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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2018-05-20 20:12:19 UTC
HMDB IDHMDB0014916
Secondary Accession Numbers
  • HMDB14916
Metabolite Identification
Common NameRoxithromycin
DescriptionRoxithromycin is a semi-synthetic macrolide antibiotic. It is very similar in composition, chemical structure and mechanism of action to erythromycin, azithromycin, or clarithromycin. Roxithromycin prevents bacteria from growing, by interfering with their protein synthesis. Roxithromycin binds to the subunit 50S of the bacterial ribosome, and thus inhibits the translocation of peptides. Roxithromycin has similar antimicrobial spectrum as erythromycin, but is more effective against certain gram-negative bacteria, particularly Legionella pneumophila. It can treat respiratory tract, urinary and soft tissue infections.
Structure
Thumb
Synonyms
ValueSource
9-[O-(2-Methoxyethoxymethyl)-oxime] OF erythromycinChEBI
1a Brand OF roxithromycinMeSH
Hoechst brand OF roxithromycinMeSH
Knoll brand OF roxithromycinMeSH
MIP brand OF roxithromycinMeSH
MacrosilMeSH
Roxi basicsMeSH
Roxi-paed 1a pharmaMeSH
RoxibetaMeSH
Wolff brand OF roxithromycinMeSH
Basics brand OF roxithromycinMeSH
Faes brand OF roxithromycinMeSH
Hexal brand OF roxithromycinMeSH
InfectoroxitMeSH
RotesanMeSH
Roxi tadMeSH
Roxi-QMeSH
Roxi-saarMeSH
RoxigrünMeSH
Roxithromycin hexal brandMeSH
Betapharm brand OF roxithromycinMeSH
RoxiduraMeSH
Aventis brand OF roxithromycinMeSH
BiaxsigMeSH
Juta brand OF roxithromycinMeSH
Merck dura brand OF roxithromycinMeSH
Roxi-wolffMeSH
RoxigammaMeSH
RulidMeSH
TAD brand OF roxithromycinMeSH
Wörwag brand OF roxithromycinMeSH
Alpharma brand OF roxithromycinMeSH
ClaramidMeSH
Grünenthal brand OF roxithromycinMeSH
Infectopharm brand OF roxithromycinMeSH
Lichtenstein brand OF roxithromycinMeSH
MTW Brand OF roxithromycinMeSH
MTW-RoxithromycinMeSH
Medeva brand OF roxithromycinMeSH
Pfizer brand OF roxithromycinMeSH
RotraminMeSH
Roxi 1a pharmaMeSH
Roxi-purenMeSH
RoxihexalMeSH
roxithro-LichMeSH
RulideMeSH
Sigma brand OF roxithromycinMeSH
CT-Arzneimittel brand OF roxithromycinMeSH
Roxi von CTMeSH
Chemical FormulaC41H76N2O15
Average Molecular Weight837.0465
Monoisotopic Molecular Weight836.524569772
IUPAC Name(3R,4S,5S,6R,7R,9R,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one
Traditional Nameroxiβ
CAS Registry Number80214-83-1
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)C(=NOCOCCOC)[C@H](C)[C@@H](O)[C@]1(C)O
InChI Identifier
InChI=1S/C41H76N2O15/c1-15-29-41(10,49)34(45)24(4)31(42-53-21-52-17-16-50-13)22(2)19-39(8,48)36(58-38-32(44)28(43(11)12)18-23(3)54-38)25(5)33(26(6)37(47)56-29)57-30-20-40(9,51-14)35(46)27(7)55-30/h22-30,32-36,38,44-46,48-49H,15-21H2,1-14H3/t22-,23-,24+,25+,26-,27+,28+,29-,30+,32-,33+,34-,35+,36-,38+,39-,40-,41-/m1/s1
InChI KeyRXZBMPWDPOLZGW-HITVVWEBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAminoglycosides
Alternative Parents
Substituents
  • Aminoglycoside core
  • Macrolide
  • Glycosyl compound
  • O-glycosyl compound
  • Monosaccharide
  • Oxane
  • Tertiary alcohol
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Lactone
  • Oxime ether
  • Secondary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Acetal
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Carbonyl group
  • Alcohol
  • Organopnictogen compound
  • Organonitrogen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.19 g/LNot Available
LogP1.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP2.9ALOGPS
logP3ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)9.08ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area216.89 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity211.24 m³·mol⁻¹ChemAxon
Polarizability91.84 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0aor-3911000000-4cbf211b5d9e86f931c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00xr-0000493040-58979c13aa08aabece66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0000090010-6a8aec8cf2250a61f51eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00fr-0000095000-b6d63d80187aeea8a81fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00b9-0000159000-4d5697a33fe979ce33e3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-2911101000-e3794cff943215a188cbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0aor-3911000000-4cbf211b5d9e86f931c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01s9-5100029140-40e43637a280a4eb46aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2200095000-16b1ef7907f8808065a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9100160000-85b185754c8ef3a49170View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2500069830-f89e7f69e1091b4b9b7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dj-5400089510-c2329a0e31fc4cd9d425View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-3200096100-351f99c960e0a3fb10daView in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00778 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00778 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00778
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5291557
KEGG Compound IDC13173
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRoxithromycin
METLIN IDNot Available
PubChem Compound6915744
PDB IDROX
ChEBI ID48844
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gentry LO: Roxithromycin, a new macrolide antibiotic, in the treatment of infections in the lower respiratory tract: an overview. J Antimicrob Chemother. 1987 Nov;20 Suppl B:145-52. [PubMed:3323166 ]
  2. South African Electronic Package Inserts [Link]

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. 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. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
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. 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. Beltinger J, Haschke M, Kaufmann P, Michot M, Terracciano L, Krahenbuhl S: Hepatic veno-occlusive disease associated with immunosuppressive cyclophosphamide dosing and roxithromycin. Ann Pharmacother. 2006 Apr;40(4):767-70. Epub 2006 Mar 7. [PubMed:16595573 ]
  2. Kaufmann P, Haschke M, Torok M, Beltinger J, Bogman K, Wenk M, Terracciano L, Krahenbuhl S: Mechanisms of venoocclusive disease resulting from the combination of cyclophosphamide and roxithromycin. Ther Drug Monit. 2006 Dec;28(6):766-74. [PubMed:17164692 ]