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Details

Stereochemistry RACEMIC
Molecular Formula C24H31NO6
Molecular Weight 429.507
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SARPOGRELATE

SMILES

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

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

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 ( + / - )

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
Serotonin potentiates angiotensin II--induced vascular smooth muscle cell proliferation.
2001 Dec
Effects of sarpogrelate hydrochloride on adenosine diphosphate- or collagen-induced platelet responses in arteriosclerosis obliterans.
2001 Jul
Assessment of affinity and dissociation ability of a newly synthesized 5-HT2 antagonist, AT-1015: comparison with other 5-HT2 antagonists.
2001 Nov
Effects of sarpogrelate, a novel 5-HT2 antagonist, on 5-HT-induced endothelium-dependent relaxations in porcine coronary artery.
2002 Aug
Effectiveness of a novel serotonin blocker, sarpogrelate, for patients with angina pectoris.
2002 Aug
DOI, a 5-HT2 receptor agonist, induces renal vasodilation via nitric oxide in anesthetized dogs.
2002 Feb 15
[Pharmacological analysis of inhibitory effect of sarpogrelate hydrochloride on human radial artery contraction].
2002 Jan
Effect of MCI-9042, a 5-HT2 receptor antagonist, on retinal ganglion cell death and retinal ischemia.
2003 Apr
A novel serotonin blocker, sarpogrelate, increases circulating adiponectin levels in diabetic patients with arteriosclerosis obliterans.
2003 Aug
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
Sarpogrelate, a 5-HT2 receptor blocker, may have a preconditioning-like effect in patients with coronary artery disease.
2004 Jan
Effect of the serotonin blocker sarpogrelate on circulating interleukin-18 levels in patients with diabetes and arteriosclerosis obliterans.
2004 Mar-Apr
Functions of 5-HT2A receptor and its antagonists in the cardiovascular system.
2004 Oct
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
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
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
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
[Effect of sarpogrelate in enteral feeding of patients with gastroesophageal reflux (GER)].
2006 Jul
Homology modelling of the serotoninergic 5-HT2c receptor.
2006 Jun
Serotonin acts as an up-regulator of acyl-coenzyme A:cholesterol acyltransferase-1 in human monocyte-macrophages.
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
Combined treatment of sustained-release basic fibroblast growth factor and sarpogrelate enhances collateral blood flow effectively in rabbit hindlimb ischemia.
2006 Sep
Synthesis and 5-HT2A, 5-HT1A and alpha1-binding affinities of 2-[2-Hydroxy-3-(pyridin-3-yl-methyl)amino]-, 2-[2-hydroxy-3-(2-pyridin-2-yl-ethyl)amino]- and 2-[2-hydroxy-3-(4-N-methyl-piperazin-1-yl)-amino]propoxybenzaldehyde-O-(substituted) benzyl oximes.
2007 Mar
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
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
[Coronary artery bypass grafting for simultaneous subacute stent thrombosis after sirolimus-eluting stent implantation].
2008 May
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
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 13:38:02 UTC 2021
Edited
by admin
on Sat Jun 26 13:38:02 UTC 2021
Record UNII
19P708E787
Record Status Validated (UNII)
Record Version
  • Download
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 Sat Jun 26 13:38:03 UTC 2021 , Edited by admin on Sat Jun 26 13:38:03 UTC 2021
NCI_THESAURUS C66885
Created by admin on Sat Jun 26 13:38:03 UTC 2021 , Edited by admin on Sat Jun 26 13:38:03 UTC 2021
Code System Code Type Description
EPA CompTox
125926-17-2
Created by admin on Sat Jun 26 13:38:03 UTC 2021 , Edited by admin on Sat Jun 26 13:38:03 UTC 2021
PRIMARY
INN
6611
Created by admin on Sat Jun 26 13:38:03 UTC 2021 , Edited by admin on Sat Jun 26 13:38:03 UTC 2021
PRIMARY
CAS
135309-80-7
Created by admin on Sat Jun 26 13:38:03 UTC 2021 , Edited by admin on Sat Jun 26 13:38:03 UTC 2021
SUPERSEDED
PUBCHEM
5160
Created by admin on Sat Jun 26 13:38:03 UTC 2021 , Edited by admin on Sat Jun 26 13:38:03 UTC 2021
PRIMARY
EVMPD
SUB10455MIG
Created by admin on Sat Jun 26 13:38:03 UTC 2021 , Edited by admin on Sat Jun 26 13:38:03 UTC 2021
PRIMARY
FDA UNII
19P708E787
Created by admin on Sat Jun 26 13:38:03 UTC 2021 , Edited by admin on Sat Jun 26 13:38:03 UTC 2021
PRIMARY
DRUG CENTRAL
2423
Created by admin on Sat Jun 26 13:38:03 UTC 2021 , Edited by admin on Sat Jun 26 13:38:03 UTC 2021
PRIMARY
MESH
C064294
Created by admin on Sat Jun 26 13:38:03 UTC 2021 , Edited by admin on Sat Jun 26 13:38:03 UTC 2021
PRIMARY
DRUG BANK
DB12163
Created by admin on Sat Jun 26 13:38:03 UTC 2021 , Edited by admin on Sat Jun 26 13:38:03 UTC 2021
PRIMARY
NCI_THESAURUS
C73158
Created by admin on Sat Jun 26 13:38:03 UTC 2021 , Edited by admin on Sat Jun 26 13:38:03 UTC 2021
PRIMARY
ChEMBL
CHEMBL52939
Created by admin on Sat Jun 26 13:38:03 UTC 2021 , Edited by admin on Sat Jun 26 13:38:03 UTC 2021
PRIMARY
IUPHAR
210
Created by admin on Sat Jun 26 13:38:03 UTC 2021 , Edited by admin on Sat Jun 26 13:38:03 UTC 2021
PRIMARY
CAS
125926-17-2
Created by admin on Sat Jun 26 13:38:03 UTC 2021 , Edited by admin on Sat Jun 26 13:38:03 UTC 2021
PRIMARY
WIKIPEDIA
SARPOGRELATE
Created by admin on Sat Jun 26 13:38:03 UTC 2021 , Edited by admin on Sat Jun 26 13:38:03 UTC 2021
PRIMARY
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