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oritavancin

Structure via PubChem · Public domain (PubChem)

EntityQ7102878· pop 16· linked from 66 articles

oritavancin

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Also known as LY-333328, Chlorobiphenyl-chloroeremomycin

Oritavancin, sold under the brand name Orbactiv among others, is a semisynthetic glycopeptide antibiotic medication for the treatment of serious Gram-positive bacterial infections. Its chemical structure as a lipoglycopeptide is similar to vancomycin.

Key facts

Drug.image
Oritavancin.svg
Drug.image_class
skin-invert-image
Drug.tradename
Orbactiv, others
Drug.MedlinePlus
a614042
Drug.DailyMedID
Oritavancin
Drug.routes_of_administration
Intravenous
Drug.ATC_prefix
J01
Drug.ATC_suffix
XA05
Drug.legal_CA
Rx-only
Drug.legal_US
Rx-only
Drug.legal_EU
Rx-only
Drug.CAS_number
171099-57-3
Drug.PubChem
16131319
Drug.DrugBank
DB04911
Drug.ChemSpiderID
31149229
Drug.UNII
PUG62FRZ2E
Drug.KEGG
D05271
Drug.ChEBI
82699

via Wikipedia infobox

Chemical data

Formula
C86H97Cl3N10O26
Molecular weight
1793.1 g/mol
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
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
InChIKey
VHFGEBVPHAGQPI-LXKZPTCJSA-N
XLogP
1.5
Polar surface area
561 Ų
H-bond donors
20
H-bond acceptors
29
Formal charge
0

via PubChem

Drug data · ChEMBL

Max clinical phase
Approved
Molecule type
Small molecule
First approval
2014
Admin. routes
parenteral
Indications
bacterial disease, skin disease

via ChEMBL · EBI

Research

545 papers

via PubMed

Wikidata facts

Mass
1790.564106
Has use
medication
Show 5 more facts
chemical formula
C₈₆H₉₇Cl₃N₁₀O₂₆
medical condition treated
cellulitis
canonical SMILES
CC1C(C(CC(O1)OC2C3C(=O)NC(C4=CC(=CC(=C4C5=C(C=CC(=C5)C(C(=O)N3)NC(=O)C6C7=CC(=C(C(=C7)OC8=C(C=C(C=C8)C(C(C(=O)NC(C(=O)N6)CC(=O)N)NC(=O)C(CC(C)C)NC)O)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=C2C=C1)Cl)O)O)O)C(=O)O)(C)N)O
isomeric SMILES
CN[C@H](CC(C)C)C(=O)N[C@@H]1[C@H](O)C2=CC(Cl)=C(OC3=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O[C@H]5C[C@](C)(NCC6=CC=C(C=C6)C7=CC=C(Cl)C=C7)[C@@H](O)[C@H](C)O5)C8=CC(=C3)[C@@H](NC(=O)[C@H](CC(N)=O)NC1=O)C(=O)N[C@@H]9C%10=CC=C(O)C(=C%10)C%11=C(C=C(O)C=C%11O)[C@H](NC(=O)[C@@H](NC9=O)[C@H](O[C@H]%12C[C@](C)(N)[C@@H](O)[C@H](C)O%12)C%13=CC(Cl)=C(O8)C=C%13)C(O)=O)C=C2
subject has role
bactericide
Sources (2)

via Wikidata · CC0

~4 min read

Encyclopedic overview

7 sections
Contents
  • Medical uses
  • ''In vitro'' activity
  • Mechanism
  • Synergism
  • Spectrum of Activity
  • History
  • References

Oritavancin, sold under the brand name Orbactiv among others, is a semisynthetic glycopeptide antibiotic medication for the treatment of serious Gram-positive bacterial infections. Its chemical structure as a lipoglycopeptide is similar to vancomycin.

The US Food and Drug Administration and the European Medicines Agency approved oritavancin for treatment of acute bacterial skin and skin structure infections.

Excerpted from Wikipedia’s “oritavancin” article, available under the CC BY-SA 4.0 licence.

Available in 16 languages

via Wikidata sitelinks · CC0