vancomycin

Also known as (2.2Sp,3.5sa,2.6sp)-O(4.2),C(3.4), Vancocin, c(5.4),O(4.6), Vancomycinum, Vancomicina, Vancomycine

Vancomycin is a glycopeptide antibiotic medication used to treat certain bacterial infections. It is administered intravenously (injection into a vein) to treat complicated skin infections, bloodstream infections, endocarditis, bone and joint infections, and meningitis caused by methicillin-resistant Staphylococcus aureus. Blood levels may be measured to determine the correct dose. Vancomycin is also taken orally (by mouth) to treat Clostridioides difficile infections. When taken orally, it is poorly absorbed.

Chemical data

Formula: C66H75Cl2N9O24
Molecular weight: 1449.2 g/mol
IUPAC name: (1S,2R,18R,19R,22S,25R,28R,40S)-48-[(2S,3R,4S,5S,6R)-3-[(2S,4S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37-pentahydroxy-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(48),9,11,14,16,29(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]([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=C9O)O)[C@H](NC(=O)[C@H]([C@@H](C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)CO)O)O)(C)N)O
InChIKey: MYPYJXKWCTUITO-LYRMYLQWSA-N
XLogP: -2.6
Polar surface area: 530 Å²
H-bond donors: 19
H-bond acceptors: 26
Formal charge: 0

via PubChem

Research

43,478 papers

Vancomycin.Mayo Clinic proceedings · 1991
Renaissance of vancomycin: approaches for breaking antibiotic resistance in multidrug-resistant bacteria.Canadian journal of microbiology · 2020
The pharmacokinetic and pharmacodynamic properties of vancomycin.Clinical infectious diseases : an official publication of the Infectious Diseases Society of America · 2006
Vancomycin mimicry: towards new supramolecular antibiotics.Organic & biomolecular chemistry · 2022
Vancomycin.The Medical clinics of North America · 1995

via PubMed

Wikidata facts

Mass: 1447.43

Show 7 more facts

chemical formula: C₆₆H₇₅Cl₂N₉O₂₄
defined daily dose: 2
Commons category: Vancomycin
canonical SMILES: CC1C(C(CC(O1)OC2C(C(C(OC2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)C(C(C(=O)NC(C(=O)NC5C(=O)NC7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9C(NC(=O)C(C(C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)O)O)CC(=O)N)NC(=O)C(CC(C)C)NC)O)Cl)CO)O)O)(C)N)O
isomeric SMILES: CN[C@H](CC(C)C)C(=O)N[C@@H]1[C@H](O)C2=CC=C(OC3=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O[C@H]5C[C@](C)(N)[C@H](O)[C@H](C)O5)C6=CC(=C3)[C@@H](NC(=O)[C@H](CC(N)=O)NC1=O)C(=O)N[C@@H]7C8=CC=C(O)C(=C8)C9=C(O)C=C(O)C=C9[C@H](NC(=O)[C@@H](NC7=O)[C@H](O)C%10=CC=C(O6)C(Cl)=C%10)C(O)=O)C(Cl)=C2
NCI Thesaurus ID: C925
MCN code: 3004.20.71

Sources (6)

via Wikidata · CC0

~32 min read

Article

27 sections

Contents

Medical uses
Spectrum of susceptibility
Side effects
Oral administration
Intravenous administration
Nephrotoxicity
Interactions with other nephrotoxins
Vancomycin Flushing Reaction (aka "Red man syndrome")
Dosing considerations
Routes of administration
Intravenous
Oral
Inhaled (off-label)
Rectal (off-label)
Therapeutic drug monitoring
Chemistry
Biosynthesis
Total synthesis
Mechanism of action
Plant tissue culture
Antibiotic resistance
Intrinsic resistance
Acquired resistance
"Regained" vancomycin
History
Research
References

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