Compounds > 3-iodo-4-aminobenzyl-5'-N-methylcarboxamidoadenosine
Page last updated: 2024-11-12

3-iodo-4-aminobenzyl-5'-N-methylcarboxamidoadenosine

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

Description

3-iodo-4-aminobenzyl-5'-N-methylcarboxamidoadenosine : A derivative of adenosine in which the 5'-hydroxymethyl group is replaced by N-ethylcarboxamido and one of the hydrogens of the exocyclic amino function is substituted by a 3-iodo-4-aminobenzyl group. [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]

Cross-References

ID SourceID
PubMed CID9958472
CHEMBL ID133566
CHEBI ID73285

Synonyms (25)

Synonym
PDSP2_000300
PDSP1_000302
i-ab-meca, solid
CHEMBL133566 ,
chebi:73285 ,
5-[6-(4-amino-3-iodo-benzylamino)-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid methylamide
iab-meca
bdbm50106543
n(6)-(4-amino-3-iodobenzyl)-adenosine-5'-n-methyluronamide
n(6)-(3-iodo-4-aminobenzyl)-adenosine-5'-n-methyluronamide
(2s,3s,4r,5r)-5-{6-[(4-amino-3-iodobenzyl)amino]-9h-purin-9-yl}-3,4-dihydroxy-n-methyltetrahydrofuran-2-carboxamide
3-iodo-4-aminobenzyl-5'-n-methylcarboxamidoadenosine
152918-27-9
i-ab-meca
beta-d-ribofuranuronamide, 1-(6-(((4-amino-3-iodophenyl)methyl)amino)-9h-purin-9-yl)-1-deoxy-n-methyl-
9wr19428j3 ,
unii-9wr19428j3
.beta.-d-ribofuranuronamide, 1-(6-(((4-amino-3-iodophenyl)methyl)amino)-9h-purin-9-yl)-1-deoxy-n-methyl-
DTXSID10165159
J-008960
NCGC00485570-01
Q27140417
i-ab-meca reference standard fo
(2s,3s,4r,5r)-5-[6-[(4-amino-3-iodophenyl)methylamino]purin-9-yl]-3,4-dihydroxy-n-methyloxolane-2-carboxamide
(2s,3s,4r,5r)-5-(6-((4-amino-3-iodobenzyl)amino)-9h-purin-9-yl)-3,4-dihydroxy-n-methyltetrahydrofuran-2-carboxamide

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)		0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
adenosinesAny purine ribonucleoside that is a derivative of adenosine.
organoiodine compoundAn organoiodine compound is a compound containing at least one carbon-iodine bond.
monocarboxylic acid amideA carboxamide derived from a monocarboxylic acid.
[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 (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A3Homo sapiens (human)Ki0.25120.00000.930610.0000AID1819796; AID34581; AID34704; AID34723
Adenosine receptor A1Rattus norvegicus (Norway rat)Ki0.00340.00011.20929.9700AID32188
Adenosine receptor A3Rattus norvegicus (Norway rat)Ki0.00130.00030.91969.0000AID33341; AID33485
Adenosine receptor A2bRattus norvegicus (Norway rat)Ki0.19700.00061.353610.0000AID33569
Adenosine receptor A2aRattus norvegicus (Norway rat)Ki0.19700.00021.494010.0000AID32878; AID33569; AID33939
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A3Rattus norvegicus (Norway rat)Kd0.00100.00100.00100.0010AID1819763
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (11)

Processvia Protein(s)Taxonomy
inflammatory responseAdenosine receptor A3Homo sapiens (human)
signal transductionAdenosine receptor A3Homo sapiens (human)
activation of adenylate cyclase activityAdenosine receptor A3Homo sapiens (human)
regulation of heart contractionAdenosine receptor A3Homo sapiens (human)
negative regulation of cell population proliferationAdenosine receptor A3Homo sapiens (human)
response to woundingAdenosine receptor A3Homo sapiens (human)
regulation of norepinephrine secretionAdenosine receptor A3Homo sapiens (human)
negative regulation of cell migrationAdenosine receptor A3Homo sapiens (human)
negative regulation of NF-kappaB transcription factor activityAdenosine receptor A3Homo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A3Homo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (1)

Processvia Protein(s)Taxonomy
G protein-coupled adenosine receptor activityAdenosine receptor A3Homo sapiens (human)
G protein-coupled adenosine receptor activityAdenosine receptor A2aRattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
plasma membraneAdenosine receptor A3Homo sapiens (human)
presynaptic membraneAdenosine receptor A3Homo sapiens (human)
Schaffer collateral - CA1 synapseAdenosine receptor A3Homo sapiens (human)
dendriteAdenosine receptor A3Homo sapiens (human)
plasma membraneAdenosine receptor A3Homo sapiens (human)
synapseAdenosine receptor A3Homo sapiens (human)
Golgi membraneAdenosine receptor A2aRattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID33939Tested for the binding affinity of A2a receptor by displacing the [3H]-CGS- 21680 in rat striatal membranes1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
2-Substitution of N6-benzyladenosine-5'-uronamides enhances selectivity for A3 adenosine receptors.
AID32513Tested for the binding affinity of A1 receptor by displacing the [3H]-PIA in rat brain membranes1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
2-Substitution of N6-benzyladenosine-5'-uronamides enhances selectivity for A3 adenosine receptors.
AID1819763Binding affinity to rat adenosine A3 receptor measured by radioligand binding assay2022ACS medicinal chemistry letters, Apr-14, Volume: 13, Issue:4
Selective A
AID229821Ratio of Ki for A1 and A3 receptors1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
2-Substitution of N6-benzyladenosine-5'-uronamides enhances selectivity for A3 adenosine receptors.
AID34704Binding affinity at wild-type Adenosine A3 receptor expressed in COS-7 cells2001Journal of medicinal chemistry, Nov-22, Volume: 44, Issue:24
Neoceptor concept based on molecular complementarity in GPCRs: a mutant adenosine A(3) receptor with selectively enhanced affinity for amine-modified nucleosides.
AID32878Binding affinity for adenosine A2A receptor as displacement of [3H]-CGS- 21680 from rat striatal membranes at 10e-4 M1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Structure-activity relationships and molecular modeling of 3, 5-diacyl-2,4-dialkylpyridine derivatives as selective A3 adenosine receptor antagonists.
AID33341Binding affinity for rat A3-adenosine receptor expressed in chinese hamster ovarian cells (assayed by the displacement of specific [125I]-N6-(4-amino-3-iodobenzyl)-adenosine-5''-N-methyluronamide)1994Journal of medicinal chemistry, Mar-04, Volume: 37, Issue:5
Structure-activity relationships of N6-benzyladenosine-5'-uronamides as A3-selective adenosine agonists.
AID34581Binding affinity at Mutant (H272E) human adenosine A3 receptor expressed in COS-7 cells2001Journal of medicinal chemistry, Nov-22, Volume: 44, Issue:24
Neoceptor concept based on molecular complementarity in GPCRs: a mutant adenosine A(3) receptor with selectively enhanced affinity for amine-modified nucleosides.
AID231119Ratio of binding affinities for A2 receptor compared to that of A3 receptor1994Journal of medicinal chemistry, Mar-04, Volume: 37, Issue:5
Structure-activity relationships of N6-benzyladenosine-5'-uronamides as A3-selective adenosine agonists.
AID230000Ratio of Ki for A2a and A3 receptors1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
2-Substitution of N6-benzyladenosine-5'-uronamides enhances selectivity for A3 adenosine receptors.
AID32021Binding affinity for A1-adenosine receptor by the displacement of specific [3H]-PIA binding in rat brain was determined1994Journal of medicinal chemistry, Mar-04, Volume: 37, Issue:5
Structure-activity relationships of N6-benzyladenosine-5'-uronamides as A3-selective adenosine agonists.
AID1819796Binding affinity to human adenosine A3 receptor measured by radioligand binding assay2022ACS medicinal chemistry letters, Apr-14, Volume: 13, Issue:4
Selective A
AID33485Tested for the binding affinity of A3 receptor by displacing N6-[[125I]-4-amino-3-iodobenzyl]-adenosine-5''-N-methyluronamide from membranes of CHO cells transfected with rat A3-cDNA1994Journal of medicinal chemistry, Oct-14, Volume: 37, Issue:21
2-Substitution of N6-benzyladenosine-5'-uronamides enhances selectivity for A3 adenosine receptors.
AID231118Ratio of binding affinities for A1 receptor compared to that of A3 receptor1994Journal of medicinal chemistry, Mar-04, Volume: 37, Issue:5
Structure-activity relationships of N6-benzyladenosine-5'-uronamides as A3-selective adenosine agonists.
AID33569Binding affinity for A2-adenosine receptor by the displacement of specific [3H]-CGS- binding in rat striatal membranes was determined1994Journal of medicinal chemistry, Mar-04, Volume: 37, Issue:5
Structure-activity relationships of N6-benzyladenosine-5'-uronamides as A3-selective adenosine agonists.
AID34723Displacement of [125I]AB-MECA from adenosine A3 receptor from HEK293 cell membranes1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Structure-activity relationships and molecular modeling of 3, 5-diacyl-2,4-dialkylpyridine derivatives as selective A3 adenosine receptor antagonists.
AID32188Binding affinity for adenosine A1 receptor as displacement of [3H]R-PIA from rat brain membranes at 10e-4 M1998Journal of medicinal chemistry, Aug-13, Volume: 41, Issue:17
Structure-activity relationships and molecular modeling of 3, 5-diacyl-2,4-dialkylpyridine derivatives as selective A3 adenosine receptor antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (37.50)18.2507
2000's1 (12.50)29.6817
2010's1 (12.50)24.3611
2020's3 (37.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.72

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 Index12.72 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.92 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.72)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
cgs 15943
9-chloro-2-(2-furyl)-(1,2,4)triazolo(1,5-c)quinazolin-5-imine: non-xanthine triazoloquinazoline adenosine antagonist. CGS 15943 : A member of the class of triazoloquinazolines that is [1,2,4]triazolo[1,5-c]quinazoline substited at positions 2, 5 and 9 by furan-2-yl, amino and chloro groups respectively. A potent antagonist at adenosine A1 and adenosine A2A receptors.		210aromatic amine;
biaryl;
furans;
organochlorine compound;
primary amino compound;
quinazolines;
triazoloquinazoline		adenosine A1 receptor antagonist;
adenosine A2A receptor antagonist;
antineoplastic agent;
central nervous system stimulant
8-(4-((2-aminoethyl)aminocarbonylmethyloxy)phenyl)-1,3-dipropylxanthine
8-(4-((2-aminoethyl)aminocarbonylmethyloxy)phenyl)-1,3-dipropylxanthine: adenosine receptor antagonist		210
2-chloroadenosine
5-chloroformycin A: structure given in first source		2.420purine nucleoside
3'-amino-3'-deoxyadenosine
[no description available]		210
n(6)-benzyladenosine
N(6)-benzyladenosine: RN given refers to parent cpd		1.9810
5'-n-methylcarboxamideadenosine
5'-N-methylcarboxamideadenosine: RN given refers to (beta-D)-isomer		1.9810
n(6)-(3-iodobenzyl)-5'-n-methylcarboxamidoadenosine
N(6)-(3-iodobenzyl)-5'-N-methylcarboxamidoadenosine: structure given in first source; a selective A(3) adenosine receptor agonist. 3-iodobenzyl-5'-N-methylcarboxamidoadenosine : A derivative of adenosine in which the 5'-hydroxymethyl group is replaced by N-ethylcarboxamido and one of the hydrogens of the exocyclic amino function is substituted by a 3-iodobenzyl group.		2.9240adenosines;
monocarboxylic acid amide;
organoiodine compound		adenosine A3 receptor agonist
2-chloro-n(6)cyclopentyladenosine
2-chloro-N(6)cyclopentyladenosine: highly selective agonist at A1 adenosine receptors		1.9810
mrs 1191
MRS 1191: a selective A3 adenosine receptor antagonist; structure given in first source		1.9910cinnamate ester
mrs 1220
9-chloro-2-(2-furyl)-5-phenylacetylamino(1,2,4)triazolo(1,5-c)quinazoline: structure in first source		2.4110quinazolines
2'-amino-2'-deoxyadenosine
[no description available]		210
adenosine-5'-(n-ethylcarboxamide)
Adenosine-5'-(N-ethylcarboxamide): A stable adenosine A1 and A2 receptor agonist. Experimentally, it inhibits cAMP and cGMP phosphodiesterase activity.. N-ethyl-5'-carboxamidoadenosine : A derivative of adenosine in which the 5'-hydroxymethyl group is replaced by an N-ethylcarboxamido group.		2.7230adenosines;
monocarboxylic acid amide		adenosine A1 receptor agonist;
adenosine A2A receptor agonist;
antineoplastic agent;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
vasodilator agent
n(6)-cyclopentyladenosine
[no description available]		1.9810
2-chloro-n(6)-(3-iodobenzyl)adenosine-5'-n-methyluronamide
2-chloro-N(6)-(3-iodobenzyl)adenosine-5'-N-methyluronamide: structure given in first source		2.9340
2-((2-aminoethylamino)carbonylethylphenylethylamino)-5'-n-ethylcarboxamidoadenosine
2-((2-aminoethylamino)carbonylethylphenylethylamino)-5'-N-ethylcarboxamidoadenosine: structure given in first source		1.9810
2-(4-(2-carboxyethyl)phenethylamino)-5'-n-ethylcarboxamidoadenosine
2-(4-(2-carboxyethyl)phenethylamino)-5'-N-ethylcarboxamidoadenosine: A2 adenosine receptor agonist; structure given in first source. CGS-21680 : A derivative of adenosine in which the 5'-hydroxymethyl group is replaced by N-ethylcarboxamido and the hydrogen at position 2 on the adenine is replaced by a 4-(2-carboxyethyl)phenethylamino group.		1.9810adenosines;
dicarboxylic acid monoamide;
monocarboxylic acid		adenosine A2A receptor agonist;
anti-inflammatory agent
mrs 1523
2,3-diethyl-4,5-dipropyl-6-phenylpyridine-3-thiocarboxylate-5-carboxylate: adenosine A3 receptor antagonist		2.4620
mre 3008-f20
MRE 3008-F20: InChIKey: CJRNHKSLHHWUAB-UHFFFAOYSA-N		2.4110
5'-amino-5'-deoxyadenosine
[no description available]		210
mrs 1097
[no description available]		1.9910
vuf 8504
[no description available]		210
n-cyclopropyl adenosine-5'-carboxamide
[no description available]		1.9810
psb 11
[no description available]		2.4110
ConditionIndicatedRelationship StrengthStudiesTrials
Congenital Zika Syndrome
[description not available]		02.2510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.2510
Zika Virus Infection
A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.		02.2510