BUNAZOSIN

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H27N5O3
Molecular Weight	373.4494
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CCCC(=O)N1CCCN(CC1)C2=NC3=C(C=C(OC)C(OC)=C3)C(N)=N2

InChI

InChIKey=RHLJLALHBZGAFM-UHFFFAOYSA-N

InChI=1S/C19H27N5O3/c1-4-6-17(25)23-7-5-8-24(10-9-23)19-21-14-12-16(27-3)15(26-2)11-13(14)18(20)22-19/h11-12H,4-10H2,1-3H3,(H2,20,21,22)

HIDE SMILES / InChI

Description

Bunazosin (E-643) is a quinazoline derivative with a1-adrenoceptor blocking activity. It has been clinically used both as a systemic antihypertensive as well as an ocular hypotensive drug. The major adverse effect associated with the use of bunazosin is orthostatic hypotension or its consequences (e.g. dizziness). Others adverse effects include headache, sweating, nausea, dry mouth, abdominal pain, diarrhea, and constipation. The effects of Bunazosin may be enhanced by diuretics and other antihypertensive agents and decreased by Rifampicin.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor alpha-1 171	Blocker 555

Conditions

Condition	Modality	Highest Phase	Product
Hypertension 575	Primary	Approved 8,583	Detantol@R
Glaucoma 57	Primary	Phase III 665	Unknown
Chronic obstructive pulmonary disease 175	Primary	Basic research	Unknown

C_max

Value	Dose	Analyte	Population
15 ng/mL	6 mg single, oral	BUNAZOSIN plasma	Homo sapiens
6.1 μg/L	6 mg single, oral	BUNAZOSIN plasma	Homo sapiens
5.4 μg/L	6 mg single, oral	BUNAZOSIN plasma	Homo sapiens
11.4 μg/L	6 mg 1 times / day multiple, oral	BUNAZOSIN plasma	Homo sapiens
17.8 μg/L	6 mg 1 times / day multiple, oral	BUNAZOSIN plasma	Homo sapiens
14.6 μg/L	6 mg 1 times / day multiple, oral	BUNAZOSIN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
106 μg × h/L	6 mg single, oral	BUNAZOSIN plasma	Homo sapiens
86.6 μg × h/L	6 mg single, oral	BUNAZOSIN plasma	Homo sapiens
147.6 μg × h/L	6 mg 1 times / day multiple, oral	BUNAZOSIN plasma	Homo sapiens
220.5 μg × h/L	6 mg 1 times / day multiple, oral	BUNAZOSIN plasma	Homo sapiens
184 μg × h/L	6 mg 1 times / day multiple, oral	BUNAZOSIN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
12 h	6 mg single, oral	BUNAZOSIN plasma	Homo sapiens
16 h	6 mg single, oral	BUNAZOSIN plasma	Homo sapiens
20.9 h	6 mg single, oral	BUNAZOSIN plasma	Homo sapiens

F_unbound

Value	Dose	Analyte	Population
3%	6 mg single, oral	BUNAZOSIN plasma	Homo sapiens
3%	6 mg single, oral	BUNAZOSIN plasma	Homo sapiens
3%	6 mg 1 times / day multiple, oral	BUNAZOSIN plasma	Homo sapiens
3%	6 mg 1 times / day multiple, oral	BUNAZOSIN plasma	Homo sapiens
3%	6 mg 1 times / day multiple, oral	BUNAZOSIN plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
0.2 % single, ophthalmic Highest studied dose	healthy, ADULT	Other AEs: conjunctival hyperemia...
12 mg 1 times / day multiple, oral Highest studied dose	unhealthy, ADULT
18 mg 1 times / day multiple, Highest studied dose	unhealthy, ADULT
0.1 % single, ophthalmic Studied dose	healthy, ADULT	Disc. AE: conjunctival hyperemia...

Showing 1 to 4 of 4 entries

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AEs

Show entries

AE	Significance	Dose	Population
conjunctival hyperemia	moderately severe	0.2 % single, ophthalmic Highest studied dose	healthy, ADULT
conjunctival hyperemia	6 patients Disc. AE	0.1 % single, ophthalmic Studied dose	healthy, ADULT

Showing 1 to 2 of 2 entries

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Cav1.2 58

Tox targets

Show entries

Target	Modality	Activity	Metabolite	Clinical evidence
Cav1.2 63	inhibitor 2,237

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PubMed

Show entries

Title	Date	PubMed
Effect of phenylephrine injected into the nucleus tractus solitarius of Sprague-Dawley rats and spontaneously hypertensive rats.	2002 Aug 15	12183010
Different effects of carvedilol, metoprolol, and propranolol on left ventricular remodeling after coronary stenosis or after permanent coronary occlusion in rats.	2002 Feb 26	11864928
Neuroprotective effects of nipradilol on purified cultured retinal ganglion cells.	2002 Jun	12140401
The alpha(1D)-adrenergic receptor directly regulates arterial blood pressure via vasoconstriction.	2002 Mar	11901185
Bunazosin hydrochloride reduces glutamate-induced neurotoxicity in rat primary retinal cultures.	2004 Apr 2	15019572

Showing 1 to 5 of 11 entries

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Patents

Sample Use Guides

In Vivo Use Guide

3 to 9 mg once daily. The administration should be started at a dose of 3 mg once daily and the maximum daily dose of 9 mg should not be exceeded.

Route of Administration: Oral

In Vitro Use Guide

[3H]bunazosin binds specifically to rat brain preparation with a Bmax value of 84.6 fmol/mg protein and a Kd value of 0.59 nM.

Show entries

Name

Type

Language

BUNAZOSIN

Official Name

English

BUNAZOSIN [MI]

Preferred Name

English

1-(4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)-4-BUTYRYLHEXAHYDRO-1H-1,4-DIAZEPINE

Systematic Name

English

bunazosin [INN]

Common Name

English

Bunazosin [WHO-DD]

Common Name

English

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Show entries

Classification Tree

Code System

Code

Adrenergic Antagonist

NCI_THESAURUS

C29713

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Show entries

Code System

Code

Type

Description

INN

5466

PRIMARY

PUBCHEM

2472

PRIMARY

DRUG BANK

DB12230

PRIMARY

EPA CompTox

DTXSID7022700

PRIMARY

CAS

80755-51-7

PRIMARY

Showing 1 to 5 of 15 entries

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ACTIVE MOIETY


					9UUW4V7G2H

BUNAZOSIN

SALT/SOLVATE (PARENT)


					18V54TZ7U6

BUNAZOSIN HYDROCHLORIDE

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Tox targets

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound