Clarithromycin

Common Name

Clarithromycin 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. Structure

Synonyms

Value Source 6-O-MethylerythromycinChEBI 6-O-Methylerythromycin aChEBI CLAChEBI ClarithromycinaChEBI ClarithromycineChEBI ClarithromycinumChEBI ClathromycinHMDB BiaxinMeSH

Chemical Formlia

C₃₈H₆₉NO₁₃ Average Molecliar Weight

747.9534 Monoisotopic Molecliar Weight

747.476891299 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 Traditional Name

clarithromycin CAS Registry Number

81103-11-9 SMILES

InChI Identifier

InChI Key

AGOYDEPGAOXOCK-KCBOHYOISA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as aminoglycosides. These are moleclies or a portion of a moleclie composed of amino-modified sugars. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic oxygen compounds Sub Class

Organooxygen compounds 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

Cyclic ketones

Lactones

Oxacyclic compounds

Acetals

Monocarboxylic acids and derivatives

Dialkyl ethers

Organopnictogen compounds

Organic oxides

Hydrocarbon derivatives

Substituents

Aminoglycoside core

Macrolide

Glycosyl compound

O-glycosyl compound

Oxane

Monosaccharide

Tertiary alcohol

1,2-aminoalcohol

Amino acid or derivatives

Carboxylic acid ester

Ketone

Cyclic ketone

Tertiary aliphatic amine

Tertiary amine

Secondary alcohol

Lactone

Acetal

Carboxylic acid derivative

Dialkyl ether

Ether

Oxacycle

Organoheterocyclic compound

Monocarboxylic acid or derivatives

Organic nitrogen compound

Carbonyl group

Hydrocarbon derivative

Alcohol

Amine

Organopnictogen compound

Organonitrogen compound

Organic oxide

Aliphatic heteromonocyclic compound

Molecliar Framework

Aliphatic heteromonocyclic compounds External Descriptors

macrolide antibiotic (CHEBI:3732 )

Macrolides and lactone polyketides (C06912 )

Macrolides and lactone polyketides (LMPK04000014 )

Ontology Status

Expected but not Quantified Origin

Drug

Biofunction

Anti-Bacterial Agents

Macrolides

Other Macrolides

Protein Synthesis Inhibitors

Application

Pharmaceutical

Cellliar locations

Membrane

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting Point217 – 220 °CNot Available Boiling PointNot AvailableNot Available Water Solubility2.17e-01 g/LNot Available LogP1.7Not Available

Predicted Properties

Property Value Source Water Solubility0.22 mg/mLALOGPS logP3.18ALOGPS logP3.24ChemAxon logS-3.5ALOGPS pKa (Strongest Acidic)12.46ChemAxon pKa (Strongest Basic)8.38ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count13ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area182.91 ŲChemAxon Rotatable Bond Count8ChemAxon Refractivity190.79 m³·mol^-1ChemAxon Polarizability82.03 ųChemAxon Number of Rings3ChemAxon Bioavailability0ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0a4i-3900020000-7d6e24fdb4aaa06a54bdView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0005-0300060900-61dad109d1b621f69b3bView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0a4i-0900020000-0595f7fefa3c09c779d2View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0a4i-0900000000-8a6bb2526f5f15604524View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0a4i-0900000000-5d02e103d637084e4b49View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0002-0000000900-9b3927ca525e74f19cecView in MoNA LC-MS/MS

LC-MS/MS Spectrum – , positivesplash10-052e-0800070900-da3f6b9dcca7ec506f23View in MoNA LC-MS/MS

LC-MS/MS Spectrum – , positivesplash10-00di-0000001900-bcb836ce99019295a00eView in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

Biological Properties Cellliar Locations

Membrane

Biofluid Locations

Blood

Urine

Tissue Location

Not Available Pathways

Name SMPDB Link KEGG Link Clarithromycin PathwaySMP00248Not Available

Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01211

21059682

details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01211

21059682

details

Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

DB01211 DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

Not Available KNApSAcK ID

Not Available Chemspider ID

10342604 KEGG Compound ID

C06912 BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Clarithromycin NuGOwiki Link

HMDB15342 Metagene Link

HMDB15342 METLIN ID

Not Available PubChem Compound

84029 PDB ID

CTY ChEBI ID

3732

Product: Pentoxifylline

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References

1. Authors unspecified: Clarithromycin. Tuberculosis (Edinb). 2008 Mar;88(2):92-5. doi: 10.1016/S1472-9792(08)70005-2. [PubMed:18486039 ]
2. 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. doi: 10.1016/j.idc.2009.06.013. [PubMed:19909895 ]
3. Piscitelli SC, Danziger LH, Rodvold KA: Clarithromycin and azithromycin: new macrolide antibiotics. Clin Pharm. 1992 Feb;11(2):137-52. [PubMed:1312921 ]
4. Peters DH, Clissold SP: Clarithromycin. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic potential. Drugs. 1992 Jul;44(1):117-64. [PubMed:1379907 ]
5. 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:9383733 ]
6. 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:17292768 ]

Enzymes

General function:

Involved in monooxygenase 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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.

Gene Name:

CYP3A4

Uniprot ID:

P08684

Molecular weight:

57255.585

References

1. 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. doi: 10.1016/j.idc.2009.06.013. [PubMed:19909895 ]
2. Authors unspecified: Clarithromycin. Tuberculosis (Edinb). 2008 Mar;88(2):92-5. doi: 10.1016/S1472-9792(08)70005-2. [PubMed:18486039 ]
3. 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 ]
4. Williams JA, Ring BJ, Cantrell VE, Jones DR, Eckstein J, Ruterbories K, Hamman MA, Hall SD, Wrighton SA: Comparative metabolic capabilities of CYP3A4, CYP3A5, and CYP3A7. Drug Metab Dispos. 2002 Aug;30(8):883-91. [PubMed:12124305 ]

General function:

Involved in monooxygenase activity

Specific function:

Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.

Gene Name:

CYP2C19

Uniprot ID:

P33261

Molecular weight:

55944.565

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 ]

General function:

Involved in monooxygenase 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.

Gene Name:

CYP3A5

Uniprot ID:

P20815

Molecular weight:

57108.065

General function:

Involved in monooxygenase 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.

Gene Name:

CYP3A7

Uniprot ID:

P24462

Molecular weight:

57525.03

General function:

Involved in monooxygenase 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.

Gene Name:

CYP1A2

Uniprot ID:

P05177

Molecular weight:

58406.915

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 ]

Transporters

General function:

Involved in ATP binding

Specific function:

Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

Gene Name:

ABCB1

Uniprot ID:

P08183

Molecular weight:

141477.3

References

1. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]
2. Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [PubMed:11716514 ]
3. Egashira K, Ohtani H, Itoh S, Koyabu N, Tsujimoto M, Murakami H, Sawada Y: Inhibitory effects of pomelo on the metabolism of tacrolimus and the activities of CYP3A4 and P-glycoprotein. Drug Metab Dispos. 2004 Aug;32(8):828-33. [PubMed:15258108 ]
4. Authors unspecified: Clarithromycin. Tuberculosis (Edinb). 2008 Mar;88(2):92-5. doi: 10.1016/S1472-9792(08)70005-2. [PubMed:18486039 ]
5. Dey S, Gunda S, Mitra AK: Pharmacokinetics of erythromycin in rabbit corneas after single-dose infusion: role of P-glycoprotein as a barrier to in vivo ocular drug absorption. J Pharmacol Exp Ther. 2004 Oct;311(1):246-55. Epub 2004 Jun 2. [PubMed:15175422 ]

General function:

Involved in transmembrane transport

Specific function:

Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate

Gene Name:

SLC22A7

Uniprot ID:

Q9Y694

Molecular weight:

60025.0

References

1. Kobayashi Y, Sakai R, Ohshiro N, Ohbayashi M, Kohyama N, Yamamoto T: Possible involvement of organic anion transporter 2 on the interaction of theophylline with erythromycin in the human liver. Drug Metab Dispos. 2005 May;33(5):619-22. Epub 2005 Feb 11. [PubMed:15708966 ]

PMID: 1317923

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