Dirithromycin

Names

[ CAS No. ]:
62013-04-1

[ Name ]:
Dirithromycin

[Synonym ]:
(2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-3-Ethyl-2,10-dihydroxy-15-[(2-methoxyethoxy)methyl]-2,6,8,10,12,17-hexamethyl-5-oxo-9-{[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy}-4,16-dio xa-14-azabicyclo[11.3.1]heptadec-7-yl 2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranoside
Noriclan
Dynabac
Dirythromycin
4,16-Dioxa-14-azabicyclo[11.3.1]heptadecan-5-one
MFCD00865041
ASE 136
4,16-Dioxa-14-azabicyclo[11.3.1]heptadecan-5-one, 7-[(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy]-3-ethyl-2,10-dihydroxy-15-[(2-methoxyethoxy)methyl]-2,6,8,10,12,17-hexamethyl-9- [[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-, (2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-
Dirithomycin
Valodin
Dirithromycin
Antibiotic AS-E 136

Biological Activity

[Description]:

Dirithromycin(LY 237216) is a macrolide glycopeptide antibiotic by binding to the 50S subunit of the 70S bacterial ribosome to inhibit the translocation of peptides.Target: AntibacterialDirithromycin is a new macrolide with a spectrum and degree of in vitro antimicrobial activity similar to that of erythromycin. Compared with erythromycin, dirithromycin has a long elimination half-life enabling once-daily administration, and it also achieves a greater cellular:extracellular concentration ratio and higher concentration in some tissues. Multicentre double-blind clinical trials have shown dirithromycin to be similar in efficacy to erythromycin in the treatment of uncomplicated bacterial infections of the respiratory tract and of skin and soft tissues [1]. Dirithromycin offers some attractive pharmacokinetic properties. The long elimination half-life of dirithromycin allows once-daily dosing and higher and more prolonged tissue concentrations than are achievable with erythromycin. The spectrum of activity, adverse effect profile, clinical efficacy, and bacteriologic eradication rate of dirithromycin may be similar to those of erythromycin [2, 3].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Infection

[References]

[1]. Brogden, R.N. and D.H. Peters, Dirithromycin. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic efficacy. Drugs, 1994. 48(4): p. 599-616.

[2]. Wintermeyer, S.M., S.M. Abdel-Rahman, and M.C. Nahata, Dirithromycin: a new macrolide. Ann Pharmacother, 1996. 30(10): p. 1141-9.

[3]. Sides, G.D., et al., Pharmacokinetics of dirithromycin. J Antimicrob Chemother, 1993. 31 Suppl C: p. 65-75.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
871.8±65.0 °C at 760 mmHg

[ Melting Point ]:
185 - 189ºC

[ Molecular Formula ]:
C₄₂H₇₈N₂O₁₄

[ Molecular Weight ]:
835.074

[ Flash Point ]:
481.0±34.3 °C

[ Exact Mass ]:
834.545288

[ PSA ]:
196.33000

[ LogP ]:
2.84

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.533

[ Storage condition ]:
-20°C

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H317

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R42/43

[ Safety Phrases ]:
S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
29419000

Customs

[ HS Code ]: 29419000

Articles

The new macrolide antibiotics: azithromycin, clarithromycin, dirithromycin, and roxithromycin.

Ann. Pharmacother. 26(1) , 46-55, (1992)

To review the chemistry, antimicrobial spectrum, pharmacokinetics, clinical trials, adverse effects, and drug interactions of four new macrolide antibiotics: azithromycin, clarithromycin, dirithromyci...

Pharmacokinetics of dirithromycin.

J. Antimicrob. Chemother. 31 Suppl C , 65-75, (1993)

Dirithromycin is a new member of the macrolide class of antibiotics and has been developed for oral administration. Dirithromycin is a 14-membered lactone ring macrolide and is the C9-oxazine derivati...

Modulation of human polymorphonuclear neutrophil function by macrolides: preliminary data concerning dirithromycin.

J. Antimicrob. Chemother. 31 Suppl C , 51-64, (1993)

Polymorphonuclear neutrophils (PMN) play a prominent role in the host response to infectious diseases. One major bactericidal mechanism used by these cells is the production of reactive oxygen species...