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124832-27-5 分子结构
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2-[(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate

ChemBase编号:459
分子式:C13H20N6O4
平均质量:324.3357
单一同位素质量:324.15460315
SMILES和InChIs

SMILES:
O(C(=O)[C@@H](N)C(C)C)CCOCn1c2[nH]c(nc(=O)c2nc1)N
Canonical SMILES:
CC([C@@H](C(=O)OCCOCn1cnc2c1[nH]c(N)nc2=O)N)C
InChI:
InChI=1S/C13H20N6O4/c1-7(2)8(14)12(21)23-4-3-22-6-19-5-16-9-10(19)17-13(15)18-11(9)20/h5,7-8H,3-4,6,14H2,1-2H3,(H3,15,17,18,20)/t8-/m0/s1
InChIKey:
HDOVUKNUBWVHOX-QMMMGPOBSA-N

引用这个纪录

CBID:459 http://www.chembase.cn/molecule-459.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
2-[(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate
IUPAC传统名
valaciclovir
商标名
Valtrex
Zelitrex
别名
Valaciclovir Hcl
Valaciclovir Hydrochloride
Valacyclover Hydrochloric
Valacyclover Hydrochloride
Valacyclovir Hydrochloride
Valacyclovir
valaciclovir
Valaciclovir
CAS号
124832-27-5
PubChem SID
46508197
160963922
PubChem CID
60773

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 DB00577 external link
PubChem 60773 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 8.103873  质子受体
质子供体 LogD (pH = 5.5) -1.9993745 
LogD (pH = 7.4) -0.486973  Log P -0.45152116 
摩尔折射率 80.6341 cm3 极化性 31.018381 Å3
极化表面积 146.85 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -0.84  LOG S -1.96 
溶解度 3.55e+00 g/l 

分子性质

分子性质

理化性质 生物活性(PubChem)
疏水性(logP)
-0.3 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB00577 external link
Item Information
Drug Groups approved; investigational
Description Valaciclovir (INN) or valacyclovir (USAN) is an antiviral drug used in the management of herpes simplex and herpes zoster (shingles). It is a prodrug, being converted in vivo to aciclovir. It is marketed by GlaxoSmithKline under the trade name Valtrex or Zelitrex. [Wikipedia]
Indication For the treatment or suppression of cold sores (herpes labialis), herpes zoster (shingles), genital herpes in immunocompetent individuals, and recurrent genital herpes in HIV-infected individuals.
Pharmacology Valaciclovir (INN) or Valacyclovir (USAN) is a prodrug and synthetic purine nucleoside analogue with inhibitory activity against herpes simplex virus types 1 (HSV-1), 2 (HSV-2), varicella-zoster virus (VZV), Epstein-Barr virus (EBV), and cytomegalovirus (CMV). Valaciclovir is almost completely converted to acyclovir and L-valine. The inhibitory activity of valaciclovir is highly selective due to its affinity for the enzyme thymidine kinase (TK) encoded by HSV and VZV. This viral enzyme converts acyclovir into acyclovir monophosphate, which is then converted into acyclovir diphosphate and triphosphate by cellular enzymes. Acyclovir is selectively converted to the active triphosphate form by cells infected with herpes viruses.
Toxicity Adverse effects of overexposure might include headache and nausea.
Affected Organisms
Human Herpes Virus
Biotransformation Valaciclovir is rapidly and almost entirely (~99%) converted to the active compound, acyclovir, and L-valine by first-pass intestinal and hepatic metabolism by enzymatic hydrolysis. Neither valaciclovir nor acyclovir is metabolized by cytochrome P450 enzymes.
Absorption After oral administration, valaciclovir hydrochloride is rapidly absorbed from the gastrointestinal tract. The absolute bioavailability of acyclovir after administration of valaciclovir is 54.5% ± 9.1%.
Half Life 2.5-3.3 hours
Protein Binding 13-18%
Elimination Acyclovir accounted for 89% of the radioactivity excreted in the urine.
Clearance * Renal cl=255 +/- ?86 mL/min [healthy]
* apparent cl=86.3 +/- 21.3 mL/min/1.73?m2 [dialysis patients]
* apparent cl=679.16 +/- 162.76 mL/min/1.73?m2 [healthy]
References
O'Brien JJ, Campoli-Richards DM: Acyclovir. An updated review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1989 Mar;37(3):233-309. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
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
  • O'Brien JJ, Campoli-Richards DM: Acyclovir. An updated review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1989 Mar;37(3):233-309. Pubmed
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专利

专利

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