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Telithromycin

Macrolide antibiotics
Telithromycin
Telithromycin structure
CAS No.
191114-48-4
Chemical Name:
Telithromycin
Synonyms
KETEK;RU 66647;HMR 3647;TELITHROMYCIN;TelithroMycin 90%;(1R,2R,4R,6S,7R,8R,10R,13R,14S)-7-[(2S,3R,4S,6R)-4-Dimethylamino-3-hydroxy-6-methyloxan-2-yl]oxy-13-ethyl-6-methoxy-2,4,6,8,10,14-hexamethyl-17-[4-(4-pyridin-3-ylimidazol-1-yl)butyl]-12,15-dioxa-17-azabicyclo[12.3.0]heptadecane-3,9,11,16-tetrone;2H-Oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(1H,7H,9H)-tetrone,4-ethyloctahydro-11-Methoxy-3a,7,9,11,13,15-hexaMethyl-1-[4-[4-(3-pyridinyl)-1H-iMidazol-1-yl]butyl]-10-[[3,4,6-trideoxy-3-(diMethylaMino)-b-D-xylo-hexopyranosyl]oxy]-,(3aS,4R,7R,9R,10R,11R,1;(3aS,4R,7R,9R,10R,11R,13R,15R,15aR)-4-Ethyloctahydro-11-Methoxy-3a,7,9,11,13,15-hexaMethyl-1-[4-[4-(3-pyridinyl)-1H-iMidazol-1-yl]butyl]-10-[[3,4,6-trideoxy-3-(diMethylaMino)-β-D-xylo-hexopyranosyl]oxy]-2H-oxacyclotetradecino[4,3-d]oxazole-2,6,8,14(1H,7H,9H)tetrone
CBNumber:
CB1482102
Molecular Formula:
C43H65N5O10
Formula Weight:
812
MOL File:
191114-48-4.mol

Telithromycin Properties

Melting point:
176-188 C
Boiling point:
966℃
RTECS 
KF4674500
Flash point:
>110°(230°F)
storage temp. 
-20?C Freezer
Water Solubility 
Sparingly soluble in water
CAS DataBase Reference
191114-48-4(CAS DataBase Reference)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36
HazardClass  9
Hazardous Substances Data 191114-48-4(Hazardous Substances Data)
Symbol(GHS):
Signal word:
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H319 Causes serious eye irritation Serious eye damage/eye irritation Category 2A Warning P264, P280, P305+P351+P338,P337+P313P
H335 May cause respiratory irritation Specific target organ toxicity, single exposure;Respiratory tract irritation Category 3 Warning
H400 Very toxic to aquatic life Hazardous to the aquatic environment, acute hazard Category 1 Warning P273, P391, P501
H410 Very toxic to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 1 Warning P273, P391, P501
Precautionary statements:
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P304+P340 IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405 Store locked up.

Telithromycin price More Price(5)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Alfa Aesar J66820 Telithromycin 95% 191114-48-4 100mg $432 2018-11-20 Buy
Cayman Chemical 17315 Telithromycin ≥98% 191114-48-4 10mg $39 2018-11-13 Buy
Cayman Chemical 17315 Telithromycin ≥98% 191114-48-4 25mg $93 2018-11-13 Buy
Cayman Chemical 17315 Telithromycin ≥98% 191114-48-4 50mg $156 2018-11-13 Buy
Cayman Chemical 17315 Telithromycin ≥98% 191114-48-4 100mg $215 2018-11-13 Buy

Telithromycin Chemical Properties,Uses,Production

Macrolide antibiotics

Telithromycin is recently developed a new kind of macrolide antibiotics. It is the first antibiotic in the family of semi synthetic macrolides, a lincomycin B (MLSB) family. It is also the first ketone lactone antibiotic to be applied to the clinic. It is developed by the French Sanofi Aventis group successfully, with broad-spectrum antimicrobial activity and low resistance selection. It can be a good treatment of Streptococcus pneumoniae and resistant to penicillin and erythromycin, pneumococcal strains, Haemophilus influenzae bacteria and bacteria morahan, The antibacterial effect is stronger than the macrolide antibiotics such as azithromycin.It is mainly used for the treatment of respiratory tract infection, bronchitis, pharyngitis, tonsillitis and pneumonia.The function mechanism of Telithromycin is similar to the that of macrolide antibiotic.Mainly by binding to the 50S subunit of the bacterial ribosome, it inhibits the synthesis of protein and inhibits its translation and assembly. It can also be combined with nucleotides of the 23S ribosome RNA II and V structural region. But the biggest difference is that the binding force of telithromycin on wild-type ribosomes is about 10 times and 6 times stronger than that of erythromycin and clarithromycin. The slight difference in modification of ribosomal structure V region has made the MLSB antibiotic tolerance to bacteria increased by 20 times, making it effective for all drug-resistant strains of macrolide mg/(L•h). Oral administration absorbs well and its bioavailability is about 57%. Food does not affect its absorption. The 70% will be metabolized by CYP3A4 into theyrite alcohol, theyrite acid, N- deoxamide derivative and N- oxpyridine derivative in the liver. T1/2 is 9.81h, and the renal clearance rate was 12.5L/h. There are many ways of excreting: 13% are excreted from the urine in the original form, 3% are excreted from the feces in the original form , and 37% of the metabolites are excreted from the liver.In patients with liver dysfunction, Cmax decreases by about 20%, T1/2 is 1.4 times longer than normal people, and the metabolic rate decreases. The average pharmacokinetic parameters in patients with community acquired pneumonia (CAP) are Cmax 2.89 mg/L, Cmin 0.19 mg/L and AUC 13.9 mg/ (L. H).The US Food and Drug Administration announced on February 12, 2007It should make certain modifications to the drug labels of on the antibiotic telithromycin (also called Kenlike) produced by Sanofi Aventis. It will remove two items of acute bacterial sinusitis and chronic bronchitis in the indications of the drug from the drug instructions. It reminds patients to be careful in using telithromycin.

Chemical Properties

Pale Beige Solid

Uses

Telithromycin represents the first member of the current generation of erythromycin descendants, belonging to the ketolide class. The ketolides are characterised by the hydrolysis of the cladinose sugar and subsequent oxidation of the alcohol to a ketone. Telithromycin is acid stabile and has good activity against erythromycin-resistant S. aureus, and improved pharmacokinetics.

Uses

A ketolide antibiotic, used to treat respiratory infections

brand name

Ketek (Sanofi Aventis).

Antimicrobial activity

The spectrum covers Gram-positive and Gramnegative cocci, Gram-positive bacilli, fastidious Gram-negative bacilli, atypical mycobacteria, M. leprae, H. pylori, anaerobes, T. pallidum, intracellular pathogens and atypical organisms.
It exhibits bactericidal activity in vitro against isolates of Str. pneumoniae regardless of the underlying resistance to penicillin G, erythromycin A and other agents. It is 2–4 times more active than clarithromycin against erythromycin A-susceptible isolates of Str. pneumoniae and other streptococci. Against H. influenzae the MIC range is 1–4 mg/L. It also exhibits good in-vitro activity against Coxiella burnetii (MIC 1 mg/L) and various Gram-positive species, including viridans streptococci (MIC ≤0.015–0.25 mg/L), C. diphtheriae (MIC 0.004–0.008 mg/L) and Listeria spp. (MIC 0.03–0.25 mg/L).

Acquired resistance

It retains activity against isolates resistant to erythromycin A. Str. pneumoniae and Str. pyogenes isolates for which the MIC of telithromycin is above the resistance breakpoint of 2 mg/L are presently rare. It is not active against Staph. aureus isolates that owe their resistance to erythromycin to constitutive methylation of adenine 2058 on domain V of the peptidyl transferase loop.

General Description

Telithromycin (Ketek) is an orally bioavailable macrolide.The antibiotic is semisynthetic. Telithromycin is classifiedas a ketolide, and it differs chemically from the macrolidegroup of antibacterials by the lack of α-L-cladinose at 3-position of the erythronolide A ring, resulting in a 3-ketofunction. It is further characterized by imidazolyl andpyridyl rings inked to the macrolide nucleus through a butylchain. The mechanism of action of telithromycin is the sameas that of the macrolide class.
Telithromycin causes a blockade of protein synthesis bybinding to domains II and V of 23S rRNA of the 50S ribosomalsubunit. Because telithromycin binds at domain II,activity against Gram-positive cocci is retained in the presenceof resistance mediated by methylases that alter thedomain V binding site. The antibiotic is also believed to inhibitthe assembly of ribosomes. Resistance to telithromycinoccurs because of riboprotein mutations.

Pharmaceutical Applications

A 14-membered-ring ketolide, obtained by semisynthesis from erythromycin A. Formulated for oral administration.

Pharmacokinetics

Oral absorption :90%
Cmax 800 mg oral :1.9–2.27 mg/L (steady state after 2–3 days)
Plasma half-life: 10–12 h
Volume of distribution :210 L
Plasma protein binding:60–70%
After oral administration the absolute bioavailability is 57% in both young and elderly subjects. The rate and extent of absorption are not influenced by food. In a study of ascending doses administered to healthy volunteers, peak plasma concentration ranged from 0.8 mg/L (400 mg dose) to 6 mg/L (2400 mg dose). The peak plasma concentration was reached after 1–2 h. The apparent elimination half-lives ranged from 10 to 14 h, with an AUC of 2.6 mg.h/L (400 mg dose) to 43.3 mg.h/L (2400 mg dose). After repeated oral doses the ratios between day 1 and day 10 ranged from 1.3 to 1.5. After once-daily oral dosing with 800 mg, the AUC is 8.25 mg.h/L.

Side effects

It is generally well tolerated. The main adverse event is diarrhea.

Telithromycin Preparation Products And Raw materials

Raw materials

Preparation Products


Telithromycin Suppliers

Global( 93)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 22043 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20786 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32651 55
Haihang Industry Co.,Ltd
86-531-88032799
+86 531 8582 1093 export@haihangchem.com CHINA 4525 58
J & K SCIENTIFIC LTD. 400-666-7788 +86-10-82848833
+86-10-82849933 jkinfo@jkchemical.com;market6@jkchemical.com China 96815 76
LGM Pharma 1-(800)-881-8210
615-250-9817 inquiries@lgmpharma.com United States 1954 70
Nanjing Chemlin Chemical Co., Ltd 025-83697070
+86-25-83453306 sales@chemlin.com.cn China 19998 64
Chemsky(shanghai)International Co.,Ltd. 021-50135380
shchemsky@sina.com China 32492 50
Hangzhou Yuhao Chemical Technology Co., Ltd 0571-82693216
+86-571-82880190 info@yuhaochemical.com China 9430 52
Beijing HuaMeiHuLiBiological Chemical 010-56205725;010-86181995
010-65763397 waley188@sohu.com China 12388 58

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