Page last updated: 2024-11-05

benzylguanidine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Benzylguanidine is a small molecule that has been studied for its potential use in various applications, including drug development. It is synthesized through a straightforward reaction of benzyl chloride with guanidine. Benzylguanidine has shown promising activity as a selective inhibitor of the enzyme O6-alkylguanine-DNA alkyltransferase (AGT), which is involved in DNA repair. This inhibitory property makes benzylguanidine a potential therapeutic agent for treating cancer, particularly for tumors that are resistant to chemotherapy. Its ability to bind to AGT and inhibit its function has also been exploited in the development of novel drug delivery systems. The compound is studied extensively to understand its pharmacological properties, including its mechanism of action, bioavailability, and potential side effects. This knowledge is crucial for developing safe and effective therapeutic strategies based on benzylguanidine.'

Cross-References

ID SourceID
PubMed CID16644
CHEMBL ID288640
SCHEMBL ID45768
MeSH IDM0302324

Synonyms (36)

Synonym
1-benzylguanidine
2211-57-6
n-benzoguanidine
guanidine, benzyl-
benzylguanidine
nsc227970
n-benzylguanidine
guanidine, (phenylmethyl)-
nsc-227970
nsc 227970
STK501305
AKOS000321591
CHEMBL288640 ,
n-benzyl-guanidine
2-benzylguanidine
bdbm50013044
1-benzyl-guanidine
n-benzylguanidinium acetate
g6537f6gqs ,
unii-g6537f6gqs
S12114
SCHEMBL45768
ABSNGNUGFQIDDO-UHFFFAOYSA-N
monobenzylguanidine
AS-54562
DTXSID20944755
guanidine,n-(phenylmethyl)-;1-benzylguanidine;n-benzylguanidine;benzylguanidine
BCP31403
BB 0323264
A878708
benzylguanidinesulfate(2:1)
n-benzylguanidineacetate
CS-0139507
EN300-73529
mfcd00461648
SY074251
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 3BMus musculus (house mouse)Ki0.00100.00130.26351.4300AID6020
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (39)

Assay IDTitleYearJournalArticle
AID304711Antiproliferative activity against human PC3 cells after 72 hrs2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Amine-guanidine switch: a promising approach to improve DNA binding and antiproliferative activities.
AID304708Antiproliferative activity against human BT474 cells after 72 hrs2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Amine-guanidine switch: a promising approach to improve DNA binding and antiproliferative activities.
AID1656186Drug uptake in human SK-N-FI cells using Cy7-labeled compound incubated for 4 hrs by confocal microscopy2020Journal of medicinal chemistry, 07-23, Volume: 63, Issue:14
Dual Targeting of Norepinephrine Transporter (NET) Function and Thyrointegrin αvβ3 Receptors in the Treatment of Neuroblastoma.
AID304718Binding affinity to calf thymus dodecamer DNA assessed as thermal stability in cacodylate buffer at 12 uM2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Amine-guanidine switch: a promising approach to improve DNA binding and antiproliferative activities.
AID352979Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.5 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID304707Antiproliferative activity against human SKBR3 cells after 72 hrs2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Amine-guanidine switch: a promising approach to improve DNA binding and antiproliferative activities.
AID352948Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.40 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID230956Ratio of the concentration levels determined for the adrenal medulla to the liver after 72 hr; [Adrenal Medulla] / [liver]1984Journal of medicinal chemistry, Feb, Volume: 27, Issue:2
Adrenal medulla imaging agents: a structure-distribution relationship study of radiolabeled aralkylguanidines.
AID352975Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.60 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID352976Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.72 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID352956Hypoglycemic activity in lean normal BALB/c mouse assessed as blood glucose level at 0.54 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID352977Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.54 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID352938Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.57 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID304717Binding affinity to calf thymus DNA assessed as thermal stability in BPE buffer at 2 uM2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Amine-guanidine switch: a promising approach to improve DNA binding and antiproliferative activities.
AID15565Distribution in dog adrenal medulla 30 min after administration.1984Journal of medicinal chemistry, Feb, Volume: 27, Issue:2
Adrenal medulla imaging agents: a structure-distribution relationship study of radiolabeled aralkylguanidines.
AID374709Hypoglycemic activity in high fat diet-induced obese BALB/c mouse model assessed as blood glucose level at 0.43 mmol/kg/day administered through diet for 28 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID352936Toxicity in lean normal BALB/c mouse assessed as overt signs of behavioural changes at equimolar dose of 0.5 mmol/kg galegine administered daily through diet for 7 days2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID352972Antiobesity activity in lean normal BALB/c mouse assessed as change in average daily weight at 0.54 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID352961Antiobesity activity in lean normal BALB/c mouse assessed as change in average daily food intake at 0.54 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID352937Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.51 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID304715Increase in caspase 3 activation in human SKBR3 cells at 20 uM after 24 hrs2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Amine-guanidine switch: a promising approach to improve DNA binding and antiproliferative activities.
AID352984Antiobesity activity in ob/ob mouse model assessed as change in average daily weight at 0.26 mmol/kg/day administered through diet for 28 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID374697Hypoglycemic activity in ob/ob mouse model assessed as blood glucose level at 0.26 mmol/kg/day administered through diet for 28 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID1656185Antitumor activity against human SK-N-FI cells xenografted in Ncr nude mouse assessed as inhibition of tumor growth by measuring suppression of tumor weight at 3 mg/kg, sc dosed daily for 15 days relative to control2020Journal of medicinal chemistry, 07-23, Volume: 63, Issue:14
Dual Targeting of Norepinephrine Transporter (NET) Function and Thyrointegrin αvβ3 Receptors in the Treatment of Neuroblastoma.
AID352978Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.62 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID304712Antiproliferative activity against human HT29 cells after 72 hrs2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Amine-guanidine switch: a promising approach to improve DNA binding and antiproliferative activities.
AID352940Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.59 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID15566Distribution in dog adrenal medulla 72 hours after administration.1984Journal of medicinal chemistry, Feb, Volume: 27, Issue:2
Adrenal medulla imaging agents: a structure-distribution relationship study of radiolabeled aralkylguanidines.
AID304710Antiproliferative activity against human LnCAP cells after 72 hrs2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Amine-guanidine switch: a promising approach to improve DNA binding and antiproliferative activities.
AID352987Antiobesity activity in ob/ob mouse model assessed as change in average daily food intake at 0.26 mmol/kg/day administered through diet for 28 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID304719Binding affinity to calf thymus dodecamer DNA assessed as thermal stability in cacodylate buffer containing 0.1 M NaCl at 12 uM2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Amine-guanidine switch: a promising approach to improve DNA binding and antiproliferative activities.
AID304709Antiproliferative activity against human T47D cells after 72 hrs2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Amine-guanidine switch: a promising approach to improve DNA binding and antiproliferative activities.
AID304716Increase in caspase 7 activation in human SKBR3 cells at 20 uM after 24 hrs2007Journal of medicinal chemistry, Dec-27, Volume: 50, Issue:26
Amine-guanidine switch: a promising approach to improve DNA binding and antiproliferative activities.
AID352939Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.70 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID374712Metabolic stability in ob/ob mouse liver microsomes assessed as oxidative hydroxylation at 50 uM after 45 mins by HPLC-MS analysis2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID374705Antiobesity activity in high fat diet-induced obese BALB/c mouse model assessed as change in average daily food intake at 0.43 mmol/kg/day administered through diet for 28 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID6020In vitro binding affinity for the 5-hydroxytryptamine 3 receptor was determined with NG-108-15 mouse neuroblastoma-glioma cells1990Journal of medicinal chemistry, Oct, Volume: 33, Issue:10
An initial three-component pharmacophore for specific serotonin-3 receptor ligands.
AID352941Antidiabetic activity in lean normal BALB/c mouse assessed as effect on blood lactate level at 0.52 mmol/kg/day administered through diet for 7 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
AID374701Antiobesity activity in high fat diet-induced obese BALB/c mouse model assessed as change in average daily body weight at 0.43 mmol/kg/day administered through diet for 28 days relative to time-matched control2009Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11
Benzylguanidines and other galegine analogues inducing weight loss in mice.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (26)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (3.85)18.7374
1990's2 (7.69)18.2507
2000's6 (23.08)29.6817
2010's12 (46.15)24.3611
2020's5 (19.23)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.79

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.79 (24.57)
Research Supply Index3.37 (2.92)
Research Growth Index5.16 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.79)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (3.57%)6.00%
Case Studies1 (3.57%)4.05%
Observational0 (0.00%)0.25%
Other26 (92.86%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]