronchitis, mild to moderate community-acquired pneuomia, Legionnaires' disease, and pertussis. Other indications include treatment of uncomplicated skin or skin structure infections, helicobacter pylori infection, duodenal ulcer disease, bartonella infections, early Lyme disease, and encephalitis caused by <i>Toxoplasma gondii</i> (in HIV infected patients in conjunction with pyrimethamine). Clarithromycin may also decrease the incidence of cryptosporidiosis, prevent the occurence of α-hemolytic (viridans group) streptococcal endocarditis, as well as serve as a primary prevention for <i>Mycobacterium avium</i> complex (MAC) bacteremia or disseminated infections (in adults, adolescents, and children with advanced HIV infection).
owl:sameAs
n9:DB01211 n19:DB01211
dcterms:title
Clarithromycin
adms:identifier
n12:DB01211 n13:3732 n14:0378-8250-91 n17:C06912 n18:D00276 n20:PA449028 n21:Clarithromycin
n3:mechanismOfAction
Clarithromycin is first metabolized to 14-OH clarithromycin, which is active and works synergistically with its parent compound. Like other macrolides, it then penetrates bacteria cell wall and reversibly binds to domain V of the 23S ribosomal RNA of the 50S subunit of the bacterial ribosome, blocking translocation of aminoacyl transfer-RNA and polypeptide synthesis. Clarithromycin also inhibits the hepatic microsomal CYP3A4 isoenzyme and P-glycoprotein, an energy-dependent drug efflux pump.
n3:packager
n10:271B56AD-363D-11E5-9242-09173F13E4C5 n10:271B56AE-363D-11E5-9242-09173F13E4C5 n10:271B56AB-363D-11E5-9242-09173F13E4C5 n10:271B56AC-363D-11E5-9242-09173F13E4C5 n10:271B56A9-363D-11E5-9242-09173F13E4C5 n10:271B56AA-363D-11E5-9242-09173F13E4C5 n10:271B56A7-363D-11E5-9242-09173F13E4C5 n10:271B56A8-363D-11E5-9242-09173F13E4C5 n10:271B56A5-363D-11E5-9242-09173F13E4C5 n10:271B56A6-363D-11E5-9242-09173F13E4C5 n10:271B56A3-363D-11E5-9242-09173F13E4C5 n10:271B56A4-363D-11E5-9242-09173F13E4C5 n10:271B56A1-363D-11E5-9242-09173F13E4C5 n10:271B56A2-363D-11E5-9242-09173F13E4C5 n10:271B569F-363D-11E5-9242-09173F13E4C5 n10:271B56A0-363D-11E5-9242-09173F13E4C5 n10:271B56B5-363D-11E5-9242-09173F13E4C5 n10:271B56B6-363D-11E5-9242-09173F13E4C5 n10:271B56B3-363D-11E5-9242-09173F13E4C5 n10:271B56B4-363D-11E5-9242-09173F13E4C5 n10:271B56B1-363D-11E5-9242-09173F13E4C5 n10:271B56B2-363D-11E5-9242-09173F13E4C5 n10:271B56AF-363D-11E5-9242-09173F13E4C5 n10:271B56B0-363D-11E5-9242-09173F13E4C5 n10:271B568D-363D-11E5-9242-09173F13E4C5 n10:271B568E-363D-11E5-9242-09173F13E4C5 n10:271B568B-363D-11E5-9242-09173F13E4C5 n10:271B568C-363D-11E5-9242-09173F13E4C5 n10:271B5689-363D-11E5-9242-09173F13E4C5 n10:271B568A-363D-11E5-9242-09173F13E4C5 n10:271B5687-363D-11E5-9242-09173F13E4C5 n10:271B5688-363D-11E5-9242-09173F13E4C5 n10:271B5685-363D-11E5-9242-09173F13E4C5 n10:271B5686-363D-11E5-9242-09173F13E4C5 n10:271B5683-363D-11E5-9242-09173F13E4C5 n10:271B5684-363D-11E5-9242-09173F13E4C5 n10:271B569D-363D-11E5-9242-09173F13E4C5 n10:271B569E-363D-11E5-9242-09173F13E4C5 n10:271B569B-363D-11E5-9242-09173F13E4C5 n10:271B569C-363D-11E5-9242-09173F13E4C5 n10:271B5699-363D-11E5-9242-09173F13E4C5 n10:271B569A-363D-11E5-9242-09173F13E4C5 n10:271B5697-363D-11E5-9242-09173F13E4C5 n10:271B5698-363D-11E5-9242-09173F13E4C5 n10:271B5695-363D-11E5-9242-09173F13E4C5 n10:271B5696-363D-11E5-9242-09173F13E4C5 n10:271B5693-363D-11E5-9242-09173F13E4C5 n10:271B5694-363D-11E5-9242-09173F13E4C5 n10:271B5691-363D-11E5-9242-09173F13E4C5 n10:271B5692-363D-11E5-9242-09173F13E4C5 n10:271B568F-363D-11E5-9242-09173F13E4C5 n10:271B5690-363D-11E5-9242-09173F13E4C5
n3:patent
n6:6010718 n6:6551616 n6:1328609 n6:2471102
n3:routeOfElimination
After a 250 mg tablet every 12 hours, approximately 20% of the dose is excreted in the urine as clarithromycin, while after a 500 mg tablet every 12 hours, the urinary excretion of clarithromycin is somewhat greater, approximately 30%.
n3:synonym
Clarithromycina 6-O-methyl erythromycin CLARITHROMYCIN CLA 6-O-Methylerythromycin Clarithromycinum Clarithromycine 6-O-Methylerythromycin a
n3:toxicity
Symptoms of toxicity include diarrhea, nausea, abnormal taste, dyspepsia, and abdominal discomfort. Transient hearing loss with high doses has been observed. Pseudomembraneous colitis has been reported with clarithromycin use. Allergic reactions ranging from urticaria and mild skin eruptions to rare cases of anaphylaxis and Stevens-Johnson syndrome have also occurred. Rare cases of severe hepatic dysfunctions also have been reported. Hepatic failure is usually reversible, but fatalities have been reported. Clarithromycin may also cause tooth decolouration which may be removed by dental cleaning. Fetal abnormalities, such as cardiovascular defects, cleft palate and fetal growth retardation, have been observed in animals. Clarithromycin may cause QT prolongation.
n22:hasAHFSCode
n23:08-12-12-92
n3:foodInteraction
Biaxin XL - take with a meal, taking it on an empty stomach is associated with total product exposure 30% inferior to that observed when administered with food. Biaxin - take without regard to meals (however absorption appears to be improved when drug is taken with food).
n3:proteinBinding
~ 70% protein bound
n3:synthesisReference
Jih-Hua Liu, David A. Riley, "Preparation of crystal form II of clarithromycin." U.S. Patent US5844105, issued May, 1997.
n27:hasConcept
n28:M0026249
foaf:page
n16:clarith.htm n26:clarithromycin.html
n3:IUPAC-Name
n5:271B56E0-363D-11E5-9242-09173F13E4C5
n3:InChI
n5:271B56E6-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n5:271B56E5-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n5:271B56E2-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n5:271B56E3-363D-11E5-9242-09173F13E4C5
n3:SMILES
n5:271B56E4-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n5:271B56DE-363D-11E5-9242-09173F13E4C5 n5:271B56F6-363D-11E5-9242-09173F13E4C5
n3:logP
n5:271B56DC-363D-11E5-9242-09173F13E4C5 n5:271B56DF-363D-11E5-9242-09173F13E4C5 n5:271B56F8-363D-11E5-9242-09173F13E4C5
n3:logS
n5:271B56DD-363D-11E5-9242-09173F13E4C5
n3:pKa
n5:271B56F9-363D-11E5-9242-09173F13E4C5
n22:hasATCCode
n25:J01FA09
n3:H-Bond-Acceptor-Count
n5:271B56EC-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n5:271B56ED-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n5:271B56E7-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n5:271B56E8-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n5:271B56EA-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n5:271B56E9-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n5:271B56EB-363D-11E5-9242-09173F13E4C5
n3:absorption
Clarithromycin is well-absorbed, acid stable and may be taken with food.
n3:affectedOrganism
Helicobacter pylori Mycobacterium leprae Mycobacterium avium Haemophilus influenzae Enteric bacteria and other eubacteria Streptococcus pneumoniae Mycobacterium Streptococcus pyogenes
n3:casRegistryNumber
81103-11-9
n3:category
n3:containedIn
n7:271B56BC-363D-11E5-9242-09173F13E4C5 n7:271B56BD-363D-11E5-9242-09173F13E4C5 n7:271B56BA-363D-11E5-9242-09173F13E4C5 n7:271B56BB-363D-11E5-9242-09173F13E4C5 n7:271B56B8-363D-11E5-9242-09173F13E4C5 n7:271B56B9-363D-11E5-9242-09173F13E4C5 n7:271B56B7-363D-11E5-9242-09173F13E4C5 n7:271B56CD-363D-11E5-9242-09173F13E4C5 n7:271B56CB-363D-11E5-9242-09173F13E4C5 n7:271B56CC-363D-11E5-9242-09173F13E4C5 n7:271B56C9-363D-11E5-9242-09173F13E4C5 n7:271B56CA-363D-11E5-9242-09173F13E4C5 n7:271B56C7-363D-11E5-9242-09173F13E4C5 n7:271B56C8-363D-11E5-9242-09173F13E4C5 n7:271B56C5-363D-11E5-9242-09173F13E4C5 n7:271B56C6-363D-11E5-9242-09173F13E4C5 n7:271B56C2-363D-11E5-9242-09173F13E4C5 n7:271B56C3-363D-11E5-9242-09173F13E4C5 n7:271B56C0-363D-11E5-9242-09173F13E4C5 n7:271B56C1-363D-11E5-9242-09173F13E4C5 n7:271B56BE-363D-11E5-9242-09173F13E4C5 n7:271B56BF-363D-11E5-9242-09173F13E4C5 n7:271B56C4-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n5:271B56F2-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n5:271B56F4-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n5:271B56F5-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n5:271B56F7-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n5:271B56F1-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n5:271B56F0-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n5:271B56F3-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n5:271B56E1-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n5:271B56EE-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n5:271B56EF-363D-11E5-9242-09173F13E4C5