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204255-11-8 分子结构
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ethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

ChemBase编号:83
分子式:C16H28N2O4
平均质量:312.40452
单一同位素质量:312.20490739
SMILES和InChIs

SMILES:
O([C@H]1[C@H](NC(=O)C)[C@@H](N)CC(=C1)C(=O)OCC)C(CC)CC
Canonical SMILES:
CCOC(=O)C1=C[C@H]([C@@H]([C@H](C1)N)NC(=O)C)OC(CC)CC
InChI:
InChI=1S/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/t13-,14+,15+/m0/s1
InChIKey:
VSZGPKBBMSAYNT-RRFJBIMHSA-N

引用这个纪录

CBID:83 http://www.chembase.cn/molecule-83.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
ethyl (3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
IUPAC传统名
oseltamivir
商标名
Tamiflu
别名
Oseltamivir phosphate
Oseltamivir
CAS号
204255-11-8
PubChem SID
160963546
46507602
PubChem CID
65028

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
DrugBank DB00198 external link
PubChem 65028 external link
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 14.033634  质子受体
质子供体 LogD (pH = 5.5) -1.8032612 
LogD (pH = 7.4) -0.7199175  Log P 1.1625985 
摩尔折射率 84.2034 cm3 极化性 33.440342 Å3
极化表面积 90.65 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 1.3  LOG S -2.66 
溶解度 6.86e-01 g/l 

分子性质

分子性质

理化性质 生物活性(PubChem)
溶解度
Soluble expand 查看数据来源
疏水性(logP)
1 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB00198 external link
Item Information
Drug Groups approved
Description An acetamido cyclohexene that is a structural homolog of sialic acid and inhibits neuraminidase. [PubChem]
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.
Pharmacology 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.
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
Biotransformation 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.
Absorption Readily absorbed from the gastrointestinal tract after oral administration with a bioavailability of 75%.
Half Life 1 to 3 hours in most subjects after oral administration.
Protein Binding Oseltamivir carboxylate: low (3%), Oseltamivir free base: 42%.
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.
Distribution * 23 to 26 L
References
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]
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]
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]
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]
External Links
Wikipedia
RxList
Drugs.com

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • 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
  • 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
  • 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
  • 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
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专利

专利

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