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CHEBI:474014 - dirithromycin

ChEBI IDCHEBI:474014
ChEBI Namedirithromycin
Stars
DefinitionThe 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.
Last Modified22 February 2017
DownloadsMolfile
FormulaC42H78N2O14
Net Charge0
Average Mass835.086
Monoisotopic Mass834.54531
SMILESCC[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](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)[C@@H]2N[C@@H](COCCOC)O[C@H]([C@H]2C)[C@]1(C)O
InChIInChI=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
InChIKeyWLOHNSSYAXHWNR-DWIOZXRMSA-N
Wikipedia
Roles Classification
Biological Role:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application:
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
ChEBI Ontology
Outgoing Relation(s)
dirithromycin (CHEBI:474014) has role prodrug (CHEBI:50266)
dirithromycin (CHEBI:474014) is a macrolide antibiotic (CHEBI:25105)
IUPAC Name 
(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)-β-D-xylo-hexopyranosyl]oxy}-4,16-dioxa-14-azabicyclo[11.3.1]heptadec-7-yl 2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranoside
INNs  Source
dirithromycinChemIDplus
dirithromycineChemIDplus
dirithromycinumChemIDplus
diritromicinaChemIDplus
Synonyms  Source
(9S)-9-deoxo-11-deoxy-9,11-(imino((1R)-2-(2-methoxyethoxy)ethylidene)oxy)erythromycinChemIDplus
dirithromycinChEMBL
Manual XrefsDatabases
925DrugCentral
BE840431Patent
D03865KEGG DRUG
DB00954DrugBank
DirithromycinWikipedia
LSM-5636LINCS
US4048306Patent
Registry NumbersSources
Beilstein:4225019Beilstein
CAS:62013-04-1KEGG DRUG
CAS:62013-04-1ChemIDplus