U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C24H31NO6.ClH
Molecular Weight 465.967
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SARPOGRELATE HYDROCHLORIDE

SMILES

Cl.COC1=CC(CCC2=CC=CC=C2OCC(CN(C)C)OC(=O)CCC(O)=O)=CC=C1

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 ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C24H31NO6
Molecular Weight 429.506
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
Effects of sarpogrelate, a novel 5-HT2 antagonist, on 5-HT-induced endothelium-dependent relaxations in porcine coronary artery.
2002 Aug
AT-1015, a newly synthesized 5-HT2 receptor antagonist, dissociates slowly from the 5-HT2 receptor sites in rabbit cerebral cortex membrane.
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
Enhancing effect of advanced glycation end products on serotonin-induced platelet aggregation in patients with diabetes mellitus.
2002 Sep 15
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
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
Attenuation of the serotonin-induced increase in intracellular calcium in rat aortic smooth muscle cells by sarpogrelate.
2003 Nov
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
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
Dual roles of 5-hydroxytryptamine in ischemia-reperfusion injury in isolated rat hearts.
2004 Mar
Electroencephalographical effects of sarpogrelate hydrochloride versus ticlopidine hydrochloride in elderly patients with peripheral atherosclerosis.
2004 May-Jun
Therapeutic potentials of sarpogrelate in cardiovascular disease.
2004 Spring
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
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
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
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
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
Identification of amino acid residues important for sarpogrelate binding to the human 5-hydroxytryptamine2A serotonin receptor.
2006 Sep
Marked improvement with sildenafil in a patient with idiopathic pulmonary arterial hypertension unresponsive to beraprost and sarpogrelate.
2007
Sarpogrelate hydrochloride, a 5-HT2A receptor antagonist, attenuates neurogenic pain induced by nucleus pulposus in rats.
2007 Feb 1
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
Antiplatelet agents sarpogrelate and cilostazol affect experimentally-induced ventricular arrhythmias and mortality.
2008 Fall
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
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 Dec 16 05:17:52 UTC 2023
Edited
by admin
on Sat Dec 16 05:17:52 UTC 2023
Record UNII
FQN8N8QP1B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SARPOGRELATE HYDROCHLORIDE
JAN   WHO-DD  
Common Name English
ANPLAG
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 [WHO-DD]
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 Dec 16 05:17:52 UTC 2023 , Edited by admin on Sat Dec 16 05:17:52 UTC 2023
NCI_THESAURUS C1327
Created by admin on Sat Dec 16 05:17:52 UTC 2023 , Edited by admin on Sat Dec 16 05:17:52 UTC 2023
Code System Code Type Description
CAS
86819-20-7
Created by admin on Sat Dec 16 05:17:52 UTC 2023 , Edited by admin on Sat Dec 16 05:17:52 UTC 2023
SUPERSEDED
NCI_THESAURUS
C132071
Created by admin on Sat Dec 16 05:17:52 UTC 2023 , Edited by admin on Sat Dec 16 05:17:52 UTC 2023
PRIMARY
FDA UNII
FQN8N8QP1B
Created by admin on Sat Dec 16 05:17:52 UTC 2023 , Edited by admin on Sat Dec 16 05:17:52 UTC 2023
PRIMARY
DRUG BANK
DBSALT002147
Created by admin on Sat Dec 16 05:17:52 UTC 2023 , Edited by admin on Sat Dec 16 05:17:52 UTC 2023
PRIMARY
ChEMBL
CHEMBL52939
Created by admin on Sat Dec 16 05:17:52 UTC 2023 , Edited by admin on Sat Dec 16 05:17:52 UTC 2023
PRIMARY
EPA CompTox
DTXSID8046662
Created by admin on Sat Dec 16 05:17:52 UTC 2023 , Edited by admin on Sat Dec 16 05:17:52 UTC 2023
PRIMARY
CAS
135159-51-2
Created by admin on Sat Dec 16 05:17:52 UTC 2023 , Edited by admin on Sat Dec 16 05:17:52 UTC 2023
PRIMARY
EVMPD
SUB04330MIG
Created by admin on Sat Dec 16 05:17:52 UTC 2023 , Edited by admin on Sat Dec 16 05:17:52 UTC 2023
PRIMARY
PUBCHEM
444005
Created by admin on Sat Dec 16 05:17:52 UTC 2023 , Edited by admin on Sat Dec 16 05:17:52 UTC 2023
PRIMARY
SMS_ID
100000084946
Created by admin on Sat Dec 16 05:17:52 UTC 2023 , Edited by admin on Sat Dec 16 05:17:52 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY