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=1S/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(O)C1NC(=O)C2NC(=O)C(NC(=O)C3NC(=O)C(NC(=O)C(NC(=O)C(NC)CC(C)C)C(O)C4=CC=C(OC5=CC3=CC(OC6=CC=C(C=C6Cl)C2O)=C5OC7OC(CO)C(O)C(O)C7OC8OC(C)C(O)C(NCCNCCCCCCCCCC)(C)C8)C(Cl)=C4)CC(=O)N)C9=CC=C(O)C(=C9)C%10=C(O)C(=C(O)C=C%101)CNCP(=O)(O)O