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药品详细

Oseltamivir(奥司他韦)

化学结构式图
中文名
奥司他韦
英文名
Oseltamivir
分子式
C16H28N2O4
化学名
ethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
分子量
Average: 312.4045
Monoisotopic: 312.204907394
CAS号
204255-11-8
ATC分类
J05A Direct acting antivirals
药物类型
small molecule
阶段
approved
商品名
Tamiflu;
同义名
Oseltamivir phosphate;
基本介绍

An acetamido cyclohexene that is a structural homolog of sialic acid and inhibits neuraminidase. [PubChem]

生产厂家
  • Hoffmann la roche inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Chokephaibulkit K, Uiprasertkul M, Puthavathana P, Chearskul P, Auewarakul P, Dowell SF, Vanprapar N: A child with avian influenza A (H5N1) infection. Pediatr Infect Dis J. 2005 Feb;24(2):162-6. Pubmed
  2. de Jong MD, Tran TT, Truong HK, Vo MH, Smith GJ, Nguyen VC, Bach VC, Phan TQ, Do QH, Guan Y, Peiris JS, Tran TH, Farrar J: Oseltamivir resistance during treatment of influenza A (H5N1) infection. N Engl J Med. 2005 Dec 22;353(25):2667-72. Pubmed
  3. Kiso M, Mitamura K, Sakai-Tagawa Y, Shiraishi K, Kawakami C, Kimura K, Hayden FG, Sugaya N, Kawaoka Y: Resistant influenza A viruses in children treated with oseltamivir: descriptive study. Lancet. 2004 Aug 28-Sep 3;364(9436):759-65. Pubmed
  4. Ward P, Small I, Smith J, Suter P, Dutkowski R: Oseltamivir (Tamiflu) and its potential for use in the event of an influenza pandemic. J Antimicrob Chemother. 2005 Feb;55 Suppl 1:i5-i21. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Carboxylic Acids and Derivatives
  • Cyclohexenes and Derivatives
Substructures
  • Carboxylic Acids and Derivatives
  • Alkanes and Alkenes
  • Acetates
  • Amino Ketones
  • Aliphatic and Aryl Amines
  • Ethers
  • Carboxamides and Derivatives
  • Cyclohexenes and Derivatives
适应症
ANTIVIRALS 抗病毒;
药理
Indication Oseltamivir (Tamiflu) is for the treatment of uncomplicated acute illness due to influenza infection in patients 1 year and older who have been symptomatic for no more than 2 days. It is also used for the prophylaxis of influenza in adult patients and adolescents 13 years and older.
Pharmacodynamics Oseltamivir is an antiviral drug, a neuraminidase inhibitor used in the treatment and prophylaxis of both influenza A and influenza B. Oseltamivir is a prodrug (usually administered as phosphate), it is hydrolysed hepatically to the active metabolite, the free carboxylate of oseltamivir (GS4071). Like zanamivir, oseltamivir acts as a transition-state analogue inhibitor of influenza neuraminidase.
Mechanism of action Oseltamivir is an ethyl ester prodrug requiring ester hydrolysis for conversion to the active form, oseltamivir carboxylate. The proposed mechanism of action of oseltamivir is inhibition of influenza virus neuraminidase with the possibility of alteration of virus particle aggregation and release.
Absorption Readily absorbed from the gastrointestinal tract after oral administration with a bioavailability of 75%.
Volume of distribution
  • 23 to 26 L
Protein binding Oseltamivir carboxylate: low (3%), Oseltamivir free base: 42%.
Metabolism
Extensively converted to oseltamivir carboxylate by esterases located predominantly in the liver. Neither oseltamivir nor oseltamivir carboxylate is a substrate for, or inhibitor of, cytochrome P450 isoforms. At least 75% of an oral dose reaches the systemic circulation as oseltamivir carboxylate.
Route of elimination Absorbed oseltamivir is primarily (>90%) eliminated by conversion to oseltamivir carboxylate. Oseltamivir carboxylate is not further metabolized and is eliminated in the urine. Oseltamivir carboxylate is eliminated entirely (>99%) by renal excretion.
Half life 1 to 3 hours in most subjects after oral administration.
Clearance Not Available
Toxicity At present, there has been no experience with overdose. Single doses of up to 1000 mg of oseltamivir have been associated with nausea and/or vomiting. Mean LD (intravenous, mouse) = 100 mg/kg.
Affected organisms
  • Influenza Virus
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
water solubility Soluble Not Available
logP 1 Not Available
Predicted Properties
Property Value Source
water solubility 6.86e-01 g/l ALOGPS
logP 1.3 ALOGPS
logP 1.16 ChemAxon
logS -2.7 ALOGPS
pKa (strongest acidic) 14.03 ChemAxon
pKa (strongest basic) 9.31 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 90.65 ChemAxon
rotatable bond count 8 ChemAxon
refractivity 84.2 ChemAxon
polarizability 34.65 ChemAxon
药物相互作用
食物相互作用
  • Take without regard to meals. Food may improve gastric tolerance.

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