Identification

Name
Adenosine
Accession Number
DB00640  (APRD00132)
Type
Small Molecule
Groups
Approved, Investigational
Description

A nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. Adenosine itself is a neurotransmitter. [PubChem]

Structure
Thumb
Synonyms
  • (2R,3R,4S,5R)-2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
  • 6-Amino-9-beta-D-ribofuranosyl-9H-purine
  • 9-beta-D-Ribofuranosidoadenine
  • 9-beta-D-Ribofuranosyl-9H-purin-6-amine
  • Ade-rib
  • Adenin riboside
  • Adenine deoxyribonucleoside
  • Adenocor
  • Adenosin
  • Adenosina
  • Adénosine
  • Adenosinum
  • Adenyldeoxyriboside
  • Ado
  • beta-D-Adenosine
  • Deoxyadenosine
  • Desoxyadenosine
External IDs
SR 96225 / SR-96225 / USAF CB-10
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AdenocardSolution3 mg/mLIntravenousRemedy Repack2015-08-182017-09-05Us
AdenocardSolution3 mg/mLIntravenousAstellas Pharma Inc1989-10-30Not applicableUs
AdenocardSolution6 mg/2mLIntravenousCardinal Health1989-10-30Not applicableUs
AdenocardSolution3 mg/mLIntravenousCardinal Health1989-10-30Not applicableUs
Adenocard - Liq Rapid Bolus IV 3mg/mlSolution3 mgIntravenousAstellas Pharma Inc1996-08-142014-12-05Canada
Adenocard Injection -pre-filled SyringeSolution3 mgIntravenousAstellas Pharma Inc1994-12-31Not applicableCanada
Adenocard Liq IV 3mg/mlLiquid3 mgIntravenousFujisawa Pharmaceutical Co, Division Of Fujisawa Canada Inc.1993-12-311996-09-09Canada
Adenocard Liq IV 3mg/ml (pre-filled Syringe)Liquid3 mgIntravenousFujisawa Pharmaceutical Co, Division Of Fujisawa Canada Inc.1994-12-311996-09-09Canada
AdenoscanSolution3 mg/mLIntravenousAstellas Pharma Inc1995-05-18Not applicableUs
AdenoscanSolution3 mg/mLIntravenousRemedy Repack2013-06-102016-10-13Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AdenosineInjection, solution3 mg/mLIntravenousRemedy Repack2014-05-232016-12-16Us
AdenosineInjection, solution3 mg/mLIntravenousGeneral Injectables & Vaccines2011-10-05Not applicableUs
AdenosineInjection3 mg/mLIntravenousWest Ward Pharmaceutical2004-06-16Not applicableUs
AdenosineInjection3 mg/mLIntravenousWockhardt2009-07-20Not applicableUs
AdenosineInjection, solution3 mg/mLIntravenousAkorn2014-10-02Not applicableUs
AdenosineInjection, solution3 mg/mLIntravenousAGILA SPECIALTIES PRIVATE LIMITED2014-03-22Not applicableUs
AdenosineInjection, solution3 mg/mLIntravenousCardinal Health2011-03-17Not applicableUs
AdenosineInjection, solution3 mg/mLIntravenousMylan Institutional2014-03-28Not applicableUs
AdenosineInjection3 mg/mLIntravenousSagent Pharmaceuticals2009-09-01Not applicableUs
AdenosineInjection, solution3 mg/mLIntravenousTeva Parenteral Medicines, Inc.2013-09-23Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
A.H.C Real Eye For FaceCream.12 mg/30mLTopicalCarver Korea Co.,Ltd.2013-06-21Not applicableUs
A.H.C. Collagen CreamCream20 mg/50mLTopicalCarver Korea Co.,Ltd.2013-08-15Not applicableUs
A.H.C. Collagen TonerLiquid48 mg/120mLTopicalCarver Korea Co.,Ltd.2013-08-15Not applicableUs
AdenosineInjection, solution3 mg/mLIntravenousCantrell Drug Company2015-02-05Not applicableUs
Advanced Snail 92 All in One CreamCream.04 mg/100mLTopicalCosrx Inc.2016-05-242017-06-29Us
AHC Collagen SerumLiquid12 mg/30mLTopicalCarver Korea Co.,Ltd.2013-08-15Not applicableUs
AHC Complex Choice EGF BoosterCream.4 mg/mLTopicalCarver Korea Co.,Ltd.2013-08-15Not applicableUs
AHC Complex Choice EGF BoosterCream.4 mg/mLTopicalCarver Korea Co.,Ltd.2013-08-15Not applicableUs
AHC Hydration Special Gen CreamCream20 mg/50mLTopicalCarver Korea Co.,Ltd.2013-07-15Not applicableUs
AHC Hydration Special Gen MaskLiquid12.8 mg/32gTopicalCarver Korea Co.,Ltd.2013-07-15Not applicableUs
International/Other Brands
Adenocard / Adenocor (Sanofi-Aventis) / Adenoject (Sun) / Adenoscan / Adenoz (Celon) / Adenozer (Purzer) / Adesin (Dae Han New Pharm) / Adrekar (Sanofi-Aventis) / Atépadène (Mayoly-Spindler) / Cardimax (AC Farma) / Cardiovert (Sanofi-Aventis) / Krenosin (Sanofi-Aventis) / Osiden (Square) / Pisdeno (Pisa)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
A.H.c Cotton 100 Mask Multi PeptideAdenosine (.01 g/25mL) + Allantoin (.025 g/25mL) + Nicotinamide (.05 g/25mL)PatchTopicalCarver Korea Co.,Ltd.2017-09-20Not applicableUs
A.H.c Cotton 100 Mask Skin CeramideAdenosine (.01 g/25mL) + Allantoin (.025 g/25mL) + Nicotinamide (.05 g/25mL)PatchTopicalCarver Korea Co.,Ltd.2017-09-05Not applicableUs
A.H.c Cotton 100 Mask Soy IsoflavoneAdenosine (.01 g/25mL) + Allantoin (.025 g/25mL) + Nicotinamide (.05 g/25mL)PatchTopicalCarver Korea Co.,Ltd.2017-09-14Not applicableUs
A.H.c Cotton 100 Mask Triple HyaluronicAdenosine (.01 g/25mL) + Allantoin (.025 g/25mL) + Nicotinamide (.05 g/25mL)PatchTopicalCarver Korea Co.,Ltd.2017-09-20Not applicableUs
Abalone Aqua Flood WaterAdenosine (.04 g/100mL) + Nicotinamide (2 g/100mL)CreamTopicalC&bcosmetic Co.,ltd.2017-02-16Not applicableUs
ABALONE CrystalDouble EXAdenosine (.04 g/100mL) + Nicotinamide (2 g/100mL)CreamTopicalC&bcosmetic Co.,ltd.2017-02-16Not applicableUs
Abalone Crystaldouble EX AmpouleAdenosine (.044 g/100mL) + Arbutin (2.2 g/100mL)LiquidTopicalC&bcosmetic Co.,ltd.2017-03-10Not applicableUs
Abalone Crystaldouble EX BbAdenosine (.04 g/100mL) + Nicotinamide (2 g/100mL) + Octinoxate (2 g/100mL) + Octocrylene (3 g/100mL) + Titanium dioxide (9.9 g/100mL)CreamTopicalC&bcosmetic Co.,ltd.2017-03-10Not applicableUs
Abalone Crystaldouble EX CcAdenosine (.04 g/100mL) + Nicotinamide (2 g/100mL) + Octinoxate (7 g/100mL) + Titanium dioxide (4.694 g/100mL)CreamTopicalC&bcosmetic Co.,ltd.2017-03-10Not applicableUs
Abalone Crystaldouble EX HommeAdenosine (.04 g/100mL) + Nicotinamide (2 g/100mL)CreamTopicalC&bcosmetic Co.,ltd.2017-02-20Not applicableUs
Categories
UNII
K72T3FS567
CAS number
58-61-7
Weight
Average: 267.2413
Monoisotopic: 267.096753929
Chemical Formula
C10H13N5O4
InChI Key
OIRDTQYFTABQOQ-KQYNXXCUSA-N
InChI
InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
IUPAC Name
(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
SMILES

Pharmacology

Indication

Used as an initial treatment for the termination of paroxysmal supraventricular tachycardia (PVST), including that associated with accessory bypass tracts, and is a drug of choice for terminating stable, narrow-complex supraventricular tachycardias (SVT). Also used as an adjunct to thallous chloride TI 201 myocardial perfusion scintigraphy (thallium stress test) in patients who are unable to exercise adequately, as well as an adjunct to vagal maneuvers and clinical assessment to establish a specific diagnosis of undefined, stable, narrow-complex SVT.

Structured Indications
Pharmacodynamics

Adenosine is an endogenous nucleoside occurring in all cells of the body and is not chemically related to other antiarrhythmic drugs. Adenosine may exert its pharmacologic effects by activation of purine (cell surface A1 and A2 adenosine) receptors, as well as relax vascular smooth muscles through the reduction in calcium uptake by inhibition of slow inward calcium current and activation of adenylate cyclase in smooth muscle cells. Adenosine may reduce vascular tone by modulation of sympathetic neurotransmission. The drug also has negative chronotropic, dromotropic, and inotropic effects on the heart by slowing conduction time throught he AV node and interrupting AV nodal reentry pathways. Adenosine is a potent vasodilator in most vascular beds, but vasoconstriction is produced in renal afferent arterioles and hepatic veins. The drug produces a net mild to moderate reduction in systolic, diastolic, and mean arterial blood pressure and a reflex increase in heart rate. Adenosine is antagonized competitively by methylxanthines such as caffeine and theophylline, and potentiated by blockers of nucleoside transport such as dipyridamole. Adenosine is not blocked by atropine.

Mechanism of action

Adenosine slows conduction time through the AV node and can interrupt the reentry pathways through the AV node, resulting in the restoration of normal sinus rhythm in patients with paroxysmal supraventricular tachycardia (PSVT), including PSVT associated with Wolff-Parkinson-White Syndrome. This effect may be mediated through the drug's activation of cell-surface A1 and A2 adenosine receptors. Adenosine also inhibits the slow inward calcium current and activation of adenylate cyclase in smooth muscle cells, thereby causing relaxation of vascular smooth muscle. By increasing blood flow in normal coronary arteries with little or no increase in stenotic arteries (with little to no increase in stenotic arteries), adenosine produces a relative difference in thallous (thallium) chloride TI 201 uptake in myocardium supplied by normal verus stenotic coronary arteries.

TargetActionsOrganism
AAdenosine receptor A2a
agonist
Human
AAdenosine receptor A2b
agonist
Human
AAdenosine receptor A3
agonist
Human
AAdenosine receptor A1
agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Intracellular adenosine is rapidly metabolized either via phosphorylation to adenosine monophosphate by adenosine kinase, or via deamination to inosine by adenosine deaminase in the cytosol.

Route of elimination
Not Available
Half life

Less than 10 secs

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)Disease
Lesch-Nyhan Syndrome (LNS)Disease
Myoadenylate deaminase deficiencyDisease
AICA-RibosiduriaDisease
Mercaptopurine Action PathwayDrug action
Thioguanine Action PathwayDrug action
Xanthinuria type IDisease
Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation typeDisease
Betaine MetabolismMetabolic
Cystathionine Beta-Synthase DeficiencyDisease
Intracellular Signalling Through Adenosine Receptor A2a and AdenosineSignaling
Gout or Kelley-Seegmiller SyndromeDisease
Azathioprine Action PathwayDrug action
Xanthinuria type IIDisease
Selenoamino Acid MetabolismMetabolic
Methionine MetabolismMetabolic
Purine MetabolismMetabolic
Adenosine Deaminase DeficiencyDisease
Xanthine Dehydrogenase Deficiency (Xanthinuria)Disease
Methionine Adenosyltransferase DeficiencyDisease
HypermethioninemiaDisease
Adenylosuccinate Lyase DeficiencyDisease
Molybdenum Cofactor DeficiencyDisease
Purine Nucleoside Phosphorylase DeficiencyDisease
S-Adenosylhomocysteine (SAH) Hydrolase DeficiencyDisease
Glycine N-methyltransferase DeficiencyDisease
Intracellular Signalling Through Adenosine Receptor A2b and AdenosineSignaling
Adenine phosphoribosyltransferase deficiency (APRT)Disease
Mitochondrial DNA depletion syndromeDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
Ambroxol acefyllinateThe therapeutic efficacy of Adenosine can be decreased when used in combination with Ambroxol acefyllinate.Experimental
AminophyllineThe therapeutic efficacy of Adenosine can be decreased when used in combination with Aminophylline.Approved
CaffeineThe therapeutic efficacy of Adenosine can be decreased when used in combination with Caffeine.Approved
CarbamazepineThe risk or severity of adverse effects can be increased when Carbamazepine is combined with Adenosine.Approved, Investigational
DigoxinThe risk or severity of adverse effects can be increased when Digoxin is combined with Adenosine.Approved
DipyridamoleThe risk or severity of adverse effects can be increased when Dipyridamole is combined with Adenosine.Approved
DyphyllineThe therapeutic efficacy of Adenosine can be decreased when used in combination with Dyphylline.Approved
NicotineNicotine may increase the atrioventricular blocking (AV block) activities of Adenosine.Approved
TheophyllineThe therapeutic efficacy of Adenosine can be decreased when used in combination with Theophylline.Approved
Food Interactions
  • Avoid caffeine containing foods and drinks.

References

Synthesis Reference

Giorgio Stramentinoli, Federico Gennari, "Process for preparing adenosine derivatives of anti-inflammatory and analgesic activity." U.S. Patent US4373097, issued October, 1965.

US4373097
General References
Not Available
External Links
Human Metabolome Database
HMDB00050
KEGG Drug
D00045
KEGG Compound
C00212
PubChem Compound
60961
PubChem Substance
46508728
ChemSpider
54923
BindingDB
14487
ChEBI
16335
ChEMBL
CHEMBL477
Therapeutic Targets Database
DAP000223
PharmGKB
PA448049
HET
ADN
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Adenosine
ATC Codes
C01EB10 — Adenosine
AHFS Codes
  • 24:04.04.24 — Class IV Antiarrythmics
  • 24:04.92 — Miscellaneous Cardiac Drugs
  • 92:00.00 — Miscellaneous Therapeutic Agents
PDB Entries
1bx4 / 1d4f / 1dgm / 1fmo / 1ho5 / 1jdv / 1jg2 / 1jg3 / 1lii / 1lik
show 138 more
FDA label
Download (154 KB)
MSDS
Download (72.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceBlood Pressures / Cognition1
0CompletedDiagnosticMyocardial Ischemia / Vascular Diseases1
1CompletedNot AvailableCoronary Artery Disease1
1CompletedDiagnosticCoronary Artery Disease1
1CompletedTreatmentAtrioventricular Block / Sinus Bradycardia1
1TerminatedOtherInflammatory Reaction1
1, 2CompletedTreatmentAdenosine / Cardiac Surgical Procedures / Heart Defects,Congenital / Myocardial Reperfusion Injury1
1, 2CompletedTreatmentAngina Pectoris1
1, 2Unknown StatusNot AvailableNeoplasms, Hepatic1
2Active Not RecruitingTreatmentCancer, Breast1
2CompletedPreventionST Elevation Myocardial Infarction (STEMI)1
2CompletedTreatmentHealthy Volunteers1
2CompletedTreatmentNonvalvular Atrial Fibrillation1
2CompletedTreatmentPain1
2CompletedTreatmentPerioperative Pain1
2CompletedTreatmentTiredness1
2RecruitingPreventionPathological Processes / Prophylaxis of cardiomyopathy1
2RecruitingTreatmentMicrovascular coronary artery disease1
2RecruitingTreatmentTakotsubo Cardiomyopathy1
2Unknown StatusNot AvailableIschaemic Heart Diseases1
2Unknown StatusTreatmentAcute ST Elevation Myocardial Infarction1
2, 3CompletedDiagnosticCoronary Artery Atherosclerosis / Heart Disease, Ischemic1
2, 3CompletedTreatmentMyocardial Infarction (MI)1
3CompletedDiagnosticCoronary Artery Disease5
3CompletedDiagnosticOrthotopic Heart Transplant1
3CompletedPreventionCoronary Angioplasty1
3CompletedTreatmentAcute Myocardial Infarction (AMI)1
3TerminatedDiagnosticCoronary Artery Disease2
3TerminatedPreventionCoronary Artery Disease / Coronary Artery Stenosis1
3Unknown StatusTreatmentPercutaneous Coronary Intervention / Stable Angina (SA)1
4RecruitingBasic ScienceHypertrophic Cardiomyopathy / Microvascular Ischaemia of Myocardium / Non-ischemic Dilated Cardiomyopathy1
4RecruitingDiagnosticPremature Ventricular Contraction (PVC)1
4RecruitingTreatmentResistant Hypertension1
Not AvailableCompletedNot AvailableCoronary Artery Disease1
Not AvailableCompletedNot AvailableType 2 Diabetes Mellitus1
Not AvailableCompletedDiagnosticBMI >30 kg/m2 / Decreased Vascular Flow / Endothelial Dysfunction1
Not AvailableCompletedDiagnosticCoronary Artery Disease2
Not AvailableCompletedScreeningDiabetes Mellitus, Insulin-Dependent / Ischemia-Reperfusion Injury1
Not AvailableCompletedSupportive CareNeoplasms, Breast / Neoplasms, Lung1
Not AvailableCompletedTreatmentHeart Failure, Unspecified / Peripheral Chemoreceptor Hypersensitivity1
Not AvailableCompletedTreatmentMicrocirculation / Physiology, Ocular1
Not AvailableRecruitingNot AvailableCoronary Artery Disease / Coronary Microvascular Disease1
Not AvailableRecruitingHealth Services ResearchMRI Scans1
Not AvailableSuspendedNot AvailableIschemia-Reperfusion Injury1
Not AvailableSuspendedNot AvailableTransient ischemia attacks1
Not AvailableUnknown StatusDiagnosticAtherosclerosis / Endothelial Dysfunction / Inflammatory Reaction / Myocardial Ischemia1
Not AvailableUnknown StatusTreatmentTachycardia, Supraventricular1

Pharmacoeconomics

Manufacturers
  • Astellas pharma us inc
  • Akorn inc
  • App pharmaceuticals llc
  • Baxter healthcare corp
  • Bedford laboratories div ben venue laboratories inc
  • Gland pharma ltd
  • Luitpold pharmaceuticals inc
  • Strides arcolab ltd
  • Teva parenteral medicines inc
  • Wockhardt ltd
Packagers
Dosage forms
FormRouteStrength
CreamTopical.12 mg/30mL
LiquidTopical48 mg/120mL
SolutionIntravenous6 mg/2mL
LiquidIntravenous3 mg
SolutionIntravenous3 mg/mL
InjectionIntravenous3 mg/mL
Injection, solutionIntravenous3 mg/mL
CreamTopical.04 mg/100mL
CreamTopical.4 mg/mL
CreamTopical20 mg/50mL
LiquidTopical12.8 mg/32g
LiquidTopical12 mg/30mL
LiquidTopical54 mg/135mL
LiquidTopical
LiquidTopical12 mg/30g
SolutionTopical.002 g/6mL
SolutionTopical2.8 mg/7mL
LiquidTopical.012 g/30mL
GelTopical
CreamTopical.04 g/100mL
LiquidTopical.05 g/130mL
CreamTopical.01 g/45mL
CreamTopical.02 g/50mL
CreamTopical.01 g/30mL
SolutionTopical1.2 mg/3mL
PatchTopical.008 g/20g
LiquidTopical.6 mg/6mL
CreamTopical.04 mL/100mL
CreamTopical.004 g/10g
GelTopical.04 g/100g
CreamTopical.03 g/95g
LiquidTopical20 mg/50mL
GelTopical.04 g/100mL
CreamTopical.04 g/100g
LiquidTopical6 mg/15mL
LiquidTopical.04 g/100mL
EmulsionTopical.04 g/100g
Solution / dropsTopical
CreamTopical
LiquidTopical.04 g/100g
KitTopical
CreamTopical.0428 g/100g
KitTopical
CreamTopical.2 g/100g
LiquidTopical2 mg/5mL
PatchTopical.01 g/25g
LiquidTopical25 mg/50mL
LiquidTopical.02 g/50mL
CreamTopical.0004 mL/mL
LiquidTopical.0004 mL/mL
CreamTopical.0004 g/g
EmulsionTopical.04 g/100mL
Kit
LotionTopical
PatchTopical.5 g/25g
CreamTopical6 g/150g
CreamTopical.004 mg/10g
CreamTopical.08 mg/20mL
PatchTopical.6 mg/3g
CreamTopical.02 mg/50mL
LiquidTopical.05 mg/125mL
PatchTopical.014 g/35g
CreamTopical.01 g/27g
LiquidTopical.04 mg/100mL
LipstickTopical.001 g/3.5g
PatchTopical
LiquidTopical.00012 mg/.3mL
CreamTopical.00012 mg/.3mL
CreamTopical.011 mg/27mL
CreamTopical.001 mg/2.5mL
OilTopical.01 g/30mL
SolutionIntravenous3 mg
CreamTopical.0004 1/100mL
OilTopical
SolutionTopical
CreamTopical.01 g/25g
PatchTopical1 g/100g
SprayTopical
CreamTopical.018 g/45mL
CreamTopical.012 g/30mL
CreamTopical.4 mg/g
CreamTopical.002 g/10g
CreamTopical.04 mL/mL
LotionTopical.05 g/100mL
CreamTopical.05 g/100mL
PatchTopical.01 g/25mL
LiquidTopical.001 g/3mL
PatchTopical.009 g/24mL
PatchTopical.008 g/20mL
LiquidTopical.001 g/4mL
LotionTopical1 mg/150mL
LiquidTopical.04 mL/100mL
CreamTopical.02 g/50g
CreamTopical.024 g/60g
PowderTopical
EmulsionTopical
EmulsionTopical.06 g/150mL
LiquidTopical.06 g/150mL
Prices
Unit descriptionCostUnit
Adenosine-5 monophosphate19.74USD g
Adenosine powder15.86USD g
Adenoscan 3 mg/ml vial10.09USD ml
Adenosine 12 mg/4 ml vial8.44USD ml
Adenosine 6 mg/2 ml vial8.1USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5731296No1995-03-242015-03-24Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)235.5 °CPhysProp
water solubility8230 mg/LNot Available
logP-1.05HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility14.0 mg/mLALOGPS
logP-1.2ALOGPS
logP-2.1ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area139.54 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.2 m3·mol-1ChemAxon
Polarizability25.27 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9227
Blood Brain Barrier+0.9383
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.7026
P-glycoprotein inhibitor INon-inhibitor0.966
P-glycoprotein inhibitor IINon-inhibitor0.9533
Renal organic cation transporterNon-inhibitor0.9444
CYP450 2C9 substrateNon-substrate0.8639
CYP450 2D6 substrateNon-substrate0.8349
CYP450 3A4 substrateNon-substrate0.5866
CYP450 1A2 substrateNon-inhibitor0.9667
CYP450 2C9 inhibitorNon-inhibitor0.9595
CYP450 2D6 inhibitorNon-inhibitor0.977
CYP450 2C19 inhibitorNon-inhibitor0.9514
CYP450 3A4 inhibitorNon-inhibitor0.962
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9701
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9182
BiodegradationNot ready biodegradable0.9738
Rat acute toxicity1.9715 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.989
hERG inhibition (predictor II)Non-inhibitor0.9102
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9.12 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)GC-MSsplash10-0f7w-1890000000-5c70a5423faa5e8eceaf
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)GC-MSsplash10-001v-0691000000-8f88854b7d5adec5c558
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-001s-0790000000-cc3bcd977e11efd4ea25
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)GC-MSsplash10-00di-9460000000-3ae19bfaa5d2df72f9b1
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0gc0-0590000000-05874cecded3009c1f4d
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-0fsv-1792000000-b37fd6826f28aaf9e825
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0f7w-1890000000-5c70a5423faa5e8eceaf
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-001v-0691000000-8f88854b7d5adec5c558
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-001s-0790000000-cc3bcd977e11efd4ea25
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-9460000000-3ae19bfaa5d2df72f9b1
GC-MS Spectrum - GC-MSGC-MSsplash10-0gc0-0590000000-05874cecded3009c1f4d
GC-MS Spectrum - GC-MSGC-MSsplash10-0fsv-1792000000-b37fd6826f28aaf9e825
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-014r-0890000000-588861a9494ab4680698
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-000i-1900000000-dd7cbed8e76c6e783831
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-000i-2900000000-c6644520b5943b59403d
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-014i-0090000000-3d4fd8ea211eaed10531
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-cb58ec56a5faa09c9a02
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-9559aa07ec13a688fb16
LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , PositiveLC-MS/MSsplash10-000i-0900000000-f7c1371d8e1058df3a32
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-001i-0940000000-da71247788bf1ba222e2
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-001i-0920000000-f2e8ec028abdd674b5e3
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-001i-0910000000-815ed65588c07415cd65
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-001i-1910000000-2780e737da8848411c4f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-053r-1900000000-c6c1128990661334c15b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-014i-0090000000-106e7131507fadd4befb
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-000i-0910000000-1c53823486cd2c23f90e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-000i-0900000000-f0313435db4847490fd6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-000i-1900000000-dcd4c2972882dcd7535a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-000i-2900000000-5ee474864189cef6df64
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-000i-0900000000-17edf36faf6eb5750912
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-000i-0900000000-0591143763a0bad31c23
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-014i-0290000000-f1d71a97ce39145c8e31
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-00kr-0950000000-9bbdbb14aed287ad5ac8
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-001i-0910000000-35f90965f1f3c2b3236b
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-000i-0900000000-f360cca994696d7ae735
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0910000000-65268017a112bc263b5e
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0900000000-375c0e137f7068cf49af
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0900000000-ad5db8e5cbaacc341347
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0900000000-718be441310a581854a6
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-0900000000-765c0fccf80d24951ef9
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-053r-2900000000-2f0ca594f7cc031e54e7
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0940000000-da71247788bf1ba222e2
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0920000000-f2e8ec028abdd674b5e3
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-0910000000-815ed65588c07415cd65
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001i-1910000000-bbdd67de0fcb7c302c8f
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-053r-1900000000-2c12434eaabba59a0a6c
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-001i-0910000000-35f90965f1f3c2b3236b
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-001i-0980000000-56af5755b924f7c42369
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-001i-0980000000-25acc7da5b6ea2bee529
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-001i-3900000000-602d3adcf68051f2992d
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-001i-4900000000-85777953862ffa85a828
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-014i-0090000000-8c7c25ea99344e167af5
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-014i-0090000000-2de6609bcaad91b510b5
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00kr-0940000000-a6eb3acc66bfb4687127
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0900000000-38a0b51e84259a90e0bf
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0900000000-95ff80024f6f3ecb8b96
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0900000000-54121dd1ddff8baeedbd
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0900000000-bc944eede02f73a9f09c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-1900000000-bf97b22e23b479deb25b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0490000000-47f7a73ecc9fc3610eac
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-e43eddf41f22caa830b7
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-5ff3043042220443b986
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-7157f8ad056eb2a71278
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-a82c9cbf7a2ae7b92911
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00kr-0960000000-c27288ef88b7c9fada7c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-b9c204c25a40d0b9d54e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-d29b79bb7074f6b6007f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-0090000000-106e7131507fadd4befb
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-0910000000-1c53823486cd2c23f90e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-0900000000-f0313435db4847490fd6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-1900000000-23bcec0b5be3fa4e10ed
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-2900000000-60219ac7d9220e297492
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-000i-0900000000-cda34117888d584ca7b7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0910000000-83e1685b54e8f76906fd
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0920000000-985897f3309c69d2acfb
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0930000000-9e6777212cb3a21a3a83
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0940000000-a9e90a868ea4f0f6fdb3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-cb58ec56a5faa09c9a02
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-9559aa07ec13a688fb16
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-f7c1371d8e1058df3a32
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0290000000-f1d71a97ce39145c8e31
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00kr-0950000000-9bbdbb14aed287ad5ac8
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-f360cca994696d7ae735
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0900000000-fef79893c00d065702b7
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0900000000-ea11cf8ac5af935bddf7
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-02t9-0294000000-abb236da520f6aef0219
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-014i-0092000000-d2d13a36535aa8fc719b
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-03fr-0039520000-ff390a49e70c3ce16d6d
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-01t9-0039810000-72148f451c6faa94b6a0
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-3900000000-d46a6ac68cff3d0c9020
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleosides
Sub Class
Not Available
Direct Parent
Purine nucleosides
Alternative Parents
Glycosylamines / Pentoses / 6-aminopurines / Aminopyrimidines and derivatives / N-substituted imidazoles / Imidolactams / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Oxacyclic compounds
show 5 more
Substituents
Purine nucleoside / Glycosyl compound / N-glycosyl compound / 6-aminopurine / Pentose monosaccharide / Imidazopyrimidine / Purine / Aminopyrimidine / Monosaccharide / N-substituted imidazole
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
adenosines (CHEBI:16335) / Ribonucleosides (C00212)

Targets

Details
1. Adenosine receptor A2a
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Identical protein binding
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
Gene Name
ADORA2A
Uniprot ID
P29274
Uniprot Name
Adenosine receptor A2a
Molecular Weight
44706.925 Da
References
  1. Trincavelli ML, Daniele S, Martini C: Adenosine receptors: what we know and what we are learning. Curr Top Med Chem. 2010;10(9):860-77. [PubMed:20370662]
  2. Schenone S, Brullo C, Musumeci F, Bruno O, Botta M: A1 receptors ligands: past, present and future trends. Curr Top Med Chem. 2010;10(9):878-901. [PubMed:20370661]
  3. Ezeamuzie CI, Khan I: The role of adenosine A(2) receptors in the regulation of TNF-alpha production and PGE(2) release in mouse peritoneal macrophages. Int Immunopharmacol. 2007 Apr;7(4):483-90. Epub 2006 Dec 29. [PubMed:17321471]
  4. Kreckler LM, Wan TC, Ge ZD, Auchampach JA: Adenosine inhibits tumor necrosis factor-alpha release from mouse peritoneal macrophages via A2A and A2B but not the A3 adenosine receptor. J Pharmacol Exp Ther. 2006 Apr;317(1):172-80. Epub 2005 Dec 9. [PubMed:16339914]
  5. Kreckler LM, Gizewski E, Wan TC, Auchampach JA: Adenosine suppresses lipopolysaccharide-induced tumor necrosis factor-alpha production by murine macrophages through a protein kinase A- and exchange protein activated by cAMP-independent signaling pathway. J Pharmacol Exp Ther. 2009 Dec;331(3):1051-61. doi: 10.1124/jpet.109.157651. Epub 2009 Sep 11. [PubMed:19749080]
  6. Buenestado A, Grassin Delyle S, Arnould I, Besnard F, Naline E, Blouquit-Laye S, Chapelier A, Bellamy JF, Devillier P: The role of adenosine receptors in regulating production of tumour necrosis factor-alpha and chemokines by human lung macrophages. Br J Pharmacol. 2010 Mar;159(6):1304-11. doi: 10.1111/j.1476-5381.2009.00614.x. Epub 2010 Feb 5. [PubMed:20136829]
  7. Funakoshi H, Zacharia LC, Tang Z, Zhang J, Lee LL, Good JC, Herrmann DE, Higuchi Y, Koch WJ, Jackson EK, Chan TO, Feldman AM: A1 adenosine receptor upregulation accompanies decreasing myocardial adenosine levels in mice with left ventricular dysfunction. Circulation. 2007 May 1;115(17):2307-15. Epub 2007 Apr 16. [PubMed:17438146]
  8. Haschemi A, Wagner O, Marculescu R, Wegiel B, Robson SC, Gagliani N, Gallo D, Chen JF, Bach FH, Otterbein LE: Cross-regulation of carbon monoxide and the adenosine A2a receptor in macrophages. J Immunol. 2007 May 1;178(9):5921-9. [PubMed:17442976]
Details
2. Adenosine receptor A2b
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
G-protein coupled adenosine receptor activity
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
Gene Name
ADORA2B
Uniprot ID
P29275
Uniprot Name
Adenosine receptor A2b
Molecular Weight
36332.655 Da
References
  1. Trincavelli ML, Daniele S, Martini C: Adenosine receptors: what we know and what we are learning. Curr Top Med Chem. 2010;10(9):860-77. [PubMed:20370662]
  2. Schenone S, Brullo C, Musumeci F, Bruno O, Botta M: A1 receptors ligands: past, present and future trends. Curr Top Med Chem. 2010;10(9):878-901. [PubMed:20370661]
  3. Ezeamuzie CI, Khan I: The role of adenosine A(2) receptors in the regulation of TNF-alpha production and PGE(2) release in mouse peritoneal macrophages. Int Immunopharmacol. 2007 Apr;7(4):483-90. Epub 2006 Dec 29. [PubMed:17321471]
  4. Kreckler LM, Wan TC, Ge ZD, Auchampach JA: Adenosine inhibits tumor necrosis factor-alpha release from mouse peritoneal macrophages via A2A and A2B but not the A3 adenosine receptor. J Pharmacol Exp Ther. 2006 Apr;317(1):172-80. Epub 2005 Dec 9. [PubMed:16339914]
  5. Buenestado A, Grassin Delyle S, Arnould I, Besnard F, Naline E, Blouquit-Laye S, Chapelier A, Bellamy JF, Devillier P: The role of adenosine receptors in regulating production of tumour necrosis factor-alpha and chemokines by human lung macrophages. Br J Pharmacol. 2010 Mar;159(6):1304-11. doi: 10.1111/j.1476-5381.2009.00614.x. Epub 2010 Feb 5. [PubMed:20136829]
  6. Funakoshi H, Zacharia LC, Tang Z, Zhang J, Lee LL, Good JC, Herrmann DE, Higuchi Y, Koch WJ, Jackson EK, Chan TO, Feldman AM: A1 adenosine receptor upregulation accompanies decreasing myocardial adenosine levels in mice with left ventricular dysfunction. Circulation. 2007 May 1;115(17):2307-15. Epub 2007 Apr 16. [PubMed:17438146]
  7. Haschemi A, Wagner O, Marculescu R, Wegiel B, Robson SC, Gagliani N, Gallo D, Chen JF, Bach FH, Otterbein LE: Cross-regulation of carbon monoxide and the adenosine A2a receptor in macrophages. J Immunol. 2007 May 1;178(9):5921-9. [PubMed:17442976]
Details
3. Adenosine receptor A3
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
G-protein coupled adenosine receptor activity
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibits adenylyl cyclase. Possible role in reproduction.
Gene Name
ADORA3
Uniprot ID
P0DMS8
Uniprot Name
Adenosine receptor A3
Molecular Weight
36184.175 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Trincavelli ML, Daniele S, Martini C: Adenosine receptors: what we know and what we are learning. Curr Top Med Chem. 2010;10(9):860-77. [PubMed:20370662]
  3. Schenone S, Brullo C, Musumeci F, Bruno O, Botta M: A1 receptors ligands: past, present and future trends. Curr Top Med Chem. 2010;10(9):878-901. [PubMed:20370661]
  4. Ezeamuzie CI, Khan I: The role of adenosine A(2) receptors in the regulation of TNF-alpha production and PGE(2) release in mouse peritoneal macrophages. Int Immunopharmacol. 2007 Apr;7(4):483-90. Epub 2006 Dec 29. [PubMed:17321471]
  5. Kreckler LM, Wan TC, Ge ZD, Auchampach JA: Adenosine inhibits tumor necrosis factor-alpha release from mouse peritoneal macrophages via A2A and A2B but not the A3 adenosine receptor. J Pharmacol Exp Ther. 2006 Apr;317(1):172-80. Epub 2005 Dec 9. [PubMed:16339914]
  6. Buenestado A, Grassin Delyle S, Arnould I, Besnard F, Naline E, Blouquit-Laye S, Chapelier A, Bellamy JF, Devillier P: The role of adenosine receptors in regulating production of tumour necrosis factor-alpha and chemokines by human lung macrophages. Br J Pharmacol. 2010 Mar;159(6):1304-11. doi: 10.1111/j.1476-5381.2009.00614.x. Epub 2010 Feb 5. [PubMed:20136829]
  7. Funakoshi H, Zacharia LC, Tang Z, Zhang J, Lee LL, Good JC, Herrmann DE, Higuchi Y, Koch WJ, Jackson EK, Chan TO, Feldman AM: A1 adenosine receptor upregulation accompanies decreasing myocardial adenosine levels in mice with left ventricular dysfunction. Circulation. 2007 May 1;115(17):2307-15. Epub 2007 Apr 16. [PubMed:17438146]
  8. Haschemi A, Wagner O, Marculescu R, Wegiel B, Robson SC, Gagliani N, Gallo D, Chen JF, Bach FH, Otterbein LE: Cross-regulation of carbon monoxide and the adenosine A2a receptor in macrophages. J Immunol. 2007 May 1;178(9):5921-9. [PubMed:17442976]
Details
4. Adenosine receptor A1
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Purine nucleoside binding
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
ADORA1
Uniprot ID
P30542
Uniprot Name
Adenosine receptor A1
Molecular Weight
36511.325 Da
References
  1. Trincavelli ML, Daniele S, Martini C: Adenosine receptors: what we know and what we are learning. Curr Top Med Chem. 2010;10(9):860-77. [PubMed:20370662]
  2. Schenone S, Brullo C, Musumeci F, Bruno O, Botta M: A1 receptors ligands: past, present and future trends. Curr Top Med Chem. 2010;10(9):878-901. [PubMed:20370661]
  3. Ezeamuzie CI, Khan I: The role of adenosine A(2) receptors in the regulation of TNF-alpha production and PGE(2) release in mouse peritoneal macrophages. Int Immunopharmacol. 2007 Apr;7(4):483-90. Epub 2006 Dec 29. [PubMed:17321471]
  4. Buenestado A, Grassin Delyle S, Arnould I, Besnard F, Naline E, Blouquit-Laye S, Chapelier A, Bellamy JF, Devillier P: The role of adenosine receptors in regulating production of tumour necrosis factor-alpha and chemokines by human lung macrophages. Br J Pharmacol. 2010 Mar;159(6):1304-11. doi: 10.1111/j.1476-5381.2009.00614.x. Epub 2010 Feb 5. [PubMed:20136829]
  5. Funakoshi H, Zacharia LC, Tang Z, Zhang J, Lee LL, Good JC, Herrmann DE, Higuchi Y, Koch WJ, Jackson EK, Chan TO, Feldman AM: A1 adenosine receptor upregulation accompanies decreasing myocardial adenosine levels in mice with left ventricular dysfunction. Circulation. 2007 May 1;115(17):2307-15. Epub 2007 Apr 16. [PubMed:17438146]
  6. Haschemi A, Wagner O, Marculescu R, Wegiel B, Robson SC, Gagliani N, Gallo D, Chen JF, Bach FH, Otterbein LE: Cross-regulation of carbon monoxide and the adenosine A2a receptor in macrophages. J Immunol. 2007 May 1;178(9):5921-9. [PubMed:17442976]

Enzymes

Details
1. Adenosine deaminase
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Zinc ion binding
Specific Function
Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, an...
Gene Name
ADA
Uniprot ID
P00813
Uniprot Name
Adenosine deaminase
Molecular Weight
40764.13 Da
References
  1. Kopff M, Kopff A, Puczkowski S: [Adenosine deaminase: isoenzymes ADA1 and ADA2]. Pol Merkur Lekarski. 1997 Dec;3(18):288-90. [PubMed:9523470]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Poly(a) rna binding
Specific Function
ATP dependent phosphorylation of adenosine and other related nucleoside analogs to monophosphate derivatives. Serves as a potential regulator of concentrations of extracellular adenosine and intrac...
Gene Name
ADK
Uniprot ID
P55263
Uniprot Name
Adenosine kinase
Molecular Weight
40545.075 Da
References
  1. Boison D: Adenosine kinase, epilepsy and stroke: mechanisms and therapies. Trends Pharmacol Sci. 2006 Dec;27(12):652-8. Epub 2006 Oct 23. [PubMed:17056128]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Pyrimidine- and adenine-specific:sodium symporter activity
Specific Function
Sodium-dependent, pyrimidine- and purine-selective. Involved in the homeostasis of endogenous nucleosides. Exhibits the transport characteristics of the nucleoside transport system cib or N3 subtyp...
Gene Name
SLC28A3
Uniprot ID
Q9HAS3
Uniprot Name
Solute carrier family 28 member 3
Molecular Weight
76929.61 Da
References
  1. Badagnani I, Chan W, Castro RA, Brett CM, Huang CC, Stryke D, Kawamoto M, Johns SJ, Ferrin TE, Carlson EJ, Burchard EG, Giacomini KM: Functional analysis of genetic variants in the human concentrative nucleoside transporter 3 (CNT3; SLC28A3). Pharmacogenomics J. 2005;5(3):157-65. [PubMed:15738947]

Drug created on June 13, 2005 07:24 / Updated on October 21, 2017 19:24