GUANIDINE

US Previously Marketed

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

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

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 7 Target ID: CHEMBL2362996 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21926190	Inhibitor 3315

Conditions

Condition	Modality	Targets	Highest Phase	Product
Eaton-Lambert syndrome 4 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=903fbd33-e5d9-41fb-9414-7bd6f42a8593	Palliative		Approved 4033	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 -9.5463362E11

PubMed

Title	Date	PubMed
Selective substrates for non-neuronal monoamine transporters.	1999 Jul	10385678
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
Structure-activity relationship (SAR) studies on oxazolidinone antibacterial agents. 1. Conversion of 5-substituent on oxazolidinone.	2001 Apr	11310656
High-sensitivity fluorescence anisotropy detection of protein-folding events: application to alpha-lactalbumin.	2001 Apr	11259312
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
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	11305927
Equilibrium unfolding of dimeric desulfoferrodoxin involves a monomeric intermediate: iron cofactors dissociate after polypeptide unfolding.	2001 Apr 24	11305909
Probing copper ligands in denatured Pseudomonas aeruginosa azurin: unfolding His117Gly and His46Gly mutants.	2001 Feb	11293412
Species-specific PCR for the identification of ovine, porcine and chicken species in meta and bone meal (MBM).	2001 Feb	11284433
Uremic concentrations of guanidino compounds inhibit neutrophil superoxide production.	2001 Feb	11168990
Apparent two-state tendamistat folding is a sequential process along a defined route.	2001 Feb 16	11237606
Rate of intrachain contact formation in an unfolded protein: temperature and denaturant effects.	2001 Feb 2	11162121
Efficient gene transfection by bisguanylated diacetylene lipid formulations.	2001 Feb 23	11181080
Phaeochromocytoma: an unusual cause of hypertension in pregnancy.	2001 Jan	11167434
Detection of enterovirus and hepatitis A virus RNA in mussels (Mytilus spp.) by reverse transcriptase-polymerase chain reaction.	2001 Jan	11155127
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
Folding-unfolding of goat alpha-lactalbumin studied by stopped-flow circular dichroism and molecular dynamics simulations.	2001 Jan 1	11093260
Conformational origin of the aggregation of recombinant human factor VIII.	2001 Jan 16	11148054
Achieving stability and conformational specificity in designed proteins via binary patterning.	2001 Jan 19	11152617
A kinetic folding intermediate probed by native state hydrogen exchange.	2001 Jan 19	11152615
Engineering conformational flexibility in the lactose permease of Escherichia coli: use of glycine-scanning mutagenesis to rescue mutant Glu325-->Asp.	2001 Jan 23	11170394
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
Elucidation of a [4Fe-4S] cluster degradation pathway: rapid kinetic studies of the degradation of Chromatium vinosum HiPIP.	2001 Mar	11315562
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
Mutagenesis of two acidic active site residues in human muscle creatine kinase: implications for the catalytic mechanism.	2001 Mar 13	11258919
Dramatic stabilization of an SH3 domain by a single substitution: roles of the folded and unfolded states.	2001 Mar 30	11273710
The dimerization of folded monomers of ribulose 1,5-bisphosphate carboxylase/oxygenase.	2001 Mar 9	11092881
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
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 `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

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Name

Type

Language

GUANIDINE

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