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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

NC(N)=N

InChI

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

HIDE SMILES / InChI

Molecular Formula CH5N3
Molecular Weight 59.0705
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

1939
PubMed

PubMed

TitleDatePubMed
The relationship of the factor V Leiden mutation or the deletion-deletion polymorphism of the angiotensin converting enzyme to postoperative thromboembolic events following total joint arthroplasty.
2001
Isolation and characterization of a xylose-glucose isomerase from a new strain Streptomyces thermovulgaris 127, var. 7-86.
2001
Topological diversity of artificial beta-barrels in water.
2001
Structure-activity relationship (SAR) studies on oxazolidinone antibacterial agents. 1. Conversion of 5-substituent on oxazolidinone.
2001 Apr
Demineralized bone matrix as a biological scaffold for bone repair.
2001 Apr
Strain-specified relative conformational stability of the scrapie prion protein.
2001 Apr
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
Second-site revertants of a low-sodium-affinity mutant of the Na+/H+ exchanger reveal the participation of TM4 into a highly constrained sodium-binding site.
2001 Apr 24
Equilibrium unfolding of dimeric desulfoferrodoxin involves a monomeric intermediate: iron cofactors dissociate after polypeptide unfolding.
2001 Apr 24
Characterization of the denatured states distribution of neocarzinostatin by small-angle neutron scattering and differential scanning calorimetry.
2001 Apr 3
Isolation and spectroscopic characterization of the structural subunits of keyhole limpet hemocyanin.
2001 Apr 7
Intensely positively charged perineuronal nets in the adult rat brain as detected by staining with anionic iron colloid.
2001 Feb
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
Role of nitric oxide in the synthesis of guanidinosuccinic acid, an activator of the N-methyl-D-aspartate receptor.
2001 Feb
Human abdominal aortic aneurysm is characterized by decreased versican concentration and specific downregulation of versican isoform V(0).
2001 Feb 1
Uracil moiety is required for toxicity of the cyanobacterial hepatotoxin cylindrospermopsin.
2001 Feb 23
Efficient gene transfection by bisguanylated diacetylene lipid formulations.
2001 Feb 23
Dichlorobis(glycocyamine-O)copper(II).
2001 Jan
Detection of enterovirus and hepatitis A virus RNA in mussels (Mytilus spp.) by reverse transcriptase-polymerase chain reaction.
2001 Jan
The relationship between visible intracellular aggregates that appear after overexpression of Sup35 and the yeast prion-like elements [PSI(+)] and [PIN(+)].
2001 Jan
Cellular responses of NG108-15 and SK-N-MC lines to sweet and bitter tastants as measured by extracellular acidification rates.
2001 Jan 1
Hydrophobic core malleability of a de novo designed three-helix bundle protein.
2001 Jan 12
The PD...(D/E)XK motif in restriction enzymes: a link between function and conformation.
2001 Jan 16
Analysis of the Desulfovibrio gigas transcriptional unit containing rubredoxin (rd) and rubredoxin-oxygen oxidoreductase (roo) genes and upstream ORFs.
2001 Jan 19
Distributions of intramolecular distances in the reduced and denatured states of bovine pancreatic ribonuclease A. Folding initiation structures in the C-terminal portions of the reduced protein.
2001 Jan 9
[Antibody avidity: use for the diagnosis of HIV early infection].
2001 Jan-Feb
Structural basis of the Na+/H+ exchanger regulatory factor PDZ1 interaction with the carboxyl-terminal region of the cystic fibrosis transmembrane conductance regulator.
2001 Jun 8
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
Structure-activity relationship of the p55 TNF receptor death domain and its lymphoproliferation mutants.
2001 Mar
Cutinase unfolding and stabilization by trehalose and mannosylglycerate.
2001 Mar 1
The synthesis of beta-peptides containing guanidino groups.
2001 Mar 12
An N-terminal three-helix fragment of the exchangeable insect apolipoprotein apolipophorin III conserves the lipid binding properties of wild-type protein.
2001 Mar 13
Mutagenesis of two acidic active site residues in human muscle creatine kinase: implications for the catalytic mechanism.
2001 Mar 13
Matrix proteins from insect pliable cuticles: are they flexible and easily deformed?
2001 Mar 15
Dramatic stabilization of an SH3 domain by a single substitution: roles of the folded and unfolded states.
2001 Mar 30
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
Cofactor-induced refolding: refolding of molten globule carbonic anhydrase induced by Zn(II) and Co(II).
2001 Mar 6
Proton and metal ion-dependent assembly of a model diiron protein.
2001 May
Guanidino-containing drugs in cancer chemotherapy: biochemical and clinical pharmacology.
2001 May 15
Replacement of thrombin residue G184 with Lys or Arg fails to mimic Na+ binding.
2001 May 15
Folding intermediates of a model three-helix bundle protein. Pressure and cold denaturation studies.
2001 May 4
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:42:51 GMT 2023
Edited
by admin
on Fri Dec 15 15:42:51 GMT 2023
Record UNII
JU58VJ6Y3B
Record Status Validated (UNII)
Record Version
  • Download
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 Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
NDF-RT N0000175772
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
NDF-RT N0000009079
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID0023117
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
PRIMARY
DRUG BANK
DB00536
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
PRIMARY
CAS
113-00-8
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
PRIMARY
RXCUI
50675
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
PRIMARY RxNorm
MESH
D019791
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
PRIMARY
EVMPD
SUB14034MIG
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
PRIMARY
NCI_THESAURUS
C77851
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
PRIMARY
HSDB
7603
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
PRIMARY
MERCK INDEX
m5867
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
PRIMARY Merck Index
CHEBI
30087
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-021-8
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
PRIMARY
FDA UNII
JU58VJ6Y3B
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
PRIMARY
WIKIPEDIA
GUANIDINE
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
PRIMARY
IUPHAR
4783
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
PRIMARY
DRUG CENTRAL
1344
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
PRIMARY
SMS_ID
100000077877
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
PRIMARY
CHEBI
42820
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
PRIMARY
PUBCHEM
3520
Created by admin on Fri Dec 15 15:42:51 GMT 2023 , Edited by admin on Fri Dec 15 15:42:51 GMT 2023
PRIMARY
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