DrugBank: Guanadrel Sulfate (DB00226)

targets (1)

Identification

Name

Guanadrel Sulfate

Accession Number

DB00226 (APRD01006)

Type

small molecule

Groups

approved

Description

Guanadrel is a postganglionic adrenergic blocking agent. Uptake of guanadrel and storage in sympathetic neurons occurs via the norepinephrine pump or transporter.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Guanadrelum [INN-Latin]

Salts

Not Available

Brand names

Name	Company
Guanadrel
Hylorel

Brand mixtures

Not Available

Categories

Antihypertensive Agents

CAS number

22195-34-2

Weight

Average: 213.2768
Monoisotopic: 213.147726867

Chemical Formula

C₁₀H₁₉N₃O₂

InChI Key

InChIKey=HPBNRIOWIXYZFK-UHFFFAOYSA-N

InChI

InChI=1S/C10H19N3O2/c11-9(12)13-6-8-7-14-10(15-8)4-2-1-3-5-10/h8H,1-7H2,(H4,11,12,13)

Plain Text

IUPAC Name

2-{1,4-dioxaspiro[4.5]decan-2-ylmethyl}guanidine

SMILES

NC(N)=NCC1COC2(CCCCC2)O1

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Dioxoles

Substructures

Acetals and Derivatives
Ethers
Dioxoles
Heterocyclic compounds
Guanidines
Carboxamidines

Pharmacology

Indication

Used to treat and control hypertension.

Pharmacodynamics

High blood pressure adds to the work load of the heart and arteries. If it continues for a long time, the heart and arteries may not function properly. This can damage the blood vessels of the brain, heart, and kidneys resulting in a stroke, heart failure, or kidney failure. High blood pressure may also increase the risk of heart attacks. These problems may be less likely to occur if blood pressure is controlled. Guanadrel works by controlling nerve impulses along certain nerve pathways. As a result, it relaxes the blood vessels so that blood passes through them more easily. This helps to lower blood pressure.

Mechanism of action

Guanadrel is a postganglionic adrenergic blocking agent. Uptake of guanadrel and storage in sympathetic neurons occurs via the norepinephrine pump or transporter. Guanadrel slowly displaces norepinephrine from its storage in nerve endings and thereby blocks the release of norepinephrine normally produced by nerve stimulation. The reduction in neurotransmitter release in response to sympathetic nerve stimulation, as a result of catecholamine depletion, leads to reduced arteriolar vasoconstriction, especially the reflex increase in sympathetic tone that occurs with a change in position.

Absorption

Rapidly and readily absorbed from the gastrointestinal tract.

Volume of distribution

Not Available

Protein binding

Low, approximately 20%

Metabolism

Primarily hepatic

Route of elimination

Not Available

Half life

10 hours

Clearance

Not Available

Toxicity

Side effects include dizziness, drowsiness, headache, constipation, diarrhea, gas pains, loss of appetite, fatigue, and nasal congestion.

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Pharmacia and upjohn co

Packagers

Pharmaceutical Utilization Management Program VA Inc.

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Experimental Properties

Property	Value	Source
logP	0.6	Not Available

Predicted Properties

Property	Value	Source
water solubility	1.93e+00 g/l	ALOGPS
logP	0.03	ALOGPS
logP	0.62	ChemAxon
logS	-2	ALOGPS
pKa (strongest acidic)	19.85	ChemAxon
pKa (strongest basic)	12.56	ChemAxon
physiological charge	1	ChemAxon
hydrogen acceptor count	5	ChemAxon
hydrogen donor count	2	ChemAxon
polar surface area	82.86	ChemAxon
rotatable bond count	2	ChemAxon
refractivity	56.54	ChemAxon
polarizability	23.23	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Drug	D00607
PubChem Compound	38521
PubChem Substance	46506457
ChemSpider	35305
Therapeutic Targets Database	DAP000059
PharmGKB	PA164745308
Drugs.com	http://www.drugs.com/mtm/guanadrel.html

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. Sodium-dependent noradrenaline transporter Pharmacological action: yes Actions: partial agonist Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals Organism class: human UniProt ID: P23975 Gene: SLC6A2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed Malinow SH: Comparison of guanadrel and guanethidine efficacy and side effects. Clin Ther. 1983;5(3):284-9. Pubmed Finnerty FA Jr, Brogden RN: Guanadrel. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic use in hypertension. Drugs. 1985 Jul;30(1):22-31. Pubmed Palmer JD, Nugent CA: Guanadrel sulfate: a postganglionic sympathetic inhibitor for the treatment of mild to moderate hypertension. Pharmacotherapy. 1983 Jul-Aug;3(4):220-9. Pubmed

Targets

1. Sodium-dependent noradrenaline transporter

Pharmacological action: yes
Actions: partial agonist

Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals

Organism class: human
UniProt ID: P23975 Link_out

Gene: SLC6A2 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
Malinow SH: Comparison of guanadrel and guanethidine efficacy and side effects. Clin Ther. 1983;5(3):284-9. Pubmed
Finnerty FA Jr, Brogden RN: Guanadrel. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic use in hypertension. Drugs. 1985 Jul;30(1):22-31. Pubmed
Palmer JD, Nugent CA: Guanadrel sulfate: a postganglionic sympathetic inhibitor for the treatment of mild to moderate hypertension. Pharmacotherapy. 1983 Jul-Aug;3(4):220-9. Pubmed

Comments

Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19