bupicomide
{{Chembox
| ImageFile = Bupicomide.svg
| ImageSize = 200px
| PIN = 5-Butylpyridine-2-carboxamide
| OtherNames = Sch-10595; Fusaramide[http://www.chemicalbook.com/ChemicalProductProperty_EN_CB6878197.htm Bupicomide], Chemical Book
|Section1={{Chembox Identifiers
| CASNo = 22632-06-0
| CASNo_Ref = {{cascite|correct|}}
| UNII = 0X3H76N0HY
| PubChem = 31447
| ChemSpiderID = 29167
| ChEMBL = 2106646
| SMILES = O=C(c1ncc(cc1)CCCC)N
| InChI = 1/C10H14N2O/c1-2-3-4-8-5-6-9(10(11)13)12-7-8/h5-7H,2-4H2,1H3,(H2,11,13)
| InChIKey = VKSPIPWLHGKJQO-UHFFFAOYAT
| StdInChI = 1S/C10H14N2O/c1-2-3-4-8-5-6-9(10(11)13)12-7-8/h5-7H,2-4H2,1H3,(H2,11,13)
| StdInChIKey = VKSPIPWLHGKJQO-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=10 | H=14 | N=2 | O=1
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
Bupicomide is a chemical compound created and manufactured by Lanospharma Laboratories Company, Ltd. It is used experimentally as a beta blocker and clinically as a strong vasodilator with the noted side effects of reduced systolic, diastolic and mean arterial pressure.{{cite journal |pmid=782220 |year=1976 |last1=Chrysant |first1=SG |last2=Adamopoulos |first2=P |last3=Tsuchiya |first3=M |last4=Frohlich |first4=ED |title=Systemic and renal hemodynamic effects of bupicomide: A new vasodilator |volume=92 |issue=3 |pages=335–9 |journal=American Heart Journal |doi=10.1016/s0002-8703(76)80114-7}}{{cite journal |pmid=1097150 |year=1975 |last1=Velasco |first1=M |last2=Gilbert |first2=CA |last3=Rutledge |first3=CO |last4=McNay |first4=JL |title=Antihypertensive effect of a dopamine beta hydroxylase inhibitor, bupicomide: A comparison with hydralazine |volume=18 |issue=2 |pages=145–53 |journal=Clinical Pharmacology and Therapeutics |doi=10.1002/cpt1975182145|s2cid=19966617 }}{{cite journal|title=Physiologic mechanisms of bupicomide- and hydralazine-induced increase in plasma renin activity in hypertensive patients.|journal=Mayo Clinic Proceedings|volume=52|issue=7|pages=430–2|pmid=875465|year=1977|last1=Velasco|first1=M.|last2=McNay|first2=J. L.}}
Synthesis
As the result of the screening program examining microbial fermentation products for pharmacological activity (other than antibiotic activity), fusaric acid was isolated from Fusarium oxysporum following the discovery that extracts were potent inhibitors of DBH, and thus interfered with the biosynthesis of the pressor neurohormone, norepinephrine. To refine this lead, amidation via the acid chloride was carried out to give antihypertensive analog bupicomide.{{Cite patent|country=DE|number=2217084|pubdate=1972-10-19|title=Verfahren zur Herstellung von 5-Alkylpyridin-derivaten [Process for the preparation of 5-alkylpyridine derivatives]|assign1=Banyu Pharmaceutical Co. Ltd.|assign2=Hiroyoshi Hidaka|inventor1-last=Kuniteru|inventor1-first=Shimizu|inventor2-last=Ushijima|inventor2-first=Ryosuke|inventor3-last=Sugiura|inventor3-first=Kohsuke|inventor4-last=Okazaki|inventor4-first=Aichi}}
References
{{reflist}}
{{Monoamine metabolism modulators}}
{{aromatic-stub}}