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Systematic (IUPAC) name
CAS number 62013-04-1
ATC code J01FA13
PubChem 5464388
DrugBank APRD00931
Chemical data
Formula C42H78N2O14 
Mol. mass 835.074 g/mol
Pharmacokinetic data
Bioavailability 10%
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Licence data


Pregnancy cat.


Legal status
Routes  ?

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.


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]


  1. ^ Dynabac Drug Details. U.S. Food and Drug Administration. Retrieved on 2007-05-25.
  2. ^ Dirithromycin. MedlinePlus. U.S. National Library of Medicine (January 1 2006). Retrieved on 2007-05-25.
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Dirithromycin". A list of authors is available in Wikipedia.
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