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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

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
Serotonin potentiates angiotensin II--induced vascular smooth muscle cell proliferation.
2001 Dec
Antithrombotic activity of AT-1015, a potent 5-HT(2A) receptor antagonist, in rat arterial thrombosis model and its effect on bleeding time.
2001 Dec 21
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
Sarpogrelate diminishes changes in energy stores and ultrastructure of the ischemic-reperfused rat heart.
2001 Sep
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
5-HT2A receptor subtype in the peripheral branch of sensory fibers is involved in the potentiation of inflammatory pain in rats.
2002 Sep
Assessment of affinities and dissociation potencies of several 5-HT2 antagonists to and from M2 muscarinic receptor in rat heart membranes.
2003 Aug
Serotonin receptor antagonist inhibits monocrotaline-induced pulmonary hypertension and prolongs survival in rats.
2003 Dec 1
Sarpogrelate HCl, a selective 5-HT2A antagonist, retards the progression of atherosclerosis through a novel mechanism.
2003 May
[Molecular pharmacology of sarpogrelate].
2003 Nov
Attenuation of the serotonin-induced increase in intracellular calcium in rat aortic smooth muscle cells by sarpogrelate.
2003 Nov
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
Therapeutic potentials of sarpogrelate in cardiovascular disease.
2004 Spring
Contribution of the peripheral 5-HT 2A receptor to mechanical hyperalgesia in a rat model of neuropathic pain.
2005 Nov
Site-directed mutagenesis of the serotonin 5-Hydroxytryptamine2c receptor: identification of amino acids responsible for sarpogrelate binding.
2006 Aug
Effects of sarpogrelate hydrochloride in a patient with chronic graft-versus-host disease: a case report.
2006 Feb
A new method for assessment of an anti-5HT(2A) agent, sarpogrelate hydrochloride, on platelet aggregation.
2006 Feb
Sarpogrelate, a 5-hT2A receptor antagonist in intermittent claudication. A phase II European study.
2006 May
Induction of indefinite survival of fully mismatched cardiac allografts and generation of regulatory cells by sarpogrelate hydrochloride.
2006 Oct 27
Combined treatment of sustained-release basic fibroblast growth factor and sarpogrelate enhances collateral blood flow effectively in rabbit hindlimb ischemia.
2006 Sep
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
Identification of a key amino acid of the human 5-HT(2B) serotonin receptor important for sarpogrelate binding.
2007 Jul
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
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
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 Fri Dec 15 16:01:29 GMT 2023
Edited
by admin
on Fri Dec 15 16:01:29 GMT 2023
Record UNII
19P708E787
Record Status Validated (UNII)
Record Version
  • Download
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 GMT 2023 , Edited by admin on Fri Dec 15 16:01:29 GMT 2023
NCI_THESAURUS C66885
Created by admin on Fri Dec 15 16:01:29 GMT 2023 , Edited by admin on Fri Dec 15 16:01:29 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID7048328
Created by admin on Fri Dec 15 16:01:29 GMT 2023 , Edited by admin on Fri Dec 15 16:01:29 GMT 2023
PRIMARY
INN
6611
Created by admin on Fri Dec 15 16:01:29 GMT 2023 , Edited by admin on Fri Dec 15 16:01:29 GMT 2023
PRIMARY
CAS
135309-80-7
Created by admin on Fri Dec 15 16:01:29 GMT 2023 , Edited by admin on Fri Dec 15 16:01:29 GMT 2023
SUPERSEDED
PUBCHEM
5160
Created by admin on Fri Dec 15 16:01:29 GMT 2023 , Edited by admin on Fri Dec 15 16:01:29 GMT 2023
PRIMARY
EVMPD
SUB10455MIG
Created by admin on Fri Dec 15 16:01:29 GMT 2023 , Edited by admin on Fri Dec 15 16:01:29 GMT 2023
PRIMARY
FDA UNII
19P708E787
Created by admin on Fri Dec 15 16:01:29 GMT 2023 , Edited by admin on Fri Dec 15 16:01:29 GMT 2023
PRIMARY
DRUG CENTRAL
2423
Created by admin on Fri Dec 15 16:01:29 GMT 2023 , Edited by admin on Fri Dec 15 16:01:29 GMT 2023
PRIMARY
MESH
C064294
Created by admin on Fri Dec 15 16:01:29 GMT 2023 , Edited by admin on Fri Dec 15 16:01:29 GMT 2023
PRIMARY
DRUG BANK
DB12163
Created by admin on Fri Dec 15 16:01:29 GMT 2023 , Edited by admin on Fri Dec 15 16:01:29 GMT 2023
PRIMARY
NCI_THESAURUS
C73158
Created by admin on Fri Dec 15 16:01:29 GMT 2023 , Edited by admin on Fri Dec 15 16:01:29 GMT 2023
PRIMARY
ChEMBL
CHEMBL52939
Created by admin on Fri Dec 15 16:01:29 GMT 2023 , Edited by admin on Fri Dec 15 16:01:29 GMT 2023
PRIMARY
SMS_ID
100000084098
Created by admin on Fri Dec 15 16:01:29 GMT 2023 , Edited by admin on Fri Dec 15 16:01:29 GMT 2023
PRIMARY
IUPHAR
210
Created by admin on Fri Dec 15 16:01:29 GMT 2023 , Edited by admin on Fri Dec 15 16:01:29 GMT 2023
PRIMARY
CAS
125926-17-2
Created by admin on Fri Dec 15 16:01:29 GMT 2023 , Edited by admin on Fri Dec 15 16:01:29 GMT 2023
PRIMARY
WIKIPEDIA
SARPOGRELATE
Created by admin on Fri Dec 15 16:01:29 GMT 2023 , Edited by admin on Fri Dec 15 16:01:29 GMT 2023
PRIMARY
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