Cinepazide

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Cinepazide
Cinepazide.svg
Systematic (IUPAC) name
1-{4-[2-Oxo-2-(pyrrolidin-1-yl)ethyl]piperazin-1-yl}-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
Identifiers
ATC code C04AX27 (WHO)
PubChem CID: 5282459
ChemSpider 4445611
UNII 67Y4P5C84X YesY
ChEMBL CHEMBL1874750
Chemical data
Formula C22H31N3O5
Molecular mass 417.49864
  • O=C(N1CCCC1)CN3CCN(C(=O)\C=C\c2cc(OC)c(OC)c(OC)c2)CC3
  • InChI=1S/C22H31N3O5/c1-28-18-14-17(15-19(29-2)22(18)30-3)6-7-20(26)25-12-10-23(11-13-25)16-21(27)24-8-4-5-9-24/h6-7,14-15H,4-5,8-13,16H2,1-3H3/b7-6+
  • Key:RCUDFXMNPQNBDU-VOTSOKGWSA-N
  (verify)

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failure, balance disorders, cerebrovascular disease, and vascular complications of diabetes.[6][8] In 1988 the drug was withdrawn from the market in Spain due to risk of agranulocytosis; other countries where the drug was available added warnings to the label.[8][9][10] It was withdrawn from the market in France in 1992.[11] The drug had also been marketed in Japan by Daiichi under the brand name "Brindel"[2] for dementia, but was withdrawn in 1999, following a review by the Japanese regulatory authorities of dementia drugs after a drug, calcium hopantenate, that had been considered the standard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]

Chemistry

Cinepazide is a pyrrolidine derivative of cinepazic acid.

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  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 2010Sihuan 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. ↑ Ruffolo RR Jr, et al. Drug receptors and control of the cardiovascular system: recent advances. Prog Drug Res. 1991;36:117-360. Review. PMID 1876708 p 304
  6. ↑ 6.0 6.1 Johnson Sun for Guotai Junan International. Sept 28, 2011. Company Report: Sihuan Pharmaceuticals
  7. ↑ Cameron BD, et al The metabolic fate of the coronary vasodilator 4-(3,4,5-Trimethoxycinnamoyl)-1-(N-pyrrolidinocarbonylmethyl)piperazine (cinepazide) in the rat, dog and man. Xenobiotica. 1976 Jul;6(7):441-55. PMID 997590
  8. ↑ 8.0 8.1 Reactions Weekly 305(1):1. June 1990 Cinepazide-related agranulocytosis
  9. ↑ Laporte JR, Capellà D, Juan J.Agranulocytosis induced by cinepazide. Eur J Clin Pharmacol. 1990;38(4):387-8. 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. ↑ Takeda M, Tanaka T, Okochi M. New drugs for Alzheimer's disease in Japan. Psychiatry Clin Neurosci. 2011 Aug;65(5):399-404. 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
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