Details
Stereochemistry | RACEMIC |
Molecular Formula | C24H31NO6.ClH |
Molecular Weight | 465.967 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.COC1=CC(CCC2=CC=CC=C2OCC(CN(C)C)OC(=O)CCC(O)=O)=CC=C1
InChI
InChIKey=POQBIDFFYCYHOB-UHFFFAOYSA-N
InChI=1S/C24H31NO6.ClH/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);1H
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 |
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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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Effects of sarpogrelate hydrochloride on adenosine diphosphate- or collagen-induced platelet responses in arteriosclerosis obliterans. | 2001 Jul |
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Effects of chronic administration of sarpogrelate on systolic blood pressure of spontaneously hypertensive rats: comparison with quinapril. | 2002 Feb |
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Blockade of 5-HT(2A) receptors by sarpogrelate protects the heart against myocardial infarction in rats. | 2002 Jan |
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Changed responsiveness of the detrusor in rabbits with alloxan induced hyperglycemia: possible role of 5-hydroxytryptamine for diabetic bladder dysfunction. | 2002 Jul |
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5-HT2A receptor subtype in the peripheral branch of sensory fibers is involved in the potentiation of inflammatory pain in rats. | 2002 Sep |
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Effect of MCI-9042, a 5-HT2 receptor antagonist, on retinal ganglion cell death and retinal ischemia. | 2003 Apr |
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[Molecular pharmacology of sarpogrelate]. | 2003 Nov |
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Attenuation of the serotonin-induced increase in intracellular calcium in rat aortic smooth muscle cells by sarpogrelate. | 2003 Nov |
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Effects of R-102444, an orally active 5-HT2A receptor antagonist, in rat models of peripheral vascular disease. | 2004 Feb |
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Effect of sarpogrelate hydrochloride, a 5-HT2 blocker, on insulin resistance in Otsuka Long-Evans Tokushima fatty rats (OLETF rats), a type 2 diabetic rat model. | 2004 Feb |
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Sarpogrelate, a 5-HT2 receptor blocker, may have a preconditioning-like effect in patients with coronary artery disease. | 2004 Jan |
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Dual roles of 5-hydroxytryptamine in ischemia-reperfusion injury in isolated rat hearts. | 2004 Mar |
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Effect of the serotonin blocker sarpogrelate on circulating interleukin-18 levels in patients with diabetes and arteriosclerosis obliterans. | 2004 Mar-Apr |
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Therapeutic potentials of sarpogrelate in cardiovascular disease. | 2004 Spring |
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Effects of a 5-HT2A receptor antagonist, sarpogrelate on thermal or inflammatory pain. | 2005 May 23 |
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Increased hypothalamic 5-HT2A receptor gene expression and effects of pharmacologic 5-HT2A receptor inactivation in obese Ay mice. | 2006 Dec 29 |
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Livedo racemosa as a cutaneous manifestation of polycythemia vera. | 2006 May-Jun |
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Inverse agonist activity of sarpogrelate, a selective 5-HT2A-receptor antagonist, at the constitutively active human 5-HT2A receptor. | 2006 Oct |
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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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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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Sarpogrelate hydrochloride, a 5-HT2A receptor antagonist, attenuates neurogenic pain induced by nucleus pulposus in rats. | 2007 Feb 1 |
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Antiplatelet agents sarpogrelate and cilostazol affect experimentally-induced ventricular arrhythmias and mortality. | 2008 Fall |
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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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Acute effects of sarpogrelate, a 5-HT2A receptor antagonist on cytokine production in endotoxin shock model of rats. | 2009 Jul 1 |
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Chronic treatment of hydroxytryptamine type 2a receptor antagonist sarpogrelate hydrochloride modulates the vasoreactivity of serotonin in experimental rabbit vein grafts. | 2009 Sep |
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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.
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NCI_THESAURUS |
C66885
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NCI_THESAURUS |
C1327
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86819-20-7
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C132071
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FQN8N8QP1B
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CHEMBL52939
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DTXSID8046662
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ACTIVE MOIETY
SUBSTANCE RECORD