Cinepazide

Cinepazide
Clinical data
ATC code
Identifiers
IUPAC name
  • (2E)-1-{4-[2-Oxo-2-(1-pyrrolidinyl)ethyl]-1-piperazinyl}-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.041.739
Edit this at Wikidata
Chemical and physical data
FormulaC22H31N3O5
Molar mass417.49864 g·mol−1
3D model (JSmol)
SMILES
  • O=C(N1CCCC1)CN3CCN(C(=O)\C=C\c2cc(OC)c(OC)c(OC)c2)CC3
InChI
  • 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+ ☒N
  • Key:RCUDFXMNPQNBDU-VOTSOKGWSA-N ☒N
 ☒NcheckY (what is this?)  (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failure, balance disorders, cerebrovascular disease, and vascular complications of diabetes.[6][8] In 1988 the drug was withdrawn from the market in Spain due to risk of agranulocytosis; other countries where the drug was available added warnings to the label.[9][10] It was withdrawn from the market in France in 1992.[11] The drug had also been marketed in Japan by Daiichi Pharmeceutical Company under the brand name "Brindel"[2] for dementia, but was withdrawn in 1999, following a review by the Japanese regulatory authorities of dementia drugs after a drug, calcium hopantenate, that had been considered the standard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". www.biocentury.com. Retrieved 2015-08-04.
  2. 1 2 Drugs.com Drugs.com International listings for cinepazide Page accessed Aug 3, 2015
  3. 1 2 3 20 Oct 2010 Sihuan Pharm – China's leading player in cardio-cerebral vascular drug – IPO Report Archived 2015-09-23 at the Wayback Machine
  4. ↑ Sihuan Pharmaceutical Kelinao/Anjieli official site Page accessed Aug 3, 2015
  5. ↑ Ruffolo RR, Hieble JP, Brooks DP, Feuerstein GZ, Nichols AJ (1991). "Drug receptors and control of the cardiovascular system: recent advances". Progress in Drug Research. Fortschritte der Arzneimittelforschung. Progrès des Recherches Pharmaceutiques. 36: 117–360. doi:10.1007/978-3-0348-7136-5_4. ISBN 978-3-0348-7138-9. PMID 1876708.
  6. 1 2 Johnson Sun for Guotai Junan International. Sept 28, 2011. Company Report: Sihuan Pharmaceuticals
  7. ↑ Cameron BD, Chasseaud LF, Hawkins DR, Taylor T (July 1976). "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. doi:10.3109/00498257609151657. PMID 997590.
  8. ↑ Reactions Weekly 305(1):1. June 1990 Cinepazide-related agranulocytosis
  9. ↑ Laporte JR, Capellà D, Juan J (1990). "Agranulocytosis induced by cinepazide". European Journal of Clinical Pharmacology. 38 (4): 387–8. doi:10.1007/bf00315580. PMID 2344862. S2CID 19427552.
  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 (August 2011). "New drugs for Alzheimer's disease in Japan". Psychiatry and Clinical Neurosciences. 65 (5): 399–404. doi:10.1111/j.1440-1819.2011.02253.x. PMID 21851448. S2CID 21519637.
  13. 1 2 Lefei Sun, Jinsong Du, and Iris Wang for Credit Suisse. October 6, 2011 China Pharma Sector
  14. 1 2 Su Zhang for Standard Chartered Bank (HK) Limited. June 27, 2014 China health care: Pharma sector comes of age
This article is issued from Offline. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.