CAS 372151-71-8

Telavancin

Description:

Telavancin is a synthetic lipoglycopeptide antibiotic primarily used for the treatment of complicated skin and skin structure infections caused by Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA). It functions by inhibiting bacterial cell wall synthesis, leading to cell lysis and death. Telavancin exhibits a dual mechanism of action: it binds to the D-alanyl-D-alanine terminus of peptidoglycan precursors, disrupting cell wall formation, and also disrupts bacterial membrane integrity. This compound is characterized by its unique structure, which includes a lipophilic side chain that enhances its binding affinity to bacterial membranes. Telavancin is administered intravenously and has a relatively long half-life, allowing for once-daily dosing. Common side effects may include nausea, vomiting, and renal impairment, necessitating monitoring of kidney function during treatment. Its use is generally reserved for cases where other antibiotics are ineffective, highlighting its importance in combating resistant bacterial strains.

Formula: C₈₀H₁₀₆Cl₂N₁₁O₂₇P

InChI: InChI=1/C80H106Cl2N11O27P/c1-7-8-9-10-11-12-13-14-21-85-22-23-87-80(5)32-57(115-37(4)71(80)103)119-70-68(102)67(101)55(34-94)118-79(70)120-69-53-28-41-29-54(69)117-52-20-17-40(27-46(52)82)65(99)63-77(109)91-61(78(110)111)43-30-50(96)44(33-86-35-121(112,113)114)66(100)58(43)42-25-38(15-18-49(42)95)59(74(106)93-63)90-75(107)60(41)89-73(105)48(31-56(83)97)88-76(108)62(92-72(104)47(84-6)24-36(2)3)64(98)39-16-19-51(116-53)45(81)26-39/h15-20,25-30,36-37,47-48,55,57,59-65,67-68,70-71,79,84-87,94-96,98-103H,7-14,21-24,31-35H2,1-6H3,(H2,83,97)(H,88,108)(H,89,105)(H,90,107)(H,91,109)(H,92,104)(H,93,106)(H,110,111)(H2,112,113,114)/t37-,47+,48-,55+,57-,59+,60+,61-,62+,63-,64+,65+,67+,68-,70+,71+,79-,80-/m0/s1

InChI key: InChIKey=ONUMZHGUFYIKPM-MXNFEBESSA-N

SMILES: O(C=1C2=CC3=CC1OC=4C(Cl)=CC(=CC4)[C@@H](O)[C@@H](NC([C@@H](CC(C)C)NC)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@]3(C(=O)N[C@@]5(C=6C=C(C=7C([C@@H](C(O)=O)NC(=O)[C@]([C@H](O)C=8C=C(Cl)C(O2)=CC8)(NC5=O)[H])=CC(O)=C(CNCP(=O)(O)O)C7O)C(O)=CC6)[H])[H])[C@H]9[C@H](O[C@H]%10C[C@@](NCCNCCCCCCCCCC)(C)[C@H](O)[C@H](C)O%10)[C@@H](O)[C@H](O)[C@@H](CO)O9

Synonyms:

• Arbelic
• Telavancin
• Vibativ
• Vancomycin, N3′′-[2-(decylamino)ethyl]-29-[[(phosphonomethyl)amino]methyl]-
• CS-712
• Telavacin
• N3''-[2-(Decylamino)ethyl]-29-[[(phosphonomethyl)amino]methyl]vancomycin
• Telavancin DISCONTINUED

Telavancin

CAS: 372151-71-8

Telavancin is a lipoglycopeptide antibiotic, which is a semi-synthetic derivative of vancomycin. Its source is derived through modifications of the glycopeptide antibiotic, specifically aimed to enhance antibacterial activity. Telavancin functions by inhibiting cell wall synthesis in Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA). It does this by binding to the D-alanyl-D-alanine terminus of cell wall precursors, disrupting peptidoglycan polymerization and, consequently, cell wall integrity. Additionally, Telavancin increases membrane permeability and disrupts membrane potential, further enhancing its bactericidal activity.

Formula: C₈₀H₁₀₆Cl₂N₁₁O₂₇P

Purity: Min. 95%

Molecular weight: 1,755.64 g/mol

Ref: 3D-AT58720