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Compound InformationSONAR Target prediction
Name:

DIRITHROMYCIN

Unique Identifier:SPE01504144
MolClass: Checkout models in ver1.5 and ver1.0
Molecular Formula:
Molecular Weight:756.454 g/mol
X log p:-2.064  (online calculus)
Lipinksi Failures2
TPSA103.38
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptors Count:16
Rotatable Bond Count:12
Canonical Smiles:CCC1OC(=O)C(C)C(OC2CC(C)(OC)C(O)C(C)O2)C(C)C(OC2OC(C)CC(C2O)N(C)C)C(C)
(O)CC(C)C2NC(COCCOC)OC(C2C)C1(C)O
Source:semisynthetic
Reference:Drugs 61: 443 (2001)
Therapeutics:antibacterial
Generic_name:Dirithromycin
Chemical_iupac_name:9-(4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl)oxy-3-ethyl-2,10-dihydroxy-7-(5-hydr
oxy-4-methoxy-4,6-dimethyl-oxan-2-yl)oxy-15-(2-methoxyethoxymethyl)-2,6,8,10,12,17-h
examethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one
Drug_type:Approved Drug
Pharmgkb_id:PA449368
Drugbank_id:APRD00931
H2o_solubility:Poor
Logp:2.833
Cas_registry_number:62013-04-1
Drug_category:Anti-infectives; Macrolides; ATC:J01FA13
Indication:For the treatment of the following mild-to-moderate infections caused by susceptible
strains of microorganisms: acute bacterial exacerbations of chronic bronchitis,
secondary bacterial infection of acute bronchitis, community-acquired pneumonia,
pharyngitis/tonsilitis, and uncomplicated skin and skin structure infections.
Pharmacology:Dirithromycin is a pro-drug which is converted non-enzymatically during intestinal
absorption into the microbiologically active moiety erythromycylamine.
Erythromycylamine exerts its activity by binding to the 50S ribosomal subunits of
susceptible mircoorganisms resulting in inhibition of protein synthesis.
Dirithromycin/erythromycylamine 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.
Mechanism_of_action:Dirithromycin prevents bacteria from growing, by interfering with their protein
synthesis. Dirithromycin binds to the 50S subunit of the 70S bacterial ribosome, and
thus inhibits the translocation of peptides. Dirithromycin has over 10 times higher
affinity to the subunit 50S than erythromycin. In addition, dirithromycin binds
simultaneously in to two domains of 23S RNA of the ribosomal subunit 50S, where
older macrolides bind only in one. Dirithromycin can also inhibit the formation of
ribosomal subunits 50S and 30S.
Organisms_affected:Enteric bacteria and other eubacteria

Found: 205 nonactive as graph: single | with analogs [1] << Back 1 2 3 4 5 6 7 8 9 10  Next >> [205]
Species: 4932
Condition: BY4741-2nd
Replicates: 2
Raw OD Value: r im 0.9690±0.014425
Normalized OD Score: sc h 0.9981±0.00738223
Z-Score: 0.8645±0.322827
p-Value: 0.399588
Z-Factor: -2.46069
Fitness Defect: 0.9173
Bioactivity Statement: Nonactive
Experimental Conditions
Library:Spectrum_ED
Plate Number and Position:8|F8
Drug Concentration:50.00 nM
OD Absorbance:595 nm
Robot Temperature:30.00 Celcius
Date:2012-05-28 YYYY-MM-DD
Plate CH Control (+):0.1095±0.00497
Plate DMSO Control (-):0.9544999999999999±0.02160
Plate Z-Factor:0.9057
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DBLink | Rows returned: 72 Next >> 
462481 (2R,3R,6R,7S,9R,10R,12R,13S,15R,17S)-9-(4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl)oxy-3-ethyl-2,10-di
hydroxy-7-(5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl)oxy-15-(2-methoxyethoxymethyl)-2,6,8,10,12,17-hexa
methyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one
4580358 9-(4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl)oxy-3-ethyl-2,10-dihydroxy-7-(5-hydroxy-4-methoxy-4,6-di
methyl-oxan-2-yl)oxy-15-(2-methoxyethoxymethyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.
1]heptadecan-5-one
5464388 (2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-9-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl]ox
y-3-ethyl-2,10-dihydroxy-7-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl]oxy-15-(2-methoxyet
hoxymethyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one
6473883 (1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-9-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl
]oxy-3-ethyl-2,10-dihydroxy-7-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl]oxy-15-(2-methox
yethoxymethyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one
6604422 (1R,2R,3S,6R,7R,8S,9S,10R,12S,13S,15S,17R)-9-[(2S,3S,4R,6S)-4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl
]oxy-3-ethyl-2,10-dihydroxy-7-[(2R,4S,5R,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl]oxy-15-(2-methox
yethoxymethyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one
6713946 (2R,3S,6R,7R,8R,9R,10S,12R,13S,15S,17S)-9-[(2S,3R,4S,6R)-4-dimethylamino-3-hydroxy-6-methyl-oxan-2-yl]ox
y-3-ethyl-2,10-dihydroxy-7-[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyl-oxan-2-yl]oxy-15-(2-methoxyet
hoxymethyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one

internal high similarity DBLink | Rows returned: 0

nonactive | Cluster 14145 | Additional Members: 11 | Rows returned: 102 Next >> 
Prest923 0.320754716981132
SPE01503276 0.264705882352941
Prest1046 0.264705882352941
SPE01500279 0.221052631578947
SPE01503679 0.206521739130435
SPE01501176 0.195652173913043

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