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药品详细

Zanamivir(扎那米韦)

化学结构式图
中文名
扎那米韦
英文名
Zanamivir
分子式
C12H20N4O7
化学名
(2R,3R,4S)-4-[(diaminomethylidene)amino]-3-acetamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
分子量
Average: 332.3098
Monoisotopic: 332.133199014
CAS号
139110-80-8
ATC分类
J05A Direct acting antivirals
药物类型
small molecule
阶段
approved
商品名
Relenza (GlaxoSmithKline);
同义名
GANA;GNA;Modified sialic acid;Zanamavir;ZMR;
基本介绍

A guanido-neuraminic acid that is used to inhibit neuraminidase. [PubChem]

生产厂家
  • Glaxosmithkline
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Meindl P, Bodo G, Palese P, Schulman J, Tuppy H: Inhibition of neuraminidase activity by derivatives of 2-deoxy-2,3-dehydro-N-acetylneuraminic acid. Virology. 1974 Apr;58(2):457-63. Pubmed
  2. von Itzstein M, Wu WY, Kok GB, Pegg MS, Dyason JC, Jin B, Van Phan T, Smythe ML, White HF, Oliver SW, et al.: Rational design of potent sialidase-based inhibitors of influenza virus replication. Nature. 1993 Jun 3;363(6428):418-23. Pubmed
  3. Hata K, Koseki K, Yamaguchi K, Moriya S, Suzuki Y, Yingsakmongkon S, Hirai G, Sodeoka M, von Itzstein M, Miyagi T: Limited Inhibitory Effects of Oseltamivir and Zanamivir on Human Sialidases. Antimicrob Agents Chemother. 2008 Aug 11. Pubmed
  4. Sugaya N, Tamura D, Yamazaki M, Ichikawa M, Kawakami C, Kawaoka Y, Mitamura K: Comparison of the clinical effectiveness of oseltamivir and zanamivir against influenza virus infection in children. Clin Infect Dis. 2008 Aug 1;47(3):339-45. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Glycerol and Derivatives
  • Pyrans
  • Ethers
  • Carboxylic Acids and Derivatives
Substructures
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Pyrans
  • Acetates
  • Amino Ketones
  • Ethers
  • Carboxylic Acids and Derivatives
  • Alcohols and Polyols
  • Heterocyclic compounds
  • Guanidines
  • Carboxamidines
  • Carboxamides and Derivatives
适应症
ANTIVIRALS 抗病毒;
药理
Indication For the prevention and treatment of influenza A and B.
Pharmacodynamics Zanamivir, an antiviral agent, is a neuraminidase inhibitor indicated for treatment of uncomplicated acute illness due to influenza A and B virus in adults and pediatric patients 7 years and older who have been symptomatic for no more than 2 days. Zanamivir has also been shown to significantly inhibit the human sialidases NEU3 and NEU2 in the micromolar range (Ki 3.7 +/-0.48 and 12.9+/-0.07 microM, respectively), which could account for some of the rare side effects of zanamivir.
Mechanism of action The proposed mechanism of action of zanamivir is via inhibition of influenza virus neuraminidase with the possibility of alteration of virus particle aggregation and release. By binding and inhibiting the neuraminidase protein, the drug renders the influenza virus unable to escape its host cell and infect others.
Absorption Absolute bioavailability is very low following oral administration (2%). Following oral inhalation, bioavailability is 4% to 17%.
Volume of distribution Not Available
Protein binding Zanamivir has limited plasma protein binding (<10%).
Metabolism
Not metabolized
Route of elimination It is excreted unchanged in the urine with excretion of a single dose completed within 24 hours. Unabsorbed drug is excreted in the feces.Zanamivir is renally excreted as unchanged drug.
Half life 2.5-5.1 hours
Clearance
  • 2.5 – 10.9 L/h [Following oral inhalation 10 mg]
  • 5.3 L/h [Normal renal function receiving IV single dose of 4 mg or 2 mg]
  • 2.7 L/h [Patients with mild and moderate renal impairement receiving IV single dose of 4 mg or 2 mg]
  • 0.8 L/h [Patients with severe renal impairement receiving IV single dose of 4 mg or 2 mg]
Toxicity Not Available
Affected organisms
  • Influenza A virus
  • Influenza B virus
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
logP -3 Not Available
Predicted Properties
Property Value Source
water solubility 7.31e+00 g/l ALOGPS
logP -2.3 ALOGPS
logP -5.8 ChemAxon
logS -1.7 ALOGPS
pKa (strongest acidic) 3.25 ChemAxon
pKa (strongest basic) 11.93 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 10 ChemAxon
hydrogen donor count 7 ChemAxon
polar surface area 200.72 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 76.19 ChemAxon
polarizability 31.24 ChemAxon
药物相互作用
食物相互作用
Not Available

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