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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

[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

HIDE SMILES / InChI

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

Description
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

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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)
Hypersensitivity (7 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no (co-administration study)
Comment: dirithromycin did not manifest significant drug interactions with cyclosporine, theophylline, terfenadine, or warfarin
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
PubMed

PubMed

TitleDatePubMed
[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

500 mg once a day for seven to fourteen days.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Dirithromycin activity against Streptococcus pneumoniae
MIC90: 16 ug/ml
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:23:42 UTC 2023
Edited
by admin
on Wed Jul 05 23:23:42 UTC 2023
Record UNII
1801D76STL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIRITHROMYCIN
EP   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
DIRITHROMYCIN [ORANGE BOOK]
Common Name English
ERYTHROMYCIN, 9-DEOXO-11-DEOXY-9,11-(IMINO(2-(2-METHOXYETHOXY)ETHYLIDENE)OXY)-, (9S(R))-
Common Name English
DIRITHROMYCIN [USP-RS]
Common Name English
Dirithromycin [WHO-DD]
Common Name English
DIRITHROMYCIN [VANDF]
Common Name English
DIRITHROMYCIN [USAN]
Common Name English
DIRITHROMYCIN [USP IMPURITY]
Common Name English
DIRITHROMYCIN [EP IMPURITY]
Common Name English
dirithromycin [INN]
Common Name English
LY 237216
Code English
DIRITHROMYCIN [MART.]
Common Name English
DIRITHROMYCIN [MI]
Common Name English
DIRITHROMYCIN [EP MONOGRAPH]
Common Name English
LY-237216
Code English
(9S)-9-Deoxo-11-deoxy-9,11-[imino[(1R)-2-(2-methoxyethoxy)ethylidene]oxy]erythromycin
Common Name English
DYNABAC
Brand Name English
NSC-758672
Code English
Classification Tree Code System Code
NCI_THESAURUS C261
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
WHO-VATC QJ01FA13
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
WHO-ATC J01FA13
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
Code System Code Type Description
INN
5694
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
PRIMARY
ChEMBL
CHEMBL3039471
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
PRIMARY
DRUG BANK
DB00954
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
PRIMARY
RS_ITEM_NUM
1220700
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
PRIMARY
WIKIPEDIA
DIRITHROMYCIN
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
PRIMARY
MERCK INDEX
M4664
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C47496
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
PRIMARY
CAS
62013-04-1
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
PRIMARY
CHEBI
474014
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
PRIMARY
EVMPD
SUB07232MIG
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
PRIMARY
PUBCHEM
6473883
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
PRIMARY
NSC
758672
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
PRIMARY
SMS_ID
100000082376
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
PRIMARY
FDA UNII
1801D76STL
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
PRIMARY
USAN
AA-97
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
PRIMARY
DRUG CENTRAL
925
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
PRIMARY
RXCUI
23437
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID7048956
Created by admin on Wed Jul 05 23:23:42 UTC 2023 , Edited by admin on Wed Jul 05 23:23:42 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY