Details
Stereochemistry | RACEMIC |
Molecular Formula | C24H31NO6 |
Molecular Weight | 429.506 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(CCC2=CC=CC=C2OCC(CN(C)C)OC(=O)CCC(O)=O)=CC=C1
InChI
InChIKey=FFYNAVGJSYHHFO-UHFFFAOYSA-N
InChI=1S/C24H31NO6/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)
Sarpogrelate (brand name Anplag; former developmental code names MCI-9042, LS-187,118) is a drug which acts as an antagonist at the 5HT2A and 5-HT2B receptors. It 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.
CNS Activity
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Effects of sarpogrelate, a novel 5-HT2 antagonist, on 5-HT-induced endothelium-dependent relaxations in porcine coronary artery. | 2002 Aug |
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The effects of vasodilators on the relaxation of guinea-pig aorta during acute recoil. | 2002 Dec |
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Pharmacological profiles of R-96544, the active form of a novel 5-HT2A receptor antagonist R-102444. | 2002 Dec 20 |
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Sarpogrelate hydrochloride, a serotonin2A receptor antagonist, reduces albuminuria in diabetic patients with early-stage diabetic nephropathy. | 2002 Nov |
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The role of serotonin in ischemic cellular damage and the infarct size-reducing effect of sarpogrelate, a 5-hydroxytryptamine-2 receptor blocker, in rabbit hearts. | 2002 Oct 2 |
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5-HT2A receptor subtype in the peripheral branch of sensory fibers is involved in the potentiation of inflammatory pain in rats. | 2002 Sep |
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Enhancing effect of advanced glycation end products on serotonin-induced platelet aggregation in patients with diabetes mellitus. | 2002 Sep 15 |
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[A 50-year history of new drugs in Japan-the development and trends of hemostatics and antithrombotic drugs]. | 2003 |
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Effect of MCI-9042, a 5-HT2 receptor antagonist, on retinal ganglion cell death and retinal ischemia. | 2003 Apr |
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Assessment of affinities and dissociation potencies of several 5-HT2 antagonists to and from M2 muscarinic receptor in rat heart membranes. | 2003 Aug |
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A novel serotonin blocker, sarpogrelate, increases circulating adiponectin levels in diabetic patients with arteriosclerosis obliterans. | 2003 Aug |
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Serotonin receptor antagonist inhibits monocrotaline-induced pulmonary hypertension and prolongs survival in rats. | 2003 Dec 1 |
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Effect of sarpogrelate on altered STZ-diabetes induced cardiovascular responses to 5-hydroxytryptamine in rats. | 2003 Jul |
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Efficacy of serotonin receptor blocker for symptomatic lumbar disc herniation. | 2003 Jun |
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Sarpogrelate treatment reduces restenosis after coronary stenting. | 2003 Mar |
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Sarpogrelate HCl, a selective 5-HT2A antagonist, retards the progression of atherosclerosis through a novel mechanism. | 2003 May |
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The role of 5-HT on the cardiovascular and renal systems and the clinical potential of 5-HT modulation. | 2003 May |
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Identification of the binding sites and selectivity of sarpogrelate, a novel 5-HT2 antagonist, to human 5-HT2A, 5-HT2B and 5-HT2C receptor subtypes by molecular modeling. | 2003 May 30 |
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[Molecular pharmacology of sarpogrelate]. | 2003 Nov |
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Attenuation of the serotonin-induced increase in intracellular calcium in rat aortic smooth muscle cells by sarpogrelate. | 2003 Nov |
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Effects of 5-HT2A receptor antagonist on blood flow in chronically compressed nerve roots. | 2004 Dec |
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Selective blockade of serotonin 5-HT2A receptor increases coronary blood flow via augmented cardiac nitric oxide release through 5-HT1B receptor in hypoperfused canine hearts. | 2004 Dec |
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Effects of R-102444, an orally active 5-HT2A receptor antagonist, in rat models of peripheral vascular disease. | 2004 Feb |
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Effect of sarpogrelate hydrochloride, a 5-HT2 blocker, on insulin resistance in Otsuka Long-Evans Tokushima fatty rats (OLETF rats), a type 2 diabetic rat model. | 2004 Feb |
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Sarpogrelate, a 5-HT2 receptor blocker, may have a preconditioning-like effect in patients with coronary artery disease. | 2004 Jan |
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Sarpogrelate: cardiovascular and renal clinical potential. | 2004 Jul |
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Dual roles of 5-hydroxytryptamine in ischemia-reperfusion injury in isolated rat hearts. | 2004 Mar |
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Effect of the serotonin blocker sarpogrelate on circulating interleukin-18 levels in patients with diabetes and arteriosclerosis obliterans. | 2004 Mar-Apr |
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Electroencephalographical effects of sarpogrelate hydrochloride versus ticlopidine hydrochloride in elderly patients with peripheral atherosclerosis. | 2004 May-Jun |
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Functions of 5-HT2A receptor and its antagonists in the cardiovascular system. | 2004 Oct |
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Therapeutic potentials of sarpogrelate in cardiovascular disease. | 2004 Spring |
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Cardiovascular disease in diabetic nephropathy patients: cell adhesion molecules as potential markers? | 2005 |
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Protective effects of sarpogrelate, a 5-HT2A antagonist, against postischemic myocardial dysfunction in guinea-pig hearts. | 2005 Apr |
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Effects of a 5-HT2A receptor antagonist, sarpogrelate on thermal or inflammatory pain. | 2005 May 23 |
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A new method for assessment of an anti-5HT(2A) agent, sarpogrelate hydrochloride, on platelet aggregation. | 2006 Feb |
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The 5-hydroxytryptamine2A receptor antagonist sarpogrelate hydrochloride inhibits acute platelet aggregation in injured endothelium. | 2006 Jan-Feb |
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[Effect of sarpogrelate in enteral feeding of patients with gastroesophageal reflux (GER)]. | 2006 Jul |
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Livedo racemosa as a cutaneous manifestation of polycythemia vera. | 2006 May-Jun |
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Persistent insulin-sensitizing effects of sarpogrelate hydrochloride, a serotonin 2A receptor antagonist, in patients with peripheral arterial disease. | 2006 Nov |
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Induction of indefinite survival of fully mismatched cardiac allografts and generation of regulatory cells by sarpogrelate hydrochloride. | 2006 Oct 27 |
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Identification of amino acid residues important for sarpogrelate binding to the human 5-hydroxytryptamine2A serotonin receptor. | 2006 Sep |
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Effect of sarpogrelate, a 5-HT(2A) antagonist, on platelet aggregation in patients with ischemic stroke: clinical-pharmacological dose-response study. | 2007 |
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Identification of a key amino acid of the human 5-HT(2B) serotonin receptor important for sarpogrelate binding. | 2007 Jul |
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New therapeutic approach for impaired arteriogenesis in diabetic mouse hindlimb ischemia. | 2008 Apr |
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Both 5-hydroxytryptamine 5-HT2A and 5-HT1B receptors are involved in the vasoconstrictor response to 5-HT in the human isolated internal thoracic artery. | 2008 Jul |
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Reduced albuminuria with sarpogrelate is accompanied by a decrease in monocyte chemoattractant protein-1 levels in type 2 diabetes. | 2008 Mar |
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Comparison of sarpogrelate and ticlopidine in bare metal coronary stent implantation. | 2008 May 7 |
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Assessment of binding affinity to 5-hydroxytryptamine 2A (5-HT2A) receptor and inverse agonist activity of naftidrofuryl: comparison with those of sarpogrelate. | 2009 Aug |
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Sarpogrelate versus aspirin in secondary prevention of cerebral infarction: differential efficacy in diabetes? Subgroup analysis from S-ACCESS. | 2009 Aug |
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Acute effects of sarpogrelate, a 5-HT2A receptor antagonist on cytokine production in endotoxin shock model of rats. | 2009 Jul 1 |
Patents
Sample Use Guides
The usual dosage for adult patients is 100 mg of sarpogrelate hydrochloride, administered after meal three times a day. The dosage may be adjusted according to the patient’s age and symptoms.
Route of Administration:
Oral
Stably expressing cell lines were constructed in HEK293 cells by transfecting with Lipofectamine 2000 reagent and selecting with 0.5 mg/ml G418-containing growth medium. Cells were split into 24-well plates at a density of 105 cells /well and labeled with 3 μCi/ml [3H]myo-inositol in serum-free DMEM for 24 h. Then the cells were washed with the assay medium (20 mM LiCl, 130 mM NaCl, 900 μM NaH2PO4, 5.4 mM KCl, 1.8 mM CaCl2, and 25 mM glucose in 20 mM HEPES, pH 7.4) and incubated with both SARPOGRELATE (10−9 – 10−4 M) at 37°C for 1 h. Cell extracts, in 10 mM formic acid, were applied to a 1-ml AG1-X8 resin (100 – 200 mesh; Assist Co., Tokyo) column before elution by buffer containing 1 M ammonium formate and 0.1 M formic acid. Radioactivity was measured by a liquid scintillation spectrophotometer.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1327
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NCI_THESAURUS |
C66885
Created by
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Code System | Code | Type | Description | ||
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125926-17-2
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6611
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135309-80-7
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5160
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SUB10455MIG
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C064294
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C73158
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CHEMBL52939
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210
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125926-17-2
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SARPOGRELATE
Created by
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)