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135159-51-2 molecular structure
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4-{[1-(dimethylamino)-3-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}propan-2-yl]oxy}-4-oxobutanoic acid hydrochloride

ChemBase ID: 73237
Molecular Formular: C24H32ClNO6
Molecular Mass: 465.96698
Monoisotopic Mass: 465.19181543
SMILES and InChIs

SMILES:
c1(CCc2cc(ccc2)OC)ccccc1OCC(OC(=O)CCC(=O)O)CN(C)C.Cl
Canonical SMILES:
COc1cccc(c1)CCc1ccccc1OCC(OC(=O)CCC(=O)O)CN(C)C.Cl
InChI:
InChI=1S/C24H31NO6.ClH/c1-25(2)16-21(31-24(28)14-13-23(26)27)17-30-22-10-5-4-8-19(22)12-11-18-7-6-9-20(15-18)29-3;/h4-10,15,21H,11-14,16-17H2,1-3H3,(H,26,27);1H
InChIKey:
POQBIDFFYCYHOB-UHFFFAOYSA-N

Cite this record

CBID:73237 http://www.chembase.cn/molecule-73237.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-{[1-(dimethylamino)-3-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}propan-2-yl]oxy}-4-oxobutanoic acid hydrochloride
IUPAC Traditional name
sarpogrelate hydrochloride
4-{[1-(dimethylamino)-3-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}propan-2-yl]oxy}-4-oxobutanoic acid hydrochloride
Synonyms
Sarpogrelate hydrochloride
Anplag
Butanedioic acid 1-[2-(dimethylamino)-1-[[2-[2-(3-methoxyphenyl)ethyl]phenoxy]methyl]ethyl] ester hydrochloride
MCI 9042
Succinic acid mono-(1-dimethylaminomethyl-2-(2-[2-(3-methoxyphenyl)et hyl]phenoxy)ethyl) ester hydrochloride
Sarpogrelate hydrochloride
CAS Number
135159-51-2
MDL Number
MFCD00887582
PubChem SID
162038157
PubChem CID
444005

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.7819445  H Acceptors
H Donor LogD (pH = 5.5) 1.1198967 
LogD (pH = 7.4) 1.0684103  Log P 1.1228089 
Molar Refractivity 117.349 cm3 Polarizability 46.033474 Å3
Polar Surface Area 85.3 Å2 Rotatable Bonds 14 
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
deionized water: ≥5 mg/mL expand Show data source
Methanol expand Show data source
Water expand Show data source
Apperance
solid expand Show data source
White Solid expand Show data source
Melting Point
145-148°C expand Show data source
Storage Condition
-20°C expand Show data source
desiccated expand Show data source
Refrigerator expand Show data source
European Hazard Symbols
Nature polluting Nature polluting (N) expand Show data source
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-50/53 expand Show data source
Safety Statements
60-61 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS09 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H400 expand Show data source
GHS Precautionary statements
P273 expand Show data source
Storage Temperature
room temp expand Show data source
Target
Serotonin receptor expand Show data source
Mechanism of Action
5HT(2A) receptor antagonist expand Show data source
Platelet aggregation inhibitor expand Show data source
Purity
≥98% (HPLC) expand Show data source
Salt Data
HCl expand Show data source
hydrochloride expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Antithrombotic expand Show data source
Empirical Formula (Hill Notation)
C24H31NO6.HCl expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
Selleck Chemicals - S2019 external link
Biological Activity:
Sarpogrelate hydrochloride is a selective 5-HT2A receptor antagonist to 5-HT2A, 5-HT2C and 5-HT2B receptors with pKi of 8.52, 7.43 and 6.57, respectively.Sarpogrelate hydrochloride reveals selectivity over 5-HT1, 5-HT3, 5-HT4 H1, H2, M3, α1-adrenergic, α2-adrenergic and β-adrenergic receptors. Additionally, Sarpogrelate hydrochloride displays cardioprotective activity in vivo. [1] Sarpogrelate hydrochloride improves vascular function in patients with peripheral arterial disease. Sarpogrelate hydrochloride blocks serotonin-induced platelet aggregation, and has applications in the treatment of many diseases including diabetes mellitus, Buerger’s disease, Raynaud’s disease, coronary artery disease, angina pectoris, and atherosclerosis. [2]References on Sarpogrelate HCl[1] J Cardiovasc Pharmacol., 2007, 49(4):221-7[2] http://en.wikipedia.org/wiki/Sarpogrelate, ,
Sigma Aldrich - S5451 external link
Biochem/physiol Actions
Sarapogrelate hydrochloride is a potent and selective 5-HT2A receptor antagonist. It exhibits analgesic effects in numerous animal studies.1
Toronto Research Chemicals - S142300 external link
Sarpogrelate hydrochloride is a potent and selective 5-HT2A receptor antagonist and is used as an antiplatelet agent. It has been reported to increase erythrocyte deformability and suppress shear stress-induced hemolysis.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Miyazaki M, et al. J Cardiovasc Pharmacol. 2007;49(4):221-7.
  • • Skoularigis, J., et al.: Am. J. Cardiol., 71, 587 (1993)
  • • Hara, H., et al.: Thromb. Haemost., 66, 484 (1993)
  • • Nagatomo, T., et al.: Pharmacol. Ther., 104, 59 (1993)
  • • Kikumoto, R. et al. , J. Med. Chem. , 1990, 33 , 1818, (synth, pharmacol)
  • • Hara, H. et al. , Arzneim.-Forsch. , 1991, 41 , 616, (pharmacol)
  • • Hara, H. et al. , Thromb. Haemostasis , 1991, 66 , 484, (pharmacol)
  • • Rabasseda, X. et al. , Drugs of Today (Barcelona) , 1994, 30 , 43, (rev)
  • • Kanamori, A. et al. , Life Sci. , 1994, 55 , PL365, (pharmacol)
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PATENTS

PATENTS

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INTERNET

INTERNET

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