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Details

Stereochemistry ACHIRAL
Molecular Formula CH5N3
Molecular Weight 59.0705
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GUANIDINE

SMILES

C(=N)(N)N

InChI

InChIKey=ZRALSGWEFCBTJO-UHFFFAOYSA-N
InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4)

HIDE SMILES / InChI
Guanidine is a small basic compound. Guanidine stimulates the neuromuscular junction presynaptically by inhibiting voltage-gated potassium (Kv) channels, leading to the enhanced release of acetylcholine in the synaptic cleft. This stimulatory effect of guanidine underlies its use in the therapy for the neuromuscular diseases. The hydrochloride salt of guanidine was approved by FDA for the reduction of the symptoms of muscle weakness and easy fatigability associated with the myasthenic syndrome of Eaton-Lambert.

CNS Activity

Curator's Comment:: The study was performed on rats.

Originator

Curator's Comment:: Original article: A. Strecker, Liebigs Ann. Chem. 1861, 118, 151-177.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
GUANIDINE HYDROCHLORIDE

Approved Use

Guanidine is indicated for the reduction of the symptoms of muscle weakness and easy fatigability associated with the myasthenic syndrome of Eaton-Lambert. It is not indicated for treating myasthenia gravis. The Eaton-Lambert syndrome is ordinarily differentiated from myasthenia gravis by the usual association of the syndrome with small cell carcinoma of the lung, but myography may be necessary to make the diagnosis.

Launch Date

-9.5463362E11
PubMed

PubMed

TitleDatePubMed
Selective substrates for non-neuronal monoamine transporters.
1999 Jul
Presynaptic imidazoline receptors. New developments in characterization and classification.
1999 Jun 21
Topological diversity of artificial beta-barrels in water.
2001
Dihydrofolate reductase from Thermotoga maritima.
2001
The structure of human mitochondrial branched-chain aminotransferase.
2001 Apr
High-sensitivity fluorescence anisotropy detection of protein-folding events: application to alpha-lactalbumin.
2001 Apr
Guanidine-induced equilibrium unfolding of a homo-hexameric enzyme 4-oxalocrotonate tautomerase (4-OT).
2001 Apr 10
Synthesis and biological activity of analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid: discovery of a novel aminoguanidinoacetic acid antidiabetic agent.
2001 Apr 12
Structure--function relationships in bovine thymus 20S proteasome: a fluorimetric study.
2001 Apr 12
Equilibrium unfolding of dimeric desulfoferrodoxin involves a monomeric intermediate: iron cofactors dissociate after polypeptide unfolding.
2001 Apr 24
Isolation and spectroscopic characterization of the structural subunits of keyhole limpet hemocyanin.
2001 Apr 7
Probing copper ligands in denatured Pseudomonas aeruginosa azurin: unfolding His117Gly and His46Gly mutants.
2001 Feb
Species-specific PCR for the identification of ovine, porcine and chicken species in meta and bone meal (MBM).
2001 Feb
Stabilization of hen egg white lysozyme by a cavity-filling mutation.
2001 Feb
Metric engineering of soft molecular host frameworks.
2001 Feb
Erythrocyte transketolase activity and guanidino compounds in hemodialysis patients.
2001 Feb
Role of nitric oxide in the synthesis of guanidinosuccinic acid, an activator of the N-methyl-D-aspartate receptor.
2001 Feb
Endogenous guanidino compounds as uremic neurotoxins.
2001 Feb
Human abdominal aortic aneurysm is characterized by decreased versican concentration and specific downregulation of versican isoform V(0).
2001 Feb 1
Spontaneous and flow-induced Ca2+ transients in retracted regions in endothelial cells.
2001 Feb 16
Phaeochromocytoma: an unusual cause of hypertension in pregnancy.
2001 Jan
Hydrophobic core malleability of a de novo designed three-helix bundle protein.
2001 Jan 12
Conformational origin of the aggregation of recombinant human factor VIII.
2001 Jan 16
Surprisingly high stability of barley lipid transfer protein, LTP1, towards denaturant, heat and proteases.
2001 Jan 19
A kinetic folding intermediate probed by native state hydrogen exchange.
2001 Jan 19
alpha Arg-237 in Methylophilus methylotrophus (sp. W3A1) electron-transferring flavoprotein affords approximately 200-millivolt stabilization of the FAD anionic semiquinone and a kinetic block on full reduction to the dihydroquinone.
2001 Jun 8
Elucidation of a [4Fe-4S] cluster degradation pathway: rapid kinetic studies of the degradation of Chromatium vinosum HiPIP.
2001 Mar
Proteoglycans and hyaluronan in human fetal membranes.
2001 Mar
Characterization of carbonic anhydrase from Neisseria gonorrhoeae.
2001 Mar
Structure-activity relationship of the p55 TNF receptor death domain and its lymphoproliferation mutants.
2001 Mar
Probing conformational changes in the estrogen receptor: evidence for a partially unfolded intermediate facilitating ligand binding and release.
2001 Mar
Cutinase unfolding and stabilization by trehalose and mannosylglycerate.
2001 Mar 1
The synthesis of beta-peptides containing guanidino groups.
2001 Mar 12
Structural alterations and inhibition of unisite and multisite ATP hydrolysis in soluble mitochondrial F1 by guanidinium chloride.
2001 Mar 20
Probing local conformational changes during equilibrium unfolding of firefly luciferase: fluorescence and circular dichroism studies of single tryptophan mutants.
2001 Mar 23
The pro domain of beta-secretase does not confer strict zymogen-like properties but does assist proper folding of the protease domain.
2001 Mar 30
Crystallographic and solution studies of an activation loop mutant of the insulin receptor tyrosine kinase: insights into kinase mechanism.
2001 Mar 30
The structure of denatured alpha-lactalbumin elucidated by the technique of disulfide scrambling: fractionation of conformational isomers of alpha-lactalbumin.
2001 Mar 30
Osmolytes protect mitochondrial F(0)F(1)-ATPase complex against pressure inactivation.
2001 Mar 9
Patents

Sample Use Guides

Initial dosage is usually between 10 and 15 mg/kg (5 to 7 mg/pound) of body weight per day in 3 or 4 divided doses. This dosage may be gradually increased to a total daily dosage of 35 mg/kg (16 mg/pound) of body weight per day or up to the development of side effects.
Route of Administration: Oral
In Vitro Use Guide
Mice spinal cord neurons were treated with guanidine at concentrations between 100 nM and 100 mM. At 100 mM induced a membrane depolarization of 10 to 25 mV and rapidly and reversibly reduced GABA responses: 23.9% decrease of GABA responses was obtained with 10 mM guanidine and complete inhibition was observed with 100 mM). It also significantly reduced Glycine response at 10 mM.
Name Type Language
GUANIDINE
HSDB   MI   VANDF   WHO-DD  
Systematic Name English
GUANIDINE [MI]
Common Name English
IMIDOUREA
Common Name English
GUANIDINE [WHO-DD]
Common Name English
GUANIDINE [HSDB]
Common Name English
GUANIDINE [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C45564
Created by admin on Fri Jun 25 22:35:41 UTC 2021 , Edited by admin on Fri Jun 25 22:35:41 UTC 2021
NDF-RT N0000175772
Created by admin on Fri Jun 25 22:35:41 UTC 2021 , Edited by admin on Fri Jun 25 22:35:41 UTC 2021
NDF-RT N0000009079
Created by admin on Fri Jun 25 22:35:41 UTC 2021 , Edited by admin on Fri Jun 25 22:35:41 UTC 2021
Code System Code Type Description
EPA CompTox
113-00-8
Created by admin on Fri Jun 25 22:35:41 UTC 2021 , Edited by admin on Fri Jun 25 22:35:41 UTC 2021
PRIMARY
DRUG BANK
DB00536
Created by admin on Fri Jun 25 22:35:41 UTC 2021 , Edited by admin on Fri Jun 25 22:35:41 UTC 2021
PRIMARY
CAS
113-00-8
Created by admin on Fri Jun 25 22:35:41 UTC 2021 , Edited by admin on Fri Jun 25 22:35:41 UTC 2021
PRIMARY
RXCUI
50675
Created by admin on Fri Jun 25 22:35:41 UTC 2021 , Edited by admin on Fri Jun 25 22:35:41 UTC 2021
PRIMARY RxNorm
MESH
D019791
Created by admin on Fri Jun 25 22:35:41 UTC 2021 , Edited by admin on Fri Jun 25 22:35:41 UTC 2021
PRIMARY
EVMPD
SUB14034MIG
Created by admin on Fri Jun 25 22:35:41 UTC 2021 , Edited by admin on Fri Jun 25 22:35:41 UTC 2021
PRIMARY
NCI_THESAURUS
C77851
Created by admin on Fri Jun 25 22:35:41 UTC 2021 , Edited by admin on Fri Jun 25 22:35:41 UTC 2021
PRIMARY
HSDB
7603
Created by admin on Fri Jun 25 22:35:41 UTC 2021 , Edited by admin on Fri Jun 25 22:35:41 UTC 2021
PRIMARY
MERCK INDEX
M5867
Created by admin on Fri Jun 25 22:35:41 UTC 2021 , Edited by admin on Fri Jun 25 22:35:41 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
204-021-8
Created by admin on Fri Jun 25 22:35:41 UTC 2021 , Edited by admin on Fri Jun 25 22:35:41 UTC 2021
PRIMARY
FDA UNII
JU58VJ6Y3B
Created by admin on Fri Jun 25 22:35:41 UTC 2021 , Edited by admin on Fri Jun 25 22:35:41 UTC 2021
PRIMARY
WIKIPEDIA
GUANIDINE
Created by admin on Fri Jun 25 22:35:41 UTC 2021 , Edited by admin on Fri Jun 25 22:35:41 UTC 2021
PRIMARY
IUPHAR
4783
Created by admin on Fri Jun 25 22:35:41 UTC 2021 , Edited by admin on Fri Jun 25 22:35:41 UTC 2021
PRIMARY
DRUG CENTRAL
1344
Created by admin on Fri Jun 25 22:35:41 UTC 2021 , Edited by admin on Fri Jun 25 22:35:41 UTC 2021
PRIMARY
PUBCHEM
3520
Created by admin on Fri Jun 25 22:35:41 UTC 2021 , Edited by admin on Fri Jun 25 22:35:41 UTC 2021
PRIMARY