BUPICOMIDE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H14N2O
Molecular Weight	178.231
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCC1=CC=C(N=C1)C(N)=O

InChI

InChIKey=VKSPIPWLHGKJQO-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/782220

Bupicomide is a vasodilator. Bupicomide significantly reduced systolic, diastolic, and mean arterial pressure and peripheral vascular resistance and this hypotensive effect was associated with a reflexive increase in heart rate, left ventricular ejection rate, and cardiac index; it had no effect upon other reflexive sympathetic adjustments induced by upright tilt and the Valsalva maneuver. Bupicomide also increased renal blood flow and decreased renal vascular resistance, but it had no effect upon the glomerular filtration rate. The hypotensive mechanism of bupicomide therefore is mediated by peripheral arteriolar dilation, through vascular smooth muscle relaxation. The more immediate clinical side effects of bupicomide are related to its strong vasodialting action and include headaches, cutaneous flushing, and tachycardia.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine beta-hydroxylase 17 Target ID: CHEMBL3102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1097150	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1097150 https://www.ncbi.nlm.nih.gov/pubmed/875465	Primary		Phase I 438	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
60 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4214231/	15 mg/kg single, oral dose: 15 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		FUSARIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
784.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4214231/	15 mg/kg single, oral dose: 15 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		FUSARIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
8.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4214231/	15 mg/kg single, oral dose: 15 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		FUSARIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
2000 mg 4 times / day multiple, oral Highest studied dose Dose: 2000 mg, 4 times / day Route: oral Route: multiple Dose: 2000 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1097150/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1097150/	Sources: https://pubmed.ncbi.nlm.nih.gov/1097150/
625 mg 3 times / day multiple, oral Studied dose Dose: 625 mg, 3 times / day Route: oral Route: multiple Dose: 625 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/782220/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/782220/	Disc. AE: Headache... Other AEs: Palpitation... AEs leading to discontinuation/dose reduction: Headache (30%) Other AEs: Palpitation (30%) Sources: https://pubmed.ncbi.nlm.nih.gov/782220/

AEs

AE	Significance	Dose	Population
Palpitation	30%	625 mg 3 times / day multiple, oral Studied dose Dose: 625 mg, 3 times / day Route: oral Route: multiple Dose: 625 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/782220/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/782220/
Headache	30% Disc. AE	625 mg 3 times / day multiple, oral Studied dose Dose: 625 mg, 3 times / day Route: oral Route: multiple Dose: 625 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/782220/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/782220/

PubMed

Title	Date	PubMed
Physiologic mechanisms of bupicomide- and hydralazine-induced increase in plasma renin activity in hypertensive patients.	1977-07	875465
Systemic and renal hemodynamic effects of bupicomide: a new vasodilator.	1976-09	782220
Rapid GLC determination of fusaric acid in biological fluids.	1976-04	5590

Patents

Sample Use Guides

In Vivo Use Guide

The mean supine arterial pressure of patients was reduced 15.2 mm Hg by bupicomide (900 to 2,000 mg/day) and 15.7 mm Hg by hydralazine (300 to 600 mg/day).

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

NSC-329138

Preferred Name

English

BUPICOMIDE

Official Name

English

BUPICOMIDE [USAN]

Common Name

English

5-Butylpicolinamide

Systematic Name

English

bupicomide [INN]

Common Name

English

SCH-10595

Code

English

2-PYRIDINECARBOXAMIDE, 5-BUTYL-

Systematic Name

English

SCH 10595

Code

English

Code System Code Type Description

SMS_ID

100000088466