グリコペプチド系抗生物質

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a chemical substance derivable from a mold or bacterium that can kill microorganisms and cure bacterial infections; "when antibiotics were first discovered they were called wonder drugs" (同)antibiotic drug
of or relating to antibiotic drugs

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抗生物質(ペニシリン,ストレプトマイシンなど) / 抗生[物質]の

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/05/28 02:43:54」(JST)

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Glycopeptide antibiotics are a class of drugs of microbial origin that are composed of glycosylated cyclic or polycyclic nonribosomal peptides. Significant glycopeptide antibiotics include the anti-infective antibiotics vancomycin, teicoplanin, telavancin, ramoplanin and decaplanin, and the antitumor antibiotic bleomycin. Vancomycin is used if infection with methicillin-resistant Staphylococcus aureus (MRSA) is suspected.

Mechanism

Some members of this class of drugs inhibit the synthesis of cell walls in susceptible microbes by inhibiting peptidoglycan synthesis. They bind to the amino acids within the cell wall preventing the addition of new units to the peptidoglycan. In particular, they bind to acyl-D-alanyl-D-alanine in peptidoglycan.

Use

Due to their toxicity, use of glycopeptide antibiotics is restricted to patients who are critically ill, who have a demonstrated hypersensitivity to the β-lactams, or who are infected with β-lactam-resistant species. These antibiotics are effective principally against Gram-positive cocci. They exhibit a narrow spectrum of action, and are bactericidal only against the enterococci. Some tissues are not penetrated very well by glycopeptides, and they do not penetrate into the cerebrospinal fluid.

History

Vancomycin was isolated in 1953, and used clinically from 1955. Approved in 1958 by FDA to treat penicillin resistant staphylococci. MRSA first seen in 1961.
Bleomycin was first discovered in 1966.
Teicoplanin was discovered in the early 1990s.
Telavancin is a semi-synthetic lipoglycopeptide derivative of vancomycin (approved by FDA in 2009).

Teicoplanin : While not approved for use in the U.S., teicoplanin was discovered in the early 1990s and is marketed in Europe. It has more fatty acid chains than vancomycin and is considered to be 50 to 100 times more lipophillic. Teicoplanin also has an increased half-life compared to vancomycin, as well as having better tissue penetration. It can be two to four times more active than vancomycin, but it does depend upon the organism. Teicoplanin is more acidic, forming water-soluble salts, so it can be given intramuscularly. Teicoplanin is much better at penetrating into leucocytes and phagocytes than vancomycin.^{[citation needed]}

Since 2002, isolates of vancomycin-resistant Staphylococcus aureus (VRSA) have been found in the USA and other countries.

[Until 2000?] Glycopeptides used to be the last effective line of defense for cases of MRSA, however several newer classes of antibiotics have proven to have activity against MRSA, including, in 2000, linezolid of the oxazolidinone class, and in 2003 daptomycin of the lipopeptide class.^[1]

Research

Several derivatives of vancomycin are currently being developed, including oritavancin and dalbavancin (both lipoglycopeptides). Possessing longer half-lives than vancomycin,^[2] these newer candidates may demonstrate improvements over vancomycin due to less frequent dosing and activity against vancomycin-resistant bacteria.

Administration

Vancomycin is usually given intravenously, as an infusion, and can cause tissue necrosis and phlebitis at the injection site if given too rapidly. Pain at site of injection is indeed a common adverse event. One of the side-effects is red man syndrome, an idiosyncratic reaction to bolus caused by histamine release. Some other side-effects of vancomycin are nephrotoxicity including renal failure and interstitial nephritis, blood disorders including neutropenia, and deafness, which is reversible once therapy has stopped. Over 90% of the dose is excreted in the urine, therefore there is a risk of accumulation in patients with renal impairment, so therapeutic drug monitoring (TDM) is recommended.

Oral preparations of vancomycin are available, however they are not absorbed from the lumen of the gut, so are of no use in treating systemic infections. The oral preparations are formulated for the treatment of infections within the gastrointestinal tract, Clostridium difficile, for example.

References

^ Loffler CA, Macdougall C, Update on prevalence and treatment of methicillin-resistant Staphylococcus aureus infections, Expert Rev Anti Infect Ther. 2007 Dec;5(6):961-81; http://www.future-drugs.com/doi/abs/10.1586/14787210.5.6.961
^ Van Bambeke F. (August 2006). "Glycopeptides and glycodepsipeptides in clinical development: a comparative review of their antibacterial spectrum, pharmacokinetics and clinical efficacy,". Curr Opin Investig Drugs. 7 (8): 740–9. PMID 16955686. http://www.facm.ucl.ac.be/Full-texts-FACM/Vanbambeke-2006-3.pdf

UpToDate Contents

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1. 成人における侵襲性メチシリン耐性黄色ブドウ球菌感染症の治療 treatment of invasive methicillin resistant staphylococcus aureus infections in adults
2. バンコマイシン過敏症 vancomycin hypersensitivity
3. メチシリン耐性黄色ブドウ球菌およびバンコマイシン耐性腸球菌の治療のための抗菌薬の薬理学 pharmacology of antimicrobial agents for treatment of methicillin resistant staphylococcus aureus and vancomycin resistant enterococcus
4. 成人におけるバンコマイシン投与および血清濃度のモニタリング vancomycin dosing and serum concentration monitoring in adults
5. バンコマイシン中等度耐性およびバンコマイシン耐性黄色ブドウ球菌感染症 vancomycin intermediate and vancomycin resistant staphylococcus aureus infections

English Journal

Optimization of particle size and encapsulation efficiency of vancomycin nanoparticles by response surface methodology.

Honary S1, Ebrahimi P, Hadianamrei R.
Pharmaceutical development and technology.Pharm Dev Technol.2014 Dec;19(8):987-98. doi: 10.3109/10837450.2013.846375. Epub 2013 Oct 23.
CONTEXT: Treating vancomycin-resistant Staphylococcus aureus strains requires high doses of vancomycin, which might lead to adverse reactions such as nephrotoxicity and "red neck syndrome". Use of nanotechnology for antibiotic delivery is a promising approach to overcome antibiotic-resistance.OBJECT
PMID 24147898

Enantioselective Determination of Protein Amino Acids in Fertilizers by Liquid Chromatography-Tandem Mass Spectrometry on Chiral Teicoplanin Stationary Phase.

Taujenis L1, Olšauskaitė V, Padarauskas A.
Journal of agricultural and food chemistry.J Agric Food Chem.2014 Nov 5. [Epub ahead of print]
High-performance liquid chromatography on a glycopeptide antibiotic teicoplanin-based chiral stationary phase coupled with tandem mass spectrometry was developed for fast and reliable enantioseparation and determination of protein amino acids in hydrolyzed fertilizer samples. The effect of the mobil
PMID 25350489

Vancomycin pharmacokinetic models: informing the clinical management of drug-resistant bacterial infections.

Stockmann C1, Roberts JK, Yu T, Constance JE, Knibbe CA, Spigarelli MG, Sherwin CM.
Expert review of anti-infective therapy.Expert Rev Anti Infect Ther.2014 Nov;12(11):1371-88. doi: 10.1586/14787210.2014.966081.
This review aims to critically evaluate the pharmacokinetic literature describing the use of vancomycin in the treatment of methicillin-resistant Staphylococcus aureus (MRSA) infections. Guidelines recommend that trough concentrations be used to guide vancomycin dosing for the treatment of MRSA infe
PMID 25301231

Japanese Journal

Possible structural role of the disaccharide unit in Fe-bleomycin before and after oxygen activation

LEHMANN Teresa E,LI Yang
Journal of antibiotics 65(1), 25-33, 2012-01-25
NAID 10030641053

抗MRSA薬適正使用のための薬学的な介入とその評価

石原慎之,西村信弘,陶山登之 [他],山本英,玉木宏樹,上村智哉,礒部威,稲垣文子,岩本喜久生,直良浩司
日本環境感染学会誌 = Japanese journal of environmental infections 25(1), 15-21, 2010-01-25
グリコペプチド系抗菌薬バンコマイシン塩酸塩(VCM)，テイコプラニン(TEIC)およびアミノグリコシド系抗菌薬アルベカシン硫酸塩(ABK)はメチシリン耐性黄色ブドウ球菌(MRSA)の治療において効果的な抗菌薬である．抗MRSA薬は治療濃度域が狭いため，治療薬物血中濃度モニタリング(TDM)の実施ならびにPharmacokinetics-Pharmacodynamics (PK-PD)理論に基づ …
NAID 10026902108

Correlation of Pharmacokinetic Parameters with Serum Vancomycin Concentration in Elderly Patients with Malignancies

佐道紳一,辻泰弘,塚元和弘
YAKUGAKU ZASSHI 130(1), 69-73, 2010
… Vancomycin (VCM) is a glycopeptide antibiotic that is generally used to treat methicillin-resistant Staphylococcus aureus (MRSA). …
NAID 130000152013