Bupicomide

Bupicomide
Names

Preferred IUPAC name 5-Butylpyridine-2-carboxamide
Other names Sch-10595; Fusaramide^[1]
Identifiers
CAS Number	22632-06-0^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2106646
ChemSpider	29167
ECHA InfoCard	100.041.024
PubChem CID	31447
UNII	0X3H76N0HY
CompTox Dashboard (EPA)	DTXSID80177168
InChI InChI=1S/C10H14N2O/c1-2-3-4-8-5-6-9(10(11)13)12-7-8/h5-7H,2-4H2,1H3,(H2,11,13) Key: VKSPIPWLHGKJQO-UHFFFAOYSA-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) Key: VKSPIPWLHGKJQO-UHFFFAOYAT
SMILES O=C(c1ncc(cc1)CCCC)N
Properties
Chemical formula	C₁₀H₁₄N₂O
Molar mass	178.235 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

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.^[2]^[3]^[4]

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.^[5]

References

^ Bupicomide, Chemical Book
^ Chrysant, SG; Adamopoulos, P; Tsuchiya, M; Frohlich, ED (1976). "Systemic and renal hemodynamic effects of bupicomide: A new vasodilator". American Heart Journal. 92 (3): 335–9. doi:10.1016/s0002-8703(76)80114-7. PMID 782220.
^ Velasco, M; Gilbert, CA; Rutledge, CO; McNay, JL (1975). "Antihypertensive effect of a dopamine beta hydroxylase inhibitor, bupicomide: A comparison with hydralazine". Clinical Pharmacology and Therapeutics. 18 (2): 145–53. doi:10.1002/cpt1975182145. PMID 1097150. S2CID 19966617.
^ Velasco, M.; McNay, J. L. (1977). "Physiologic mechanisms of bupicomide- and hydralazine-induced increase in plasma renin activity in hypertensive patients". Mayo Clinic Proceedings. 52 (7): 430–2. PMID 875465.
^ DE 2217084, Kuniteru, Shimizu; Ushijima, Ryosuke & Sugiura, Kohsuke et al., "Verfahren zur Herstellung von 5-Alkylpyridin-derivaten [Process for the preparation of 5-alkylpyridine derivatives]", published 1972-10-19, assigned to Banyu Pharmaceutical Co. Ltd. and Hiroyoshi Hidaka

Monoamine metabolism modulators

Non-specific

AAADTooltip Aromatic L-amino acid decarboxylase

Substrates→Products: L-DOPA (levodopa)→Dopamine
5-HTP→Serotonin
L-Histidine→Histamine
Phenylalanine→Phenethylamine
L-Tyrosine→Tyramine
Tryptophan→Tryptamine

MAOTooltip Monoamine oxidase

Substrates→Products (with ALDHTooltip Aldehyde dehydrogenase/ALRTooltip ALR): Epinephrine (adrenaline)→DHMA Metanephrine→MHPG/VMA Norepinephrine (noradrenaline)→DHMA Normetanephrine→MHPG/VMA Dopamine→DOPAC 3-Methoxytyramine→HVA Serotonin→5-HIAA Inhibitors: Non-selective: Benmoxin Caroxazone Echinopsidine Furazolidone Guineesine Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivhydrazine Procarbazine Safrazine Tranylcypromine
Inhibitors: MAO-A-selective: Amiflamine Bazinaprine Befloxatone Brofaromine Cimoxatone Clorgiline CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone
Inhibitors: MAO-B selective: Adarigiline Almoxatone D-Deprenyl Ethanol Ladostigil Lazabemide Milacemide Mofegiline Nicotine Pargyline^‡ Rasagiline Safinamide Selegiline (L-Deprenyl) Sembragiline

Phenethylamines
(dopamine, epinephrine,
norepinephrine)

PAHTooltip Phenylalanine hydroxylase	Substrates→Products: Phenylalanine→Tyrosine Inhibitors: 3,4-Dihydroxystyrene
THTooltip Tyrosine hydroxylase	Substrates→Products: Tyrosine→L-DOPA (levodopa) Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone
DBHTooltip Dopamine beta-monooxygenase	Substrates→Products: Dopamine→Norepinephrine (Noradrenaline) Inhibitors: Bupicomide Disulfiram Dopastin Fusaric acid Nepicastat Phenopicolinic acid Tropolone
PNMTTooltip Phenylethanolamine N-methyltransferase	Substrates→Products: Norepinephrine (noradrenaline)→Epinephrine (adrenaline) Inhibitors: CGS-19281A SKF-64139 SKF-7698
COMTTooltip Catechol-O-methyl transferase	Substrates→Products: Dopamine→3-Methoxytyramine DOPAC→Homovanillic acid Norepinephrine→Normetanephrine Epinephrine→Metanephrine DOPEG→MOPEG DOMA→VMA 2-Hydroxyestradiol→2-Methoxyestradiol 2-Hydroxyestrone→2-Methoxyestrone 4-Hydroxyestradiol→4-Methoxyestradiol 4-Hydroxyestrone→4-Methoxyestrone Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone Entacapone Neluxicapone Nitecapone Opicapone Quinalizarin Tolcapone

Tryptamines
(serotonin, melatonin)

TPHTooltip Tryptophan hydroxylase	Substrates→Products: Tryptophan→5-HTP Inhibitors: AGN-2979 Fenclonine (PCPA) Telotristat ethyl
AANATTooltip Serotonin N-acetyl transferase	Substrates→Products: Serotonin→N-Acetylserotonin
ASMTTooltip Acetylserotonin O-methyltransferase	Substrates→Products: N-Acetylserotonin→Melatonin

Histamine

HDCTooltip Histidine decarboxylase	Substrates→Products: L-Histidine→Histamine Inhibitors: Catechin Alpha-Fluoromethylhistidine Histidine methyl ester Meciadanol Naringenin Tritoqualine
HNMTTooltip Histamine N-methyltransferase	Substrates→Products: Histamine→N-Methylhistamine Inhibitors: Amodiaquine Diphenhydramine Harmaline Metoprine Quinacrine SKF-91488 Tacrine
DAOTooltip Diamine oxidase	Substrates→Products: Histamine→Imidazole acetic acid Inhibitors: Pimagedine (aminoguanidine)

See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine neurotoxins