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
SMILES
[H][C@@]2(O[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)[C@@H](C)C(=O)O[C@H](CC)[C@@](C)(O)[C@@H]3O[C@H](COCCOC)N[C@H]([C@@H]3C)[C@H](C)C[C@@](C)(O)[C@]([H])(O[C@@H]4O[C@H](C)C[C@@H]([C@H]4O)N(C)C)[C@H]2C
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
Molecular Formula | C42H78N2O14 |
Molecular Weight | 835.0737 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 20 / 20 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/8735838Curator's Comment: Description was created using several sources including:
http://www.ncbi.nlm.nih.gov/pubmed/15544496;
http://www.ncbi.nlm.nih.gov/pubmed/8303037;
http://www.hindawi.com/journals/isrn/2012/859473/;
http://www.ncbi.nlm.nih.gov/pubmed/8893122
Sources: http://www.ncbi.nlm.nih.gov/pubmed/8735838
Curator's Comment: Description was created using several sources including:
http://www.ncbi.nlm.nih.gov/pubmed/15544496;
http://www.ncbi.nlm.nih.gov/pubmed/8303037;
http://www.hindawi.com/journals/isrn/2012/859473/;
http://www.ncbi.nlm.nih.gov/pubmed/8893122
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
Curator's Comment: Dirithromycin was synthesized by Peter Luger and Roland Maier that published their report in 1979. In 1991 Eli Lilly and Company submitted the patent on a novel process for the synthesis of dirithromycin. In 1998 Dynabac (R) (dirithromycin tablets) received FDA clearance for expanded coverage within certain indications filed by Eli Lilly and Company. Sanofi markets Dynabac in the U.S. under an agreement with Lilly (http://www.prnewswire.com/news-releases/expanded-indications-approved-for-dynabacr-dirithromycin-tablets-antibiotic-marketed-by-sanofi-76962592.html). Discontinued.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2363135 Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=11324679 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Dynabac (R) Approved UseUnknown Launch Date1996 |
|||
Curative | Dynabac (R) Approved UseUnknown Launch Date1996 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.4 μg/mL |
250 mg 2 times / day steady-state, oral dose: 250 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ERYTHROMYCYLAMINE unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
0.3 μg/mL |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
ERYTHROMYCYLAMINE unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.8 μg × h/mL |
250 mg 2 times / day steady-state, oral dose: 250 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ERYTHROMYCYLAMINE unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
0.9 μg × h/mL |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
ERYTHROMYCYLAMINE unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8 h |
250 mg 2 times / day steady-state, oral dose: 250 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ERYTHROMYCYLAMINE unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
8 h |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
ERYTHROMYCYLAMINE unknown | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
500 mg 1 times / day steady, oral Recommended Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: |
unhealthy, 16 - 65 years n = 193 Health Status: unhealthy Condition: infectious diseases Age Group: 16 - 65 years Sex: M+F Population Size: 193 Sources: |
Disc. AE: Gastrointestinal disturbance... AEs leading to discontinuation/dose reduction: Gastrointestinal disturbance (5 patients) Sources: |
500 mg 1 times / day steady, oral Recommended Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: |
unhealthy, adult n = 2825 Health Status: unhealthy Condition: infectious diseases Age Group: adult Sex: M+F Population Size: 2825 Sources: |
Disc. AE: Gastrointestinal disorder NOS, Hypersensitivity... AEs leading to discontinuation/dose reduction: Gastrointestinal disorder NOS (53 patients) Sources: Hypersensitivity (7 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Gastrointestinal disturbance | 5 patients Disc. AE |
500 mg 1 times / day steady, oral Recommended Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: |
unhealthy, 16 - 65 years n = 193 Health Status: unhealthy Condition: infectious diseases Age Group: 16 - 65 years Sex: M+F Population Size: 193 Sources: |
Gastrointestinal disorder NOS | 53 patients Disc. AE |
500 mg 1 times / day steady, oral Recommended Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: |
unhealthy, adult n = 2825 Health Status: unhealthy Condition: infectious diseases Age Group: adult Sex: M+F Population Size: 2825 Sources: |
Hypersensitivity | 7 patients Disc. AE |
500 mg 1 times / day steady, oral Recommended Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: |
unhealthy, adult n = 2825 Health Status: unhealthy Condition: infectious diseases Age Group: adult Sex: M+F Population Size: 2825 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | no (co-administration study) Comment: dirithromycin did not manifest significant drug interactions with cyclosporine, theophylline, terfenadine, or warfarin Sources: https://pubmed.ncbi.nlm.nih.gov/9066944/ |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no |
PubMed
Title | Date | PubMed |
---|---|---|
[Extra and intracellular activity of dirithromycin against Mycobacterium avium]. | 1995 Apr |
|
Comparative study of dirithromycin and azithromycin in the treatment of acute bacterial exacerbations of chronic bronchitis. | 1999 Apr |
|
Actual therapeutic management of allergic and hyperreactive nasal disorders. | 2004 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/cons/dirithromycin.html
500 mg once a day for seven to fourteen days.
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/10212755
Curator's Comment: Dirithromycin activity against Streptococcus pneumoniae
MIC90: 16 ug/ml
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 15:55:22 GMT 2023
by
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on
Fri Dec 15 15:55:22 GMT 2023
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Record UNII |
1801D76STL
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C261
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J01FA13
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5694
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CHEMBL3039471
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DIRITHROMYCIN
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m4664
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C47496
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DTXSID7048956
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