CHEBI:5555 - guanadrel

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ChEBI Name guanadrel
ChEBI ID CHEBI:5555
Definition A spiroketal resulting from the formal condensation of the keto group of cyclohexanone with the hydroxy groups of 1-(2,3-dihydroxypropyl)guanidine. A postganglionic adrenergic blocking agent formerly used (generally as the sulfate salt) for the management of hypertension, it has been largely superseded by other drugs less likely to cause orthostatic hypotension (dizzy spells on standing up or stretching).
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C10H19N3O2
Net Charge 0
Average Mass 213.27680
Monoisotopic Mass 213.148
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)
InChIKey HPBNRIOWIXYZFK-UHFFFAOYSA-N
SMILES NC(=N)NCC1COC2(CCCCC2)O1
Roles Classification
Biological Role(s): adrenergic antagonist
An agent that binds to but does not activate adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists.
Application(s): antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
adrenergic antagonist
An agent that binds to but does not activate adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists.
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ChEBI Ontology
Outgoing guanadrel (CHEBI:5555) has role adrenergic antagonist (CHEBI:37887)
guanadrel (CHEBI:5555) has role antihypertensive agent (CHEBI:35674)
guanadrel (CHEBI:5555) is a guanidines (CHEBI:24436)
guanadrel (CHEBI:5555) is a spiroketal (CHEBI:72600)
guanadrel (CHEBI:5555) is conjugate base of guanadrel(1+) (CHEBI:72602)
Incoming guanadrel(1+) (CHEBI:72602) is conjugate acid of guanadrel (CHEBI:5555)
IUPAC Name
1-(1,4-dioxaspiro[4.5]dec-2-ylmethyl)guanidine
INNs Sources
guanadrel ChemIDplus
guanadrel WHO MedNet
guanadrel WHO MedNet
guanadrelum ChemIDplus
Synonym Source
Guanadrel KEGG COMPOUND
Database Links Databases
1339 DrugCentral
C07035 KEGG COMPOUND
D08029 KEGG DRUG
DB00226 DrugBank
Guanadrel Wikipedia
HMDB0014371 HMDB
US3547951 Patent
View more database links
Registry Numbers Types Sources
40580-59-4 CAS Registry Number ChemIDplus
8325419 Reaxys Registry Number Reaxys
8325419 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
3896742 PubMed citation Europe PMC
6621504 PubMed citation Europe PMC
7206175 PubMed citation Europe PMC
Last Modified
22 February 2017