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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
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
Sarpogrelate inhibits serotonin-induced proliferation of porcine coronary artery smooth muscle cells: implications for long-term graft patency.
2001 Jun
Binding affinity of a newly synthesized 5-HT2 antagonist, AT-1015 (N-[2-[4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-piperidino]ethyl]-1-formyl-4-piperidinecarboxamide monohydrochloride monohydrate), in the rabbit platelet membrane.
2001 Oct
The effects of vasodilators on the relaxation of guinea-pig aorta during acute recoil.
2002 Dec
DOI, a 5-HT2 receptor agonist, induces renal vasodilation via nitric oxide in anesthetized dogs.
2002 Feb 15
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
[A 50-year history of new drugs in Japan-the development and trends of hemostatics and antithrombotic drugs].
2003
Effect of sarpogrelate on altered STZ-diabetes induced cardiovascular responses to 5-hydroxytryptamine in rats.
2003 Jul
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
Sarpogrelate: cardiovascular and renal clinical potential.
2004 Jul
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
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
Impaired potency of bone marrow mononuclear cells for inducing therapeutic angiogenesis in obese diabetic rats.
2006 Apr
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
Induction of indefinite survival of fully mismatched cardiac allografts and generation of regulatory cells by sarpogrelate hydrochloride.
2006 Oct 27
Identification of a key amino acid of the human 5-HT(2B) serotonin receptor important for sarpogrelate binding.
2007 Jul
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
[Coronary artery bypass grafting for simultaneous subacute stent thrombosis after sirolimus-eluting stent implantation].
2008 May
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
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.
Name Type Language
SARPOGRELATE
INN   WHO-DD  
INN  
Official Name English
Sarpogrelate [WHO-DD]
Common 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
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 Fri Dec 15 16:01:29 UTC 2023 , Edited by admin on Fri Dec 15 16:01:29 UTC 2023
NCI_THESAURUS C66885
Created by admin on Fri Dec 15 16:01:29 UTC 2023 , Edited by admin on Fri Dec 15 16:01:29 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID7048328
Created by admin on Fri Dec 15 16:01:29 UTC 2023 , Edited by admin on Fri Dec 15 16:01:29 UTC 2023
PRIMARY
INN
6611
Created by admin on Fri Dec 15 16:01:29 UTC 2023 , Edited by admin on Fri Dec 15 16:01:29 UTC 2023
PRIMARY
CAS
135309-80-7
Created by admin on Fri Dec 15 16:01:29 UTC 2023 , Edited by admin on Fri Dec 15 16:01:29 UTC 2023
SUPERSEDED
PUBCHEM
5160
Created by admin on Fri Dec 15 16:01:29 UTC 2023 , Edited by admin on Fri Dec 15 16:01:29 UTC 2023
PRIMARY
EVMPD
SUB10455MIG
Created by admin on Fri Dec 15 16:01:29 UTC 2023 , Edited by admin on Fri Dec 15 16:01:29 UTC 2023
PRIMARY
FDA UNII
19P708E787
Created by admin on Fri Dec 15 16:01:29 UTC 2023 , Edited by admin on Fri Dec 15 16:01:29 UTC 2023
PRIMARY
DRUG CENTRAL
2423
Created by admin on Fri Dec 15 16:01:29 UTC 2023 , Edited by admin on Fri Dec 15 16:01:29 UTC 2023
PRIMARY
MESH
C064294
Created by admin on Fri Dec 15 16:01:29 UTC 2023 , Edited by admin on Fri Dec 15 16:01:29 UTC 2023
PRIMARY
DRUG BANK
DB12163
Created by admin on Fri Dec 15 16:01:29 UTC 2023 , Edited by admin on Fri Dec 15 16:01:29 UTC 2023
PRIMARY
NCI_THESAURUS
C73158
Created by admin on Fri Dec 15 16:01:29 UTC 2023 , Edited by admin on Fri Dec 15 16:01:29 UTC 2023
PRIMARY
ChEMBL
CHEMBL52939
Created by admin on Fri Dec 15 16:01:29 UTC 2023 , Edited by admin on Fri Dec 15 16:01:29 UTC 2023
PRIMARY
SMS_ID
100000084098
Created by admin on Fri Dec 15 16:01:29 UTC 2023 , Edited by admin on Fri Dec 15 16:01:29 UTC 2023
PRIMARY
IUPHAR
210
Created by admin on Fri Dec 15 16:01:29 UTC 2023 , Edited by admin on Fri Dec 15 16:01:29 UTC 2023
PRIMARY
CAS
125926-17-2
Created by admin on Fri Dec 15 16:01:29 UTC 2023 , Edited by admin on Fri Dec 15 16:01:29 UTC 2023
PRIMARY
WIKIPEDIA
SARPOGRELATE
Created by admin on Fri Dec 15 16:01:29 UTC 2023 , Edited by admin on Fri Dec 15 16:01:29 UTC 2023
PRIMARY