Dirithromycin

Dirithromycin

File:Dirithromycin.svg
Clinical data
[[Regulation of therapeutic goods |Template:Engvar data]]	US FDA: Clarithromycin
Pregnancy category	B
ATC code	J01FA13 (WHO)
Pharmacokinetic data
Bioavailability	10%
Identifiers
IUPAC name (1S,2R,4R,5R,6S,7S,8R,11R,12R,15R,17S)- 5-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy- 6-methyl-oxan-2-yl]oxy-11-ethyl-4,12-dihydroxy- 7-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy- 4,6-dimethyl-oxan-2-yl]oxy-15-(2-methoxyethoxymethyl)- 2,4,6,8,12,17-hexamethyl-10,14-dioxa-16- azabicyclo[11.3.1]heptadecan-9-one
CAS Number	62013-04-1
PubChem CID	5464388
DrugBank	APRD00931
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C42H78N2O14
Molar mass	835.074 g/mol

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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. The U.S. National Institutes of Health recommend that people taking dirithromycin consult their physicians to discuss switching to another treatment.