Dirithromycin

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Dirithromycin
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Clinical data
Trade namesDynabac
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa604026
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Pregnancy
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  • B
Routes of
administration		Oral
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Pharmacokinetic data
Bioavailability10%
Protein binding15 to 30%
MetabolismHyrolized to erythromycyclamine in 1.5 hours
Identifiers
  • (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
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Chemical and physical data
FormulaC42H78N2O14
Molar mass835.086 g·mol−1
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Melting point186 to 189 °C (367 to 372 °F) (dec.)
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  • 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 checkY
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Data page
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Dirithromycin is a macrolide glycopeptide antibiotic.[1]

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.[2] Since the production of dirithromycin is discontinued in the U.S., National Institutes of Health recommend that people taking dirithromycin should consult their physicians to discuss switching to another treatment.[3] However, dirithromycin is still available in many European countries.

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.McConnell SA, Amsden GW (April 1999). "Review and comparison of advanced-generation macrolides clarithromycin and dirithromycin". Pharmacotherapy. 19 (4): 404–15. doi:10.1592/phco.19.6.404.31054. PMID 10212011. S2CID 25018468.
  2. ^ Page Module:Citation/CS1/styles.css has no content."Dynabac Drug Details". U.S. Food and Drug Administration. Retrieved 2007-05-25.[dead link]
  3. ^ Page Module:Citation/CS1/styles.css has no content."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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