Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C24H31NO6.ClH |
| Molecular Weight | 465.9678 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CC(COc1ccccc1CCc2cccc(c2)OC)OC(=O)CCC(=O)O.Cl
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
| 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 | ( + / - ) |
| Molecular Formula | ClH |
| Molecular Weight | 36.4609 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator'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
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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL224 |
8.38 nM [Ki] | ||
Target ID: CHEMBL1833 |
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 |
|---|---|---|
| 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 |
|
| Site-directed mutagenesis of the serotonin 5-Hydroxytryptamine2c receptor: identification of amino acids responsible for sarpogrelate binding. | 2006 Aug |
|
| Increased hypothalamic 5-HT2A receptor gene expression and effects of pharmacologic 5-HT2A receptor inactivation in obese Ay mice. | 2006 Dec 29 |
|
| Effects of sarpogrelate hydrochloride in a patient with chronic graft-versus-host disease: a case report. | 2006 Feb |
|
| Sarpogrelate hydrochloride, an antagonist of 5-hydroxytryptamine receptor, improves skin flap survival and suppresses thrombus formation in injured microvessels of rabbits. | 2006 Jan |
|
| Inhibition of 5-hydroxytryptamine receptor prevents occlusive thrombus formation on neointima of the rabbit femoral artery. | 2006 Jan |
|
| The 5-hydroxytryptamine2A receptor antagonist sarpogrelate hydrochloride inhibits acute platelet aggregation in injured endothelium. | 2006 Jan-Feb |
|
| Homology modelling of the serotoninergic 5-HT2c receptor. | 2006 Jun |
|
| Sarpogrelate, a 5-hT2A receptor antagonist in intermittent claudication. A phase II European study. | 2006 May |
|
| Peripheral 5-HT2A receptor antagonism attenuates primary thermal hyperalgesia and secondary mechanical allodynia after thermal injury in rats. | 2006 May |
|
| Livedo racemosa as a cutaneous manifestation of polycythemia vera. | 2006 May-Jun |
|
| Persistent insulin-sensitizing effects of sarpogrelate hydrochloride, a serotonin 2A receptor antagonist, in patients with peripheral arterial disease. | 2006 Nov |
|
| Inverse agonist activity of sarpogrelate, a selective 5-HT2A-receptor antagonist, at the constitutively active human 5-HT2A receptor. | 2006 Oct |
|
| Induction of indefinite survival of fully mismatched cardiac allografts and generation of regulatory cells by sarpogrelate hydrochloride. | 2006 Oct 27 |
|
| Identification of amino acid residues important for sarpogrelate binding to the human 5-hydroxytryptamine2A serotonin receptor. | 2006 Sep |
|
| 5-HT2 receptor blocker sarpogrelate prevents downregulation of antiapoptotic protein Bcl-2 and protects the heart against ischemia-reperfusion injury. | 2006 Sep 27 |
|
| 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 |
|
| Sarpogrelate hydrochloride, a selective 5-HT2A antagonist, improves vascular function in patients with peripheral arterial disease. | 2007 Apr |
|
| Sarpogrelate hydrochloride, a 5-HT2A receptor antagonist, attenuates neurogenic pain induced by nucleus pulposus in rats. | 2007 Feb 1 |
|
| Identification of a key amino acid of the human 5-HT(2B) serotonin receptor important for sarpogrelate binding. | 2007 Jul |
|
| Antiplatelet therapy mitigates cardiac remodeling and dysfunction in congestive heart failure due to myocardial infarction. | 2008 Apr |
|
| New therapeutic approach for impaired arteriogenesis in diabetic mouse hindlimb ischemia. | 2008 Apr |
|
| 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 |
|
| Serotonin induces vasoconstriction of smooth muscle cell-rich neointima through 5-hydroxytryptamine2A receptor in rabbit femoral arteries. | 2008 Jul |
|
| 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 |
|
| 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 |
|
| Reduced albuminuria with sarpogrelate is accompanied by a decrease in monocyte chemoattractant protein-1 levels in type 2 diabetes. | 2008 Mar |
|
| [Coronary artery bypass grafting for simultaneous subacute stent thrombosis after sirolimus-eluting stent implantation]. | 2008 May |
|
| 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 |
|
| Sarpogrelate versus aspirin in secondary prevention of cerebral infarction: differential efficacy in diabetes? Subgroup analysis from S-ACCESS. | 2009 Aug |
|
| Acute effects of sarpogrelate, a 5-HT2A receptor antagonist on cytokine production in endotoxin shock model of rats. | 2009 Jul 1 |
|
| Sarpogrelate hydrochloride reduced intimal hyperplasia in experimental rabbit vein graft. | 2009 May |
|
| 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
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
Edited
Sat Jun 26 05:39:08 UTC 2021
by
admin
on
Sat Jun 26 05:39:08 UTC 2021
|
| Record UNII |
FQN8N8QP1B
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C66885
Created by
admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
|
||
|
NCI_THESAURUS |
C1327
Created by
admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
86819-20-7
Created by
admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
|
SUPERSEDED | |||
|
C132071
Created by
admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
|
PRIMARY | |||
|
FQN8N8QP1B
Created by
admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
|
PRIMARY | |||
|
DBSALT002147
Created by
admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
|
PRIMARY | |||
|
CHEMBL52939
Created by
admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
|
PRIMARY | |||
|
135159-51-2
Created by
admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
|
PRIMARY | |||
|
135159-51-2
Created by
admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
|
PRIMARY | |||
|
SUB04330MIG
Created by
admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
|
PRIMARY | |||
|
444005
Created by
admin on Sat Jun 26 05:39:08 UTC 2021 , Edited by admin on Sat Jun 26 05:39:08 UTC 2021
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |