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.

OverviewAI-generated

Vancomycin is a chemical compound with the formula C₆₆H₇₅Cl₂N₉O₂₄. It has a mass of 1447.43 and a defined daily dose of 2. The substance carries a charge of 0 and features an xlogp value of -2.6. Its topological polar surface area is 530, with 19 hydrogen bond donors and 26 hydrogen bond acceptors.

The compound is associated with the NCI Thesaurus ID C925 and MCN codes 3003.20.71 and 3004.20.71. A search for vancomycin on PubMed yields 43478 results. The subject is referenced by 431 other encyclopedia articles.

Synthesized by Vinony from 17 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

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

~32 min read

Encyclopedic overview

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

{{drugbox | Watchedfields = changed | verifiedrevid = 470628926 | image = Vancomycin structure.svg | image_class = skin-invert-image | width = 300 | alt = | image2 = Vancomycin-from-xtal-1996-3D-balls.png | image_class2 = bg-transparent | width2 = 300 | alt2 = | drug_name =

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