Oritavancin , CAS No.171099-57-3

CAS: 171099-57-3 Cat. No.: O1419185 PubChem CID: 16136912

Storage

Room temperature

Overview

Oritavancin (LY 333328), a semisynthetic derivative of Vancomycin , is an orally active glycopeptide antibiotic with bactericidal activity against gram-positive organisms. Oritavancin shows antibacterial effect against B. anthracis , such as Ames strain with a MIC value of 0.015 g/mL. Oritavancin inhibits cell wall synthesis and disrupts the membrane potential. Oritavancin inhibits ArlS kinase activity thereby interfering the signal transduction. Oritavancin enters cells by adsorptive endocytosis, which drives it to lysosomes, where it exerts antibiotic activity.

Specifications

Storage

Room temperature

Action Type

INHIBITOR

Names and Identifiers

• Canonical Smiles: CC1C(C(CC(O1)OC2C3C(=O)NC(C4=C(C(=CC(=C4)O)O)C5=C(C=CC(=C5)C(C(=O)N3)NC(=O)C6C7=CC(=C(C(=C7)OC8=C(C=C2C=C8)Cl)OC9C(C(C(C(O9)CO)O)O)OC1CC(C(C(O1)C)O)(C)NCC1=CC=C(C=C1)C1=CC=C(C=C1)Cl)OC1=C(C=C(C=C1)C(C(C(=O)NC(C(=O)N6)CC(=O)N)NC(=O)C(CC(C)C)NC)O)Cl)O)C(=O)O)(C)N)O
• IUPAC Name: (1S,2R,18R,19R,22S,25R,28R,40S)-2-[(2R,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-22-(2-amino-2-oxoethyl)-5,15-dichloro-48-[(2S,3R,4S,5S,6R)-3-[(2S,4S,5R,6S)-4-[[4-(4-chlorophenyl)phenyl]methylamino]-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-18,32,35,37-tetrahydroxy-19-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8,10,12(48),14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid
• InChIKey: VHFGEBVPHAGQPI-LXKZPTCJSA-N
• 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
• Isomeric 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]1C[C@]([C@H]([C@@H](O1)C)O)(C)NCC1=CC=C(C=C1)C1=CC=C(C=C1)Cl)OC1=C(C=C(C=C1)[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
• Alternate CAS: 171099-57-3
• PubChem CID: 16136912
• MeSH Entry Terms: (4''R)-22-O-(3-amino-2,3,6-trideoxy-3-C-methyl-alpha-L-arabinohexopyranosyl)-N3''-(p-(p-chlorophenyl)benzyl)vancomycin;LY 333328;LY-333328;LY333328;Orbactiv;oritavancin

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Peptides
          • Level6 Oligopeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Peptides
• Direct Parent: Oligopeptides
• Alternative Parents: Cyclic peptides Aminoglycosides Phenolic glycosides Leucine and derivatives Chlorinated biphenyls N-acyl-alpha amino acids and derivatives Alpha amino acid amides Diarylethers Disaccharides O-glycosyl compounds Benzylamines Phenylmethylamines Aralkylamines Chlorobenzenes 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Aryl chlorides Oxanes N-acyl amines Amino acids Secondary carboxylic acid amides 1,2-aminoalcohols Primary carboxylic acid amides Secondary alcohols Lactams Acetals Oxacyclic compounds Dialkylamines Polyols Carboxylic acids Azacyclic compounds Monocarboxylic acids and derivatives Carbonyl compounds Hydrocarbon derivatives Monoalkylamines Organic oxides Organochlorides Organopnictogen compounds Primary alcohols
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Alpha-oligopeptide - Cyclic alpha peptide - Aminoglycoside core - Phenolic glycoside - Leucine or derivatives - N-acyl-alpha amino acid or derivatives - Chlorinated biphenyl - Biphenyl - Alpha-amino acid amide - O-glycosyl compound - Diaryl ether - Disaccharide - Glycosyl compound - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Benzylamine - Phenylmethylamine - 1-hydroxy-2-unsubstituted benzenoid - 1-hydroxy-4-unsubstituted benzenoid - Chlorobenzene - Aralkylamine - Amino saccharide - Halobenzene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Fatty acyl - Benzenoid - Fatty amide - N-acyl-amine - Oxane - Carboxamide group - Amino acid - 1,2-aminoalcohol - Secondary carboxylic acid amide - Lactam - Amino acid or derivatives - Secondary alcohol - Primary carboxylic acid amide - Oxacycle - Ether - Azacycle - Secondary amine - Carboxylic acid - Secondary aliphatic amine - Monocarboxylic acid or derivatives - Polyol - Organoheterocyclic compound - Acetal - Primary alcohol - Carbonyl group - Hydrocarbon derivative - Organic nitrogen compound - Alcohol - Organic oxygen compound - Organopnictogen compound - Organic oxide - Organohalogen compound - Organochloride - Organonitrogen compound - Organooxygen compound - Primary aliphatic amine - Primary amine - Amine - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
• External Descriptors: disaccharide derivative - glycopeptide

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

References

1. Yechang Guo, Shaofeng Wang, Peiyue Li, Pan Zhang, Wei Wang.  (2023)  Rapid Colloidal Gold Immunoassay for Pharmacokinetic Evaluation of Vancomycin in the Cerebrospinal Fluid and Plasma of Beagle Dogs.  SENSORS,  23  (21): (8978).  [PMID:37960677] [10.3390/s23218978]