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药品详细

Vancomycin(万古霉素)

化学结构式图
中文名
万古霉素
英文名
Vancomycin
分子式
C66H75Cl2N9O24
化学名
(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-(carbamoylmethyl)-5,47-dichloro-2,18,32,35,37-pentahydroxy-19-[(2R)-4-methyl-2-(methylamino)pentanamido]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2^{3,6}.2^{14,17}.1^{8,12}.1^{29,33}.0^{10,25}.0^{34,39}]pentaconta-3,5,8,10,12(48),14,16,29(45),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid
分子量
Average: 1449.254
Monoisotopic: 1447.430199787
CAS号
1404-90-6
ATC分类
A07A 未知;J01X Other Antibacterials
药物类型
small molecule
阶段
approved
商品名
Vancocin;Vancocin HCL;Vancoled;Vancor;
同义名
Vancomycin HCL;
基本介绍

Antibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to ristocetin that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear. [PubChem]

生产厂家
  • Akorn strides llc
  • App pharmaceuticals llc
  • Baxter healthcare corp
  • Baxter healthcare corp anesthesia and critical care
  • Bioniche pharma usa llc
  • Hospira inc
  • Lederle parenterals inc
  • Pharmacia and upjohn co
  • Sandoz inc
  • Viropharma inc
封装厂家
参考
Synthesis Reference
  1. Boger DL. Vancomycin, teicoplanin, and ramoplanin: synthetic and mechanistic studies. Med Res Rev. 2001 Sep;21(5):356-81. Pubmed
General Reference
  1. Schäfer, Martina, Thomas R Schneider, and George M Sheldrick. 1996. Crystal structure of vancomycin. Structure 4, no. 12 (December 15): 1509-1515. DOI:10.1016/S0969-2126(96)00156-6.
  2. Levine DP: Vancomycin: a history. Clin Infect Dis. 2006 Jan 1;42 Suppl 1:S5-12. Pubmed
  3. Small PM, Chambers HF: Vancomycin for Staphylococcus aureus endocarditis in intravenous drug users. Antimicrob Agents Chemother. 1990 Jun;34(6):1227-31. Pubmed
  4. Gonzalez C, Rubio M, Romero-Vivas J, Gonzalez M, Picazo JJ: Bacteremic pneumonia due to Staphylococcus aureus: A comparison of disease caused by methicillin-resistant and methicillin-susceptible organisms. Clin Infect Dis. 1999 Nov;29(5):1171-7. Pubmed
  5. Sivagnanam S, Deleu D: Red man syndrome. Crit Care. 2003 Apr;7(2):119-20. Epub 2002 Dec 23. Pubmed
  6. Cantu TG, Yamanaka-Yuen NA, Lietman PS: Serum vancomycin concentrations: reappraisal of their clinical value. Clin Infect Dis. 1994 Apr;18(4):533-43. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Carbohydrates
  • Biphenyl and Derivatives
  • Polypeptides
  • Lactams
  • Catecholamines and Derivatives
Substructures
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Phenols and Derivatives
  • Pyrans
  • Benzyl Alcohols and Derivatives
  • Acetates
  • Acetals and Derivatives
  • Aliphatic and Aryl Amines
  • Amino Ketones
  • Carbohydrates
  • Carboxylic Acids and Derivatives
  • Phenylpropenes
  • Phenylacetates
  • Ethers
  • Benzene and Derivatives
  • Biphenyl and Derivatives
  • Aryl Halides
  • Halobenzenes
  • Carbamates and Derivatives
  • Alcohols and Polyols
  • Amino Alcohols
  • Catechols
  • Phenethylamines
  • Polypeptides
  • Heterocyclic compounds
  • Aromatic compounds
  • Anisoles
  • Carboxamides and Derivatives
  • Phenylpropylamines
  • Amino Acids
  • Lactams
  • Phenyl Esters
  • Amphetamines
  • Resorcinols
  • Catecholamines and Derivatives
适应症
antibacterials 抗细菌;
药理
Indication For the treatment of serious or severe infections caused by susceptible strains of methicillin-resistant (beta-lactam-resistant) staphylococci.
Pharmacodynamics Vancomycin is a branched tricyclic glycosylated nonribosomal peptide produced by the fermentation of the Actinobacteria species Amycolatopsis orientalis (formerly Nocardia orientalis). It is often reserved as the "drug of last resort", used only after treatment with other antibiotics had failed. Vancomycin has been shown to be active against most strains of the following microorganisms, both in vitro and in clinical infections: Listeria monocytogenes, Streptococcus pyogenes, Streptococcus pneumoniae (including penicillin-resistant strains), Streptococcus agalactiae, Actinomyces species, and Lactobacillus species. The combination of vancomycin and an aminoglycoside acts synergistically in vitro against many strains of Staphylococcus aureus, Streptococcus bovis, enterococci, and the viridans group streptococci.
Mechanism of action The bactericidal action of vancomycin results primarily from inhibition of cell-wall biosynthesis. Specifically, vancomycin prevents incorporation of N-acetylmuramic acid (NAM)- and N-acetylglucosamine (NAG)-peptide subunits from being incorporated into the peptidoglycan matrix; which forms the major structural component of Gram-positive cell walls. The large hydrophilic molecule is able to form hydrogen bond interactions with the terminal D-alanyl-D-alanine moieties of the NAM/NAG-peptides. Normally this is a five-point interaction. This binding of vancomycin to the D-Ala-D-Ala prevents the incorporation of the NAM/NAG-peptide subunits into the peptidoglycan matrix. In addition, vancomycin alters bacterial-cell-membrane permeability and RNA synthesis. There is no cross-resistance between vancomycin and other antibiotics. Vancomycin is not active in vitro against gram-negative bacilli, mycobacteria, or fungi.
Absorption Poorly absorbed from gastrointestinal tract, however systemic absorption (up to 60%) may occur following intraperitoneal administration.
Volume of distribution Not Available
Protein binding Approximately 55% serum protein bound.
Metabolism
Not Available
Route of elimination In the first 24 hours, about 75% of an administered dose of vancomycin is excreted in urine by glomerular filtration.
Half life Half-life in normal renal patients is approximately 6 hours (range 4 to 11 hours). In anephric patients, the average half-life of elimination is 7.5 days.
Clearance
  • 0.06 L/kg/h
Toxicity The oral LD50 in mice is 5000 mg/kg. The median lethal intravenous dose is 319 mg/kg in rats and 400 mg/kg in mice.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
logP -3.1 Not Available
Predicted Properties
Property Value Source
water solubility 2.25e-01 g/l ALOGPS
logP 1.11 ALOGPS
logP -4.4 ChemAxon
logS -3.8 ALOGPS
pKa (strongest acidic) 2.99 ChemAxon
pKa (strongest basic) 9.93 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 24 ChemAxon
hydrogen donor count 19 ChemAxon
polar surface area 530.49 ChemAxon
rotatable bond count 13 ChemAxon
refractivity 346.61 ChemAxon
polarizability 138.7 ChemAxon
药物相互作用
Drug Interaction
Colistimethate Additive nephrotoxic effects may occur. Consider alternate therapy or monitor for renal function during concomitant therapy.
Gallium nitrate Additive nephrotoxic effects may occur. Avoid concomitant therapy.
Tobramycin Increased risk of nephrotoxicity
食物相互作用
Not Available

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