Chemistry:Cinepazide

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Short description: Chemical compound
Cinepazide
Cinepazide.svg
Clinical data
ATC code
Identifiers
CAS Number
PubChem CID
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ChEMBL
Chemical and physical data
FormulaC22H31N3O5
Molar mass417.49864 g·mol−1
3D model (JSmol)
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Cinepazide or cinepazide maleate[1] (Kelinao or Anjieli in China[2][3]) is a vasodilator used in China for the treatment of cardiovascular and cerebrovascular diseases, and peripheral vascular diseases.[4] It appears to work by potentiating A2 adenosine receptors.[5]

History

Cinepazide was discovered by scientists at Laboratoires Delalande (now part of Sanofi) in 1969 in an effort to explore useful substituted cinnamoyl-piperazine compounds.[6][7] The drug, in the form of a pill taken orally, was launched by Delalande in 1976 under the tradename Vasodistal, for treatment of heart failure, balance disorders, cerebrovascular disease, and vascular complications of diabetes.[6][8] In 1988 the drug was withdrawn from the market in Spain due to risk of agranulocytosis; other countries where the drug was available added warnings to the label.[9][10] It was withdrawn from the market in France in 1992.[11] The drug had also been marketed in Japan by Daiichi Pharmeceutical Company under the brand name "Brindel"[2] for dementia, but was withdrawn in 1999, following a review by the Japanese regulatory authorities of dementia drugs after a drug, calcium hopantenate, that had been considered the standard of care and against which cinepazide and other dementia drugs had been compared, had failed to demonstrate efficacy in a re-evaluation.[12]

In 2002 Sihuan Pharmaceutical brought an injectable form of the drug to market in China;[13] Sihuan had acquired the drug from a military hospital in China that had developed the formulation.[14] In 2010 it was the highest selling drug in China, with about 1 billion RMB in sales in the 3rd quarter, outselling Plavix in China.[13][3] This made Sihuan Pharm the largest company in China in the cardio-cerebral vascular drug market in 2010.[3] In 2014 it was the tenth highest-selling drug in China.[14]

References

  1. "Anjieli, Kelinao, cinepazide maleate - Product Profile - BioCentury". http://www.biocentury.com/products/anjieli. 
  2. 2.0 2.1 Drugs.com Drugs.com International listings for cinepazide Page accessed Aug 3, 2015
  3. 3.0 3.1 3.2 20 Oct 2010 Sihuan Pharm – China's leading player in cardio-cerebral vascular drug – IPO Report
  4. Sihuan Pharmaceutical Kelinao/Anjieli official site Page accessed Aug 3, 2015
  5. "Drug receptors and control of the cardiovascular system: recent advances". Progress in Drug Research. Fortschritte der Arzneimittelforschung. Progrès des Recherches Pharmaceutiques 36: 117–360. 1991. doi:10.1007/978-3-0348-7136-5_4. ISBN 978-3-0348-7138-9. PMID 1876708. https://books.google.com/books?id=tWT0BwAAQBAJ&pg=PA304. 
  6. 6.0 6.1 Johnson Sun for Guotai Junan International. Sept 28, 2011. Company Report: Sihuan Pharmaceuticals
  7. "The metabolic fate of the coronary vasodilator 4-(3,4,5-Trimethoxycinnamoyl)-1-(N-pyrrolidinocarbonylmethyl)piperazine (cinepazide) in the rat, dog and man". Xenobiotica; the Fate of Foreign Compounds in Biological Systems 6 (7): 441–55. July 1976. doi:10.3109/00498257609151657. PMID 997590. 
  8. Reactions Weekly 305(1):1. June 1990 Cinepazide-related agranulocytosis
  9. "Agranulocytosis induced by cinepazide". European Journal of Clinical Pharmacology 38 (4): 387–8. 1990. doi:10.1007/bf00315580. PMID 2344862. 
  10. Department of Economic and Social Affairs of the United Nations Secretariat Consolidated List of Products Whose Consumption and/or Sale Have Been Banned, Withdrawn, Severely Restricted or not Approved by Governments Twelfth Issue: Pharmaceuticals United Nations – New York, 2005
  11. Sidney M. Wolfe, M.D. for the Public Citizen's Health Research Group. February 2, 1995. Differences in the Number of Drug Safety Withdrawals: United States, United Kingdom, Germany and France 1970-1992
  12. "New drugs for Alzheimer's disease in Japan". Psychiatry and Clinical Neurosciences 65 (5): 399–404. August 2011. doi:10.1111/j.1440-1819.2011.02253.x. PMID 21851448. 
  13. 13.0 13.1 Lefei Sun, Jinsong Du, and Iris Wang for Credit Suisse. October 6, 2011 China Pharma Sector
  14. 14.0 14.1 Su Zhang for Standard Chartered Bank (HK) Limited. June 27, 2014 China health care: Pharma sector comes of age