World Library  
Flag as Inappropriate
Email this Article

Guanadrel

Article Id: WHEBN0020685972
Reproduction Date:

Title: Guanadrel  
Author: World Heritage Encyclopedia
Language: English
Subject:
Collection:
Publisher: World Heritage Encyclopedia
Publication
Date:
 

Guanadrel

Guanadrel
Identifiers
CAS number 40580-59-4 YesY
PubChem 38521
KEGG D08029 YesY
ChEBI CHEBI:5555 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H19N3O2
Molar mass 213.27676
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Guanadrel is an antihypertensive agent.[1] It is used in the form of its sulfate.

Mechanism of action

Guanadrel is a postganglionic adrenergic blocking agent. Uptake of guanadrel and storage in sympathetic neurons occurs via the norepinephrine pump; 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. Guanadrel is rapidly and well absorbed from gastrointestinal tract.[2]

In 1981 the JAMA reported guanadrel as an effective step II or step III treatment of hypertension.[3]

Chemistry

Guanadrel, (1,4-dioxaspiro[4,5]dec-2-ylmethyl)guanidine, is synthesized when cyclohexanone undergoes ketalization by 3-chloro-1,2-proandiol, forming 2-chloromethyl-1,4-dioxyspiro[4,5]decane, which is further reacted with sodium phthalimide. After alkaline hydrazinolysis, the resulting phthalimide derivative is transformed into 2-aminomethyl-1,4-dioxyspiro[4,5]decane, which is reacted with S-methylthiourea, giving the desired guanadrel.

  • W.R. Hardie, J.E. Aaron, FR 1522153  (1968).
  • W.R. Hardie, J.E. Aaron, S. Afr. Pat. 67 06.328 (1968).
  • J.E. Aaron, W.R. Hardie, U.S. Patent 3,547,951 (1970).

References

External links

  • Mayo Clinic
This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and USA.gov, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for USA.gov and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
 
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
 
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.
 


Copyright © World Library Foundation. All rights reserved. eBooks from Project Gutenberg are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.