Guanidine

US Previously Marketed

First approved in 1939

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 Search

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

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=903fbd33-e5d9-41fb-9414-7bd6f42a8593

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-gated potassium channel 17 Target ID: CHEMBL2362996 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21926190	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Eaton-Lambert syndrome 5 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=903fbd33-e5d9-41fb-9414-7bd6f42a8593	Palliative		Approved 8583	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

Title	Date	PubMed
Protein compactness measured by fluorescence resonance energy transfer. Human carbonic anhydrase ii is considerably expanded by the interaction of GroEL.	2001-06-15	11278767
Structural basis of the Na+/H+ exchanger regulatory factor PDZ1 interaction with the carboxyl-terminal region of the cystic fibrosis transmembrane conductance regulator.	2001-06-08	11304524
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.	2001-06-08	11285259
Guanidino-containing drugs in cancer chemotherapy: biochemical and clinical pharmacology.	2001-05-15	11322922
Replacement of thrombin residue G184 with Lys or Arg fails to mimic Na+ binding.	2001-05-15	11288181
Cyclic green fluorescent protein produced in vivo using an artificially split PI-PfuI intein from Pyrococcus furiosus.	2001-05-11	11278952
Folding intermediates of a model three-helix bundle protein. Pressure and cold denaturation studies.	2001-05-04	11278529
Proton and metal ion-dependent assembly of a model diiron protein.	2001-05	11316876
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.	2001-04-24	11305927
Equilibrium unfolding of dimeric desulfoferrodoxin involves a monomeric intermediate: iron cofactors dissociate after polypeptide unfolding.	2001-04-24	11305909
Synthesis and biological activity of analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid: discovery of a novel aminoguanidinoacetic acid antidiabetic agent.	2001-04-12	11312922
Structure--function relationships in bovine thymus 20S proteasome: a fluorimetric study.	2001-04-12	11311722
Guanidine-induced equilibrium unfolding of a homo-hexameric enzyme 4-oxalocrotonate tautomerase (4-OT).	2001-04-10	11284706
Isolation and spectroscopic characterization of the structural subunits of keyhole limpet hemocyanin.	2001-04-07	11295438
Characterization of the denatured states distribution of neocarzinostatin by small-angle neutron scattering and differential scanning calorimetry.	2001-04-03	11300776
Structure-activity relationship (SAR) studies on oxazolidinone antibacterial agents. 1. Conversion of 5-substituent on oxazolidinone.	2001-04	11310656
Demineralized bone matrix as a biological scaffold for bone repair.	2001-04	11304452
Kinetics of unfolding and folding from amide hydrogen exchange in native ubiquitin.	2001-04	11276253
Total chemical synthesis of human matrix Gla protein.	2001-04	11274477
Strain-specified relative conformational stability of the scrapie prion protein.	2001-04	11274476
The structure of human mitochondrial branched-chain aminotransferase.	2001-04	11264579
High-sensitivity fluorescence anisotropy detection of protein-folding events: application to alpha-lactalbumin.	2001-04	11259312
Dramatic stabilization of an SH3 domain by a single substitution: roles of the folded and unfolded states.	2001-03-30	11273710
The pro domain of beta-secretase does not confer strict zymogen-like properties but does assist proper folding of the protease domain.	2001-03-30	11266439
Probing local conformational changes during equilibrium unfolding of firefly luciferase: fluorescence and circular dichroism studies of single tryptophan mutants.	2001-03-23	11263966
Structural alterations and inhibition of unisite and multisite ATP hydrolysis in soluble mitochondrial F1 by guanidinium chloride.	2001-03-20	11258961
Membrane-associated respiratory syncytial virus F protein expressed from a human rhinovirus type 14 vector is immunogenic.	2001-03-15	11277694
The major synovial targets of the rheumatoid arthritis-specific antifilaggrin autoantibodies are deiminated forms of the alpha- and beta-chains of fibrin.	2001-03-15	11238669
An N-terminal three-helix fragment of the exchangeable insect apolipoprotein apolipophorin III conserves the lipid binding properties of wild-type protein.	2001-03-13	11258930
Mutagenesis of two acidic active site residues in human muscle creatine kinase: implications for the catalytic mechanism.	2001-03-13	11258919
The synthesis of beta-peptides containing guanidino groups.	2001-03-12	11266170
[Y97V substitution in the horse cytochrome c causes accumulation of the equilibrium intermediate].	2001-03-10	11236561
Osmolytes protect mitochondrial F(0)F(1)-ATPase complex against pressure inactivation.	2001-03-09	11257519
Cofactor-induced refolding: refolding of molten globule carbonic anhydrase induced by Zn(II) and Co(II).	2001-03-06	11258876
Elucidation of a [4Fe-4S] cluster degradation pathway: rapid kinetic studies of the degradation of Chromatium vinosum HiPIP.	2001-03	11315562
Virus inactivation of plasma-derived proteins by pasteurization in the presence of guanidine hydrochloride.	2001-03	11274595
Proteoglycans and hyaluronan in human fetal membranes.	2001-03	11262472
Characterization of carbonic anhydrase from Neisseria gonorrhoeae.	2001-03	11248679
Uracil moiety is required for toxicity of the cyanobacterial hepatotoxin cylindrospermopsin.	2001-02-23	11245397
Apparent two-state tendamistat folding is a sequential process along a defined route.	2001-02-16	11237606
Intensely positively charged perineuronal nets in the adult rat brain as detected by staining with anionic iron colloid.	2001-02	11310504
Probing copper ligands in denatured Pseudomonas aeruginosa azurin: unfolding His117Gly and His46Gly mutants.	2001-02	11293412
Species-specific PCR for the identification of ovine, porcine and chicken species in meta and bone meal (MBM).	2001-02	11284433
Human recombinant interferon-inducible protein-10: intact disulfide bridges are not required for inhibition of hematopoietic progenitors and chemotaxis of T lymphocytes and monocytes.	2001-02	11276368
Stabilization of hen egg white lysozyme by a cavity-filling mutation.	2001-02	11266617
Metric engineering of soft molecular host frameworks.	2001-02	11263869
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	11311153
Isolation and characterization of a xylose-glucose isomerase from a new strain Streptomyces thermovulgaris 127, var. 7-86.	2001	11310567
Topological diversity of artificial beta-barrels in water.	2001	11270328
Dihydrofolate reductase from Thermotoga maritima.	2001	11265474

Patents

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 18:06:25 GMT 2025` Edited by `admin` on `Mon Mar 31 18:06:25 GMT 2025`
Record UNII	JU58VJ6Y3B
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

GUANIDINE [HSDB]

Preferred Name

English

Guanidine

Systematic Name

English

GUANIDINE [MI]

Common Name

English

IMIDOUREA

Common Name

English

Guanidine [WHO-DD]

Common Name

English

GUANIDINE [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C45564