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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

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

-954633600000
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
Topological diversity of artificial beta-barrels in water.
2001
Dihydrofolate reductase from Thermotoga maritima.
2001
Evolution and physiological roles of phosphagen systems.
2001
Kinetics of unfolding and folding from amide hydrogen exchange in native ubiquitin.
2001 Apr
Total chemical synthesis of human matrix Gla protein.
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
Human recombinant interferon-inducible protein-10: intact disulfide bridges are not required for inhibition of hematopoietic progenitors and chemotaxis of T lymphocytes and monocytes.
2001 Feb
Stabilization of hen egg white lysozyme by a cavity-filling mutation.
2001 Feb
Metric engineering of soft molecular host frameworks.
2001 Feb
[Discovery of cis-preference of aromatic N-methylamides and its application to molecular constructions].
2001 Feb
Uremic concentrations of guanidino compounds inhibit neutrophil superoxide production.
2001 Feb
Spontaneous and flow-induced Ca2+ transients in retracted regions in endothelial cells.
2001 Feb 16
Molecular specificities of antibodies against ovine and murine recombinant prion proteins.
2001 Feb 16
Solid-phase guanidinylation as a diversification strategy of poly-L-proline type II peptide mimic scaffolds.
2001 Feb 22
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
Collision-induced dissociation of ring-opened cyclic depsipeptides with a guanidino group by electrospray ionization/ion trap mass spectrometry.
2001 Jan
Dichlorobis(glycocyamine-O)copper(II).
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
Engineering conformational flexibility in the lactose permease of Escherichia coli: use of glycine-scanning mutagenesis to rescue mutant Glu325-->Asp.
2001 Jan 23
[Y97V substitution in the horse cytochrome c causes accumulation of the equilibrium intermediate].
2001 Jan-Feb
[Antibody avidity: use for the diagnosis of HIV early infection].
2001 Jan-Feb
Protein compactness measured by fluorescence resonance energy transfer. Human carbonic anhydrase ii is considerably expanded by the interaction of GroEL.
2001 Jun 15
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
Virus inactivation of plasma-derived proteins by pasteurization in the presence of guanidine hydrochloride.
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
Mutagenesis of two acidic active site residues in human muscle creatine kinase: implications for the catalytic mechanism.
2001 Mar 13
Membrane-associated respiratory syncytial virus F protein expressed from a human rhinovirus type 14 vector is immunogenic.
2001 Mar 15
The major synovial targets of the rheumatoid arthritis-specific antifilaggrin autoantibodies are deiminated forms of the alpha- and beta-chains of fibrin.
2001 Mar 15
Matrix proteins from insect pliable cuticles: are they flexible and easily deformed?
2001 Mar 15
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
Dramatic stabilization of an SH3 domain by a single substitution: roles of the folded and unfolded states.
2001 Mar 30
Cofactor-induced refolding: refolding of molten globule carbonic anhydrase induced by Zn(II) and Co(II).
2001 Mar 6
Osmolytes protect mitochondrial F(0)F(1)-ATPase complex against pressure inactivation.
2001 Mar 9
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
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 Jun 25 22:35:41 UTC 2021
Edited
by admin
on Fri Jun 25 22:35:41 UTC 2021
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 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
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Vmax
TRANSPORTER -> SUBSTRATE
Km
TRANSPORTER -> SUBSTRATE
Km
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
Vmax
Related Record Type Details
ACTIVE MOIETY