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
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
Topological diversity of artificial beta-barrels in water.	2001	11270328
Dihydrofolate reductase from Thermotoga maritima.	2001	11265474
Total chemical synthesis of human matrix Gla protein.	2001 Apr	11274477
The structure of human mitochondrial branched-chain aminotransferase.	2001 Apr	11264579
High-sensitivity fluorescence anisotropy detection of protein-folding events: application to alpha-lactalbumin.	2001 Apr	11259312
Guanidine-induced equilibrium unfolding of a homo-hexameric enzyme 4-oxalocrotonate tautomerase (4-OT).	2001 Apr 10	11284706
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	11312922
Structure--function relationships in bovine thymus 20S proteasome: a fluorimetric study.	2001 Apr 12	11311722
Characterization of the denatured states distribution of neocarzinostatin by small-angle neutron scattering and differential scanning calorimetry.	2001 Apr 3	11300776
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	11276368
Stabilization of hen egg white lysozyme by a cavity-filling mutation.	2001 Feb	11266617
Metric engineering of soft molecular host frameworks.	2001 Feb	11263869
Role of nitric oxide in the synthesis of guanidinosuccinic acid, an activator of the N-methyl-D-aspartate receptor.	2001 Feb	11168991
Specific neosaxitoxin interactions with the Na+ channel outer vestibule determined by mutant cycle analysis.	2001 Feb	11159437
Apparent two-state tendamistat folding is a sequential process along a defined route.	2001 Feb 16	11237606
Spontaneous and flow-induced Ca2+ transients in retracted regions in endothelial cells.	2001 Feb 16	11178976
Solid-phase guanidinylation as a diversification strategy of poly-L-proline type II peptide mimic scaffolds.	2001 Feb 22	11178825
Uracil moiety is required for toxicity of the cyanobacterial hepatotoxin cylindrospermopsin.	2001 Feb 23	11245397
Dichlorobis(glycocyamine-O)copper(II).	2001 Jan	11173378
Cellular responses of NG108-15 and SK-N-MC lines to sweet and bitter tastants as measured by extracellular acidification rates.	2001 Jan 1	11169615
The influence of ATP on the association and unfolding of the tyrosine repressor ligand response domain of Haemophilus influenzae.	2001 Jan 12	11162481
Achieving stability and conformational specificity in designed proteins via binary patterning.	2001 Jan 19	11152617
Engineering conformational flexibility in the lactose permease of Escherichia coli: use of glycine-scanning mutagenesis to rescue mutant Glu325-->Asp.	2001 Jan 23	11170394
[Y97V substitution in the horse cytochrome c causes accumulation of the equilibrium intermediate].	2001 Jan-Feb	11236561
[Antibody avidity: use for the diagnosis of HIV early infection].	2001 Jan-Feb	11174099
A rigid linker-scaffold for solid-phase synthesis of dimeric pharmacophores.	2001 Jan-Feb	11148071
Protein compactness measured by fluorescence resonance energy transfer. Human carbonic anhydrase ii is considerably expanded by the interaction of GroEL.	2001 Jun 15	11278767
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	11285259
Elucidation of a [4Fe-4S] cluster degradation pathway: rapid kinetic studies of the degradation of Chromatium vinosum HiPIP.	2001 Mar	11315562
Virus inactivation of plasma-derived proteins by pasteurization in the presence of guanidine hydrochloride.	2001 Mar	11274595
Characterization of carbonic anhydrase from Neisseria gonorrhoeae.	2001 Mar	11248679
Structure-activity relationship of the p55 TNF receptor death domain and its lymphoproliferation mutants.	2001 Mar	11231290
Probing conformational changes in the estrogen receptor: evidence for a partially unfolded intermediate facilitating ligand binding and release.	2001 Mar	11222743
Cutinase unfolding and stabilization by trehalose and mannosylglycerate.	2001 Mar 1	11170208
Major differences in stability and dimerization properties of two chimeric mutants of human stefins.	2001 Mar 1	11170205
The synthesis of beta-peptides containing guanidino groups.	2001 Mar 12	11266170
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	11258930
Membrane-associated respiratory syncytial virus F protein expressed from a human rhinovirus type 14 vector is immunogenic.	2001 Mar 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 Mar 15	11238669
Matrix proteins from insect pliable cuticles: are they flexible and easily deformed?	2001 Mar 15	11222954
Probing local conformational changes during equilibrium unfolding of firefly luciferase: fluorescence and circular dichroism studies of single tryptophan mutants.	2001 Mar 23	11263966
Dramatic stabilization of an SH3 domain by a single substitution: roles of the folded and unfolded states.	2001 Mar 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 Mar 30	11266439
Osmolytes protect mitochondrial F(0)F(1)-ATPase complex against pressure inactivation.	2001 Mar 9	11257519
Proton and metal ion-dependent assembly of a model diiron protein.	2001 May	11316876
Cyclic green fluorescent protein produced in vivo using an artificially split PI-PfuI intein from Pyrococcus furiosus.	2001 May 11	11278952
Guanidino-containing drugs in cancer chemotherapy: biochemical and clinical pharmacology.	2001 May 15	11322922
Replacement of thrombin residue G184 with Lys or Arg fails to mimic Na+ binding.	2001 May 15	11288181
Folding intermediates of a model three-helix bundle protein. Pressure and cold denaturation studies.	2001 May 4	11278529

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

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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