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convert into a sulfate
a salt or ester of sulphuric acid (同)sulphate

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/05/21 11:55:02」(JST)

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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 can be synthesized when cyclohexanone undergoes ketalization by 3-chloro-1,2-propanediol, forming 2-chloromethyl-1,4-dioxyspiro[4,5]decane, which is further reacted with sodium phthalimide.^[4]^[5]^[6] 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.

Guanadrel synthesis

References

^ 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.
^ Guanadrel, from Pharmacogenetics Knowledge Base
^ 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.
^ 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)

External links

webpage on guanadrel, from Mayo Clinic

UpToDate Contents

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English Journal

N-hydroxyl derivatives of guanidine based drugs as enzymatic NO donors.

Xian M1, Li X, Tang X, Chen X, Zheng Z, Galligan JJ, Kreulen DL, Wang PG.
Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2001 Sep 3;11(17):2377-80.
Recent research suggests that NO may play a role in the physiological effects of some guanidine-containing drugs. In this report, three guanidine-containing drugs (guanadrel, guanoxan, and guanethidine) together with their N-hydroxyl derivatives were synthesized and their NO-releasing abilities cata
PMID 11527735

Arterial alpha-adrenergic responsiveness is decreased and SNS activity is increased in older humans.

Hogikyan RV1, Supiano MA.
The American journal of physiology.Am J Physiol.1994 May;266(5 Pt 1):E717-24.
We tested the hypotheses that 1) there is an age-associated decrease in arterial alpha-adrenergic responsiveness and 2) there is upregulation of this response during suppression of sympathetic nervous system (SNS) activity. We measured forearm blood flow (FABF) by plethysmography during brachial art
PMID 8203510

Ultracentrifugal subclasses of low and intermediate density lipoproteins.

Opplt JJ1, Holzberg ES.
Journal of lipid research.J Lipid Res.1994 Mar;35(3):510-23.
Low density lipoprotein (LDL) and intermediate density lipoprotein (IDL) classes have been shown to be composed of discrete metabolic entities or subclasses. Present ultracentrifugal methods are unable to precisely determine these subclasses. A new analytical micro-ultracentrifugal method was develo
PMID 8014586

「グアナドレル」

Guanadrel
Names
	IUPAC name 2-(1,4-Dioxaspiro[4.5]decan-2-ylmethyl)guanidine
Identifiers
CAS Number	40580-59-4
ChEBI	CHEBI:5555
ChEMBL	ChEMBL1037
ChemSpider	35305
IUPHAR/BPS	7193
Jmol 3D model	Interactive image
KEGG	D08029
MeSH	C004945
PubChem	38521
UNII	765C9332T4
	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) Key: HPBNRIOWIXYZFK-UHFFFAOYSA-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 ;
	SMILES C1CCC2(CC1)OCC(O2)CN=C(N)N ;
Properties
Chemical formula	C10H19N3O2
Molar mass	213.28 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