Telavancin

Synonym(s): TD-6424 (Vibrativ)

Class: Lipoglycopeptide

Spectrum of activity:	Gram-positive
Details of activity:	Binds to the D-Ala-D-Ala terminus of the peptidoglycan in the growing cell wall and interferes with bacterial cell wall integrity and synthesis. Additionally, it dissipates the bacterial cell membrane potential at higher concentrations, leading to membrane permeabilization and leakage of ATP and potassium ions.
Description:	Semisynthetic lipoglycopeptide derived from vancomycin
Institute where first reported:	Theravance
Year first mentioned:	2002
Development status:	Approved

Chemical structure(s):
Canonical SMILES:	CCCCCCCCCCNCCN[C@@]1(C)C[C@@H](O[C@@H](C)[C@H]1O)O[C@@H]2[C@H]([C@@H]([C@@H](CO)O[C@H]2OC3=C4C=C5C=C3OC6=CC=C(C=C6Cl)[C@H]([C@H](C(=O)N[C@@H](CC(=O)N)C(=O)N[C@H]5C(=O)N[C@@H]7C8=CC=C(C(=C8)C9=C(C(=C(C=C9[C@@H](C(=O)O)NC(=O)[C@H]([C@@H](C%10=CC=C(C(=C%10)Cl)O4)O)NC7=O)O)CNCP(=O)(O)O)O)O)NC(=O)[C@@H](CC(C)C)NC)O)O)O
Isomeric SMILES:	CCCCCCCCCCNCCN[C@]1(C[C@@H](O[C@H]([C@H]1O)C)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]7C8=CC(=C(C=C8)O)C9=C(C(=C(C=C9[C@H](NC(=O)[C@H]([C@@H](C%10=CC(=C(O4)C=C%10)Cl)O)NC7=O)C(=O)O)O)CNCP(=O)(O)O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)CO)O)O)C
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:	ONUMZHGUFYIKPM-MXNFEBESSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/3081362

External links:
Guide to Pharmacology:	telavancin
Main Source:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1251517/
Citations:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3127350/ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9379927/ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9382732/