Sarpogrelat

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Structural formula
Structural formula of sarpogrelate
Simplified structural formula without stereochemistry
General
Non-proprietary name Sarpogrelat
other names
  • MCI-9042
  • LS-187118
  • 4- [2- (Dimethylamino) -1 - ({2- [2- (3-methoxyphenyl) ethyl] phenoxy} methyl) ethoxy] -4-oxobutyric acid ( IUPAC )
Molecular formula C 24 H 31 NO 6
External identifiers / databases
CAS number
  • 125926-17-2
  • 135159-51-2 (hydrochloride)
PubChem 5160
ChemSpider 4976
DrugBank DB12163
Wikidata Q44931
Drug information
Drug class

Antiplatelet drugs

properties
Molar mass 429.51 g · mol -1
safety instructions
GHS labeling of hazardous substances

Hydrochloride

07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 302-400
P: 273
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sarpogrelate is a drug that is used as a platelet aggregation inhibitor to treat strokes , heart attacks and other circulatory disorders . Sarpogrelat has also been shown to inhibit the progression of atherosclerosis and to be effective in the treatment of coronary artery disease and angina pectoris in clinical studies . Its effectiveness is based on the inhibition of serotonin receptors of the 5-HT 2A and 5-HT 2B types on the platelets and blood vessels .

synthesis

Sarpogrelate is synthesized in several stages starting from 2-hydroxy-3'-methoxybibenzyl. In the first step, the intermediate product 2- (2,3-epoxypropoxy) -3'-methoxybibenzyl is obtained by reacting the starting material with epichlorohydrin in the presence of sodium hydride . This is then reacted with dimethylamine to give 2- [3- (dimethylamino) -2-hydroxypropoxy] -3'-methoxybibenzyl. The free hydroxyl group is esterified with the help of succinic anhydride to the end product sarpogrelate.

Trade names

Sarpogrelat has been sold on the Asian market by Mitsubishi-Tokyo Pharmaceuticals since 1993 under the brand name Anplag .

Individual evidence

  1. a b Datasheet Sarpogrelate hydrochloride from Sigma-Aldrich , accessed on April 22, 2011 ( PDF ).
  2. T. Hayashi, D. Sumi, H. Matsui Hirai, A. Fukatsu, PJ Arockia-Rani, H. Kano, T. Tsunekawa, A. Iguchi: Sarpogrelate HCl, a selective 5-HT2A antagonist, retards the progression of atherosclerosis through a novel mechanism. In: Atherosclerosis. 168 (1), May 2003, pp. 23-31. PMID 12732383
  3. K. Satomura, B. Takase, A. Hamabe, K. Ashida, H. Hosaka, F. Ohsuzu, A. Kurita: Sarpogrelate, a specific 5HT2-receptor antagonist, improves the coronary microcirculation in coronary artery disease. In: Clinical Cardiology. 25 (1), Jan 2002, pp. 28-32. PMID 11808836
  4. T. Kinugawa, M. Fujita, JD Lee, H. Nakajima, H. Hanada, S. Miyamoto: Effectiveness of a novel serotonin blocker, sarpogrelate, for patients with angina pectoris. In: American Heart Journal . 144 (2), Aug 2002, p. E1. PMID 12177659
  5. H. Pertz, S. Elz: 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. In: Journal of Pharmacy and Pharmacology . 47 (4), Apr 1995, pp. 310-316. PMID 7791029
  6. H. Nishio, A. Inoue, Y. Nakata: Binding affinity of sarpogrelate, a new antiplatelet agent, and its metabolite for serotonin receptor subtypes. In: Archives internationales de Pharmacodynamie et de Thérapie . 331 (2), Mar-Apr 1996, pp. 189-202. PMID 8937629
  7. HA Muntasir, M. Hossain, MA Bhuiyan, T. Komiyama, T. Nakamura, M. Ozaki, T. Nagatomo: Identification of a key amino acid of the human 5-HT (2B) serotonin receptor important for sarpogrelate binding. In: Journal of Pharmacological Sciences . 104 (3), Jul 2007, pp. 274-277. PMID 17609583
  8. M. Osakabe, H. Fukami, M. Sugano, R. Kikumoto, K. Ninomiya, Y. Tamao, H. Hara: Syntheses and platelet aggregation inhibitory and antithrombotic properties of [2 - [(omega-aminoalkoxy) phenyl] ethyl ] benzenes. In: J. Med. Chem. 33 (6), 1990, p. 1818.