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
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)
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 | ( + / - ) |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/17438407Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17438407
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10980267
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
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8937629 |
8.38 nM [Ki] | ||
Target ID: CHEMBL1833 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17609583 |
6.11 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Anplag Approved UseINDICATIONS. Improvement of ischemic symptoms including ulcer, pain and feeling of coldness, associated with chronic arterial occlusion |
|||
Preventing | Anplag Approved UseINDICATIONS. Improvement of ischemic symptoms including ulcer, pain and feeling of coldness, associated with chronic arterial occlusion |
PubMed
Title | Date | PubMed |
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Effects of sarpogrelate hydrochloride on adenosine diphosphate- or collagen-induced platelet responses in arteriosclerosis obliterans. | 2001 Jul |
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Assessment of affinity and dissociation ability of a newly synthesized 5-HT2 antagonist, AT-1015: comparison with other 5-HT2 antagonists. | 2001 Nov |
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Sarpogrelate diminishes changes in energy stores and ultrastructure of the ischemic-reperfused rat heart. | 2001 Sep |
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Involvement of rho-kinase in agonists-induced contractions of arteriosclerotic human arteries. | 2002 Feb 1 |
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[Pharmacological analysis of inhibitory effect of sarpogrelate hydrochloride on human radial artery contraction]. | 2002 Jan |
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Sarpogrelate hydrochloride, a serotonin2A receptor antagonist, reduces albuminuria in diabetic patients with early-stage diabetic nephropathy. | 2002 Nov |
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[A 50-year history of new drugs in Japan-the development and trends of hemostatics and antithrombotic drugs]. | 2003 |
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Efficacy of serotonin receptor blocker for symptomatic lumbar disc herniation. | 2003 Jun |
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Sarpogrelate treatment reduces restenosis after coronary stenting. | 2003 Mar |
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Sarpogrelate HCl, a selective 5-HT2A antagonist, retards the progression of atherosclerosis through a novel mechanism. | 2003 May |
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The role of 5-HT on the cardiovascular and renal systems and the clinical potential of 5-HT modulation. | 2003 May |
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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 |
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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 |
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Electroencephalographical effects of sarpogrelate hydrochloride versus ticlopidine hydrochloride in elderly patients with peripheral atherosclerosis. | 2004 May-Jun |
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Functions of 5-HT2A receptor and its antagonists in the cardiovascular system. | 2004 Oct |
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Therapeutic potentials of sarpogrelate in cardiovascular disease. | 2004 Spring |
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Cardiovascular disease in diabetic nephropathy patients: cell adhesion molecules as potential markers? | 2005 |
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New treatment of lumbar disc herniation involving 5-hydroxytryptamine2A receptor inhibitor: a randomized controlled trial. | 2005 Apr |
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5-HT2A receptor antagonist increases circulating adiponectin in patients with type 2 diabetes. | 2005 Sep |
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Impaired potency of bone marrow mononuclear cells for inducing therapeutic angiogenesis in obese diabetic rats. | 2006 Apr |
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Site-directed mutagenesis of the serotonin 5-Hydroxytryptamine2c receptor: identification of amino acids responsible for sarpogrelate binding. | 2006 Aug |
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Homology modelling of the serotoninergic 5-HT2c receptor. | 2006 Jun |
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Sarpogrelate, a 5-hT2A receptor antagonist in intermittent claudication. A phase II European study. | 2006 May |
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Livedo racemosa as a cutaneous manifestation of polycythemia vera. | 2006 May-Jun |
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Identification of amino acid residues important for sarpogrelate binding to the human 5-hydroxytryptamine2A serotonin receptor. | 2006 Sep |
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Combined treatment of sustained-release basic fibroblast growth factor and sarpogrelate enhances collateral blood flow effectively in rabbit hindlimb ischemia. | 2006 Sep |
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5-HT2 receptor blocker sarpogrelate prevents downregulation of antiapoptotic protein Bcl-2 and protects the heart against ischemia-reperfusion injury. | 2006 Sep 27 |
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Effect of sarpogrelate, a 5-HT(2A) antagonist, on platelet aggregation in patients with ischemic stroke: clinical-pharmacological dose-response study. | 2007 |
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Marked improvement with sildenafil in a patient with idiopathic pulmonary arterial hypertension unresponsive to beraprost and sarpogrelate. | 2007 |
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Sarpogrelate hydrochloride, a 5-HT2A receptor antagonist, attenuates neurogenic pain induced by nucleus pulposus in rats. | 2007 Feb 1 |
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Identification of a key amino acid of the human 5-HT(2B) serotonin receptor important for sarpogrelate binding. | 2007 Jul |
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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 |
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Blockade of serotonin 2A receptor improves glomerular endothelial function in rats with streptozotocin-induced diabetic nephropathy. | 2008 Apr |
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Antiplatelet agents sarpogrelate and cilostazol affect experimentally-induced ventricular arrhythmias and mortality. | 2008 Fall |
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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 |
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Serotonin induces vasoconstriction of smooth muscle cell-rich neointima through 5-hydroxytryptamine2A receptor in rabbit femoral arteries. | 2008 Jul |
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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 |
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Antiplatelet therapy attenuates subcellular remodelling in congestive heart failure. | 2008 Sep-Oct |
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Beneficial effects of sarpogrelate hydrochloride, a 5-HT2A receptor antagonist, supplemented with pioglitazone on diabetic model mice. | 2009 |
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Sarpogrelate versus aspirin in secondary prevention of cerebral infarction: differential efficacy in diabetes? Subgroup analysis from S-ACCESS. | 2009 Aug |
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Acute effects of sarpogrelate, a 5-HT2A receptor antagonist on cytokine production in endotoxin shock model of rats. | 2009 Jul 1 |
|
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
Sample Use Guides
In Vivo Use Guide
Sources: http://www.e-search.ne.jp/~jpr/PDF/MT02.PDF
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17609583
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
Edited
Wed Jul 05 23:29:31 UTC 2023
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Record UNII |
19P708E787
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C1327
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NCI_THESAURUS |
C66885
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135309-80-7
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19P708E787
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C064294
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DB12163
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C73158
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CHEMBL52939
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100000084098
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SARPOGRELATE
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METABOLIC ENZYME -> INHIBITOR |
COMPETITIVE INHIBITOR
IC50
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO
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ACTIVE MOIETY |