Compound ID | 132

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Oritavancin

Synonym(s): LY333328  |  Orbactiv

Class: Glycopeptide

Agent Type: Semisynthetic; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Cell wall synthesis inhibitor. Binds to D-alanyl-D-alanine stem termini and the pentaglycyl bridging segment of Gram-positive peptidoglycan (transglycosylation and transpeptidation steps inhibitor); additionally membrane-active agent as in telavancin
Target Pathogen: Active against Gram-positives including methicillin-resistant Staphylococcus aureus causing acute bacterial skin and skin structure infections (ABSSSI)
Institute where first reported: The Medicines Company, USA
Year first mentioned: 1996
Highest development stage: Approved by FDA in 2014
Development status: Approved
Chemical structure(s):
Click here for structure editor
Molecular weight: 1793.1
Iso. SMILES: C[C@H]1[C@@H]([C@@](C[C@@H](O1)O[C@H]2[C@H]3C(=O)N[C@@H](C4=C(C(=CC(=C4)O)O)C5=C(C=CC(=C5)[C@H](C(=O)N3)NC(=O)[C@H]6C7=CC(=C(C(=C7)OC8=C(C=C2C=C8)Cl)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O[C@H]%10C[C@]([C@H]([C@@H](O%10)C)O)(C)NCC%11=CC=C(C=C%11)C%12=CC=C(C=C%12)Cl)OC%13=C(C=C(C=C%13)[C@H]([C@H](C(=O)N[C@H](C(=O)N6)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)O)C(=O)O)(C)N)O
InChI Key: VHFGEBVPHAGQPI-LXKZPTCJSA-N
Can. SMILES: CC(C)C[C@H](C(=O)N[C@@H]1[C@@H](C2=CC=C(C(=C2)Cl)OC3=CC4=CC(=C3O[C@H]5[C@@H]([C@H]([C@@H]([C@@H](CO)O5)O)O)O[C@H]6C[C@@](C)([C@H]([C@H](C)O6)O)NCC7=CC=C(C=C7)C8=CC=C(C=C8)Cl)OC9=CC=C(C=C9Cl)[C@H]([C@H]%10C(=O)N[C@@H](C%11=CC(=CC(=C%11C%12=CC(=CC=C%12O)[C@H](C(=O)N%10)NC(=O)[C@@H]4NC(=O)[C@H](CC(=O)N)NC1=O)O)O)C(=O)O)O[C@H]%13C[C@@](C)([C@H]([C@H](C)O%13)O)N)O)NC
InChI: InChI=1S/C86H97Cl3N10O26/c1-35(2)22-51(92-7)77(110)98-67-69(105)42-15-20-55(49(88)24-42)120-57-26-44-27-58(73(57)125-84-74(71(107)70(106)59(34-100)122-84)124-62-32-86(6,76(109)37(4)119-62)93-33-38-8-10-39(11-9-38)40-12-17-45(87)18-13-40)121-56-21-16-43(25-50(56)89)72(123-61-31-85(5,91)75(108)36(3)118-61)68-82(115)97-66(83(116)117)48-28-46(101)29-54(103)63(48)47-23-41(14-19-53(47)102)64(79(112)99-68)96-80(113)65(44)95-78(111)52(30-60(90)104)94-81(67)114/h8-21,23-29,35-37,51-52,59,61-62,64-72,74-76,84,92-93,100-103,105-109H,22,30-34,91H2,1-7H3,(H2,90,104)(H,94,114)(H,95,111)(H,96,113)(H,97,115)(H,98,110)(H,99,112)(H,116,117)/t36-,37-,51+,52-,59+,61-,62-,64+,65+,66-,67+,68-,69+,70+,71-,72+,74+,75-,76-,84-,85-,86-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/16136912
Guide to Pharmacology: oritavancin
Citations:
  • http://aac.asm.org/content/58/5/2921.full
  • https://www.jstage.jst.go.jp/article/antibiotics1968/49/6/49_6_575/_pdf
  • https://www.pnas.org/doi/10.1073/pnas.0931492100#sec-2
  • https://journals.asm.org/doi/epdf/10.1128/aac.40.9.2194

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