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Details

Stereochemistry ABSOLUTE
Molecular Formula C42H78N2O14
Molecular Weight 835.0737
Optical Activity UNSPECIFIED
Defined Stereocenters 20 / 20
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIRITHROMYCIN

SMILES

CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@](C)(O)C[C@@H](C)[C@@H]4N[C@@H](COCCOC)O[C@H]([C@H]4C)[C@]1(C)O

InChI

InChIKey=WLOHNSSYAXHWNR-DWIOZXRMSA-N
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

HIDE SMILES / InChI

Description

Dirithromycin (Dynabac) is a macrolide glycopeptide antibiotic used to treat different types of bacterial infections, such as bronchitis, pneumonia, tonsillitis, skin infections. Dirithromycin is a semi-synthetic derivative of erythromycin - the hemi-aminal resulting from the condensation of (9S)-erythromycyclamine with 2-(2-methoxyethoxy) acetaldehyde. Being unstable under both acidic and alkaline conditions, dirithromycin functions as a more lipid-soluble prodrug for (9S)-erythromycyclamine. Erythromycylamine exerts its activity by binding to the 50S ribosomal subunits of susceptible mircoorganisms resulting in inhibition of protein synthesis. Dirithromycin has been shown to be active against most strains of the following microorganisms both in vitro and in clinical infections: Staphylococcus aureus (methicillin-susceptible strains only), Streptococcus pneumoniae, Streptococcus pyogenes, Haemophilus influenzae, Legionella pneumophila, Moraxella catarrhalis, and Mycoplasma pneumoniae. Dirithromycin showed better activity in vitro against Campylobacter jejuni and Borrelia burgdorferi than erythromycin or clarithromycin but in general demonstrated less activity than erythromycin, clarithromycin, or azithromycin against a majority of microorganisms. The pharmacokinetic profile of dirithromycin has advantages over other microlides of once-daily dosing and high and prolonged tissue concentrations but adverse effect profiles similar to those of the other macrolides, with reported problems most often related to the gastrointestinal tract.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Dynabac (R)
Curative
Dynabac (R)

Cmax

ValueDoseCo-administeredAnalytePopulation
0.3 μg/mL
500 mg single, oral
ERYTHROMYCYLAMINE plasma
Homo sapiens
0.4 μg/mL
500 mg 1 times / day steady-state, oral
ERYTHROMYCYLAMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
0.9 μg × h/mL
500 mg single, oral
ERYTHROMYCYLAMINE plasma
Homo sapiens
1.8 μg × h/mL
500 mg 1 times / day steady-state, oral
ERYTHROMYCYLAMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
8 h
500 mg single, oral
ERYTHROMYCYLAMINE plasma
Homo sapiens
8 h
500 mg 1 times / day steady-state, oral
ERYTHROMYCYLAMINE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
500 mg once a day for seven to fourteen days.
Route of Administration: Oral
In Vitro Use Guide
MIC90: 16 ug/ml