萬古黴素

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

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1964
Admin. routes: oral, parenteral
Indications: cellulitis, infection, sclerosing cholangitis, skin disease

via ChEMBL · EBI

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

Subclass of: glycopeptide
Mass: 1447.43
Has use: medication

Show 13 more facts

chemical formula: C₆₆H₇₅Cl₂N₉O₂₄
found in taxon: Nostoc
medical condition treated: septic arthritis
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
subject has role: bactericide
MCN code: 3004.20.71
has characteristic: bitterness
significant drug interaction: tobramycin
legal status (medicine): boxed warning

Sources (6)

via Wikidata · CC0

Article · 中文

萬古黴素（Vancomycin，INN）是一種糖肽類抗生素，用來治療許多细菌感染的抗细菌药抗生素。治療皮膚感染、敗血症、心內膜炎、骨關節感染以及因耐甲氧西林金黄色葡萄球菌（MRSA）引起的脑膜炎時，通常建議採用靜脈注射作為第一線治療；而投藥時，劑量將依患者的血液濃度作調整。萬古黴素也是一種治療嚴重偽膜性結腸炎的口服藥，然而口服時藥效將會大為降低。，用來預防和治療革蘭氏陽性菌所造成的感染。傳統上，萬古黴素被用作「」，用來治療所有抗生素均無效的嚴重感染。但由於越來越多的抗萬古黴素耐藥性病菌的出現，其地位漸漸被利奈唑胺和達托黴素所取代。常見的副作用包含注射至局部時的疼痛、过敏，有時候也可能引發聽力問題、低血壓或骨髓抑制等問題；對母乳餵養的患者似乎沒有問題，而對於懷孕患者的影響尚不明確，但目前沒有證據顯示會造成危害。萬古黴素是一種糖肽類抗生素，藉由阻斷細胞壁生成來發揮作用。萬古黴素於1954年上市，在最基本的健康照護系統中最必要的藥物清單世界卫生组织基本药物标准清单登錄有案，是一種常見藥物，一劑靜脈注射的批發價約在1.70-6美元左右；因為在美國靜脈注射劑型相當昂貴，靜脈注射的投藥方式可能會被取代。萬古黴素目前由土壤細菌培養得來。

Abstract from DBpedia / Wikipedia · CC BY-SA