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
License data	US FDA: Clarithromycin
Pregnancy category	B
Routes of administration	Oral
Pharmacokinetic data
Bioavailability	10%
Protein binding	15 to 30%
Metabolism	Hyrolized to erythromycyclamine in 1.5 hours
Identifiers
CAS Number	62013-04-1
ATC code	J01FA13 (WHO)
PubChem	CID 6917067
DrugBank	DB00954
ChemSpider	5292341
UNII	1801D76STL
KEGG	D03865
ChEBI	CHEBI:474014
ChEMBL	CHEMBL3039471
Chemical data
Formula	C42H78N2O14
Molar mass	835.074 g/mol
SMILES O=C4O[C@@H]([C@](O)(C)[C@H]1O[C@@H](N[C@H]([C@@H]1C)[C@H](C)C[C@](O)(C)[C@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@H]([C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@](OC)(C)C3)[C@H]4C)C)COCCOC)CC
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 Key:WLOHNSSYAXHWNR-NXPDYKKBSA-N
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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] 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.^[2] However, dirithromycin is still available in many european countries.

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.