cinepazide
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 447331147
| IUPAC_name = (2E)-1-{4-[2-Oxo-2-(1-pyrrolidinyl)ethyl]-1-piperazinyl}-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one
| image = Cinepazide.svg
| tradename =
| pregnancy_AU =
| pregnancy_US =
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
| ATC_prefix = C04
| ATC_suffix = AX27
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 67Y4P5C84X
| PubChem = 5282459
| CAS_number = 23887-46-9
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1874750
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4445611
| smiles = O=C(N1CCCC1)CN3CCN(C(=O)\C=C\c2cc(OC)c(OC)c(OC)c2)CC3
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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+
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = RCUDFXMNPQNBDU-VOTSOKGWSA-N
| C=22 | H=31 | N=3 | O=5
}}
Cinepazide or cinepazide maleate{{Cite web|title = Anjieli, Kelinao, cinepazide maleate - Product Profile - BioCentury|url = http://www.biocentury.com/products/anjieli|website = www.biocentury.com|access-date = 2015-08-04}} (Kelinao or Anjieli in ChinaDrugs.com [https://www.drugs.com/international/cinepazide.html Drugs.com International listings for cinepazide] Page accessed Aug 3, 201520 Oct 2010 [http://www.bocomgroup.com/mediafiles/documents/p2_4743_en.pdf Sihuan Pharm – China's leading player in cardio-cerebral vascular drug – IPO Report] {{Webarchive|url=https://web.archive.org/web/20150923193017/http://www.bocomgroup.com/mediafiles/documents/p2_4743_en.pdf |date=2015-09-23 }}) is a vasodilator used in China for the treatment of cardiovascular and cerebrovascular diseases, and peripheral vascular diseases.Sihuan Pharmaceutical [http://www.sihuanpharm.com/index.php?a=show&m=Product&id=60&l=en Kelinao/Anjieli official site] Page accessed Aug 3, 2015 It appears to work by potentiating A2 adenosine receptors.{{cite book | vauthors = Ruffolo RR, Hieble JP, Brooks DP, Feuerstein GZ, Nichols AJ | chapter = Drug receptors and control of the cardiovascular system: Recent advances | title = Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques | journal = Progress in Drug Research. Fortschritte der Arzneimittelforschung. Progres des Recherches Pharmaceutiques | volume = 36 | pages = 117–360 | date = 1991 | pmid = 1876708 | doi = 10.1007/978-3-0348-7136-5_4| chapter-url = https://books.google.com/books?id=tWT0BwAAQBAJ&pg=PA304 | isbn = 978-3-0348-7138-9 | chapter-url-access = subscription }}
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.{{cite journal | vauthors = Cameron BD, Chasseaud LF, Hawkins DR, Taylor T | title = The metabolic fate of the coronary vasodilator 4-(3,4,5-Trimethoxycinnamoyl)-1-(N-pyrrolidinocarbonylmethyl)piperazine (cinepazide) in the rat, dog and man | journal = Xenobiotica; the Fate of Foreign Compounds in Biological Systems | volume = 6 | issue = 7 | pages = 441–55 | date = July 1976 | pmid = 997590 | doi = 10.3109/00498257609151657 }} 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.Johnson Sun for Guotai Junan International. Sept 28, 2011. [http://pg.jrj.com.cn/acc/Res%5CHK_RES%5CSTOCK%5C2011%5C9%5C28%5C5025ec90-2ed1-473d-bc50-4bc5affe1d83.pdf Company Report: Sihuan Pharmaceuticals]Reactions Weekly 305(1):1. June 1990 [https://link.springer.com/article/10.2165/00128415-199003050-00001 Cinepazide-related agranulocytosis] 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.{{cite journal | vauthors = Laporte JR, Capellà D, Juan J | title = Agranulocytosis induced by cinepazide | journal = European Journal of Clinical Pharmacology | volume = 38 | issue = 4 | pages = 387–8 | date = 1990 | pmid = 2344862 | doi = 10.1007/bf00315580 | s2cid = 19427552 }}Department of Economic and Social Affairs of the United Nations Secretariat [https://www.un.org/esa/coordination/CL12.pdf 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 It was withdrawn from the market in France in 1992.Sidney M. Wolfe, M.D. for the Public Citizen's Health Research Group. February 2, 1995. [https://www.citizen.org/documents/1360.pdf Differences in the Number of Drug Safety Withdrawals: United States, United Kingdom, Germany and France 1970-1992] The drug had also been marketed in Japan by Daiichi Pharmeceutical Company under the brand name "Brindel" 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.{{cite journal | vauthors = Takeda M, Tanaka T, Okochi M | title = New drugs for Alzheimer's disease in Japan | journal = Psychiatry and Clinical Neurosciences | volume = 65 | issue = 5 | pages = 399–404 | date = August 2011 | pmid = 21851448 | doi = 10.1111/j.1440-1819.2011.02253.x | s2cid = 21519637 | doi-access = }}
In 2002 Sihuan Pharmaceutical brought an injectable form of the drug to market in China; Sihuan had acquired the drug from a military hospital in China that had developed the formulation.Su Zhang for Standard Chartered Bank (HK) Limited. June 27, 2014 [http://www.fullertreacymoney.com/system/data/files/PDFs/2014/July/4th/China%20Healthcare.pdf China health care: Pharma sector comes of age] 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.Lefei Sun, Jinsong Du, and Iris Wang for Credit Suisse. October 6, 2011 [https://doc.research-and-analytics.csfb.com/docView?language=ENG&source=ulg&format=PDF&document_id=917625241&serialid=jeGG48ExOvdMDxhWCQXH2AnbdTfWWpDCCuIE71n2tDU%3D China Pharma Sector] This made Sihuan Pharm the largest company in China in the cardio-cerebral vascular drug market in 2010. In 2014 it was the tenth highest-selling drug in China.
References
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{{Peripheral vasodilators}}