Compounds > n-((1s,trans)-2-hydroxycyclopentyl)adenosine
Page last updated: 2024-08-02 11:03:46

n-((1s,trans)-2-hydroxycyclopentyl)adenosine

Description

N-((1S,trans)-2-hydroxycyclopentyl)adenosine: structure given in first source; an adenosine A1 receptor agonist [MeSH]

(2R,3R,4S,5R)-2-[6-[[(1S,2S)-2-hydroxycyclopentyl]amino]-9-purinyl]-5-(hydroxymethyl)oxolane-3,4-diol : no description available [CHeBI]

Cross-References

ID SourceID
PubMed CID9884817
CHEMBL ID2163568
SCHEMBL ID2779184
CHEBI ID92714
MeSH IDM0219334

Synonyms (37)

Synonym
124555-18-6
HMS3268O08
BRD-K40578143-001-01-8
gr79236
gr-79236
n-((1s,2s)-2-hydroxycyclopentyl)adenosine
gr 79236x
n-((1s,trans)-2-hydroxycyclopentyl)adenosine
adenosine, n-(2-hydroxycyclopentyl)-, (1s-trans)-
bdbm50395126
CHEMBL2163568 ,
q4h682b2vz ,
unii-q4h682b2vz
n-[(1s,2s)-2-hydroxycyclopentyl adenosine
(2r,3r,4s,5r)-2-(6-{[(1s,2s)-2-hydroxycyclopentyl]amino}-9h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
gtpl3288
HY-18978
CS-4965
SCHEMBL2779184
GYWXTRVEUURNEW-TVDBPQCTSA-N
n-[(1s,trans)-2-hydroxycyclopentyl]adenosine
adenosine, n-((1s,2s)-2-hydroxycyclopentyl)-
n-[(1s,2s)-2-hydroxycyclopentyl]adenosine
AKOS024456878
DTXSID10154427
n-[(1s,2s)-2-hydroxy-cyclopentyl]-adenosne
J-523291
CHEBI:92714
gr 79236x, >=99% (hplc), solid
gr79236x
HMS3676N18
Q27077849
HMS3412N18
(2r,3r,4s,5r)-2-[6-[[(1s,2s)-2-hydroxycyclopentyl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
MS-25429
ZEA55518
adenosine, n-[(1s,2s)-2-hydroxycyclopentyl]-

Drug Classes (1)

ClassDescription
purine nucleoside

Pathways (1)

n-((1s,trans)-2-hydroxycyclopentyl)adenosine is involved in 1 pathway(s), involving a total of 0 unique proteins and 53 unique compounds

PathwayProteinsCompounds
Purinergic signaling053

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Adenosine receptor A1Rattus norvegicus (Norway rat)Ki0.0031AID1571131
Adenosine receptor A2aHomo sapiens (human)Ki1.3300AID1571134
Adenosine receptor A1Homo sapiens (human)Ki0.0039AID1571129

Activation Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Adenosine receptor A1Homo sapiens (human)EC500.0059AID699043
Cannabinoid receptor 2Rattus norvegicus (Norway rat)EC500.0059AID699043

Bioassays (7)

Assay IDTitleYearJournalArticle
AID1571138Displacement of [125I]I-AB-MECA from recombinant human adenosine A3 receptor expressed in CHO cell membranes2018MedChemComm, Nov-01, Volume: 9, Issue:11
ISSN: 2040-2511		Structure activity relationship of 2-arylalkynyl-adenine derivatives as human A
AID1571134Displacement of [3H]ZM241385 from human A2A receptor expressed in HEK293 cell membranes2018MedChemComm, Nov-01, Volume: 9, Issue:11
ISSN: 2040-2511		Structure activity relationship of 2-arylalkynyl-adenine derivatives as human A
AID1571129Displacement of [3H]DPCPX from recombinant human A1 receptor expressed in CHO cell membranes2018MedChemComm, Nov-01, Volume: 9, Issue:11
ISSN: 2040-2511		Structure activity relationship of 2-arylalkynyl-adenine derivatives as human A
AID1571131Displacement of [3H]DPCPX from rat A1 receptor2018MedChemComm, Nov-01, Volume: 9, Issue:11
ISSN: 2040-2511		Structure activity relationship of 2-arylalkynyl-adenine derivatives as human A
AID699043Agonist activity at human A1AR expressed in HEK293T/17 cells assessed as inhibition of forskolin-induced cAMP accumulation incubated for 10 mins by luciferase reporter assay2012Journal of medicinal chemistry, Jul-26, Volume: 55, Issue:14
ISSN: 1520-4804		Orally active adenosine A(1) receptor agonists with antinociceptive effects in mice.
AID1345630Rat A1 receptor (Adenosine receptors)2006Nature reviews. Drug discovery, Mar, Volume: 5, Issue:3
ISSN: 1474-1776		Adenosine receptors as therapeutic targets.
AID1345618Human A2A receptor (Adenosine receptors)2006Nature reviews. Drug discovery, Mar, Volume: 5, Issue:3
ISSN: 1474-1776		Adenosine receptors as therapeutic targets.

Research

Studies (29)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's15 (51.72)18.2507
2000's12 (41.38)29.6817
2010's2 (6.90)24.3611
2020's0 (0.00)2.80

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (13.79%)5.53%
Reviews1 (3.45%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other24 (82.76%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
9-xylosyladenine
0
purine nucleoside00low000000
2-[6-(cyclohexylamino)-9-purinyl]-5-(hydroxymethyl)oxolane-3,4-diol
0
purine nucleoside00low000000
apnea
0
purine nucleoside00low000000
2-chloroadenosine
0
purine nucleoside00low000000
hyaluronoglucosaminidase
0
purine nucleoside00low000000
vidarabine
0
beta-D-arabinoside;
purine nucleoside		antineoplastic agent;
bacterial metabolite;
nucleoside antibiotic		00low000000
isoguanosine
0
purine nucleoside00low000000
psicofuranine
0
psicose derivative;
purine nucleoside		00low000000
4-nitrobenzylthioinosine
0
purine nucleoside00low000000
2-aminoadenosine
0
purine nucleoside00low000000
phenylisopropyladenosine
0
aromatic amine;
benzenes;
hydrocarbyladenosine;
purine nucleoside;
secondary amino compound		adenosine A1 receptor agonist;
neuroprotective agent		00low000000
8-bromoadenosine
0
purine nucleoside00low000000
n-allyladenosine
0
purine nucleoside00low000000
adenosine-5'-carboxylic acid
0
purine nucleoside00low000000
n(6)-phenyladenosine
0
purine nucleoside00low000000
1,7-dimethylguanosine
0
purine nucleoside00low000000
8-methyladenosine
0
purine nucleoside00low000000
regadenoson
0
purine nucleoside00low000000
fludarabine
0
purine nucleoside00low000000
6-thioguanosine
0
purine nucleoside00low000000
5-(6-aminopurin-9-yl)-N-ethyl-3,4-dihydroxy-2-oxolanecarboxamide
0
purine nucleoside00low000000
nelarabine
0
beta-D-arabinoside;
monosaccharide derivative;
purine nucleoside		antineoplastic agent;
DNA synthesis inhibitor;
prodrug		00low000000
(2R,4R,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
0
purine nucleoside00low000000
cv 1808
0
purine nucleoside00low000000
ver 155008
0
purine nucleoside00low000000
8-hydroxyguanosine
0
purine nucleoside00low000000
8-bromoguanosine
0
purine nucleoside00low000000
9-arabinofuranosylguanine
0
beta-D-arabinoside;
purine nucleoside		antineoplastic agent;
DNA synthesis inhibitor		00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
adenosine monophosphate
1
adenosine 5'-phosphate;
purine ribonucleoside 5'-monophosphate		adenosine A1 receptor agonist;
cofactor;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
EC 3.1.3.11 (fructose-bisphosphatase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical		2012201212.0low000010
adenosine
1
adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent		2012201212.0low000010
n(6)-(3-iodobenzyl)-5'-n-methylcarboxamidoadenosine
1
adenosines;
monocarboxylic acid amide;
organoiodine compound		adenosine A3 receptor agonist2006200618.0low000100
2-chloro-n(6)cyclopentyladenosine
2
2006201215.0low000110
tecadenoson
1
201820186.0low000010
zm 241385
1
diamino-1,3,5-triazine2006200618.0low000100
sch 58261
1
triazolopyrimidines2006200618.0low000100
regadenoson
1
purine nucleoside2006200618.0low000100
n(6)-cyclopentyladenosine
3
2006201812.0low000120
2-chloro-n(6)-(3-iodobenzyl)adenosine-5'-n-methyluronamide
1
2006200618.0low000100
2-(4-(2-carboxyethyl)phenethylamino)-5'-n-ethylcarboxamidoadenosine
1
adenosines;
dicarboxylic acid monoamide;
monocarboxylic acid		adenosine A2A receptor agonist;
anti-inflammatory agent		2006200618.0low000100
mre 3008-f20
1
2006200618.0low000100
fk 453
1
2006200618.0low000100
atl 146e
1
2006200618.0low000100
sch 442416
1
triazolopyrimidines2006200618.0low000100
mrs 3558
1
2006200618.0medium000100
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
lactic acid
2
2-hydroxy monocarboxylic acidalgal metabolite;
Daphnia magna metabolite		1993199430.5low002000
glycerol
1
alditol;
triol		algal metabolite;
detergent;
Escherichia coli metabolite;
geroprotector;
human metabolite;
mouse metabolite;
osmolyte;
Saccharomyces cerevisiae metabolite;
solvent		1995199529.0low001000
1,3-diethyl-8-phenylxanthine
1
1993199331.0low001000
1,3-dipropyl-8-cyclopentylxanthine
6
oxopurineadenosine A1 receptor antagonist;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor		1998200224.0low004200
8-phenyltheophylline
1
1993199331.0low001000
theophylline
1
dimethylxanthineadenosine receptor antagonist;
anti-asthmatic drug;
anti-inflammatory agent;
bronchodilator agent;
drug metabolite;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
fungal metabolite;
human blood serum metabolite;
immunomodulator;
muscle relaxant;
vasodilator agent		1993199331.0low001000
bethanechol
1
carbamate ester;
quaternary ammonium ion		muscarinic agonist1998199826.0low001000
cgs 15943
1
aromatic amine;
biaryl;
furans;
organochlorine compound;
primary amino compound;
quinazolines;
triazoloquinazoline		adenosine A1 receptor antagonist;
adenosine A2A receptor antagonist;
antineoplastic agent;
central nervous system stimulant		1994199430.0low001000
diclofenac
1
amino acid;
aromatic amine;
dichlorobenzene;
monocarboxylic acid;
secondary amino compound		antipyretic;
drug allergen;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
environmental contaminant;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
xenobiotic		2007200717.0low100100
fentanyl
1
anilide;
monocarboxylic acid amide;
piperidines		adjuvant;
anaesthesia adjuvant;
anaesthetic;
intravenous anaesthetic;
mu-opioid receptor agonist;
opioid analgesic		2001200123.0low000100
sumatriptan
1
sulfonamide;
tryptamines		serotonergic agonist;
vasoconstrictor agent		2001200123.0low000100
phenylephrine
1
phenols;
phenylethanolamines;
secondary amino compound		alpha-adrenergic agonist;
cardiotonic drug;
mydriatic agent;
nasal decongestant;
protective agent;
sympathomimetic agent;
vasoconstrictor agent		2000200024.0low001000
quinuclidines
1
quinuclidines;
saturated organic heterobicyclic parent		2006200618.0low000100
3-o-methylglucose
1
D-aldohexose derivative1995199529.0low001000
quinazolines
1
azaarene;
mancude organic heterobicyclic parent;
ortho-fused heteroarene;
quinazolines		1994199430.0low001000
substance p
1
peptideneurokinin-1 receptor agonist;
neurotransmitter;
vasodilator agent		2006200618.0low000100
colforsin
1
acetate ester;
cyclic ketone;
labdane diterpenoid;
organic heterotricyclic compound;
tertiary alpha-hydroxy ketone;
triol		adenylate cyclase agonist;
anti-HIV agent;
antihypertensive agent;
plant metabolite;
platelet aggregation inhibitor;
protein kinase A agonist		2001200123.0low000100
adenosine
26
adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent		1993200725.3high4017900
metrifudil
2
1993199430.5medium002000
triazoles
1
1,2,3-triazole1994199430.0low001000
sr 140333
1
2006200618.0low000100
gr 73632
1
2006200618.0low000100
n(6)-(3-iodobenzyl)-5'-n-methylcarboxamidoadenosine
1
adenosines;
monocarboxylic acid amide;
organoiodine compound		adenosine A3 receptor agonist1998199826.0low001000
adenosine-5'-(n-ethylcarboxamide)
4
adenosines;
monocarboxylic acid amide		adenosine A1 receptor agonist;
adenosine A2A receptor agonist;
antineoplastic agent;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
vasodilator agent		1993199829.5low004000
n(6)-cyclopentyladenosine
2
1995199827.5low002000
capsaicin
1
capsaicinoidnon-narcotic analgesic;
TRPV1 agonist;
voltage-gated sodium channel blocker		2005200519.0low000100
D-fructopyranose
1
cyclic hemiketal;
D-fructose;
fructopyranose		sweetening agent1997199727.0low001000
2-chloro-n(6)-(3-iodobenzyl)adenosine-5'-n-methyluronamide
1
2001200123.0low000100
2-(4-(2-carboxyethyl)phenethylamino)-5'-n-ethylcarboxamidoadenosine
4
adenosines;
dicarboxylic acid monoamide;
monocarboxylic acid		adenosine A2A receptor agonist;
anti-inflammatory agent		1993200127.5low003100
cv 1808
2
purine nucleoside1993199430.5low002000
piperidines
1
2006200618.0low000100
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Acidosis, Diabetic0
2
1994199529.5low002000
Acute Post-operative Pain0
1
2007200717.0low100100
Adjuvant Arthritis0
1
1998199826.0low001000
Alloxan Diabetes0
2
1994199529.5low002000
Anesthesia0
3
1999200024.7low003000
Angina Pectoris0
1
2002200222.0low100100
Angor Pectoris0
1
2002200222.0low100100
Apnea, Sleep0
1
1997199727.0low001000
Arteriosclerosis, Coronary0
1
2002200222.0low100100
Blood Pressure, Low0
1
2002200222.0low000100
Bradyarrhythmia0
1
2002200222.0low000100
Bradycardia0
1
2002200222.0low000100
Cardiovascular Stroke0
3
1999200024.7low003000
Coronary Artery Disease0
1
2002200222.0low100100
Coronary Disease0
2
1999200223.5low101100
Coronary Heart Disease0
2
1999200223.5low101100
Diabetic Ketoacidosis0
2
1994199529.5low002000
Disease0
1
2006200618.0low000100
Disease Models, Animal0
1
2006200618.0low000100
Experimental Radiation Injuries0
1
2006200618.0low000100
Heart Disease, Ischemic0
3
1999200223.0low201200
Hypotension0
1
2002200222.0low000100
Injury, Ischemia-Reperfusion0
1
1999199925.0low001000
Injury, Myocardial Reperfusion0
2
1999200024.5low002000
Insulin Resistance0
1
1997199727.0low001000
Insulin Sensitivity0
1
1997199727.0low001000
Left Ventricular Dysfunction0
1
2002200222.0low100100
Myocardial Infarction0
3
1999200024.7low003000
Myocardial Ischemia0
3
1999200223.0low201200
Necrosis0
1
2002200222.0low100100
Pain, Postoperative0
1
2007200717.0low100100
Reperfusion Injury0
1
1999199925.0low001000
Sleep Apnea Syndromes0
1
1997199727.0low001000
Ventricular Dysfunction0
1
1999199925.0low001000
Ventricular Dysfunction, Left0
1
2002200222.0low100100

Dosage (2)

ArticleYear
In vitro effect of adenosine agonist GR79236 on the insulin sensitivity of glucose utilisation in rat soleus and human rectus abdominus muscle.
Biochimica et biophysica acta, , Jun-07, Volume: 1316, Issue:2		1996
The effects of GR79236 on plasma fatty acid concentrations, heart rate and blood pressure in the conscious rat.
European journal of pharmacology, , May-12, Volume: 257, Issue:1-2		1994