您当前所在的位置:首页 > 产品中心 > 产品详细信息
137862-53-4 分子结构
点击图片或这里关闭

(2S)-3-methyl-2-[N-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)pentanamido]butanoic acid

ChemBase编号:62
分子式:C24H29N5O3
平均质量:435.51876
单一同位素质量:435.22703981
SMILES和InChIs

SMILES:
OC(=O)[C@@H](N(Cc1ccc(cc1)c1c(cccc1)c1n[nH]nn1)C(=O)CCCC)C(C)C
Canonical SMILES:
CCCCC(=O)N([C@H](C(=O)O)C(C)C)Cc1ccc(cc1)c1ccccc1c1n[nH]nn1
InChI:
InChI=1S/C24H29N5O3/c1-4-5-10-21(30)29(22(16(2)3)24(31)32)15-17-11-13-18(14-12-17)19-8-6-7-9-20(19)23-25-27-28-26-23/h6-9,11-14,16,22H,4-5,10,15H2,1-3H3,(H,31,32)(H,25,26,27,28)/t22-/m0/s1
InChIKey:
ACWBQPMHZXGDFX-QFIPXVFZSA-N

引用这个纪录

CBID:62 http://www.chembase.cn/molecule-62.html

Collapse All Expand All

名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(2S)-3-methyl-2-[N-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)pentanamido]butanoic acid
(2S)-3-methyl-2-[N-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)pentanamido]butanoic acid
IUPAC传统名
(2S)-3-methyl-2-[N-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)pentanamido]butanoic acid
diovan
valsartan
商标名
Diovan
Valsarran
别名
Valtan
L-Valsartan
(S)-2-(N-((2'-(1H-Tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)pentanamido)-3-methylbutanoic acid
N-(1-Oxopentyl)-N-[[2′-(2H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]methyl]-L-valine
Valsartan
valsartan
Valsartan
Diovan
CAS号
137862-53-4
MDL号
MFCD00865840
PubChem SID
160963525
46509000
PubChem CID
60846

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 4.3663416  质子受体
质子供体 LogD (pH = 5.5) 4.1015096 
LogD (pH = 7.4) 2.052606  Log P 5.269379 
摩尔折射率 134.7733 cm3 极化性 48.579018 Å3
极化表面积 112.07 Å2 可自由旋转的化学键 10 
里宾斯基五规则 false 
Log P 3.68  LOG S -4.27 
溶解度 2.34e-02 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
DMSO: ≥20 mg/mL expand 查看数据来源
外观
white to tan powder expand 查看数据来源
比旋光度
[α]/D -55 to -70°, c = 1 in methanol expand 查看数据来源
疏水性(logP)
5.8 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
desiccated expand 查看数据来源
保存注意事项
IRRITANT expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
TSCA收录
false expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
作用靶点
Angiotensin recep expand 查看数据来源
生物活性机理
Angiotensin 2 receptor antagonist expand 查看数据来源
纯度
≥98% (HPLC) expand 查看数据来源
95+% expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
应用领域
Antihypertensive agent expand 查看数据来源
Empirical Formula (Hill Notation)
C24H29N5O3 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Selleck Chemicals Selleck Chemicals
DrugBank -  DB00177 external link
Item Information
Drug Groups approved; investigational
Description Valsartan is an angiotensin-receptor blocker (ARB) that may be used to treat a variety of cardiac conditions including hypertension, diabetic nephropathy and heart failure. Valsartan lowers blood pressure by antagonizing the renin-angiotensin-aldosterone system (RAAS); it competes with angiotensin II for binding to the type-1 angiotensin II receptor (AT1) subtype and prevents the blood pressure increasing effects of angiotensin II. Unlike angiotensin-converting enzyme (ACE) inhibitors, ARBs do not have the adverse effect of dry cough. Valsartan may be used to treat hypertension, isolated systolic hypertension, left ventricular hypertrophy and diabetic nephropathy. It may also be used as an alternative agent for the treatment of heart failure, systolic dysfunction, myocardial infarction and coronary artery disease.
Indication May be used as a first line agent to treat uncomplicated hypertension, isolated systolic hypertension and left ventricular hypertrophy. May be used as a first line agent to delay progression of diabetic nephropathy. Losartan may be also used as a second line agent in the treatment of congestive heart failure, systolic dysfunction, myocardial infarction and coronary artery disease in those intolerant of ACE inhibitors.
Pharmacology Valsartan belongs to a class of antihypertensive agents called angiotensin II receptor blockers (ARBs). Valsartan is a specific and selective type-1 angiotensin II receptor (AT1) antagonist which blocks the blood pressure increasing effects angiotensin II via the renin-angiotensin-aldosterone system (RAAS). RAAS is a homeostatic mechanism for regulating hemodynamics, water and electrolyte balance. During sympathetic stimulation or when renal blood pressure or blood flow is reduced, renin is released from granular cells of the juxtaglomerular apparatus in the kidneys. Renin cleaves circulating angiotensinogen to angiotensin I, which is cleaved by angiotensin converting enzyme (ACE) to angiotensin II. Angiotensin II increases blood pressure by increasing total peripheral resistance, increasing sodium and water reabsorption in the kidneys via aldosterone secretion, and altering cardiovascular structure. Angiotensin II binds to two receptors: AT1 and type-2 angiotensin II receptor (AT2). AT1 is a G-protein coupled receptor (GPCR) that mediates the vasoconstrictive and aldosterone-secreting effects of angiotensin II. Studies performed in recent years suggest that AT2 antagonizes AT1-mediated effects and directly affects long-term blood pressure control by inducing vasorelaxation and increasing urinary sodium excretion. Angiotensin receptor blockers (ARBs) are non-peptide competitive inhibitors of AT1. ARBs block the ability of angiotensin II to stimulate pressor and cell proliferative effects. Unlike ACE inhibitors, ARBs do not affect bradykinin-induced vasodilation. The overall effect of ARBs is a decrease in blood pressure.
Affected Organisms
Humans and other mammals
Biotransformation Valsartan is excreted largely as unchanged drug (80%) and is minimally metabolized in humans. The primary circulating metabolite, 4-OH-valsartan, is pharmacologically inactive and produced CYP2C9. 4-OH-valsartan accounts for approximately 9% of the circulating dose of valsartan. Although valsartan is metabolized by CYP2C9, CYP-mediated drug-drug interactions between valsartan and other drugs is unlikely.
Absorption Absolute bioavailability = 23% with high variability
Half Life The initial phase t1/2 α is < 1 hour while the terminal phase t1/2 β is 5-9 hours.
Protein Binding 94 - 97% bound to serum proteins, primarily serum albumin
Elimination 83% of absorbed valsartan is excreted in feces and 13% is excreted in urine, primarily as unchanged drug
Distribution * 17 L (low tissue distribution)
Clearance * 2 L/h [IV administration]
* 4.5 L/h [heart Failure patients receiving oral administration 40 to 160 mg twice a day]
References
Bader, M. (2004). Renin-angiotensin-aldosterone system. In S. Offermanns, & W. Rosenthal (Eds.). _Encyclopedic reference of molecular pharmacology_ (pp. 810-814). Berlin, Germany: Springer.
Diovan. (2009). [Electronic version]. e-CPS. Retrieved December 28, 2009.
Stanfield, C.L., & Germann, W.J. (2008). _Principles of human physiology_ (3 ^rd^ ed.). San Francisco, CA: Pearson Education, Inc.
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals -  S1894 external link
Research Area: Cardiovascular Disease
Biological Activity:
Valsartan (Diovan) is an angiotensin II receptor antagonist with IC50 of ranging from 39.5 to116 µM. By blocking the action of angiotensin, valsartan dilates blood vessels and reduces blood pressure. In the Value trial, the angiotensin II receptor blocker valsartan produced a statistically significant 19% (p=0.02) relative increase in the prespecified secondary end point of myocardial infarction (fatal and non-fatal) compared with amlodipine. The CHARM-alternative trial showed a significant +52% (p=0.025) increase in myocardial infarction with candesartan (versus placebo) despite a reduction in blood pressure. [1]

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Diovan. (2009). [Electronic version]. e-CPS. Retrieved December 28, 2009.
  • Stanfield, C.L., & Germann, W.J. (2008). _Principles of human physiology_ (3 ^rd^ ed.). San Francisco, CA: Pearson Education, Inc.
  • Bader, M. (2004). Renin-angiotensin-aldosterone system. In S. Offermanns, & W. Rosenthal (Eds.). _Encyclopedic reference of molecular pharmacology_ (pp. 810-814). Berlin, Germany: Springer.
  • http://en.wikipedia.org/wiki/Valsartan
  • Eur. Pat., 1991, Ciba-Geigy, 443 983; CA, 116, 151772t, (synth, pharmacol)
  • Criscione, L. et al., Br. J. Pharmacol., 1993, 110, 761, (pharmacol)
  • Wood, J.M. et al., Hypertension (Dallas), 1993, 21, 1056, (pharmacol)
  • Buhlmayer, P. et al., Bioorg. Med. Chem. Lett., 1994, 4, 29, (synth)
  • Markham, A. et al., Drugs, 1997, 54, 299-311, (rev)
  • Langley, H.D. et al., Drugs, 1999, 57, 751-755, (rev)
  • Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 960
正在搜索,请耐心等待...(如果遇到网页错误或者长时间没有结果,请刷新页面[F5])

专利

专利

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

互联网资源

互联网资源

百度图标百度 google iconGoogle