BioModels Ontology

Last uploaded: April 3, 2012
Preferred Name

dirithromycin

Synonyms
Definitions

The hemi-aminal resulting from the condensation of the erythromycin derivative (9S)-erythromycyclamine with 2-(2-methoxyethoxy)acetaldehyde. As the oxazine ring containing the hemi-aminal group is unstable under both acidic and alkaline conditions, dirithromycin functions as a more lipid-soluble prodrug for (9S)-erythromycyclamine. Administered as enteric coated tablets to protect it from acid catalysed hydrolysis in the stomach, it is used to treat respiratory tract, skin, and soft tissue infections caused by susceptible organisms.

ID

http://purl.obolibrary.org/obo/CHEBI_474014

alternative term

(1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-3-ethyl-2,10-dihydroxy-15-[(2-methoxyethoxy)methyl]-2,6,8,10,12,17-hexamethyl-5-oxo-9-{[3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl]oxy}-4,16-dioxa-14-azabicyclo[11.3.1]heptadec-7-yl 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranoside

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@@H]2N[C@@H](COCCOC)O[C@H]([C@H]2C)[C@]1(C)O

dirithromycine

dirithromycinum

diritromicina

InChI=1S/C42H78N2O14/c1-15-29-42(10,49)37-24(4)32(43-30(56-37)21-52-17-16-50-13)22(2)19-40(8,48)36(58-39-33(45)28(44(11)12)18-23(3)53-39)25(5)34(26(6)38(47)55-29)57-31-20-41(9,51-14)35(46)27(7)54-31/h22-37,39,43,45-46,48-49H,15-21H2,1-14H3/t22-,23-,24+,25+,26-,27+,28+,29-,30-,31+,32+,33-,34+,35+,36-,37-,39+,40-,41-,42-/m1/s1

dirithromycin

(9S)-9-deoxo-11-deoxy-9,11-(imino((1R)-2-(2-methoxyethoxy)ethylidene)oxy)erythromycin

C42H78N2O14

InChIKey=WLOHNSSYAXHWNR-DWIOZXRMSA-N

definition

The hemi-aminal resulting from the condensation of the erythromycin derivative (9S)-erythromycyclamine with 2-(2-methoxyethoxy)acetaldehyde. As the oxazine ring containing the hemi-aminal group is unstable under both acidic and alkaline conditions, dirithromycin functions as a more lipid-soluble prodrug for (9S)-erythromycyclamine. Administered as enteric coated tablets to protect it from acid catalysed hydrolysis in the stomach, it is used to treat respiratory tract, skin, and soft tissue infections caused by susceptible organisms.

has role

http://purl.obolibrary.org/obo/CHEBI_50266

label

dirithromycin

prefixIRI

CHEBI:474014

prefLabel

dirithromycin

subClassOf

http://purl.obolibrary.org/obo/CHEBI_25105

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Delete Mapping To Ontology Source
http://purl.obolibrary.org/obo/CHEBI_474014 PDRO SAME_URI
http://purl.obolibrary.org/obo/CHEBI_474014 DINTO SAME_URI
http://purl.obolibrary.org/obo/CHEBI_474014 BERO SAME_URI
http://purl.obolibrary.org/obo/CHEBI_474014 DRON SAME_URI
http://purl.obolibrary.org/obo/CHEBI_474014 CHEBI SAME_URI
http://purl.obolibrary.org/obo/CHEBI_474014 GENEPIO SAME_URI
http://stirdf.jst.go.jp/id/200907017462567421 IOBC LOOM
http://purl.bioontology.org/ontology/VANDF/4020907 VANDF LOOM
http://purl.bioontology.org/ontology/MESH/C053853 MESH LOOM
http://purl.bioontology.org/ontology/SNOMEDCT/96035007 SNOMEDCT LOOM
http://purl.bioontology.org/ontology/ATC/J01FA13 ATC LOOM
http://purl.bioontology.org/ontology/NDFRT/N0000148396 NDFRT LOOM
http://purl.obolibrary.org/obo/CHEBI_474014 PDRO LOOM
http://purl.obolibrary.org/obo/CHEBI_474014 DINTO LOOM
http://purl.obolibrary.org/obo/CHEBI_474014 BERO LOOM
http://purl.obolibrary.org/obo/CHEBI_474014 DRON LOOM
http://purl.obolibrary.org/obo/CHEBI_474014 CHEBI LOOM
http://purl.obolibrary.org/obo/CHEBI_474014 GENEPIO LOOM
http://purl.jp/bio/4/id/200906029732854520 IOBC LOOM
http://purl.bioontology.org/ontology/RXNORM/23437 RXNORM LOOM
http://purl.bioontology.org/ontology/SNMI/C-52A30 SNMI LOOM
http://sbmi.uth.tmc.edu/ontology/ochv#13905 OCHV LOOM
http://purl.obolibrary.org/obo/NCIT_C47496 BERO LOOM
http://purl.bioontology.org/ontology/LNC/MTHU016192 LOINC LOOM
http://sbmi.uth.tmc.edu/ontology/ochv#C0058445 OCHV LOOM
http://purl.bioontology.org/ontology/NDDF/005044 NDDF LOOM
http://phenomebrowser.net/ontologies/mesh/mesh.owl#C053853 RH-MESH LOOM
http://purl.obolibrary.org/obo/ARO_3000176 ARO LOOM
http://purl.bioontology.org/ontology/LNC/LP17270-7 LOINC LOOM
https://go.drugbank.com/drugs/DB00954 MDM LOOM
http://ncicb.nci.nih.gov/xml/owl/EVS/Thesaurus.owl#C47496 NCIT LOOM
http://www.phoc.org.cn/pmo/class/PMO_00026070 PMAPP-PMO LOOM