Compound: Sarpogrelate
SMILES: O=C(OC(COc1c(cccc1)CCc2cc(OC)ccc2)CN(C)C)CCC(=O)O
InChIKey: FFYNAVGJSYHHFO-UHFFFAOYSA-N
Synonyms: Sarpogrelate, 125926-17-2, sarpogrelato, 19P708E787, DTXSID7048328, 4-{[1-(dimethylamino)-3-{2-[2-(3-methoxyphenyl)ethyl]phenoxy}propan-2-yl]oxy}-4-oxobutanoic acid, sarpogrelatum, 4-((1-(dimethylamino)-3-(2-(2-(3-methoxyphenyl)ethyl)phenoxy)propan-2-yl)oxy)-4-oxobutanoic acid, 4-(1-dimethylamino-3-(2-(2-(3-methoxyphenyl)ethyl)phenoxy)propan-2-yl)oxy-4-oxobutanoic acid, 4-[1-dimethylamino-3-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]propan-2-yl]oxy-4-oxobutanoic acid, RefChem:181463, DTXCID2028303, 2-(dimethylamino)-1-((2-(3-methoxyphenyl)phenoxy)methyl)ethyl hydrogensuccinate hydrochloride, mono-(2-(dimethylamino)-1-((2-(2-(3-methoxyphenyl)ethyl)phenoxy)methyl)ethyl)succinate hydrochloride, Sarpogrelate [INN], 4-[1-(dimethylamino)-3-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]propan-2-yl]oxy-4-oxobutanoic acid, Sarpogrelate (INN), CHEMBL541829, UNII-19P708E787, NCGC00167489-01, NCGC00167489-03, SCHEMBL49197, GTPL210, CHEMBL52939, SARPOGRELATE [WHO-DD], orb1687669, SCHEMBL29703848, SCHEMBL30001082, CHEBI:135697, BDBM50093789, STK631325, AKOS005563803, DB12163, NCGC00167489-02, DA-67415, FS157999, HY-10563, 5384B, 5441B, CS-0002654, LS-187,118, D08508, Q44931, SBI-0653865.0001, L000858, SR-01000883998, SR-01000883998-1, BRD-A34358106-003-01-6, (+-)-2-(Dimethylamino)-1-((o-(m-methoxyphenethyl)phenoxy)methyl)ethyl hydrogen succinate, (- )-2-(Dimethylamino)-1-((o-(m-methoxyphenethyl)phenoxy)methyl)ethyl hydrogen succinate., (S)-4- (1- (2- (3- Methoxyphenethyl) phenoxy) - 3- (dimethylamino) propan- 2- yloxy) - 4- oxobutanoic acid, 4-(1-(2-(3-METHOXYPHENETHYL)PHENOXY)-3-(DIMETHYLAMINO)PROPAN-2-YLOXY)-4-OXOBUTANOIC ACID SARPOGRELATE, BUTANEDIOIC ACID, MONO(2-(DIMETHYLAMINO)-1-((2-(2-(3-METHOXYPHENYL)ETHYL)PHENOXY)METHYL)ETHYL) ESTER, Succinic acid mono-(2-dimethylamino-1-{2-[2-(3-methoxy-phenyl)-ethyl]-phenoxymethyl}-ethyl) ester; hydrochloride
Theoretical properties:
molecular_formula: C24H31NO6
molecular_weight: 429.5 g/mol
exact_mass: 429.21513771 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 7
rotatable_bond_count: 14
heavy_atom_count: 31
topological_polar_surface_area: 85.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Sarpogrelate is a hemisuccinate and a stilbenoid.
chembl: SARPOGRELATE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Sarpogrelate (INNTooltip International Nonproprietary Name, JANTooltip Japanese Accepted Name), sold under the brand names Anplag and Sapodifil, is a serotonin 5-HT2 receptor antagonist which is used in the treatment of arterial occlusive disorders such as peripheral artery disease in Japan, South Korea, and China. Development in the United States and the European Union was discontinued and it is not available in these regions.
The drug acts as an antagonist at the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. However, its affinities for the human 5-HT2C and 5-HT2B receptors are about one and two orders of magnitude lower than for the human 5-HT2A receptor, respectively. The drug blocks serotonin-induced platelet aggregation, and has potential applications in the treatment of many diseases including diabetes mellitus, Buerger's disease, Raynaud's disease, coronary artery disease, angina pectoris, and atherosclerosis.
The predicted log P (XLogP3) of sarpogrelate is 1.2. A 2004 review stated that it was unknown whether sarpogrelate crosses the blood–brain barrier. However, other papers have stated that sarpogrelate minimally crosses into the brain and hence is peripherally selective. Accordingly, a rat study found that peak sarpogrelate levels were 50-fold lower in the brain and spinal cord than in the circulation.