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Showing drug card for Clarithromycin (DB01211)

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Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:03:53
Primary Accession Number DB01211
Secondary Accession Number
  • APRD00181
Name Clarithromycin
Drug Type
  • Approved
  • Small Molecule
Description A semisynthetic macrolide antibiotic derived from erythromycin that is active against a variety of microorganisms. It can inhibit protein synthesis in bacteria by reversibly binding to the 50S ribosomal subunits. This inhibits the translocation of aminoacyl transfer-RNA and prevents peptide chain elongation. [PubChem]
Synonyms
  1. CLA
  2. Clarithromycine
  3. Clathromycin
Brand Names
  1. Biaxin
  2. Biaxin XL
  3. Klacid
  4. Klaricid
  5. Macladin
  6. Naxy
  7. Veclam
  8. Zeclar
Brand Mixtures Not Available
Chemical IUPAC Name (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
Chemical Formula C38H69NO13
Chemical Structure Structure
CAS Registry Number 81103-11-9
InChI Identifier InChI=1/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21-,22+,23-,24+,25+,26+,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
InChI Key AGOYDEPGAOXOCK-NEFHOYQBBL
KEGG Drug D00276 Link Image
KEGG Compound C06912 Link Image
PubChem Compound 84029 Link Image
PubChem Substance 602963 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02244756 Link Image
RxList Link http://www.rxlist.com/cgi/generic/clarith.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Clarithromycin Link Image
FDA Label
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Y. Watanabe et al.; U.S. Pat. 4,331803 (1982)
Average Molecular Weight 747.9534
Monoisotopic Molecular Weight 747.4769
State Solid
Melting Point 217 - 220 oC
Experimental Water Solubility 0.33 mg/L Source: PhysProp
Predicted Water Solubility 2.17e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 1.7 Source: PhysProp
Predicted LogP 3.18 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -3.54 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point 8.99
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric 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)(C[C@@H](C)C(=O)[C@@H](C)[C@@H](O)[C@]1(C)O)OC
Canonical SMILES CCC1OC(=O)C(C)C(OC2CC(C)(OC)C(O)C(C)O2)C(C)C(OC2OC(C)CC(C2O)N(C)C)C(C)(CC(C)C(=O)C(C)C(O)C1(C)O)OC
Drug Category
  • Anti-Bacterial Agents
  • Macrolides
  • Other Macrolides
  • Protein Synthesis Inhibitors
ATC Codes
AHFS Codes
  • 08:12.12.92
Indication For the treatment of bacterial infection of (pharyngitis/tonsillitis, sinusitis, bronchitis, pneumonia, uncomplicated skin and skin structure infections) caused by H. influenzae, M. catarrhalis, M. pneumoniae, S. pneumoniae, C. pneumoniae (TWAR), S. aureus, S. pyogenes, Mycobacterium avium and Mycobacterium intracellulare
Pharmacology Clarithromycin, a macrolide antibiotic similar to erythromycin and azithromycin, is effective against Mycobacterium avium complex (MAC) and is used for the treatment of Helicobacter pylori-associated peptic ulcer disease, community-acquired pneumonia, sinusitis, and chronic bronchitis. Clarithromycin is also used to treat respiratory tract, sexually transmitted, otitis media, and AIDS-related infections.
Mechanism of Action Clarithromycin is first metabolized to 14-OH clarithromycin. Like other macrolides, it then binds to the 50 S subunit of the 70 S ribosome of the bacteria, blocking RNA-mediated bacterial protein synthesis. Clarithromycin also inhibits the hepatic microsomal CYP3A4 isoenzyme and P-glycoprotein, an energy-dependent drug efflux pump.
Absorption 50%
Toxicity Symptoms of toxicity include diarrhea, nausea, abnormal taste, dyspepsia, and abdominal discomfort. 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 occurred. Rare cases of severe hepatic dysfunctions also have been reported. Hepatic failure is usually reversible, but fatalities have been reported.
Protein Binding Low protein binding
Biotransformation Hepatic
Half Life 3-4 hours
Dosage Forms
Form Route
Tablet Oral
Tablet, extended release Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Acenocoumarol The macrolide increases anticoagulant effect
Alprazolam The macrolide increases the effect of the benzodiazepine
Aminophylline Increases the effect and toxicity of theophylline
Amiodarone Increased risk of cardiotoxicity and arrhythmias
Anisindione The macrolide increases the anticoagulant effect
Aprepitant This CYP3A4 inhibitor increases the effect and toxicity of aprepitant
Astemizole Increased risk of cardiotoxicity and arrhythmias
Atazanavir Atazanavir increases levels of clarithromycin
Atorvastatin The macrolide possibly increases the statin toxicity
Bretylium Increased risk of cardiotoxicity and arrhythmias
Buspirone Increases the effect and toxicity of buspirone
Carbamazepine The macrolide increases the effect of carbamazepine
Cerivastatin The macrolide possibly increases the statin toxicity
Cisapride Increased risk of cardiotoxicity and arrhythmias
Citalopram Possible serotoninergic syndrome with this combination
Colchicine Severe colchicine toxicity can occur
Cyclosporine The macrolide increases the effect of cyclosporine
Darifenacin This potent CYP3A4 inhibitor slows darifenacin/solifenacin metabolism
Darunavir Increased levels of clarithromycin
Diazepam The macrolide increases the effect of the benzodiazepine
Dicumarol The macrolide increases anticoagulant effect
Digoxin The macrolide increases the effect of digoxin in 10% of patients
Dihydroergotamine Risk of ergotism and severe ischemia with this association
Disopyramide Increased risk of cardiotoxicity and arrhythmias
Dofetilide Increased risk of cardiotoxicity and arrhythmias
Dyphylline Increases the effect and toxicity of theophylline
Dyphylline Increases the effect and toxicity of theophylline
Efavirenz Efavirenz decreases levels of clarithromycin
Eletriptan This macrolide increases the effect and toxicity of eletriptan
Eplerenone This macrolide increases the effect and toxicity of eplerenone
Ergotamine Risk of ergotism and severe ischemia with this association
Erlotinib This CYP3A4 inhibitor increases levels/toxicity of erlotinib
Everolimus The macrolide increases everolimus levels/toxicity
Fluoxetine Possible serotoninergic syndrome with this combination
Fosphenytoin Increases the effect and toxicity of phenytoin
Gefitinib This CYP3A4 inhibitor increases levels/toxicity of gefitinib
Imatinib The macrolide increases levels of imatinib
Indinavir Increases the effect and toxicity of indinavir
Itraconazole The macrolide increases the effect and toxicity of itraconazole
Lovastatin The macrolide possibly increases the statin toxicity
Methylprednisolone The macrolide increases the effect of corticosteroid
Methysergide Risk of ergotism and severe ischemia with this association
Midazolam The macrolide increases the effect of the benzodiazepine
Oxtriphylline Increases the effect and toxicity of theophylline
Phenytoin Increases the effect and toxicity of phenytoin
Pimozide Increased risk of cardiotoxicity and arrhythmias
Quetiapine This macrolide increases the effect/toxicity of quetiapine
Quinidine Increased risk of cardiotoxicity and arrhythmias
Quinidine barbiturate Increased risk of cardiotoxicity and arrhythmias
Quinupristin This combination presents an increased risk of toxicity
Ranolazine Increased levels of ranolazine- risk of toxicity
Repaglinide Increases the effect of repaglinide
Rifabutin The rifamycin decreases the effect of the macrolide
Rifampin The rifamycin decreases the effect of the macrolide
Sertraline Possible serotoninergic syndrome with this combination
Sildenafil Increases the effect and toxicity of sildenafil
Simvastatin The macrolide possibly increases the statin toxicity
Sirolimus The macrolide increases sirolimus levels
Solifenacin This potent CYP3A4 inhibitor slows darifenacin/solifenacin metabolism
Sotalol Increased risk of cardiotoxicity and arrhythmias
Sunitinib Possible increase in sunitinib levels
Tacrolimus This antibiotic increases the effect and toxicity of tacrolimus
Terfenadine Increased risk of cardiotoxicity and arrhythmias
Theophylline Increases the effect and toxicity of theophylline
Triazolam The macrolide increases the effect of the benzodiazepine
Vardenafil Increases the effect and toxicity of vardenafil
Warfarin The macrolide increases anticoagulant effect
Food Interactions
  • Biaxin - take without regard to meals (however absorption appears to be improved when drug is taken with food).
  • 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.
Pathways
Name SMPDB Link KEGG Link
Clarithromycin Pathway SMP00248 Link Image
General References
  1. 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 Link Image]
  2. Drugs.com Link Image
  3. Wikipedia Link Image
  4. RxList Link Image
Organisms Affected
  • Enteric bacteria and other eubacteria
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 2C19 (CYP2C19)
  2. Cytochrome P450 3A4 (CYP3A4)
Targets
  1. 50S ribosomal protein L10
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 2C19 (CYP2C19)
Enzyme 1 Gene Name CYP2C19
Enzyme 1 SwissProt ID P33261 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P33261|CP2CJ_HUMAN Cytochrome P450 2C19 (EC 1.14.13.80) 
MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDVSKSLTNLSKI
YGPVFTLYFGLERMVVLHGYEVVKEALIDLGEEFSGRGHFPLAERANRGFGIVFSNGKRW
KEIRRFSLMTLRNFGMGKRSIEDRVQEEARCLVEELRKTKASPCDPTFILGCAPCNVICS
IIFQKRFDYKDQQFLNLMEKLNENIRIVSTPWIQICNNFPTIIDYFPGTHNKLLKNLAFM
ESDILEKVKEHQESMDINNPRDFIDCFLIKMEKEKQNQQSEFTIENLVITAADLLGAGTE
TTSTTLRYALLLLLKHPEVTAKVQEEIERVVGRNRSPCMQDRGHMPYTDAVVHEVQRYID
LIPTSLPHAVTCDVKFRNYLIPKGTTILTSLTSVLHDNKEFPNPEMFDPRHFLDEGGNFK
KSNYFMPFSAGKRICVGEGLARMELFLFLTFILQNFNLKSLIDPKDLDTTPVVNGFASVP
PFYQLCFIPV
Phase 1 Metabolizing Enzyme 2 [top]
Enzyme 2 Name Cytochrome P450 3A4 (CYP3A4)
Enzyme 2 Gene Name CYP3A4
Enzyme 2 SwissProt ID P08684 Link Image
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 Protein Sequence >sp|P08684|CP3A4_HUMAN Cytochrome P450 3A4 (EC 1.14.13.67) 
ALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNILSYHKGFCMFD
MECHKKYGKVWGFYDGQQPVLAITDPDMIKTVLVKECYSVFTNRRPFGPVGFMKSAISIA
EDEEWKRLRSLLSPTFTSGKLKEMVPIIAQYGDVLVRNLRREAETGKPVTLKDVFGAYSM
DVITSTSFGVNIDSLNNPQDPFVENTKKLLRFDFLDPFFLSITVFPFLIPILEVLNICVF
PREVTNFLRKSVKRMKESRLEDTQKHRVDFLQLMIDSQNSKETESHKALSDLELVAQSII
FIFAGYETTSSVLSFIMYELATHPDVQQKLQEEIDAVLPNKAPPTYDTVLQMEYLDMVVN
ETLRLFPIAMRLERVCKKDVEINGMFIPKGWVVMIPSYALHRDPKYWTEPEKFLPERFSK
KNKDNIDPYIYTPFGSGPRNCIGMRFALMNMKLALIRVLQNFSFKPCKETQIPLKLSLGG
LLQPEKPVVLKVESRDGTVSGA
Drug Target 1 [top]
Target 1 ID 818
Target 1 Name 50S ribosomal protein L10
Target 1 Synonyms Not Available
Target 1 Gene Name rplJ
Target 1 Protein Sequence >50S ribosomal protein L10 
ALNLQDKQAIVAEVSEVAKGALSAVVADSRGVTVDKMTELRKAGREAGVYMRVVRNTLLR
RAVEGTPFECLKDAFVGPTLIAYSMEHPGAAARLFKEFAKANAKFEVKAAAFEGELIPAS
QIDRLATLPTYEEAIARLMATMKEASAGKLVRTLAAVRDAKEAA
Target 1 Number of Residues 166
Target 1 Molecular Weight 17581
Target 1 Theoretical pI 9.51
Target 1 GO Classification
Function
structural molecule activity
structural constituent of ribosome
Process
metabolism
macromolecule metabolism
macromolecule biosynthesis
protein biosynthesis
physiological process
cellular physiological process
cell organization and biogenesis
organelle organization and biogenesis
ribosome biogenesis and assembly
Component
protein complex
ribonucleoprotein complex
ribosome
cell
intracellular
Target 1 General Function Translation, ribosomal structure and biogenesis
Target 1 Specific Function Protein L10 is also a translational repressor protein. It controls the translation of the rplJL-rpoBC operon by binding to its mRNA
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 24054563 Link Image
Target 1 UniProtKB/Swiss-Prot ID P0A7J6 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name RL10_SHIFL Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location Not Available
Target 1 Gene Sequence >498 bp 
ATGGCTTTAAATCTTCAAGACAAACAAGCGATTGTTGCTGAAGTCAGCGAAGTAGCCAAA
GGCGCGCTGTCTGCAGTAGTTGCGGATTCCCGTGGCGTAACTGTAGATAAAATGACTGAA
CTGCGTAAAGCAGGTCGCGAAGCTGGCGTATACATGCGTGTTGTTCGTAACACCCTGCTG
CGCCGTGCTGTTGAAGGTACTCCGTTCGAGTGCCTGAAAGACGCGTTTGTTGGTCCGACC
CTGATTGCATACTCTATGGAACACCCGGGCGCTGCTGCTCGTCTGTTCAAAGAGTTCGCG
AAAGCGAATGCAAAATTTGAGGTCAAAGCCGCTGCCTTTGAAGGTGAGCTGATCCCGGCG
TCTCAGATCGACCGCCTGGCAACTCTGCCGACCTACGAAGAAGCAATTGCACGCCTGATG
GCAACCATGAAAGAAGCTTCGGCTGGCAAACTGGTTCGTACTCTGGCTGCTGTACGCGAT
GCGAAAGAAGCTGCTTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Jin Q, Yuan Z, Xu J, Wang Y, Shen Y, Lu W, Wang J, Liu H, Yang J, Yang F, Zhang X, Zhang J, Yang G, Wu H, Qu D, Dong J, Sun L, Xue Y, Zhao A, Gao Y, Zhu J, Kan B, Ding K, Chen S, Cheng H, Yao Z, He B, Chen R, Ma D, Qiang B, Wen Y, Hou Y, Yu J: Genome sequence of Shigella flexneri 2a: insights into pathogenicity through comparison with genomes of Escherichia coli K12 and O157. Nucleic Acids Res. 2002 Oct 15;30(20):4432-41. [PubMed Link Image]
  2. Wei J, Goldberg MB, Burland V, Venkatesan MM, Deng W, Fournier G, Mayhew GF, Plunkett G 3rd, Rose DJ, Darling A, Mau B, Perna NT, Payne SM, Runyen-Janecky LJ, Zhou S, Schwartz DC, Blattner FR: Complete genome sequence and comparative genomics of Shigella flexneri serotype 2a strain 2457T. Infect Immun. 2003 May;71(5):2775-86. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.