Compound ID | 1972

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Telavancin

Synonym(s): TD-6424 (Vibrativ)

Class: Lipoglycopeptide

Agent Type: Semisynthetic; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Cell wall synthesis inhibitor. Binds to the D-Ala-D-Ala terminus of the peptidoglycan in the growing cell wall; additionally 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
Highest development stage: Approved
Development status: Approved
Chemical structure(s):
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Molecular weight: 1755.64
Iso. 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 Key: ONUMZHGUFYIKPM-MXNFEBESSA-N
Can. 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
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/3081362
Guide to Pharmacology: telavancin
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/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1251517/

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