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Details

Stereochemistry RACEMIC
Molecular Formula C24H31NO6.ClH
Molecular Weight 465.9678
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SARPOGRELATE HYDROCHLORIDE

SMILES

CN(C)CC(COc1ccccc1CCc2cccc(c2)OC)OC(=O)CCC(=O)O.Cl

InChI

InChIKey=POQBIDFFYCYHOB-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C24H31NO6
Molecular Weight 429.507
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: description was created based on several sources, including https://www.drugs.com/international/sarpogrelate.html | https://www.ncbi.nlm.nih.gov/pubmed/10980267 | https://clinicaltrials.gov/ct2/show/NCT01165567 | http://www.e-search.ne.jp/~jpr/PDF/MT02.PDF

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

Curator's Comment:: According to information supplied by the manufacturers, the brain tissue concentration of sarpogrelate was 0.25–0.5% of the plasma concentration, in a w14 tracer experiment using Cx-labeled sarpogrelate

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.38 nM [Ki]
6.11 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Anplag

Approved Use

INDICATIONS. Improvement of ischemic symptoms including ulcer, pain and feeling of coldness, associated with chronic arterial occlusion
Preventing
Anplag

Approved Use

INDICATIONS. Improvement of ischemic symptoms including ulcer, pain and feeling of coldness, associated with chronic arterial occlusion
PubMed

PubMed

TitleDatePubMed
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
Sarpogrelate: cardiovascular and renal clinical potential.
2004 Jul
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
Protective effects of sarpogrelate, a 5-HT2A antagonist, against postischemic myocardial dysfunction in guinea-pig hearts.
2005 Apr
New treatment of lumbar disc herniation involving 5-hydroxytryptamine2A receptor inhibitor: a randomized controlled trial.
2005 Apr
Effects of a 5-HT2A receptor antagonist, sarpogrelate on thermal or inflammatory pain.
2005 May 23
Contribution of the peripheral 5-HT 2A receptor to mechanical hyperalgesia in a rat model of neuropathic pain.
2005 Nov
5-HT2A receptor antagonist increases circulating adiponectin in patients with type 2 diabetes.
2005 Sep
Impaired potency of bone marrow mononuclear cells for inducing therapeutic angiogenesis in obese diabetic rats.
2006 Apr
Site-directed mutagenesis of the serotonin 5-Hydroxytryptamine2c receptor: identification of amino acids responsible for sarpogrelate binding.
2006 Aug
Increased hypothalamic 5-HT2A receptor gene expression and effects of pharmacologic 5-HT2A receptor inactivation in obese Ay mice.
2006 Dec 29
Effects of sarpogrelate hydrochloride in a patient with chronic graft-versus-host disease: a case report.
2006 Feb
Sarpogrelate hydrochloride, an antagonist of 5-hydroxytryptamine receptor, improves skin flap survival and suppresses thrombus formation in injured microvessels of rabbits.
2006 Jan
Inhibition of 5-hydroxytryptamine receptor prevents occlusive thrombus formation on neointima of the rabbit femoral artery.
2006 Jan
The 5-hydroxytryptamine2A receptor antagonist sarpogrelate hydrochloride inhibits acute platelet aggregation in injured endothelium.
2006 Jan-Feb
Homology modelling of the serotoninergic 5-HT2c receptor.
2006 Jun
Sarpogrelate, a 5-hT2A receptor antagonist in intermittent claudication. A phase II European study.
2006 May
Peripheral 5-HT2A receptor antagonism attenuates primary thermal hyperalgesia and secondary mechanical allodynia after thermal injury in rats.
2006 May
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
Inverse agonist activity of sarpogrelate, a selective 5-HT2A-receptor antagonist, at the constitutively active human 5-HT2A receptor.
2006 Oct
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
5-HT2 receptor blocker sarpogrelate prevents downregulation of antiapoptotic protein Bcl-2 and protects the heart against ischemia-reperfusion injury.
2006 Sep 27
Effect of sarpogrelate, a 5-HT(2A) antagonist, on platelet aggregation in patients with ischemic stroke: clinical-pharmacological dose-response study.
2007
Marked improvement with sildenafil in a patient with idiopathic pulmonary arterial hypertension unresponsive to beraprost and sarpogrelate.
2007
Sarpogrelate hydrochloride, a selective 5-HT2A antagonist, improves vascular function in patients with peripheral arterial disease.
2007 Apr
Sarpogrelate hydrochloride, a 5-HT2A receptor antagonist, attenuates neurogenic pain induced by nucleus pulposus in rats.
2007 Feb 1
Identification of a key amino acid of the human 5-HT(2B) serotonin receptor important for sarpogrelate binding.
2007 Jul
Antiplatelet therapy mitigates cardiac remodeling and dysfunction in congestive heart failure due to myocardial infarction.
2008 Apr
New therapeutic approach for impaired arteriogenesis in diabetic mouse hindlimb ischemia.
2008 Apr
Blockade of serotonin 2A receptor improves glomerular endothelial function in rats with streptozotocin-induced diabetic nephropathy.
2008 Apr
Antiplatelet agents sarpogrelate and cilostazol affect experimentally-induced ventricular arrhythmias and mortality.
2008 Fall
The effects of a 5-HT2A receptor antagonist on blood flow in lumbar disc herniation: application of nucleus pulposus in a canine model.
2008 Feb
Serotonin induces vasoconstriction of smooth muscle cell-rich neointima through 5-hydroxytryptamine2A receptor in rabbit femoral arteries.
2008 Jul
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
Sarpogrelate-Aspirin Comparative Clinical Study for Efficacy and Safety in Secondary Prevention of Cerebral Infarction (S-ACCESS): A randomized, double-blind, aspirin-controlled trial.
2008 Jun
Reduced albuminuria with sarpogrelate is accompanied by a decrease in monocyte chemoattractant protein-1 levels in type 2 diabetes.
2008 Mar
[Coronary artery bypass grafting for simultaneous subacute stent thrombosis after sirolimus-eluting stent implantation].
2008 May
Comparison of sarpogrelate and ticlopidine in bare metal coronary stent implantation.
2008 May 7
Antiplatelet therapy attenuates subcellular remodelling in congestive heart failure.
2008 Sep-Oct
Beneficial effects of sarpogrelate hydrochloride, a 5-HT2A receptor antagonist, supplemented with pioglitazone on diabetic model mice.
2009
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
Sarpogrelate hydrochloride reduced intimal hyperplasia in experimental rabbit vein graft.
2009 May
Chronic treatment of hydroxytryptamine type 2a receptor antagonist sarpogrelate hydrochloride modulates the vasoreactivity of serotonin in experimental rabbit vein grafts.
2009 Sep
Sarpogrelate hydrochloride, a selective 5-hydroxytryptamine(2A) antagonist, augments autologous bone marrow mononuclear cell implantation-induced improvement in endothelium-dependent vasodilation in patients with critical limb ischemia.
2010 Jan
Patents

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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:39:08 UTC 2021
Edited
by admin
on Sat Jun 26 05:39:08 UTC 2021
Record UNII
FQN8N8QP1B
Record Status Validated (UNII)
Record Version
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Name Type Language
SARPOGRELATE HYDROCHLORIDE
JAN   WHO-DD  
Common Name English
ANPLAG
Common Name English
SARPOGRELATE HYDROCHLORIDE [WHO-DD]
Common Name English
MCI-9042
Code English
BUTANEDIOIC ACID, 1-(2-(DIMETHYLAMINO)-1-((2-(2-(3-METHOXYPHENYL)ETHYL)PHENOXY)METHYL)ETHYL) ESTER, HYDROCHLORIDE (1:1)
Systematic Name English
BUTANEDIOIC ACID, MONO(2-(DIMETHYLAMINO)-1-((2-(2-(3-METHOXYPHENYL)ETHYL)PHENOXY)METHYL)ETHYL) ESTER, HYDROCHLORIDE, (+/-)-
Common Name English
(+/-)-SARPOGRELATE HYDROCHLORIDE
Common Name English
BUTANEDIOIC ACID, MONO(2-(DIMETHYLAMINO)-1-((2-(2-(3-METHOXYPHENYL)ETHYL)PHENOXY)METHYL)ETHYL) ESTER, HYDROCHLORIDE
Common Name English
SARPOGRELATE HYDROCHLORIDE [JAN]
Common Name English
MCI 9042
Code English
SARPOGRELATE HYDROCHLORIDE, (+/-)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66885
Created by admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
NCI_THESAURUS C1327
Created by admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
Code System Code Type Description
CAS
86819-20-7
Created by admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
SUPERSEDED
NCI_THESAURUS
C132071
Created by admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
PRIMARY
FDA UNII
FQN8N8QP1B
Created by admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
PRIMARY
DRUG BANK
DBSALT002147
Created by admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
PRIMARY
ChEMBL
CHEMBL52939
Created by admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
PRIMARY
EPA CompTox
135159-51-2
Created by admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
PRIMARY
CAS
135159-51-2
Created by admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
PRIMARY
EVMPD
SUB04330MIG
Created by admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
PRIMARY
PUBCHEM
444005
Created by admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
PRIMARY
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