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)
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 |
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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 |
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Primary | Anplag Approved UseINDICATIONS. Improvement of ischemic symptoms including ulcer, pain and feeling of coldness, associated with chronic arterial occlusion |
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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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Serotonin potentiates angiotensin II--induced vascular smooth muscle cell proliferation. | 2001 Dec |
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Sarpogrelate inhibits serotonin-induced proliferation of porcine coronary artery smooth muscle cells: implications for long-term graft patency. | 2001 Jun |
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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 |
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The effects of vasodilators on the relaxation of guinea-pig aorta during acute recoil. | 2002 Dec |
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DOI, a 5-HT2 receptor agonist, induces renal vasodilation via nitric oxide in anesthetized dogs. | 2002 Feb 15 |
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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 |
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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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Effect of sarpogrelate on altered STZ-diabetes induced cardiovascular responses to 5-hydroxytryptamine in rats. | 2003 Jul |
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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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Sarpogrelate: cardiovascular and renal clinical potential. | 2004 Jul |
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Functions of 5-HT2A receptor and its antagonists in the cardiovascular system. | 2004 Oct |
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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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Effects of a 5-HT2A receptor antagonist, sarpogrelate on thermal or inflammatory pain. | 2005 May 23 |
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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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Homology modelling of the serotoninergic 5-HT2c receptor. | 2006 Jun |
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Serotonin acts as an up-regulator of acyl-coenzyme A:cholesterol acyltransferase-1 in human monocyte-macrophages. | 2006 Jun |
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Induction of indefinite survival of fully mismatched cardiac allografts and generation of regulatory cells by sarpogrelate hydrochloride. | 2006 Oct 27 |
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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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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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[Coronary artery bypass grafting for simultaneous subacute stent thrombosis after sirolimus-eluting stent implantation]. | 2008 May |
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Assessment of binding affinity to 5-hydroxytryptamine 2A (5-HT2A) receptor and inverse agonist activity of naftidrofuryl: comparison with those of sarpogrelate. | 2009 Aug |
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Sarpogrelate versus aspirin in secondary prevention of cerebral infarction: differential efficacy in diabetes? Subgroup analysis from S-ACCESS. | 2009 Aug |
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.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1327
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NCI_THESAURUS |
C66885
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DTXSID7048328
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6611
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135309-80-7
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5160
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SUB10455MIG
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19P708E787
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2423
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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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210
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125926-17-2
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SARPOGRELATE
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE ACTIVE (PARENT)
SALT/SOLVATE (PARENT)