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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
Structure of SARPOGRELATE

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)

HIDE SMILES / InChI

Description

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

PubMed

TitleDatePubMed
Effects of sarpogrelate, a novel 5-HT2 antagonist, on 5-HT-induced endothelium-dependent relaxations in porcine coronary artery.
2002 Aug
The effects of vasodilators on the relaxation of guinea-pig aorta during acute recoil.
2002 Dec
Pharmacological profiles of R-96544, the active form of a novel 5-HT2A receptor antagonist R-102444.
2002 Dec 20
Sarpogrelate hydrochloride, a serotonin2A receptor antagonist, reduces albuminuria in diabetic patients with early-stage diabetic nephropathy.
2002 Nov
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
5-HT2A receptor subtype in the peripheral branch of sensory fibers is involved in the potentiation of inflammatory pain in rats.
2002 Sep
Enhancing effect of advanced glycation end products on serotonin-induced platelet aggregation in patients with diabetes mellitus.
2002 Sep 15
[A 50-year history of new drugs in Japan-the development and trends of hemostatics and antithrombotic drugs].
2003
Effect of MCI-9042, a 5-HT2 receptor antagonist, on retinal ganglion cell death and retinal ischemia.
2003 Apr
Assessment of affinities and dissociation potencies of several 5-HT2 antagonists to and from M2 muscarinic receptor in rat heart membranes.
2003 Aug
A novel serotonin blocker, sarpogrelate, increases circulating adiponectin levels in diabetic patients with arteriosclerosis obliterans.
2003 Aug
Serotonin receptor antagonist inhibits monocrotaline-induced pulmonary hypertension and prolongs survival in rats.
2003 Dec 1
Effect of sarpogrelate on altered STZ-diabetes induced cardiovascular responses to 5-hydroxytryptamine in rats.
2003 Jul
Efficacy of serotonin receptor blocker for symptomatic lumbar disc herniation.
2003 Jun
Sarpogrelate treatment reduces restenosis after coronary stenting.
2003 Mar
Sarpogrelate HCl, a selective 5-HT2A antagonist, retards the progression of atherosclerosis through a novel mechanism.
2003 May
The role of 5-HT on the cardiovascular and renal systems and the clinical potential of 5-HT modulation.
2003 May
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
[Molecular pharmacology of sarpogrelate].
2003 Nov
Attenuation of the serotonin-induced increase in intracellular calcium in rat aortic smooth muscle cells by sarpogrelate.
2003 Nov
Effects of 5-HT2A receptor antagonist on blood flow in chronically compressed nerve roots.
2004 Dec
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
Effects of R-102444, an orally active 5-HT2A receptor antagonist, in rat models of peripheral vascular disease.
2004 Feb
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
Sarpogrelate, a 5-HT2 receptor blocker, may have a preconditioning-like effect in patients with coronary artery disease.
2004 Jan
Sarpogrelate: cardiovascular and renal clinical potential.
2004 Jul
Dual roles of 5-hydroxytryptamine in ischemia-reperfusion injury in isolated rat hearts.
2004 Mar
Effect of the serotonin blocker sarpogrelate on circulating interleukin-18 levels in patients with diabetes and arteriosclerosis obliterans.
2004 Mar-Apr
Electroencephalographical effects of sarpogrelate hydrochloride versus ticlopidine hydrochloride in elderly patients with peripheral atherosclerosis.
2004 May-Jun
Functions of 5-HT2A receptor and its antagonists in the cardiovascular system.
2004 Oct
Therapeutic potentials of sarpogrelate in cardiovascular disease.
2004 Spring
Cardiovascular disease in diabetic nephropathy patients: cell adhesion molecules as potential markers?
2005
Protective effects of sarpogrelate, a 5-HT2A antagonist, against postischemic myocardial dysfunction in guinea-pig hearts.
2005 Apr
Effects of a 5-HT2A receptor antagonist, sarpogrelate on thermal or inflammatory pain.
2005 May 23
A new method for assessment of an anti-5HT(2A) agent, sarpogrelate hydrochloride, on platelet aggregation.
2006 Feb
The 5-hydroxytryptamine2A receptor antagonist sarpogrelate hydrochloride inhibits acute platelet aggregation in injured endothelium.
2006 Jan-Feb
[Effect of sarpogrelate in enteral feeding of patients with gastroesophageal reflux (GER)].
2006 Jul
Livedo racemosa as a cutaneous manifestation of polycythemia vera.
2006 May-Jun
Persistent insulin-sensitizing effects of sarpogrelate hydrochloride, a serotonin 2A receptor antagonist, in patients with peripheral arterial disease.
2006 Nov
Induction of indefinite survival of fully mismatched cardiac allografts and generation of regulatory cells by sarpogrelate hydrochloride.
2006 Oct 27
Identification of amino acid residues important for sarpogrelate binding to the human 5-hydroxytryptamine2A serotonin receptor.
2006 Sep
Effect of sarpogrelate, a 5-HT(2A) antagonist, on platelet aggregation in patients with ischemic stroke: clinical-pharmacological dose-response study.
2007
Identification of a key amino acid of the human 5-HT(2B) serotonin receptor important for sarpogrelate binding.
2007 Jul
New therapeutic approach for impaired arteriogenesis in diabetic mouse hindlimb ischemia.
2008 Apr
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
Reduced albuminuria with sarpogrelate is accompanied by a decrease in monocyte chemoattractant protein-1 levels in type 2 diabetes.
2008 Mar
Comparison of sarpogrelate and ticlopidine in bare metal coronary stent implantation.
2008 May 7
Assessment of binding affinity to 5-hydroxytryptamine 2A (5-HT2A) receptor and inverse agonist activity of naftidrofuryl: comparison with those of sarpogrelate.
2009 Aug
Sarpogrelate versus aspirin in secondary prevention of cerebral infarction: differential efficacy in diabetes? Subgroup analysis from S-ACCESS.
2009 Aug
Acute effects of sarpogrelate, a 5-HT2A receptor antagonist on cytokine production in endotoxin shock model of rats.
2009 Jul 1
Patents

Patents

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
Name Type Language
SARPOGRELATE
INN   WHO-DD  
INN  
Official Name English
BUTANEDIOIC ACID, 1-(2-(DIMETHYLAMINO)-1-((2-(2-(3-METHOXYPHENYL)ETHYL)PHENOXY)METHYL)ETHYL) ESTER
Systematic Name English
4-(1-(2-(3-METHOXYPHENETHYL)PHENOXY)-3-(DIMETHYLAMINO)PROPAN-2-YLOXY)-4-OXOBUTANOIC ACID SARPOGRELATE
Common Name English
SARPOGRELATE [WHO-DD]
Common Name English
BUTANEDIOIC ACID, MONO(2-(DIMETHYLAMINO)-1-((2-(2-(3-METHOXYPHENYL)ETHYL)PHENOXY)METHYL)ETHYL) ESTER
Common Name English
SARPOGRELATE [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1327
Created by admin on Tue Oct 22 00:13:18 UTC 2019 , Edited by admin on Tue Oct 22 00:13:18 UTC 2019
NCI_THESAURUS C66885
Created by admin on Tue Oct 22 00:13:18 UTC 2019 , Edited by admin on Tue Oct 22 00:13:18 UTC 2019
Code System Code Type Description
EPA CompTox
125926-17-2
Created by admin on Tue Oct 22 00:13:18 UTC 2019 , Edited by admin on Tue Oct 22 00:13:18 UTC 2019
PRIMARY
INN
6611
Created by admin on Tue Oct 22 00:13:18 UTC 2019 , Edited by admin on Tue Oct 22 00:13:18 UTC 2019
PRIMARY
CAS
135309-80-7
Created by admin on Tue Oct 22 00:13:18 UTC 2019 , Edited by admin on Tue Oct 22 00:13:18 UTC 2019
SUPERSEDED
PUBCHEM
5160
Created by admin on Tue Oct 22 00:13:18 UTC 2019 , Edited by admin on Tue Oct 22 00:13:18 UTC 2019
PRIMARY
EVMPD
SUB10455MIG
Created by admin on Tue Oct 22 00:13:18 UTC 2019 , Edited by admin on Tue Oct 22 00:13:18 UTC 2019
PRIMARY
MESH
C064294
Created by admin on Tue Oct 22 00:13:18 UTC 2019 , Edited by admin on Tue Oct 22 00:13:18 UTC 2019
PRIMARY
NCI_THESAURUS
C73158
Created by admin on Tue Oct 22 00:13:18 UTC 2019 , Edited by admin on Tue Oct 22 00:13:18 UTC 2019
PRIMARY
ChEMBL
CHEMBL52939
Created by admin on Tue Oct 22 00:13:18 UTC 2019 , Edited by admin on Tue Oct 22 00:13:18 UTC 2019
PRIMARY
IUPHAR
210
Created by admin on Tue Oct 22 00:13:18 UTC 2019 , Edited by admin on Tue Oct 22 00:13:18 UTC 2019
PRIMARY
CAS
125926-17-2
Created by admin on Tue Oct 22 00:13:18 UTC 2019 , Edited by admin on Tue Oct 22 00:13:18 UTC 2019
PRIMARY
WIKIPEDIA
SARPOGRELATE
Created by admin on Tue Oct 22 00:13:18 UTC 2019 , Edited by admin on Tue Oct 22 00:13:18 UTC 2019
PRIMARY