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Dirithromycin

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Dirithromycin

Dirithromycin
Systematic (IUPAC) name
(2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-9-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-3-ethyl-2,10-dihydroxy-7-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-15-[(2-methoxyethoxy)methyl]-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one
Clinical data
Trade names Dynabac
AHFS/Drugs.com
MedlinePlus
Licence data US FDA:
Pregnancy cat.
  • B
Legal status
?
Routes Oral
Pharmacokinetic data
Bioavailability 10%
Protein binding 15 to 30%
Metabolism Hyrolized to erythromycyclamine in 1.5 hours
Identifiers
CAS number  Y
ATC code J01
PubChem
DrugBank
ChemSpider  Y
UNII  Y
KEGG  Y
ChEBI  N
ChEMBL  N
Chemical data
Formula C42H78N2O14 
Mol. mass 835.074 g/mol
 N   

Dirithromycin is a macrolide glycopeptide antibiotic.

Dirithromycin (Dynabac) is a more lipid-soluble prodrug derivative of 9S-erythromycyclamine prepared by condensation of the latter with 2-(2-methoxyethoxy)acetaldehyde. The 9N, 11O-oxazine ring thus formed is a hemi-aminal that is unstable under both acidic and alkaline aqueous conditions and undergoes spontaneous hydrolysis to form erythromycyclamine. Erythromycyclamine is a semisynthetic derivative of erythromycin in which the 9-ketogroup of the erythronolide ring has been converted to an amino group. Erythromycyclamine retains the antibacterial properties of erythromycin oral administration. The prodrug, dirithromycin, is provided as enteric coated tablets to protect it from acid catalyzed hydrolysis in the stomach. Orally administered dirithromycin is absorbed rapidly into the plasma, largely from the small intestine. Spontaneous hydrolysis to erythromycyclamine occurs in the plasma. Oral bioavailability is estimated to be about 10%, but food does not affect absorption of the prodrug.

Discontinuation

Dirithromycin is no longer available in the United States.[1] The U.S. National Institutes of Health recommend that people taking dirithromycin consult their physicians to discuss switching to another treatment.[2]

References

  1. ^ "Dynabac Drug Details". U.S. Food and Drug Administration. Retrieved 2007-05-25. 
  2. ^ "Dirithromycin". MedlinePlus. U.S. National Library of Medicine. January 1, 2006. Archived from the original on 2007-03-29. Retrieved 2007-05-25. 
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