Guanethidine


Guanethidine
Guanethidine
Systematic (IUPAC) name
2-[2-(azocan-1-yl)ethyl]guanidine
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a600027
Pregnancy cat.  ?
Legal status  ?
Pharmacokinetic data
Half-life 1.5 days
Identifiers
CAS number 645-43-2 YesY
ATC code C02CC02 S01EX01
PubChem CID 3518
DrugBank APRD01007
ChemSpider 3398 YesY
UNII 5UBY8Y002G YesY
KEGG D08030 YesY
ChEBI CHEBI:5557 YesY
ChEMBL CHEMBL765 YesY
Chemical data
Formula C10H22N4 
Mol. mass 198.309 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

Guanethidine is an antihypertensive drug that reduces the release of catecholamines, such as norepinephrine. Guanethidine is transported across the sympathetic nerve membrane by the same mechanism that transports norepinephrine itself (NET, uptake 1), and uptake is essential for the drug's action. Once guanethidine has entered the nerve, it is concentrated in transmitter vesicles, where it replaces norepinephrine.

Contents

Side effects

Side effects include orthostatic and exercise hypotension, sexual dysfunction (delayed or retrograde ejaculation), and diarrhea.

Pharmacology

Guanethidine is transported by uptake 1 into the presynaptic terminal transported by Norepinephrine transporter (NET). (In this it competes with norepinephrine so can potentiate exogenously applied norepinephrine). It becomes concentrated in norepinephrine transmitter vesicles, replacing norepinephrine in these vesicles. This leads to a gradual depletion of norepinephrine stores in the nerve endings. Once inside the terminal it blocks the release of norepinephrine in response to arrival of an action potential. Spontaneous release is not affected.

Uses

Guanethidine was once a mainstay for hypertension resistant to other agents, and was often used safely during pregnancy, but it is no longer used in the US due to lack of availability. It is still licensed in some countries, e.g., UK, for the rapid control of blood pressure in a hypertensive emergency.

Intravenous nerve block (Bier block) using guanethidine has been used to treat chronic pain caused by complex regional pain syndrome.[1]

Chemistry

Th starting material for synthetizing guanethidine, Azocine is alkylated by chloroacetonitrile. This reaction which forms 1-azocinylacetonitrile, which can be reduced into 1-(2-aminoethyl)azocine by using lithium aluminum hydride as a reductant. This compound reacts with S-methylthiourea forming guanethidine. Guanethidine synthesis.png

References


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Look at other dictionaries:

  • guanethidine — noun Etymology: guanidine + eth Date: 1959 a drug C10H22N4 used especially in the form of its sulfate to treat hypertension …   New Collegiate Dictionary

  • guanethidine — /gwon eth i deen /, n. Pharm. a potent adrenergic neuron blocking agent, C10H22N4, used in the treatment of hypertension. [1955 60; by insertion of ETH(YL) into GUANIDINE] * * * …   Universalium

  • guanethidine — gua·neth·i·dine gwä neth ə .dēn n a drug used esp. in the form of its sulfate C10H22N4·H2SO4 to treat severe high blood pressure * * * n. a drug that is used to reduce high blood pressure (see sympatholytic). It is administered by mouth; common… …   Medical dictionary

  • guanethidine — gua·neth·i·dine …   English syllables

  • guanethidine — n. a drug that is occasionally used for the rapid reduction of high blood pressure resistant to other treatments (see sympatholytic). It is administered by injection; common side effects are diarrhoea, faintness, and dizziness. Trade names:… …   The new mediacal dictionary

  • guanethidine — gwäˈnethə̇ˌdēn, ə̇də̇n noun ( s) Etymology: guanidine + eth : a synthetic guanidine derivative C10H22N4 used especially in the form of its sulfate in treating severe high blood pressure …   Useful english dictionary

  • guanethidine sulfate — A potent antihypertensive agent. It appears to interfere with the release of the chemical mediator (norepinephrine) at the sympathetic neuroeffector junction; it does not produce ganglionic or parasympathetic blockade with recommended dos …   Medical dictionary

  • guanethidine monosulfate — guan·eth·i·dine mo·no·sul·fate (gwahn ethґĭ dēn) [USP] an adrenergic neuron blocking agent used as an antihypertensive; administered orally …   Medical dictionary

  • Гуанетидин (Guanethidine) — лекарственное вещество; применяется для снижения повышенного артериального давления (см. Симпатолитическое средство). Назначается внутрь; возможные побочные эффекты: понос, обморок и головокружение. Торговое название: исмелин (Ismelin). Источник …   Медицинские термины

  • ГУАНЕТИДИН — (guanethidine) лекарственное вещество; применяется для снижения повышенного артериального давления (см. Симпатолитическое средство). Назначается внутрь; возможные побочные эффекты: понос, обморок и головокружение. Торговое название: исмелин… …   Толковый словарь по медицине


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