Telithromycin

CAS# 191114-48-4

Telithromycin

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Chemical structure

Telithromycin

3D structure

Chemical Properties of Telithromycin

Cas No. 191114-48-4 SDF Download SDF
PubChem ID 3002190 Appearance Powder
Formula C43H65N5O10 M.Wt 812.0
Type of Compound N/A Storage Desiccate at -20°C
Synonyms HMR3647; RU66647
Solubility DMSO : ≥ 100 mg/mL (123.15 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (1S,2R,5R,7R,8R,9R,11R,13R,14R)-8-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-9-methoxy-1,5,7,9,11,13-hexamethyl-15-[4-(4-pyridin-3-ylimidazol-1-yl)butyl]-3,17-dioxa-15-azabicyclo[12.3.0]heptadecane-4,6,12,16-tetrone
SMILES CCC1C2(C(C(C(=O)C(CC(C(C(C(=O)C(C(=O)O1)C)C)OC3C(C(CC(O3)C)N(C)C)O)(C)OC)C)C)N(C(=O)O2)CCCCN4C=C(N=C4)C5=CN=CC=C5)C
Standard InChIKey LJVAJPDWBABPEJ-PNUFFHFMSA-N
Standard InChI InChI=1S/C43H65N5O10/c1-12-33-43(8)37(48(41(53)58-43)19-14-13-18-47-23-31(45-24-47)30-16-15-17-44-22-30)27(4)34(49)25(2)21-42(7,54-11)38(28(5)35(50)29(6)39(52)56-33)57-40-36(51)32(46(9)10)20-26(3)55-40/h15-17,22-29,32-33,36-38,40,51H,12-14,18-21H2,1-11H3/t25-,26-,27+,28+,29-,32+,33-,36-,37-,38-,40+,42-,43-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Telithromycin

DescriptionTelithromycin(HMR3647) is a ketolide antibiotic to treat community acquired pneumonia of mild to moderate severity. Target: Antibacterial Telithromycin prevents bacteria from growing, by interfering with their protein synthesis. Telithromycin binds to the subunit 50S of the bacterial ribosome, and blocks the progression of the growing polypeptide chain. Telithromycin has over 10 times higher affinity to the subunit 50S than erythromycin. In addition, telithromycin strongly bind simultaneously to two domains of 23S RNA of the 50 S ribosomal subunit, where older macrolides bind strongly only to one domain and weakly to the second domain. Telithromycin can also inhibit the formation of ribosomal subunits 50S and 30S. From Wikipedia.

References:
[1]. http://en.wikipedia.org/wiki/Telithromycin

Telithromycin Dilution Calculator

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Telithromycin Molarity Calculator

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Preparing Stock Solutions of Telithromycin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.2315 mL 6.1576 mL 12.3153 mL 24.6305 mL 30.7882 mL
5 mM 0.2463 mL 1.2315 mL 2.4631 mL 4.9261 mL 6.1576 mL
10 mM 0.1232 mL 0.6158 mL 1.2315 mL 2.4631 mL 3.0788 mL
50 mM 0.0246 mL 0.1232 mL 0.2463 mL 0.4926 mL 0.6158 mL
100 mM 0.0123 mL 0.0616 mL 0.1232 mL 0.2463 mL 0.3079 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Telithromycin

ketolide antibiotic to treat community acquired pneumonia of mild to moderate severity.

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References on Telithromycin

Ketolide agents HMR 3004 and HMR 3647 (telithromycin) inhibit the growth of Plasmodium falciparum in vitro.[Pubmed:26958030]

Afr Health Sci. 2015 Dec;15(4):1271-6.

BACKGROUND: Malaria is on the increase due to emergence of parasite drug resistance and there is thus an urgent need for the development of new antiparasitic drugs effective at low concentrations. Ketolides antibiotics are used for treatment of various ailments and are relevant candidates to establish antiparasitic activity. OBJECTIVES: The present study investigates the activity of ketolide compounds HMR 3004 and HMR 3647 (Telithromycin) (0.025-12.5 microM) for activity against chloroquine-sensitive and resistant strains of Plasmodium falciparum in vitro. METHODS: The antiplasmodial activity of the two ketolide agents were determined using microscopic and colorimetric [lactate dehydrogenase assay] procedures. RESULTS: Both HMR 3004 and HMR 3647 caused a dose-dependent inhibition of growth of both parasite strains with IC50 values 3 and 15 nM, respectively. Suppression of parasite growth was evident after 8 hours of exposure to both agents at 12.5 microM with total parasite clearance achieved at 40 hours. CONCLUSION: The results indicate lack of cross-resistance between the ketolide compounds and chloroquine, implying presence of a drug target different from that of chloroquine. The particular drug target has still to be investigated but the stage-specific results indicate that it is expressed in all parasite growth phases. These observations demonstrate the anti-malarial potential of the ketolide antimicrobial agents.

Telithromycin: review of adverse effects.[Pubmed:25954793]

Prescrire Int. 2014 Nov;23(154):264-6.

Telithromycin is a macrolide antibiotic that has been marketed since the early 2000s. It has not been shown to be more effective against any bacteria than other macrolide antibiotics. Its antibacterial activity is in no way remarkable. In early 2014, we reviewed its adverse effect profile using data from periodic safety update reports, drug regulatory agencies, and detailed published case reports. In addition to the adverse effect profile Telithromycin shares with the other macrolides, it provokes several specific adverse effects: visual disturbances due to impaired accommodation; taste and smell disorders; severe liver damage; worsening of myasthenia gravis; rhabdomyolysis; and loss of consciousness. Prolongation of the QT interval with standard oral doses is a worrisome adverse effect. In practice, it is better not to use Telithromycin as it exposes patients to disproportionate, serious adverse effects. When treatment with a macrolide antibiotic appears necessary, it is prudent to choose a different macrolide, such as spiramycin or azithromycin, which have fewer adverse effects.

RlmCD-mediated U747 methylation promotes efficient G748 methylation by methyltransferase RlmAII in 23S rRNA in Streptococcus pneumoniae; interplay between two rRNA methylations responsible for telithromycin susceptibility.[Pubmed:26365244]

Nucleic Acids Res. 2015 Oct 15;43(18):8964-72.

Adenine at position 752 in a loop of helix 35 from positions 745 to 752 in domain II of 23S rRNA is involved in binding to the ribosome of Telithromycin (TEL), a member of ketolides. Methylation of guanine at position 748 by the intrinsic methyltransferase RlmA(II) enhances binding of Telithromycin (TEL) to A752 in Streptococcus pneumoniae. We have found that another intrinsic methylation of the adjacent uridine at position 747 enhances G748 methylation by RlmA(II), rendering TEL susceptibility. U747 and another nucleotide, U1939, were methylated by the dual-specific methyltransferase RlmCD encoded by SP_1029 in S. pneumoniae. Inactivation of RlmCD reduced N1-methylated level of G748 by RlmA(II) in vivo, leading to TEL resistance when the nucleotide A2058, located in domain V of 23S rRNA, was dimethylated by the dimethyltransferase Erm(B). In vitro methylation of rRNA showed that RlmA(II) activity was significantly enhanced by RlmCD-mediated pre-methylation of 23S rRNA. These results suggest that RlmCD-mediated U747 methylation promotes efficient G748 methylation by RlmA(II), thereby facilitating TEL binding to the ribosome.

Description

Telithromycin(HMR3647) is a ketolide antibiotic to treat community acquired pneumonia of mild to moderate severity.

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