Vancomicina

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

farmaco

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

Article · Italiano

La vancomicina è un farmaco antibiotico prodotto da che fa parte, insieme con la teicoplanina, della classe dei glicopeptidi. Sono molecole ad alto peso molecolare, che agiscono inibendo la polimerizzazione della parete del peptidoglicano dei batteri gram positivi. L'alto peso molecolare non consente a tali molecole l'attraversamento della membrana cellulare esterna dei germi Gram negativi, per cui la vancomicina è inefficace contro questi batteri; unica eccezione sono i Flavobacterium. Essendo stata diffusamente impiegata per debellare infezioni da Staphylococcus aureus si sono sviluppate resistenze, fino alla nascita di ceppi di S. Aureus particolarmente resistenti come il VISA: (Vancomycin Intermediate S. Aureus) e il VRSA (Vancomycin Resistant S. Aureus).

Abstract from DBpedia / Wikipedia · CC BY-SA