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142387-99-3 molecular structure
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N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide

ChemBase ID: 128
Molecular Formular: C24H33N3O4
Molecular Mass: 427.53652
Monoisotopic Mass: 427.24710655
SMILES and InChIs

SMILES:
OC(CN1CCN(CC1)CC(=O)Nc1c(cccc1C)C)COc1c(OC)cccc1
Canonical SMILES:
COc1ccccc1OCC(CN1CCN(CC1)CC(=O)Nc1c(C)cccc1C)O
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

Cite this record

CBID:128 http://www.chembase.cn/molecule-128.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide
IUPAC Traditional name
@ranolazine
ranolazine
Brand Name
Ranexa
Synonyms
(-)-Ranolazine
Ranolazine 2HCl
Ranolazine Dihydrochloride
ranolazine
Ranolazine
N-(2,6-Dimethylphenyl)-2-(4-(2-hydroxy-3-(2-methoxy-phenoxy)propyl)piperazin-1-yl)acetamide
N-(2,6-Dimethylphenyl)-4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]-1-piperazineacetamide
(+/-))-Ranolazine
CVT 303
RS 43285-003
N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide
Renexa
N-(2,6-Dimethylphenyl)-2-(4-(2-hydroxy-3-(2-methoxyphenoxy)propyl)piperazin-1-yl)acetamide
Ranexa
CAS Number
142387-99-3
95635-55-5
MDL Number
MFCD00864690
PubChem SID
46505145
160963591
PubChem CID
56959

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.600031  H Acceptors
H Donor LogD (pH = 5.5) 1.1640991 
LogD (pH = 7.4) 2.633176  Log P 2.8324604 
Molar Refractivity 123.4604 cm3 Polarizability 47.363354 Å3
Polar Surface Area 74.27 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.08  LOG S -3.59 
Solubility (Water) 1.10e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Very slightly soluble expand Show data source
Apperance
White Solid expand Show data source
Melting Point
119-120°C expand Show data source
Hydrophobicity(logP)
1.012 expand Show data source
1.6 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
Storage Warning
IRRITANT expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
TSCA Listed
false expand Show data source
Purity
95% expand Show data source
95+% expand Show data source
97% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals TRC TRC
DrugBank - DB00243 external link
Item Information
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 external link
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]
Toronto Research Chemicals - R122500 external link
Ranolazine is an anti-ischemic agent which modulates myocardial metabolism. Antianginal.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Chaitman, B.R., et al.: J. Am. Coll. Cardial., 43, 1375 (2004)
  • • McCormack, J.G., et al.: Gen. Pharmacol., 30, 639 (2004)
  • • Schofield, J.A.H., et al.: Expert Opin. Invest. Drugs, 11, 117 (2004)
  • • 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
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