Guanadrel

Guanadrel
Names
IUPAC name
2-(1,4-Dioxaspiro[4.5]decan-2-ylmethyl)guanidine
Identifiers
CAS Number
  • 40580-59-4 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:5555 ☒N
ChEMBL
  • ChEMBL1037 ☒N
ChemSpider
  • 35305 ☒N
IUPHAR/BPS
  • 7193
KEGG
  • D08029 checkY
MeSH C004945
PubChem CID
  • 38521
UNII
  • 765C9332T4 ☒N
CompTox Dashboard (EPA)
  • DTXSID2048533 Edit this at Wikidata
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) ☒N
    Key: HPBNRIOWIXYZFK-UHFFFAOYSA-N ☒N
  • InChI=1/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)
    Key: HPBNRIOWIXYZFK-UHFFFAOYAB
  • C1CCC2(CC1)OCC(O2)CN=C(N)N
Properties
Chemical formula
 C10H19N3O2
Molar mass 213.281 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
Chemical compound

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]

References

  1. ^ Oren A, Rotmensch HH, Vlasses PH, et al. (1985). "A dose-titration trial of guanadrel as step-two therapy in essential hypertension". J Clin Pharmacol. 25 (5): 343–6. doi:10.1002/j.1552-4604.1985.tb02852.x. PMID 4031111.[permanent dead link]
  2. ^ Guanadrel, from Pharmacogenetics Knowledge Base
  3. ^ M. I. Dunn and J. L. Dunlap (1981). "Guanadrel. A new antihypertensive drug". JAMA. 245 (16): 1639–42. doi:10.1001/jama.1981.03310410017019. PMID 7206175.

External links

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Sympatholytic (and closely related) antihypertensives (C02)
Sympatholytics
(antagonize α-adrenergic
vasoconstriction)
Central
α2-Adrenergic receptor agonists
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Ganglion-blocking/nicotinic antagonists
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Direct
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Non-selective α-adrenergic receptor blockers
Other antagonists
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Endothelin receptor antagonists (for PHTooltip Pulmonary hypertension)