Bupicomide

Bupicomide
Names

IUPAC name 5-Butyl-2-pyridinecarboxamide
Other names Sch-10595; Fusaramide^[1]
Identifiers
CAS Number	22632-06-0^Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL2106646
ChemSpider	29167
ECHA InfoCard	100.041.024
PubChem	31447
UNII	0X3H76N0HY
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	178.24 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

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]

Synthesis

As the result of the screening program examining microbial fermentation products for pharmacological acitivity (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.^[4]

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. PMID 1097150.
↑ DE 2217084

Monoamine metabolism modulators

Common
(non-specific)

AAAD

MAO

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: Almoxatone D-Deprenyl Ethanol Ladostigil Lazabemide Milacemide Mofegiline Nicotine Pargyline^‡ Rasagiline Safinamide Selegiline (L-Deprenyl)

Phenethylamines
(dopamine, epinephrine,
norepinephrine)

PAH	Inhibitors: 3,4-Dihydroxystyrene

TH	Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone

DBH	Inhibitors: Bupicomide Disulfiram Dopastin Fusaric acid Nepicastat Phenopicolinic acid Tropolone

PNMT	Inhibitors: CGS-19281A SKF-64139 SKF-7698

COMT	Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone Entacapone Nitecapone Tolcapone

Tryptamines
(serotonin, melatonin)

TPH	Inhibitors: AGN-2979 Fenclonine (PCPA) Telotristat

See also: Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake and release modulators • Monoamine neurotoxins

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