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Telithromycin
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Name

Telithromycin

 EINECS 682-750-4
CAS No. 191114-48-4 Density 1.26 g/cm3
PSA 171.85000 LogP 4.86710
Solubility Sparingly soluble in water Melting Point 176-188 °C
Formula C43H65N5O10 Boiling Point 966.2 °C at 760 mmHg
Molecular Weight 812.017 Flash Point 538.2 °C
Transport Information N/A Appearance N/A
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 191114-48-4 (Telithromycin) Hazard Symbols IrritantXi
Synonyms

Erythromycin,3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-a-L-ribo-hexopyranosyl)oxy]-11,12-dideoxy-6-O-methyl-3-oxo-12,11-[oxycarbonyl[[4-[4-(3-pyridinyl)-1H-imidazol-1-yl]butyl]imino]]-;HMR 3647;Ketek;RU 66647;

Article Data 8

Telithromycin Synthetic route

2'-hydroxy-11-amino-11-N-[4-[4-(3-pyridyl)imidazol-1-yl]butyl]-11-deoxy-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate

191114-48-4

telithromycin

Conditions
ConditionsYield
Stage #1: 2'-hydroxy-11-amino-11-N-[4-[4-(3-pyridyl)imidazol-1-yl]butyl]-11-deoxy-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate With Dess-Martin periodane In dichloromethane at 20℃; for 0.5h;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water for 0.5h; Product distribution / selectivity;		90%
Stage #1: 2'-hydroxy-11-amino-11-N-[4-[4-(3-pyridyl)imidazol-1-yl]butyl]-11-deoxy-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate With Dess-Martin periodane In dichloromethane at 20℃; for 0.5h;
Stage #2: With sodium hydrogencarbonate In dichloromethane for 0.5h; Product distribution / selectivity;		90%
With Dess-Martin periodane In dichloromethane at 20℃; for 0.5h; Product distribution / selectivity;
With pyridine hydrochloride; dimethyl sulfoxide; cyclohexyl-dimethyl-aminopropylcarbodimide hydrochloride In dichloromethane at 20 - 30℃; for 6h; Product distribution / selectivity; Pfitzner-Moffatt Oxidation;
Stage #1: 2'-hydroxy-11-amino-11-N-[4-[4-(3-pyridyl)imidazol-1-yl]butyl]-11-deoxy-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate With N-chloro-succinimide; dimethylsulfide In dichloromethane at -25 - 0℃; for 2.5h; Corey-Kim Oxidation;
Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.5h; Product distribution / selectivity;
1001326-77-7

2',4"-di-O-bis(trimethylsilyl)-11-amino-11-N-[4-[4-(3-pyridyl)imidazol-1-yl]butyl]-11-deoxy-6-O-methylerythromycin A-11,12-cycliccarbamate

191114-48-4

telithromycin

Conditions
ConditionsYield
With methanol at 20℃; for 7h; Product distribution / selectivity; Heating / reflux;98.9%
306770-60-5

10-(4-dimethylamino-6-methyl-3-trimethylsilanyloxy-tetrahydro-pyran-2-yloxy)-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-1-[4-(4-pyridin-3-yl-imidazol-1-yl)-butyl]-octahydro-3,5-dioxa-1-aza-cyclopentacyclotetradecene-2,6,8,14-tetraone

191114-48-4

telithromycin

Conditions
ConditionsYield
With methanol at 20℃; for 7h; Product distribution / selectivity; Heating / reflux;98.9%

C36H55N3O12

173838-63-6

4-[4-(3-pyridyl)imidazol-1-yl]butylamine

191114-48-4

telithromycin

Conditions
ConditionsYield
In methanol; water; acetonitrile at 23 - 65℃; for 38h;
306770-59-2

2'-O-acetyl-3-de[(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribohexopyranosyl)oxy]-11,12-dideoxy-6-O-methyl-3-oxo-12,11-[oxycarbonyl[[4-[4-(3-pyridinyl)-1H-imidazol-1-yl]butyl]imino]]erythromycin

191114-48-4

telithromycin

Conditions
ConditionsYield
With methanol at 20℃; for 16h; Product distribution / selectivity;
With isopropyl alcohol at 20℃; for 24h; Product distribution / selectivity;
With sodium hydroxide; water In ethanol at 0℃;

2'-benzoyl-11-amino-11-N-[4-[4-(3-pyridyl)imidazol-1-yl]butyl]-11-deoxy-5-O-desosaminyl-6-O-methylerythronolide A 11,12-cyclic carbamate

191114-48-4

telithromycin

Conditions
ConditionsYield
With methanol for 7h; Heating / reflux;
160145-83-5

2'-O-acetyl-10,11-didehydro-11-deoxy-12-O-(1H-1-imidazoylcarbonyl)-3-O-descladinosyl-3-oxo-6-O-methyl-erythromycin A

173838-63-6

4-[4-(3-pyridyl)imidazol-1-yl]butylamine

191114-48-4

telithromycin

Conditions
ConditionsYield
In water; acetonitrile at 60℃; Substitution;50%

2'-O-acetate-3-O-descladinosyl-3-keto-10,11-anhydro-12-O-imidazolylcarbonyl-6-O-methylerythromycin

173838-63-6

4-[4-(3-pyridyl)imidazol-1-yl]butylamine

191114-48-4

telithromycin

Conditions
ConditionsYield
In water; acetonitrile at 50℃; for 24h;72%
51746-85-1

3-(1H-imidazol-4-yl)pyridine

191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaH / dimethylformamide
2: aq. NH2NH2 / ethanol
3: 50 percent / acetonitrile; H2O / 60 °C
View Scheme
173838-67-0

4-(3-pyridyl)-1H-imidazol-1-butanamide phthalimide

191114-48-4

telithromycin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NH2NH2 / ethanol
2: 50 percent / acetonitrile; H2O / 60 °C
View Scheme

Telithromycin History

French pharmaceutical company Hoechst Marion Roussel (later Sanofi-Aventis) began phase II/III clinical trials of telithromycin (HMR-3647) in 1998. Telithromycin was approved by the European Commission in July 2001 and subsequently went on sale in October 2001. In the US, telithromycin received FDA approval on April 1, 2004 .

Telithromycin Specification

The Telithromycin is an organic compound with the formula C43H65N5O10. The IUPAC name of this chemical is (1R,2S,4R,6R,7R,8R,10S,13S,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. With the CAS registry number 191114-48-4, it is also named as 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)-β-D-xylo-hexopyranosyl]oxy]-, (3aS,4S,7R,9R,10R,11S,13R,15S,15aR)-. The product's classification codes are Anti-Bacterial Agents; Anti-Infective Agents; Antibacterial; Antimicrobial. Besides, it is the first ketolide antibiotic to enter clinical use. It is used to treat mild to moderate respiratory infections.

Physical properties about Telithromycin are: (1)ACD/LogP: 3.58; (2)# of Rule of 5 Violations: 2; (3)#H bond acceptors: 15; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 12; (6)Polar Surface Area: 160.85 Å2; (7)Index of Refraction: 1.588; (8)Molar Refractivity: 216.19 cm3; (9)Molar Volume: 641.7 cm3; (10)Polarizability: 85.7×10-24cm3; (11)Surface Tension: 44 dyne/cm; (12)Density: 1.26 g/cm3; (13)Flash Point: 538.2 °C; (14)Enthalpy of Vaporization: 147.43 kJ/mol; (15)Boiling Point: 966.2 °C at 760 mmHg.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2[C@@H]([C@@H](O[C@@H]1O[C@@H](C[C@H](N(C)C)[C@H]1O)C)[C@](OC)(C)C[C@H](C(=O)[C@@H](C)[C@H]3N(C(=O)O[C@]3(C)[C@@H](OC(=O)[C@@H]2C)CC)CCCCn4cc(nc4)c5cccnc5)C)C
(2)InChI: InChI=1/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
(3)InChIKey: LJVAJPDWBABPEJ-WIFJXVANBD
(4)Std. 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
(5)Std. InChIKey: LJVAJPDWBABPEJ-WIFJXVANSA-N

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