CHEBI:474014 - dirithromycin

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ChEBI Name dirithromycin
ChEBI ID CHEBI:474014
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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C42H78N2O14
Net Charge 0
Average Mass 835.07370
Monoisotopic Mass 834.54531
InChI 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
InChIKey WLOHNSSYAXHWNR-DWIOZXRMSA-N
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@@H]2N[C@@H](COCCOC)O[C@H]([C@H]2C)[C@]1(C)O
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via macrolide antibiotic )
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
dirithromycin ChemIDplus
dirithromycine ChemIDplus
dirithromycinum ChemIDplus
diritromicina ChemIDplus
Synonyms Sources
(9S)-9-deoxo-11-deoxy-9,11-(imino((1R)-2-(2-methoxyethoxy)ethylidene)oxy)erythromycin ChemIDplus
dirithromycin ChEMBL
Manual Xrefs Databases
925 DrugCentral
BE840431 Patent
D03865 KEGG DRUG
DB00954 DrugBank
Dirithromycin Wikipedia
LSM-5636 LINCS
US4048306 Patent
View more database links
Registry Numbers Types Sources
4225019 Beilstein Registry Number Beilstein
62013-04-1 CAS Registry Number ChemIDplus
62013-04-1 CAS Registry Number KEGG DRUG
Last Modified
22 February 2017