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	Micromedex Detailed Consumer Information
MedlinePlus	a604026
Licence data	US FDA:link
Pregnancy cat.	B
Legal status	?
Pharmacokinetic data
Bioavailability	10%
Identifiers
CAS number	62013-04-1 Y
ATC code	J01FA13
PubChem	CID 6917067
DrugBank	APRD00931
ChemSpider	5292341 Y
UNII	1801D76STL Y
KEGG	D03865 Y
ChEMBL	CHEMBL1200505 N
Chemical data
Formula	C42H78N2O14
Mol. mass	835.074 g/mol
SMILES	eMolecules & PubChem
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 Y Key:WLOHNSSYAXHWNR-NXPDYKKBSA-N Y
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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.^[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. http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.SearchAction&SearchTerm=Dirithromycin&SearchType=BasicSearch. Retrieved 2007-05-25. 
2. ^ "Dirithromycin". MedlinePlus. U.S. National Library of Medicine. January 1, 2006. Archived from the original on 2007-03-29. http://web.archive.org/web/20070329044740/http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a696021.html. Retrieved 2007-05-25. 

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