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

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 study of the Ca2+ role in cytotoxic response of human cells in culture to the action of xenobiotics].	2000	10752119
Total chemical synthesis of human matrix Gla protein.	2001 Apr	11274477
High-sensitivity fluorescence anisotropy detection of protein-folding events: application to alpha-lactalbumin.	2001 Apr	11259312
Erythrocyte transketolase activity and guanidino compounds in hemodialysis patients.	2001 Feb	11168992
Specific neosaxitoxin interactions with the Na+ channel outer vestibule determined by mutant cycle analysis.	2001 Feb	11159437
The folding nucleus of a fibronectin type III domain is composed of core residues of the immunoglobulin-like fold.	2001 Feb 2	11162123
Rate of intrachain contact formation in an unfolded protein: temperature and denaturant effects.	2001 Feb 2	11162121
Solid-phase guanidinylation as a diversification strategy of poly-L-proline type II peptide mimic scaffolds.	2001 Feb 22	11178825
Limited tryptic hydrolysis of pea legumin: molecular mass and conformational stability of legumin-T.	2001 Jan 10	11164235
Surprisingly high stability of barley lipid transfer protein, LTP1, towards denaturant, heat and proteases.	2001 Jan 19	11163761
Achieving stability and conformational specificity in designed proteins via binary patterning.	2001 Jan 19	11152617
Protein compactness measured by fluorescence resonance energy transfer. Human carbonic anhydrase ii is considerably expanded by the interaction of GroEL.	2001 Jun 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 Jun 8	11304524
Proteoglycans and hyaluronan in human fetal membranes.	2001 Mar	11262472
Probing conformational changes in the estrogen receptor: evidence for a partially unfolded intermediate facilitating ligand binding and release.	2001 Mar	11222743
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
Structural alterations and inhibition of unisite and multisite ATP hydrolysis in soluble mitochondrial F1 by guanidinium chloride.	2001 Mar 20	11258961

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 [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