Sarpogrelate

Sarpogrelate (former developmental code names MCI-9042, LS-187,118) is a drug which acts as an antagonist at the 5HT2A[1][2] and 5-HT2B[3] receptors. It blocks serotonin-induced platelet aggregation, and has applications in the treatment of many diseases including diabetes mellitus,[4][5] Buerger's disease,[6] Raynaud's disease,[7] coronary artery disease,[8] angina pectoris,[9] and atherosclerosis.[10]

Sarpogrelate
Clinical data
Other namesSarpogrelate, (−)-4-[1-dimethylamino-3-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]propan-2-yl]oxy-4-oxobutanoic acid
AHFS/Drugs.comInternational Drug Names
ATC code
  • none
Identifiers
IUPAC name
  • 4-[2-(dimethylamino)-1-({2-[2-(3-methoxyphenyl)ethyl]phenoxy}methyl)ethoxy]-4-oxobutanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H31NO6
Molar mass429.513 g·mol−1
3D model (JSmol)
SMILES
  • CN(C)CC(COC1=CC=CC=C1CCC2=CC(=CC=C2)OC)OC(=O)CCC(=O)O
InChI
  • 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) N
  • Key:FFYNAVGJSYHHFO-UHFFFAOYSA-N N
 NY (what is this?)  (verify)

See also

References
  1. Pertz H, Elz S (April 1995). "In-vitro pharmacology of sarpogrelate and the enantiomers of its major metabolite: 5-HT2A receptor specificity, stereoselectivity and modulation of ritanserin-induced depression of 5-HT contractions in rat tail artery". The Journal of Pharmacy and Pharmacology. 47 (4): 310–6. doi:10.1111/j.2042-7158.1995.tb05801.x. PMID 7791029. S2CID 25311518.
  2. Nishio H, Inoue A, Nakata Y (1996). "Binding affinity of sarpogrelate, a new antiplatelet agent, and its metabolite for serotonin receptor subtypes". Archives Internationales de Pharmacodynamie et de Therapie. 331 (2): 189–202. PMID 8937629.
  3. Muntasir HA, Hossain M, Bhuiyan MA, Komiyama T, Nakamura T, Ozaki M, Nagatomo T (July 2007). "Identification of a key amino acid of the human 5-HT(2B) serotonin receptor important for sarpogrelate binding". Journal of Pharmacological Sciences. 104 (3): 274–7. doi:10.1254/jphs.sc0060241. PMID 17609583.
  4. Pietraszek MH, Takada Y, Taminato A, Yoshimi T, Watanabe I, Takada A (April 1993). "The effect of MCI-9042 on serotonin-induced platelet aggregation in type 2 diabetes mellitus". Thrombosis Research. 70 (2): 131–8. doi:10.1016/0049-3848(93)90154-g. PMID 8322284.
  5. Ogawa S, Takeuchi K, Sugimura K, Sato C, Fukuda M, Lee R, et al. (1999). "The 5-HT2 receptor antagonist sarpogrelate reduces urinary and plasma levels of thromboxane A2 and urinary albumin excretion in non-insulin-dependent diabetes mellitus patients". Clinical and Experimental Pharmacology & Physiology. 26 (5–6): 461–4. doi:10.1111/j.1440-1681.1999.03056.x. PMID 10386239. S2CID 31041268.
  6. Rydzewski A, Urano T, Hachiya T, Kaneko H, Baba S, Takada Y, Takada A (December 1996). "The effect of a 5HT2 receptor antagonist sarpogrelate (MCI-9042) treatment on platelet function in Buerger's disease". Thrombosis Research. 84 (6): 445–52. doi:10.1016/s0049-3848(96)00212-5. PMID 8987165.
  7. Igarashi M, Okuda T, Oh-i T, Koga M (October 2000). "Changes in plasma serotonin concentration and acceleration plethysmograms in patients with Raynaud's phenomenon after long-term treatment with a 5-HT2 receptor antagonist". The Journal of Dermatology. 27 (10): 643–50. doi:10.1111/j.1346-8138.2000.tb02246.x. PMID 11092268. S2CID 24884976.
  8. Satomura K, Takase B, Hamabe A, Ashida K, Hosaka H, Ohsuzu F, Kurita A (January 2002). "Sarpogrelate, a specific 5HT2-receptor antagonist, improves the coronary microcirculation in coronary artery disease". Clinical Cardiology. 25 (1): 28–32. doi:10.1002/clc.4950250108. PMC 6654074. PMID 11808836.
  9. Kinugawa T, Fujita M, Lee JD, Nakajima H, Hanada H, Miyamoto S (August 2002). "Effectiveness of a novel serotonin blocker, sarpogrelate, for patients with angina pectoris". American Heart Journal. 144 (2): A1–A6. doi:10.1067/mhj.2002.124056. PMID 12177659.
  10. Hayashi T, Sumi D, Matsui-Hirai H, Fukatsu A, Arockia Rani PJ, Kano H, et al. (May 2003). "Sarpogrelate HCl, a selective 5-HT2A antagonist, retards the progression of atherosclerosis through a novel mechanism". Atherosclerosis. 168 (1): 23–31. doi:10.1016/s0021-9150(03)00054-6. PMID 12732383.
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