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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
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
[Involvement of peripheral 5-HT2A receptor activation in inflammatory pain].
2001 Sep
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
Pharmacological profiles of R-96544, the active form of a novel 5-HT2A receptor antagonist R-102444.
2002 Dec 20
Effects of chronic administration of sarpogrelate on systolic blood pressure of spontaneously hypertensive rats: comparison with quinapril.
2002 Feb
DOI, a 5-HT2 receptor agonist, induces renal vasodilation via nitric oxide in anesthetized dogs.
2002 Feb 15
Sarpogrelate, a specific 5HT2-receptor antagonist, improves the coronary microcirculation in coronary artery disease.
2002 Jan
Binding and functional affinity of sarpogrelate, its metabolite m-1 and ketanserin for human recombinant alpha-1-adrenoceptor subtypes.
2002 May
Serotonin receptor antagonist inhibits monocrotaline-induced pulmonary hypertension and prolongs survival in rats.
2003 Dec 1
The role of 5-HT on the cardiovascular and renal systems and the clinical potential of 5-HT modulation.
2003 May
[Molecular pharmacology of 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
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
Serotonin acts as an up-regulator of acyl-coenzyme A:cholesterol acyltransferase-1 in human monocyte-macrophages.
2006 Jun
Peripheral 5-HT2A receptor antagonism attenuates primary thermal hyperalgesia and secondary mechanical allodynia after thermal injury in rats.
2006 May
Sarpogrelate hydrochloride, a selective 5-HT2A antagonist, improves vascular function in patients with peripheral arterial disease.
2007 Apr
Blockade of serotonin 2A receptor improves glomerular endothelial function in rats with streptozotocin-induced diabetic nephropathy.
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
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
Assessment of binding affinity to 5-hydroxytryptamine 2A (5-HT2A) receptor and inverse agonist activity of naftidrofuryl: comparison with those of sarpogrelate.
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.
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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