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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
Selective substrates for non-neuronal monoamine transporters.
1999 Jul
Presynaptic imidazoline receptors. New developments in characterization and classification.
1999 Jun 21
The picornavirus replication inhibitors HBB and guanidine in the echovirus-9 system: the significance of viral protein 2C.
2000 Apr
Isolation and characterization of a xylose-glucose isomerase from a new strain Streptomyces thermovulgaris 127, var. 7-86.
2001
Demineralized bone matrix as a biological scaffold for bone repair.
2001 Apr
Strain-specified relative conformational stability of the scrapie prion protein.
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
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
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
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
[Discovery of cis-preference of aromatic N-methylamides and its application to molecular constructions].
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
Uremic concentrations of guanidino compounds inhibit neutrophil superoxide production.
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
Structure of an intermediate in the unfolding of creatine kinase.
2001 Feb 1
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
Phaeochromocytoma: an unusual cause of hypertension in pregnancy.
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
Limited tryptic hydrolysis of pea legumin: molecular mass and conformational stability of legumin-T.
2001 Jan 10
Hydrophobic core malleability of a de novo designed three-helix bundle protein.
2001 Jan 12
Counteracting effects of renal solutes on amyloid fibril formation by immunoglobulin light chains.
2001 Jan 12
Disulfide-dependent folding and export of Escherichia coli DsbC.
2001 Jan 12
Conformational origin of the aggregation of recombinant human factor VIII.
2001 Jan 16
Protein compactness measured by fluorescence resonance energy transfer. Human carbonic anhydrase ii is considerably expanded by the interaction of GroEL.
2001 Jun 15
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
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
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
Probing local conformational changes during equilibrium unfolding of firefly luciferase: fluorescence and circular dichroism studies of single tryptophan mutants.
2001 Mar 23
The structure of denatured alpha-lactalbumin elucidated by the technique of disulfide scrambling: fractionation of conformational isomers of alpha-lactalbumin.
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
Cyclic green fluorescent protein produced in vivo using an artificially split PI-PfuI intein from Pyrococcus furiosus.
2001 May 11
Replacement of thrombin residue G184 with Lys or Arg fails to mimic Na+ binding.
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 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
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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
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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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