Page last updated: 2024-12-05

benzathine

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

Description

Benzathine is a large, bulky molecule that acts as a depot formulation for various medications, extending their duration of action. It is synthesized by reacting benzylpenicillin with benzathine, a diamine. Benzathine forms a salt with the penicillin, leading to a poorly soluble compound that is slowly absorbed from the injection site. This slow absorption ensures prolonged release of the drug, resulting in sustained therapeutic levels for weeks. Benzathine penicillin G, a common example, is used to treat syphilis and rheumatic fever due to its extended duration of action. Research on benzathine focuses on its potential to deliver other drugs with extended release profiles, expanding its therapeutic applications. Its importance lies in its ability to provide long-acting therapeutic effects, reducing the need for frequent administration and improving patient compliance.'

benzathine: RN given refers to parent cpd with specified locants for phenylmethyl groups; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID8793
CHEMBL ID193646
CHEBI ID51344
SCHEMBL ID5764
MeSH IDM0055284

Synonyms (65)

Synonym
AC-13104
n,n'-dibenzyl-1,2-ethylenediamine
CHEBI:51344 ,
1, n,n'-bis(phenylmethyl)-
n,n'-dibenzylethylenediamine
ethylenediamine,n'-dibenzyl-
nsc-5632
benzatin
benzathine
nsc5632
dbed
wln: r1m2m1r
140-28-3
1,2-bis(benzylamino)ethane
usaf do-53
n,n'-dibenzylethane-1,2-diamine
nsc62936
nsc-62936
ai3-23851
nsc 5632
einecs 205-408-4
brn 0786668
1,2-ethanediamine, n,n'-bis(phenylmethyl)-
ethylenediamine, n,n'-dibenzyl-
n,n'-dibenzylethylenediamine, 97%
NCGC00166222-01
STK379515
CHEMBL193646
D1807
n',n'-dibenzylethane-1,2-diamine;n1,n2-dibenzylethane-1,2-diamine
A807638
AKOS005306729
BBL002994
benzyl-[2-(benzylamino)-ethyl]-amine
n,n'-bis(phenylmethyl)-1,2-ethanediamine
MLS004800109
smr001547335
c659vz7p7t ,
1,2-ethanediamine, n1,n2-bis(phenylmethyl)-
unii-c659vz7p7t
4-12-00-02321 (beilstein handbook reference)
FT-0629380
n1,n2-dibenzylethane-1,2-diamine
SCHEMBL5764
benzathine [mi]
n1,n2-bis(phenylmethyl)-1,2-ethanediamine
n,n'-dibenzyl-1,2-diaminoethane
DTXSID4048359
n,n'-dibenzyl-ethane-1,2-diamine
n,n'-dibenzylethylene-diamine
n,n'-dibenzylethylene diamine
W-108207
n,n'-dibenzylethylene-d4-diamine
1219795-20-6
n,n'-dibenzyl-1,2-ethanediamine
mfcd00004771
F0001-0480
CCG-248022
Q2896784
ethylenediamine-n,n'-dibenzyl
benzyl[2-(benzylamino)ethyl]amine
STR05175
SB33325
EN300-207802
CS-0008847

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Also the relative bioavailability of the potassium salt was greatest, as indicated by the areas under the serum concentration/time curves (AUC)."( Absorption of phenoxymethylpenicillin from mixtures and tablets in healthy volunteers.
Josefsson, K; Magni, L, 1983
)
0.27

Dosage Studied

ExcerptRelevanceReference
" Our analysis indicated noncompliance, incorrect selection and insufficient dosing of antibiotics, and causative pathogens other than streptococci as demonstrable causes of the recurrence of erysipelas."( Recurrent erysipelas despite antibiotic prophylaxis: an analysis from case studies.
Koster, JB; Kullberg, BJ; van der Meer, JW, 2007
)
0.34
" Based on this information, the right antibiotic with adequate dosing and timing can be selected."( Recurrent erysipelas despite antibiotic prophylaxis: an analysis from case studies.
Koster, JB; Kullberg, BJ; van der Meer, JW, 2007
)
0.34
"A water-insoluble complex between diltiazem HCl and Na deoxycholate was prepared to achieve sustained release dosage forms."( Drug-organic electrolyte complexes as controlled release systems.
Alexander, KS; Fifer, EK; Kim, CJ; Vadlapatla, R, 2009
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
diamineAny polyamine that contains two amino groups.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency0.01000.003245.467312,589.2998AID2517
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency70.79460.004023.8416100.0000AID485290
DNA polymerase kappa isoform 1Homo sapiens (human)Potency16.83360.031622.3146100.0000AID588579
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID1055494Cytotoxicity against human HuH7 cells2013European journal of medicinal chemistry, , Volume: 70Synthesis and evaluation of hexahydropyrimidines and diamines as novel hepatitis C virus inhibitors.
AID1055495Antiviral activity against cell culture derived HCV expressing NS5A-GFP fusion protein infected in human HuH7 cells assessed as inhibition of viral life cycle after 72 hrs by Hoechst-33342 staining-based confocal microscopy2013European journal of medicinal chemistry, , Volume: 70Synthesis and evaluation of hexahydropyrimidines and diamines as novel hepatitis C virus inhibitors.
AID245054In vitro minimum inhibitory concentration measured against Mycobacterium tuberculosis H37Rv strain2005Bioorganic & medicinal chemistry letters, May-02, Volume: 15, Issue:9
Synthesis and antimycobacterial activity of ferrocenyl ethambutol analogues and ferrocenyl diamines.
AID388924Antitubercular activity against Mycobacterium tuberculosis H37Rv after 2 days by mycobacteria growth indicator tube system2008Bioorganic & medicinal chemistry, Nov-01, Volume: 16, Issue:21
Synthesis and antitubercular activity of ferrocenyl diaminoalcohols and diamines.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (178)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990153 (85.96)18.7374
1990's3 (1.69)18.2507
2000's9 (5.06)29.6817
2010's11 (6.18)24.3611
2020's2 (1.12)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 83.98

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index83.98 (24.57)
Research Supply Index5.23 (2.92)
Research Growth Index4.76 (4.65)
Search Engine Demand Index147.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (83.98)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews6 (3.24%)6.00%
Case Studies7 (3.78%)4.05%
Observational0 (0.00%)0.25%
Other172 (92.97%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]