CAS 95635-55-5|CAS 142387-99-3|Ranolazine|Ranexa|N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide|@ranolazine|(-)-Ranolazine|ranolazine|Ranolazine Dihydroch...

基本信息

化学结构

分子式

C₂₄H₃₃N₃O₄

分子量

427.53652

精确质量

427.24710655

电荷

InChI

InChI=1S/C24H33N3O4/c1-18-7-6-8-19(2)24(18)25-23(29)16-27-13-11-26(12-14-27)15-20(28)17-31-22-10-5-4-9-21(22)30-3/h4-10,20,28H,11-17H2,1-3H3,(H,25,29)

InChIKey

XKLMZUWKNUAPSZ-UHFFFAOYSA-N

Canonic Smiles

COc1ccccc1OCC(CN1CCN(CC1)CC(=O)Nc1c(C)cccc1C)O

Isomeric Smiles

OC(CN1CCN(CC1)CC(=O)Nc1c(cccc1C)C)COc1c(OC)cccc1

计算属性

JChem

LogD (pH = 7.4)

2.74

LogD (pH = 5.5)

1.55

Log P

2.83

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

6.77

极化表面积

74.27

极化性

48.36

摩尔折射率

123.46

LOG S

-3.16

数据来源

名称和标识

别名

RanolazineRanexa(-)-RanolazineranolazineRanolazine DihydrochlorideRanolazine 2HClN-(2,6-Dimethylphenyl)-2-(4-(2-hydroxy-3-(2-methoxy-phenoxy)propyl)piperazin-1-yl)acetamideN-(2,6-Dimethylphenyl)-2-(4-(2-hydroxy-3-(2-methoxyphenoxy)propyl)piperazin-1-yl)acetamideN-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide(+/-))-RanolazineN-(2,6-Dimethylphenyl)-4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]-1-piperazineacetamideRS 43285-003CVT 303Renexa

IUPAC标准名

N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide

IUPAC传统名

@ranolazine ranolazine

商标名

Ranexa

API名称

Ranolazine

名称和标识

数据登录号

CAS号

95635-55-5142387-99-3

MDL号

MFCD00864690

PubChem CID

56959

PubChem SID

46505145160963591252238170

DrugBank ID

DB00243

ACToR数据库

95635-55-5142387-99-3

BKMS React数据库

LINCS数据库

SureChEMBL数据库

BRENDA数据库

CHEMBL

BRENDA Ligand数据库

CHEBI ID

CompTox数据库

数据登录号

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

DrugBank

DB00243

Drug Groups

approved; investigational

Description

Ranolazine is an antianginal medication. On January 31, 2006, ranolazine was approved for use in the United States by the FDA for the treatment of chronic angina. [Wikipedia]

Indication

For the treatment of chronic angina. It should be used in combination with amlodipine, beta-blockers or nitrates.

Pharmacology

Ranolazine has antianginal and anti-ischemic effects that do not depend upon reductions in heart rate or blood pressure. It is the first new anti-anginal developed in over 20 years.

Toxicity

In the event of overdose, the expected symptoms would be dizziness, nausea/vomiting, diplopia, paresthesia, and confusion. Syncope with prolonged loss of consciousness may develop.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic, metabolized mainly by CYP3A and to a lesser extent by CYP2D6. The pharmacologic activity of the metabolites has not been well characterized.

Absorption

Absorption is highly variable. After oral administration of ranolazine as a solution, 73% of the dose is systemically available as ranolazine or metabolites. The bioavailability of oral ranolazine relative to that from a solution is 76%.

Half Life

7 hours

Protein Binding

62%

Elimination

Ranolazine is metabolized rapidly and extensively in the liver and intestine; less than 5% is excreted unchanged in urine and feces.

References

• Hale SL, Kloner RA: Ranolazine, an inhibitor of the late sodium channel current, reduces postischemic myocardial dysfunction in the rabbit. J Cardiovasc Pharmacol Ther. 2006 Dec;11(4):249-55. [Pubmed]

• Fraser H, Belardinelli L, Wang L, Light PE, McVeigh JJ, Clanachan AS: Ranolazine decreases diastolic calcium accumulation caused by ATX-II or ischemia in rat hearts. J Mol Cell Cardiol. 2006 Dec;41(6):1031-8. Epub 2006 Oct 5. [Pubmed]

• Stone PH, Gratsiansky NA, Blokhin A, Huang IZ, Meng L: Antianginal efficacy of ranolazine when added to treatment with amlodipine: the ERICA (Efficacy of Ranolazine in Chronic Angina) trial. J Am Coll Cardiol. 2006 Aug 1;48(3):566-75. Epub 2006 Jun 15. [Pubmed]

• Chaitman BR, Pepine CJ, Parker JO, Skopal J, Chumakova G, Kuch J, Wang W, Skettino SL, Wolff AA: Effects of ranolazine with atenolol, amlodipine, or diltiazem on exercise tolerance and angina frequency in patients with severe chronic angina: a randomized controlled trial. JAMA. 2004 Jan 21;291(3):309-16. [Pubmed]

• Morrow DA, Scirica BM, Karwatowska-Prokopczuk E, Murphy SA, Budaj A, Varshavsky S, Wolff AA, Skene A, McCabe CH, Braunwald E: Effects of ranolazine on recurrent cardiovascular events in patients with non-ST-elevation acute coronary syndromes: the MERLIN-TIMI 36 randomized trial. JAMA. 2007 Apr 25;297(16):1775-83. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S1799

Research Area: Cardiovascular Disease
Biological Activity:
Ranolazine(Ranexa) is an antianginal medication. Ranolazine is believed to have its effects via altering the trans-cellular late sodium current. It is by altering the intracellular sodium level that ranolazine affects the sodium-dependent calcium channels during myocardial ischemia in rabbits. Thus, ranolazine indirectly prevents the calcium overload that causes cardiac ischemia in rats. [1]

TRC

R122500

Ranolazine is an anti-ischemic agent which modulates myocardial metabolism. Antianginal.

ChEBI

CHEBI:87690

An aromatic amide obtained by formal condensation of the carboxy group of 2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetic acid with the amino group of 2,6-dimethylaniline.

描述信息

参考文献

PubChem文献

数据源提供

• McCormack, J.G., et al.: Gen. Pharmacol., 30, 639 (2004)

• Schofield, J.A.H., et al.: Expert Opin. Invest. Drugs, 11, 117 (2004)

• Chaitman, B.R., et al.: J. Am. Coll. Cardial., 43, 1375 (2004)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC标准名

N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide

IUPAC传统名

@ranolazine ranolazine

商标名

Ranexa

API名称

Ranolazine

数据登录号

CAS号

95635-55-5142387-99-3

MDL号

MFCD00864690

PubChem CID

56959

PubChem SID

46505145160963591252238170

DrugBank ID

DB00243

ACToR数据库

95635-55-5142387-99-3

BKMS React数据库

LINCS数据库

SureChEMBL数据库

BRENDA数据库

CHEMBL

BRENDA Ligand数据库

CHEBI ID

CompTox数据库

化合物性质

描述信息

DrugBank

DB00243

Drug Groups

approved; investigational

Description

Ranolazine is an antianginal medication. On January 31, 2006, ranolazine was approved for use in the United States by the FDA for the treatment of chronic angina. [Wikipedia]

Indication

For the treatment of chronic angina. It should be used in combination with amlodipine, beta-blockers or nitrates.

Pharmacology

Ranolazine has antianginal and anti-ischemic effects that do not depend upon reductions in heart rate or blood pressure. It is the first new anti-anginal developed in over 20 years.

Toxicity

In the event of overdose, the expected symptoms would be dizziness, nausea/vomiting, diplopia, paresthesia, and confusion. Syncope with prolonged loss of consciousness may develop.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic, metabolized mainly by CYP3A and to a lesser extent by CYP2D6. The pharmacologic activity of the metabolites has not been well characterized.

Absorption

Half Life

7 hours

Protein Binding

62%

Elimination

Ranolazine is metabolized rapidly and extensively in the liver and intestine; less than 5% is excreted unchanged in urine and feces.

References

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S1799

TRC

R122500

Ranolazine is an anti-ischemic agent which modulates myocardial metabolism. Antianginal.

ChEBI

CHEBI:87690

An aromatic amide obtained by formal condensation of the carboxy group of 2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetic acid with the amino group of 2,6-dimethylaniline.

参考文献

PubChem文献

数据源提供

• McCormack, J.G., et al.: Gen. Pharmacol., 30, 639 (2004)

• Schofield, J.A.H., et al.: Expert Opin. Invest. Drugs, 11, 117 (2004)

• Chaitman, B.R., et al.: J. Am. Coll. Cardial., 43, 1375 (2004)

生物活性

PubChem BioAssay

化合物信息

ID:128