Telithromycin
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| Category | Antibiotics |
| Catalog number | BBF-03847 |
| CAS | 191114-48-4 |
| Molecular Weight | 812.00 |
| Molecular Formula | C43H65N5O10 |
| Purity | >98% |
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Description
Telithromycin is a semi-synthetic erythromycin derivative. It is created by substituting a ketogroup for the cladinose sugar and adding a carbamate ring in the lactone ring. An alkyl-aryl moiety is attached to this carbamate ring. Furthermore, the carbon at position 6 has been methylated, as is the case in clarithromycin, to achieve better acid-stability. It is used to treat community acquired pneumonia of mild to moderate severity.
Specification
| Related CAS | 173838-31-8 (Deleted CAS) |
| Synonyms | HMR-3647; HMR 3647; HMR3647; RU-66647; RU 66647; RU66647; Ketek |
| Storage | Store at -20°C |
| IUPAC 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 |
| Canonical 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 |
| 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 |
| InChI Key | LJVAJPDWBABPEJ-XZVSULPPSA-N |
| Source | Semi-synthetic |
Properties
| Appearance | White to Light Yellow Powder |
| Application | Antibacterial |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 966.2°C at 760 mmHg |
| Melting Point | 176-188°C |
| Density | 1.26 g/cm3 |
| Solubility | Soluble in DMF, DMSO, Ethanol, Methanol, Water |
| LogP | 3 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Telithromycin acts by binding to domains II and V of 23S rRNA of the 50S ribosomal subunit. By binding at domain II, telithromycin retains activity against gram-positive cocci (e.g., Streptococcus pneumoniae) in the presence of resistance mediated by methylases (erm genes) that alter the domain V binding site of telithromycin. Telithromycin may also inhibit the assembly of nascent ribosomal units. Compared to erythromycin A, telithromycin binds to the 23S rRNA with 10 times greater affinity in erythromycin-susceptible organisms and 25 times greater affinity in macrolide-resistant strains. This increased binding affinity may be conferred by the C11-12 carbamate side chain of telithromycin. The side chain appears to maintain binding at domain II in the presence of resistance mediated by alterations in domain V. |
| Toxicity | LD50 > 2000 mg/kg (PO in rats). |
Reference Reading
1. Dissociation–equilibrium constant and bound conformation for weak antibiotic binding interaction with different bacterial ribosomes
Laurent Verdier, Josyane Gharbi-Benarous, Jean-Pierre Girault *. J. Chem. Soc., Perkin Trans. 2, 2000, 2363–2371
Antibiotics were added to E. coli ribosomes at molar ratios (antibiotic–ribosome) ranging from 600 to 2600. The antibiotic protons relaxed slower (enhanced T2obs) with a relative increase in antibiotic concentration (Fig. 2b). Fig. 3a shows titration plots of the observed selective T2obs of the 6-OMe, the 3 -Me and the S-Me protons of telithromycin, roxithromycin and clindamycin, respectively. In 0.8 µM E. coli ribosome solution, antibiotic concentration dependence was evident (Figs. 2b, 3a, S1 and S2). The linearity of the plots illustrates the binding of the antibiotics to the bacterial ribosomes according to eqn. (1). The binding constant KD can thus be obtained from the y-intercept of the linear plot; for telithromycin, roxithromycin and clindamycin binding to the E. coli ribosomes, KD = 1.2 × 10-3, 1.3 × 10-3 and 1.3 × 10-2, respectively (Table 1). The value of KD was closely related to the antibacterial activity. Telithromycin (1) displayed a significantly better overall anti-biotic activity than did clindamycin (3), and at the same time, the KD(1)/KD(3) ratio (Fig. 4a) was in the range of 0.1–0.2 for their weak E. coli ribosomal interaction.
Spectrum
Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C43H65N5O10
Molecular Weight (Monoisotopic Mass): 811.4731 Da
Molecular Weight (Avergae Mass): 812.0037 Da
Derivative Type: TMS_1_1
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C43H65N5O10
Molecular Weight (Monoisotopic Mass): 811.4731 Da
Molecular Weight (Avergae Mass): 812.0037 Da
Derivative Type: TMS_1_1
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C43H65N5O10
Molecular Weight (Monoisotopic Mass): 811.4731 Da
Molecular Weight (Avergae Mass): 812.0037 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C43H65N5O10
Molecular Weight (Monoisotopic Mass): 811.4731 Da
Molecular Weight (Avergae Mass): 812.0037 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
