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Dirithromycin

Pharmaceutical drug

Field	Value
Verifiedfields	changed
verifiedrevid	460794200
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
image	Dirithromycin.svg
image_class	skin-invert-image
width	280
tradename	Dynabac
Drugs.com
MedlinePlus	a604026
licence_US	Clarithromycin
pregnancy_AU
pregnancy_US
pregnancy_category	B
legal_AU
legal_UK
legal_US
routes_of_administration	Oral
bioavailability	10%
protein_bound	15 to 30%
metabolism	Hyrolized to erythromycyclamine in 1.5 hours
CAS_number_Ref
CAS_number	62013-04-1
ATC_prefix	J01
ATC_suffix	FA13
PubChem	6917067
DrugBank_Ref
DrugBank	DB00954
ChemSpiderID_Ref
ChemSpiderID	5292341
UNII_Ref
UNII	1801D76STL
ChEBI_Ref
ChEBI	474014
KEGG_Ref
KEGG	D03865
ChEMBL_Ref
ChEMBL	3039471
C	42	H=78	N=2	O=14
smiles	O=C4OC@@HCC
StdInChI_Ref
StdInChI	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
StdInChIKey_Ref
StdInChIKey	WLOHNSSYAXHWNR-NXPDYKKBSA-N
melting_point	186
melting_high	189
melting_notes	(dec.)

| Drugs.com =

| elimination_half-life =

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. 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. However, dirithromycin is still available in many European countries.

References

(April 1999). "Review and comparison of advanced-generation macrolides clarithromycin and dirithromycin". Pharmacotherapy.
(May 2025). "Dynabac Drug Details". U.S. [[Food and Drug Administration]].
(January 1, 2006). "Dirithromycin". U.S. [[National Library of Medicine]].

Info: Wikipedia Source

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macrolide-antibiotics prodrugs fourteen-membered-rings tetrols lactones tetrahydropyrans methoxy-compounds

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