GUANIDINE CARBONATE

US Previously Marketed

First approved in 1939

Details

Stereochemistry	ACHIRAL
Molecular Formula	2CH5N3.CH2O3
Molecular Weight	180.1658
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(N)=N.NC(N)=N.OC(O)=O

InChI

InChIKey=STIAPHVBRDNOAJ-UHFFFAOYSA-N

InChI=1S/2CH5N3.CH2O3/c3*2-1(3)4/h2*(H5,2,3,4);(H2,2,3,4)

HIDE SMILES / InChI

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 16 Target ID: CHEMBL2362996 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21926190	Inhibitor 8297

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 8429	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
Presynaptic imidazoline receptors. New developments in characterization and classification.	1999 Jun 21	10415912
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
Dihydrofolate reductase from Thermotoga maritima.	2001	11265474
Expression and refolding of full-length human TIMP-1.	2001	11217305
Kinetics of unfolding and folding from amide hydrogen exchange in native ubiquitin.	2001 Apr	11276253
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
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
[Discovery of cis-preference of aromatic N-methylamides and its application to molecular constructions].	2001 Feb	11218725
Uremic concentrations of guanidino compounds inhibit neutrophil superoxide production.	2001 Feb	11168990
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
Molecular specificities of antibodies against ovine and murine recombinant prion proteins.	2001 Feb 16	11178966
The folding nucleus of a fibronectin type III domain is composed of core residues of the immunoglobulin-like fold.	2001 Feb 2	11162123
Efficient gene transfection by bisguanylated diacetylene lipid formulations.	2001 Feb 23	11181080
Equilibrium unfolding of Bombyx mori glycyl-tRNA synthetase.	2001 Feb 9	11056158
Dichlorobis(glycocyamine-O)copper(II).	2001 Jan	11173378
Detection of enterovirus and hepatitis A virus RNA in mussels (Mytilus spp.) by reverse transcriptase-polymerase chain reaction.	2001 Jan	11155127
The influence of ATP on the association and unfolding of the tyrosine repressor ligand response domain of Haemophilus influenzae.	2001 Jan 12	11162481
Hydrophobic core malleability of a de novo designed three-helix bundle protein.	2001 Jan 12	11124911
Conformational origin of the aggregation of recombinant human factor VIII.	2001 Jan 16	11148054
Analysis of the Desulfovibrio gigas transcriptional unit containing rubredoxin (rd) and rubredoxin-oxygen oxidoreductase (roo) genes and upstream ORFs.	2001 Jan 19	11162545
Engineering conformational flexibility in the lactose permease of Escherichia coli: use of glycine-scanning mutagenesis to rescue mutant Glu325-->Asp.	2001 Jan 23	11170394
Distributions of intramolecular distances in the reduced and denatured states of bovine pancreatic ribonuclease A. Folding initiation structures in the C-terminal portions of the reduced protein.	2001 Jan 9	11141061
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
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
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
Membrane-associated respiratory syncytial virus F protein expressed from a human rhinovirus type 14 vector is immunogenic.	2001 Mar 15	11277694
Structural alterations and inhibition of unisite and multisite ATP hydrolysis in soluble mitochondrial F1 by guanidinium chloride.	2001 Mar 20	11258961
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
Cofactor-induced refolding: refolding of molten globule carbonic anhydrase induced by Zn(II) and Co(II).	2001 Mar 6	11258876
Osmolytes protect mitochondrial F(0)F(1)-ATPase complex against pressure inactivation.	2001 Mar 9	11257519
The dimerization of folded monomers of ribulose 1,5-bisphosphate carboxylase/oxygenase.	2001 Mar 9	11092881
Replacement of thrombin residue G184 with Lys or Arg fails to mimic Na+ binding.	2001 May 15	11288181

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.

Name

Type

Language

GUANIDINE CARBONATE

Official Name

English

NSC-2171

Code

English

GUANIDINE CARBONATE [INCI]

Common Name

English

CARBONIC ACID, COMPD. WITH GUANIDINE (1:2)

Common Name

English

DIGUANIDINIUM CARBONATE

Systematic Name

English

GUANIDINE CARBONATE (2:1)

Systematic Name

English

BISGUANIDINIUM CARBONATE

Systematic Name

English

GUANIDINIUM CARBONATE

Systematic Name

English

Code System Code Type Description

ECHA (EC/EINECS)

209-813-7