Adenosine

Identification

Summary

Adenosine is a medication used in myocardial perfusion scintigraphy and to treat supraventricular tachycardia.

Brand Names
Adenocard, Viva-drops Lubricating Eye Drops
Generic Name
Adenosine
DrugBank Accession Number
DB00640
Background

The structure of adenosine was first described in 1931,7 though the vasodilating effects were not described in literature until the 1940s.8 Adenosine is indicated as an adjunct to thallium-201 in myocardial perfusion scintigraphy,12 though it is rarely used in this indication, having largely been replaced by dipyridamole and [regadenson].9,10 Adenosine is also indicated in the treatment of supraventricular tachycardia.13

Adenosine was granted FDA approval on 30 October 1989.11

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 267.2413
Monoisotopic: 267.096753929
Chemical Formula
C10H13N5O4
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
  • 9-β-D-ribofuranosyl-9H-purin-6-amine
  • Ade-Rib
  • Adenin riboside
  • Adenine Deoxyribonucleoside
  • Adenogesic
  • Adenosin
  • Adenosina
  • Adénosine
  • Adenosine
  • Adenosinum
  • Ado
  • beta-D-Adenosine
External IDs
  • SR 96225
  • SR-96225
  • USAF CB-10

Pharmacology

Indication

Adenosine is indicated as an adjunct to thallium-201 in myocardial perfusion scintigraphy in patients unable to adequately exercise.12 It is also indicated to convert sinus rhythm of paroxysmal supraventricular tachycardia.13

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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Adenosine is indicated as an adjunct to thallium-201 in myocardial perfusion scintigraphy and also indicated for conversion of sinus rhythm of paroxysmal supraventricular tachycardia.12,13 Adenosine has a short duration of action as the half life is <10 seconds, and a wide therapeutic window.12,13 Patients should be counselled regarding the risk of cardiovascular side effects, bronchoconstriction, seizures, and hypersensitivity.12,13

Mechanism of action

Agonism of adenosine receptors A1 and A2 reduces conduction time in the atrioventricular node of the heart.4,6,12 Conduction time is decreased by inducing potassium efflux and inhibiting calcium influx through channels in nerve cells, leading to hyperpolarization and and increased threshold for calcium dependent action potentials.4 Decreased conduction time leads to an antiarrhythmic effect.4 Inhibition of calcium influx, reduces the activity of adenylate cyclase, relaxing vascular smooth muscle.6 Relaxed vascular smooth muscle leads to increased blood flow through normal coronary arteries but not stenotic arteries, allowing thallium-201 to be more readily uptaken in normal coronary arteries.12

TargetActionsOrganism
AAdenosine receptor A1
agonist
Humans
AAdenosine receptor A2a
agonist
Humans
AAdenosine receptor A2b
agonist
Humans
AAdenosine receptor A3
agonist
Humans
Absorption

Data regarding the absorption of adenosine are not readily available.5

Volume of distribution

Data regarding the volume of distribution of adenosine are not readily available.5

Protein binding

Adenosine is bound to albumin in plasma, however data regarding the extent of binding are not readily available.3

Metabolism

Adenosine can be phosphorylated by adenosine kinase to form adenosine monophosphate.1,12 From there, it is phosphorylated again by adenylate kinase 1 to form adenosine diphosphate, and again by nucleoside diphosphate kinase A or B to form adenosine triphosphate.1,12

Alternatively, adenosine can be deaminated by adenosine deaminase to form inosine.1,12 Iosine is phosphorylated by purine nucleoside phosphorylase to form hypoxanthine.1,12 Hypoxanthine undergoes oxidation by xanthine dehydrogenase twice to form the metabolites xanthine, followed by uric acid.2,12

Hover over products below to view reaction partners

Route of elimination

Adenosine is predominantly eliminated in the urine as uric acid.2,12

Half-life

The half life of adenosine in blood is less than 10 seconds.12

Clearance

Data regarding the clearance of adenosine are not readily available.5

Adverse Effects
Adverseeffects
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Toxicity

Patients experiencing an overdose of adenosine may present with asystole, heart block, or cardiac ischemia; though the effects are generally short lived.4 Patients experiencing an overdose should be treated with symptomatic and supportive care, which may include a slow intravenous injection of theophylline.12

The LD50 in mice is >20 g/kg subcutaneously, 500mg/kg intraperitoneally, and 39.6 µg/kg subcutaneously.[L32048]

Pathways
PathwayCategory
Methionine MetabolismMetabolic
Adenosine Deaminase DeficiencyDisease
AICA-RibosiduriaDisease
Molybdenum Cofactor DeficiencyDisease
Methionine Adenosyltransferase DeficiencyDisease
Azathioprine Action PathwayDrug action
Thioguanine Action PathwayDrug action
Xanthinuria Type IIDisease
Adenylosuccinate Lyase DeficiencyDisease
S-Adenosylhomocysteine (SAH) Hydrolase DeficiencyDisease
Xanthine Dehydrogenase Deficiency (Xanthinuria)Disease
Glycine N-Methyltransferase DeficiencyDisease
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD)Disease
HypermethioninemiaDisease
Xanthinuria Type IDisease
Mitochondrial DNA Depletion SyndromeDisease
Myoadenylate Deaminase DeficiencyDisease
Homocystinuria-Megaloblastic Anemia Due to Defect in Cobalamin Metabolism, cblG Complementation TypeDisease
Selenoamino Acid MetabolismMetabolic
Purine MetabolismMetabolic
Betaine MetabolismMetabolic
Cystathionine beta-Synthase DeficiencyDisease
Purine Nucleoside Phosphorylase DeficiencyDisease
Intracellular Signalling Through Adenosine Receptor A2a and AdenosineSignaling
Intracellular Signalling Through Adenosine Receptor A2b and AdenosineSignaling
Lesch-Nyhan Syndrome (LNS)Disease
Gout or Kelley-Seegmiller SyndromeDisease
Mercaptopurine Action PathwayDrug action
Adenine Phosphoribosyltransferase Deficiency (APRT)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololAdenosine may increase the arrhythmogenic activities of Acebutolol.
AcetyldigitoxinAcetyldigitoxin may increase the arrhythmogenic activities of Adenosine.
AclidiniumThe risk or severity of Tachycardia can be increased when Adenosine is combined with Aclidinium.
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Adenosine.
AjmalineAdenosine may increase the arrhythmogenic activities of Ajmaline.
AlfuzosinThe risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Adenosine.
AlimemazineThe risk or severity of QTc prolongation can be increased when Alimemazine is combined with Adenosine.
AmantadineThe risk or severity of QTc prolongation can be increased when Amantadine is combined with Adenosine.
AmifampridineThe risk or severity of QTc prolongation can be increased when Adenosine is combined with Amifampridine.
AminophyllineThe therapeutic efficacy of Adenosine can be decreased when used in combination with Aminophylline.
Interactions
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Food Interactions
  • Avoid caffeine. Caffeine may antagonise the activity of adenosine.

Products

Products2
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International/Other Brands
Adenocor (Sanofi-Aventis) / Adenoject (Sun) / 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)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AdenocardSolution3 mg/1mLIntravenousAstellas Pharma US, Inc.1989-10-30Not applicableUS flag
AdenocardSolution6 mg/2mLIntravenousCardinal Health1989-10-302019-01-31US flag
AdenocardSolution3 mg/1mLIntravenousCardinal Health1989-10-302018-01-31US flag
AdenocardSolution3 mg/1mLIntravenousRemedy Repack2015-08-182016-08-18US flag
Adenocard - Liq Rapid Bolus IV 3mg/mlSolution3 mg / mLIntravenousAstellas Pharma Inc1996-08-142014-12-05Canada flag
Adenocard Injection -pre-filled SyringeSolution3 mg / mLIntravenousAstellas Pharma Inc1994-12-31Not applicableCanada flag
Adenocard Liq IV 3mg/mlLiquid3 mg / mLIntravenousFujisawa Pharmaceutical Co, Division Of Fujisawa Canada Inc.1993-12-311996-09-09Canada flag
Adenocard Liq IV 3mg/ml (pre-filled Syringe)Liquid3 mg / mLIntravenousFujisawa Pharmaceutical Co, Division Of Fujisawa Canada Inc.1994-12-311996-09-09Canada flag
AdenoscanSolution3 mg/1mLIntravenousAstellas Pharma US, Inc.1995-05-182018-07-01US flag
AdenoscanSolution3 mg/1mLIntravenousRemedy Repack2013-06-102014-06-10US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AdenosineInjection, solution3 mg/1mLIntravenousNorthstar RxLLC2021-06-15Not applicableUS flag
AdenosineInjection, solution3 mg/1mLIntravenousGeneral Injectables & Vaccines, Inc2011-10-05Not applicableUS flag
AdenosineInjection3 mg/1mLIntravenousRemedy Repack2018-03-052018-03-05US flag
AdenosineInjection, solution3 mg/1mLIntravenousA-S Medication Solutions2011-03-15Not applicableUS flag
AdenosineInjection, solution3 mg/1mLIntravenousTeva Parenteral Medicines, Inc.2013-09-23Not applicableUS flag
AdenosineInjection3 mg/1mLIntravenousWockhardt2009-07-20Not applicableUS flag
AdenosineInjection, solution60 mg/20mLIntravenousMylan Institutional LLC2020-04-15Not applicableUS flag
AdenosineInjection, solution90 mg/30mLIntravenousAuroMedics Pharma LLC2017-11-02Not applicableUS flag
AdenosineInjection, solution3 mg/1mLIntravenousBedford Pharmaceuticals2004-06-172012-01-31US flag
AdenosineInjection3 mg/1mLIntravenousHF Acquisition Co LLC, DBA HealthFirst2021-01-21Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
9tails Premium Wrinkle Power LiftingLiquid0.04 g/100gTopicalELUO.CO.,Ltd.2019-10-28Not applicableUS flag
A.H.C Real Eye For FaceCream0.12 mg/30mLTopicalCarver Korea Co Ltd2013-06-212018-12-01US flag
A.H.C. Collagen CreamCream20 mg/50mLTopicalCarver Korea Co.,Ltd2013-08-152018-12-01US flag
A.H.C. Collagen TonerLiquid48 mg/120mLTopicalCarver Korea Co.,Ltd2013-08-152018-12-01US flag
Advanced Snail 92 All in One CreamCream0.04 mg/100mLTopicalCosrx Inc.2016-05-242017-06-28US flag
AHC Collagen SerumLiquid12 mg/30mLTopicalCarver Korea Co.,Ltd2013-08-152018-12-01US flag
AHC Complex Choice EGF BoosterCream0.4 mg/1mLTopicalCarver Korea Co.,Ltd.2013-08-152017-11-20US flag
AHC Complex Choice EGF BoosterCream0.4 mg/1mLTopicalCarver Korea Co.,Ltd.2013-08-152017-11-20US flag
AHC Hydration Special Gen CreamCream20 mg/50mLTopicalCarver Korea Co.,Ltd.2013-07-152017-11-04US flag
AHC Hydration Special Gen MaskLiquid12.8 mg/32gTopicalCarver Korea Co.,Ltd.2013-07-152017-11-04US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
A.H.c Cotton 100 Mask Multi PeptideAdenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL)PatchTopicalCarver Korea Co.,Ltd.2017-09-202018-12-01US flag
A.H.c Cotton 100 Mask Skin CeramideAdenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL)PatchTopicalCarver Korea Co.,Ltd.2017-09-052018-12-01US flag
A.H.c Cotton 100 Mask Soy IsoflavoneAdenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL)PatchTopicalCarver Korea Co.,Ltd.2017-09-142018-12-01US flag
A.H.c Cotton 100 Mask Triple HyaluronicAdenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL)PatchTopicalCarver Korea Co.,Ltd.2017-09-202018-12-01US flag
A.H.c Cotton 100 Mask Triple HyaluronicAdenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL)PatchTopicalCarver Korea Co.,Ltd.2017-09-202017-09-21US flag
A.mAdenosine (0.04 g/100mL) + Nicotinamide (2 g/100mL)CreamTopicalJ&J COMPANY2021-04-25Not applicableUS flag
AAPE Continuous RenewalAdenosine (0.02 g/50mL) + Nicotinamide (1.00 g/50mL)CreamTopicalProstemics Co., Ltd.2019-08-01Not applicableUS flag
AAPE Continuous Renewal EyeAdenosine (0.008 g/20mL) + Nicotinamide (0.40 g/20mL)CreamTopicalProstemics Co., Ltd.2019-08-01Not applicableUS flag
AAPE Continuous Renewal SerumAdenosine (0.01 g/40mL) + Nicotinamide (0.80 g/40mL)LiquidTopicalProstemics Co., Ltd.2019-08-01Not applicableUS flag
Abalone Aqua Flood WaterAdenosine (0.04 g/100mL) + Nicotinamide (2 g/100mL)CreamTopicalC&bcosmetic Co.,ltd.2017-02-16Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
9tails Premium Wrinkle Power LiftingAdenosine (0.04 g/100g)LiquidTopicalELUO.CO.,Ltd.2019-10-28Not applicableUS flag
A.H.c Cotton 100 Mask Multi PeptideAdenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL)PatchTopicalCarver Korea Co.,Ltd.2017-09-202018-12-01US flag
A.H.c Cotton 100 Mask Skin CeramideAdenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL)PatchTopicalCarver Korea Co.,Ltd.2017-09-052018-12-01US flag
A.H.c Cotton 100 Mask Soy IsoflavoneAdenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL)PatchTopicalCarver Korea Co.,Ltd.2017-09-142018-12-01US flag
A.H.c Cotton 100 Mask Triple HyaluronicAdenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL)PatchTopicalCarver Korea Co.,Ltd.2017-09-202017-09-21US flag
A.H.c Cotton 100 Mask Triple HyaluronicAdenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL)PatchTopicalCarver Korea Co.,Ltd.2017-09-202018-12-01US flag
A.H.C Real Eye For FaceAdenosine (0.12 mg/30mL)CreamTopicalCarver Korea Co Ltd2013-06-212018-12-01US flag
A.H.C. Collagen CreamAdenosine (20 mg/50mL)CreamTopicalCarver Korea Co.,Ltd2013-08-152018-12-01US flag
A.H.C. Collagen TonerAdenosine (48 mg/120mL)LiquidTopicalCarver Korea Co.,Ltd2013-08-152018-12-01US flag
A.mAdenosine (0.04 g/100mL) + Nicotinamide (2 g/100mL)CreamTopicalJ&J COMPANY2021-04-25Not applicableUS flag

Categories

ATC Codes
C01EB10 — Adenosine
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
6-aminopurine / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound / Heteroaromatic compound / Hydrocarbon derivative
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
adenosines (CHEBI:16335) / Ribonucleosides (C00212)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
K72T3FS567
CAS number
58-61-7
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
NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1

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
  1. Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. [Article]
  2. Maiuolo J, Oppedisano F, Gratteri S, Muscoli C, Mollace V: Regulation of uric acid metabolism and excretion. Int J Cardiol. 2016 Jun 15;213:8-14. doi: 10.1016/j.ijcard.2015.08.109. Epub 2015 Aug 14. [Article]
  3. Cui F, Wang J, Li F, Fan J, Qu G, Yao X, Lei B: Investigation of the Interaction between Adenosine and Human Serum Albumin by Fluorescent Spectroscopy and Molecular Modeling Chinese Journal of Chemistry. 2008 Apr 16;26(4):661-665. [Article]
  4. Singh S, McKintosh R: Adenosine . [Article]
  5. Uematsu T, Kozawa O, Matsuno H, Niwa M, Yoshikoshi H, Oh-uchi M, Kohno K, Nagashima S, Kanamaru M: Pharmacokinetics and tolerability of intravenous infusion of adenosine (SUNY4001) in healthy volunteers. Br J Clin Pharmacol. 2000 Aug;50(2):177-81. doi: 10.1046/j.1365-2125.2000.00214.x. [Article]
  6. Iskandrian AS: Adenosine myocardial perfusion imaging. J Nucl Med. 1994 Apr;35(4):734-6. [Article]
  7. Levene PA, Tipson RS: THE RING STRUCTURE OF ADENOSINE. Science. 1931 Nov 20;74(1925):521. doi: 10.1126/science.74.1925.521. [Article]
  8. SINGHER HO, MILLMAN N: The adenosine-triphosphatase activity of smooth muscle. Fed Proc. 1946;5(1 Pt 2):202. [Article]
  9. Notghi A, Low CS: Myocardial perfusion scintigraphy: past, present and future. Br J Radiol. 2011 Dec;84 Spec No 3:S229-36. doi: 10.1259/bjr/14625142. [Article]
  10. Palani G, Ananthasubramaniam K: Regadenoson: review of its established role in myocardial perfusion imaging and emerging applications. Cardiol Rev. 2013 Jan-Feb;21(1):42-8. doi: 10.1097/CRD.0b013e3182613db6. [Article]
  11. FDA Approved Drug Products: Adenocard (Adenosine) Intravenous Injection (Discontinued) [Link]
  12. FDA Approved Drug Products: Adenoscan (Adenosine) Intravenous Injection (Discontinued) [Link]
  13. Dailymed: Adenocard (Adenosine) Intravenous Injection [Link]
Human Metabolome Database
HMDB0000050
KEGG Drug
D00045
KEGG Compound
C00212
PubChem Compound
60961
PubChem Substance
46508728
ChemSpider
54923
BindingDB
14487
RxNav
296
ChEBI
16335
ChEMBL
CHEMBL477
ZINC
ZINC000002169830
Therapeutic Targets Database
DAP000223
PharmGKB
PA448049
PDBe Ligand
ADN
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Adenosine
PDB Entries
1bx4 / 1d4f / 1dgm / 1fmo / 1ho5 / 1jdv / 1jg2 / 1jg3 / 1lii / 1lik
show 166 more
FDA label
Download (154 KB)
MSDS
Download (72.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentAcute Coronary Syndrome (ACS) / No Reflow Phenomenon / Normotensive1
4CompletedTreatmentSupraventricular Tachycardia (SVT)1
4RecruitingDiagnosticPercutaneous Coronary Intervention (PCI)1
4RecruitingDiagnosticPremature Ventricular Contraction (PVC)1
4TerminatedBasic ScienceHypertrophic Cardiomyopathy (HCM) / Microvascular Ischaemia of Myocardium / Nonischemic Dilated Cardiomyopathy1
4TerminatedTreatmentResistant Hypertension1
3CompletedDiagnosticCoronary Artery Disease (CAD)6
3CompletedDiagnosticOrthotopic Heart Transplant1
3CompletedPreventionCoronary Angioplasty1
3CompletedTreatmentAcute Myocardial Infarction (AMI)1

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
  • APP Pharmaceuticals
  • A-S Medication Solutions LLC
  • Astellas Pharma Inc.
  • Baxter International Inc.
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • General Injectables and Vaccines Inc.
  • Gland Pharma Ltd.
  • Hospira Inc.
  • Physicians Total Care Inc.
  • Sagent Pharmaceuticals
  • Spectrum Pharmaceuticals
  • Strides Arcolab Limited
  • Teva Pharmaceutical Industries Ltd.
  • Wockhardt Ltd.
Dosage Forms
FormRouteStrength
CreamTopical0.12 mg/30mL
LiquidTopical48 mg/120mL
SoapTopical
SolutionIntravenous6 mg/2mL
LiquidIntravenous3 mg / mL
Injection, solutionIntravenous bolus
InjectionIntravenous6.0 mg/2ml
Solution
Solution3 mg/1ml
InjectionIntravenous30 mg/10ml
SolutionIntravenous3 mg/1mL
Injection, solutionParenteral
Injection, solutionIntravenous
SolutionIntravenous6 mg
Injection, solution6 MG/2ML
Injection, solution30 MG/10ML
Injection, solution3 MG/ML
InjectionIntravenous3 mg/1mL
Injection, solutionIntravenous3 mg/1mL
Injection, solutionIntravenous60 mg/20mL
Injection, solutionIntravenous90 mg/30mL
InjectionParenteral3 mg
CreamTopical0.04 mg/100mL
CreamTopical0.4 mg/1mL
CreamTopical20 mg/50mL
LiquidTopical12.8 mg/32g
LiquidTopical12 mg/30mL
LiquidTopical54 mg/135mL
LiquidTopical12 mg/30g
SolutionTopical0.002 g/6mL
SolutionTopical2.8 mg/7mL
CreamTopical0.012 g/30mL
LiquidTopical0.012 g/30mL
GelTopical
LiquidTopical0.05 g/130mL
CreamTopical0.01 g/45mL
CreamTopical0.02 g/50mL
CreamTopical0.01 g/30mL
SolutionTopical1.2 mg/3mL
CreamTopical0.03 g/100mL
PatchTopical0.04 g/100mL
EmulsionTopical0.04 g/120mL
EmulsionTopical0.0006 g/1.5mL
CreamTopical0.01 g/50mL
CreamTopical0.0003 g/1.5mL
LiquidTopical0.04 g/120mL
LiquidTopical0.0006 g/1.5mL
LiquidTopical0.6 mg/6mL
CreamTopical0.04 mL/100mL
CreamTopical0.004 g/10g
LiquidTopical0.04 g/100mL
GelTopical0.04 g/100g
PatchTopical0.01 g/25mL
CreamTopical0.03 g/95g
PatchTopical0.006 g/15g
PatchTopical0.008 g/20g
StickTopical0.003 g/9g
SolutionTopical
LiquidTopical20 mg/50mL
GelTopical0.04 g/100mL
CreamTopical0.04 g/100g
PatchTopical0.0016 g/4g
LotionTopical0.04 g/100g
LiquidTopical0.002 g/6mL
LiquidTopical0.001 g/3mL
CreamOral0.04 g/100mL
LiquidTopical6 mg/15mL
CreamTopical0.004 g/10mL
EmulsionTopical0.04 g/100g
CreamTopical0.04 g/100mL
PatchTopical0.001 g/2.8g
PatchTopical0.014 g/35g
PatchTopical0.003 g/8g
LiquidTopical0.04 g/100g
Solution / dropsTopical
CreamTopical0.0428 g/100g
CreamTopical0.2 g/100g
LiquidTopical2.0 mg/5mL
LiquidTopical25 mg/50mL
PatchTopical0.005 g/0.55g
KitTopical
EmulsionTopical
CreamTopical0.0004 g/1g
CreamTopical0.0004 g/1mL
LiquidTopical0.0004 g/1mL
LiquidVaginal15 g/100mL
EmulsionTopical0.05 g/130mL
CreamTopical0.04 g/120mL
Injection, solutionIntravenous6 MG/2ML
LotionTopical
Aerosol, sprayTopical
LiquidOral0.0435 g/100mL
PatchTopical0.5 g/25g
PatchTopical0.012 g/30g
CreamTopical6 g/150g
CreamTopical0.004 mg/10g
CreamTopical0.08 mg/20mL
StickTopical
PatchTopical0.6 mg/3g
CreamTopical0.02 mg/50mL
LiquidTopical0.05 mg/125mL
PatchTopical13.2 mg/33mL
CreamTopical10 mg/25mL
LiquidTopical16 mg/40mL
CreamTopical0.03 g/75mL
CreamTopical0.01 g/25mL
CreamTopical0.018 g/45mL
InjectionIntravenous bolus
CreamTopical
CreamTopical0.01 g/27g
LiquidTopical0.04 mg/100mL
LipstickTopical0.001 g/3.5g
LiquidTopical0.00012 mg/0.3mL
CreamTopical0.00012 mg/0.3mL
CreamTopical0.011 mg/27mL
CreamTopical0.001 mg/2.5mL
PatchTopical0.01 g/25g
OilTopical0.01 g/30mL
PatchTopical
LiquidTopical
CreamTopical0.012 g/30g
SolutionIntravenous3 mg / mL
CreamTopical0.0004 1/100mL
OilTopical
LiquidTopical0.02 g/50mL
PatchTopical0.01 g/27g
LiquidTopical0.02 g/50g
PatchTopical0.008 g/20mL
CreamTopical0.01 g/25g
PatchTopical1 g/100g
SprayTopical
CreamTopical0.4 mg/1g
CreamTopical0.002 g/10g
CreamTopical0.01 g/50g
CreamTopical0.04 mL/1mL
LiquidTopical0.0004 mL/1mL
LotionTopical0.05 g/100mL
CreamTopical0.05 g/100mL
LiquidTopical0.05 g/100mL
SolutionIntravenous3 mg
LiquidTopical0.001 g/4mL
PatchTopical0.009 g/24mL
EmulsionTopical0.04 g/100mL
LiquidTopical0.005 g/13mL
LotionTopical1 mg/150mL
LiquidTopical0.04 mL/100mL
CreamTopical0.02 g/50g
CreamTopical0.024 g/60g
PowderTopical
EmulsionTopical0.06 g/150mL
LiquidTopical0.06 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)Region
US5731296No1998-03-242015-03-24US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)235.5 °CPhysProp
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)3.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area139.54 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.2 m3·mol-1ChemAxon
Polarizability25.28 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

Targets

Drugtargets2
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Details
1. Adenosine receptor A1
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Details
2. Adenosine receptor A2a
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Details
3. Adenosine receptor A2b
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Details
4. Adenosine receptor A3
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]

Enzymes

Details
1. Adenosine deaminase
Kind
Protein
Organism
Humans
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. [Article]
  2. Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  2. Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Nucleoside diphosphate kinase activity
Specific Function
Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Also displays broad nucleoside diphosphate kinase activity. Plays an important role in cellular energy homeost...
Gene Name
AK1
Uniprot ID
P00568
Uniprot Name
Adenylate kinase isoenzyme 1
Molecular Weight
21634.725 Da
References
  1. Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Ribosomal small subunit binding
Specific Function
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-sit...
Gene Name
NME1
Uniprot ID
P15531
Uniprot Name
Nucleoside diphosphate kinase A
Molecular Weight
17148.635 Da
References
  1. Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Transcription factor activity, sequence-specific dna binding
Specific Function
Major role in the synthesis of nucleoside triphosphates other than ATP. Negatively regulates Rho activity by interacting with AKAP13/LBC. Acts as a transcriptional activator of the MYC gene; binds ...
Gene Name
NME2
Uniprot ID
P22392
Uniprot Name
Nucleoside diphosphate kinase B
Molecular Weight
17297.935 Da
References
  1. Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Purine-nucleoside phosphorylase activity
Specific Function
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine ...
Gene Name
PNP
Uniprot ID
P00491
Uniprot Name
Purine nucleoside phosphorylase
Molecular Weight
32117.69 Da
References
  1. Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xanthine oxidase activity
Specific Function
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Ha...
Gene Name
XDH
Uniprot ID
P47989
Uniprot Name
Xanthine dehydrogenase/oxidase
Molecular Weight
146422.99 Da
References
  1. Maiuolo J, Oppedisano F, Gratteri S, Muscoli C, Mollace V: Regulation of uric acid metabolism and excretion. Int J Cardiol. 2016 Jun 15;213:8-14. doi: 10.1016/j.ijcard.2015.08.109. Epub 2015 Aug 14. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Wzorek J, Bednarek R, Watala C, Boncler M: Binding of adenosine derivatives to carrier proteins may reduce their antiplatelet activity. Biochem Pharmacol. 2020 Apr;174:113827. doi: 10.1016/j.bcp.2020.113827. Epub 2020 Jan 25. [Article]
  2. Cui F, Wang J, Cui Y, Yao X, Qu G, Lu Y: Investigation of interaction between human serum albumin and N6-(2-hydroxyethyl)-adenosine by fluorescence spectroscopy and molecular modelling. Luminescence. 2007 Nov-Dec;22(6):546-53. doi: 10.1002/bio.999. [Article]
  3. Cui F, Wang J, Li F, Fan J, Qu G, Yao X, Lei B: Investigation of the Interaction between Adenosine and Human Serum Albumin by Fluorescent Spectroscopy and Molecular Modeling Chinese Journal of Chemistry. 2008 Apr 16;26(4):661-665. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Nucleoside transmembrane transporter activity
Specific Function
Mediates both influx and efflux of nucleosides across the membrane (equilibrative transporter). It is sensitive (ES) to low concentrations of the inhibitor nitrobenzylmercaptopurine riboside (NBMPR...
Gene Name
SLC29A1
Uniprot ID
Q99808
Uniprot Name
Equilibrative nucleoside transporter 1
Molecular Weight
50218.805 Da
References
  1. Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Nucleoside transmembrane transporter activity
Specific Function
Mediates equilibrative transport of purine, pyrimidine nucleosides and the purine base hypoxanthine. Very less sensitive than SLC29A1 to inhibition by nitrobenzylthioinosine (NBMPR), dipyridamole, ...
Gene Name
SLC29A2
Uniprot ID
Q14542
Uniprot Name
Equilibrative nucleoside transporter 2
Molecular Weight
50112.335 Da
References
  1. Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Mediates both influx and efflux of nucleosides across the membrane (equilibrative transporter). Mediates transport of adenine, adenosine and uridine, as well as several nucleoside analog drugs, such as anticancer and antiviral agents, including cladribine, cordycepin, tubercidin and AZT. Does not transport hypoxanthine.
Specific Function
Nucleoside transmembrane transporter activity
Gene Name
SLC29A3
Uniprot ID
Q9BZD2
Uniprot Name
Equilibrative nucleoside transporter 3
Molecular Weight
51813.89 Da
References
  1. Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Nucleoside transmembrane transporter activity
Specific Function
Functions as a polyspecific organic cation transporter, efficiently transporting many organic cations such as monoamine neurotransmitters 1-methyl-4-phenylpyridinium and biogenic amines including s...
Gene Name
SLC29A4
Uniprot ID
Q7RTT9
Uniprot Name
Equilibrative nucleoside transporter 4
Molecular Weight
58058.005 Da
References
  1. Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Pyrimidine- and adenine-specific:sodium symporter activity
Specific Function
Sodium-dependent and pyrimidine-selective. Exhibits the transport characteristics of the nucleoside transport system cit or N2 subtype (N2/cit) (selective for pyrimidine nucleosides and adenosine)....
Gene Name
SLC28A1
Uniprot ID
O00337
Uniprot Name
Sodium/nucleoside cotransporter 1
Molecular Weight
71583.18 Da
References
  1. Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Purine nucleoside transmembrane transporter activity
Specific Function
Sodium-dependent and purine-selective transporter. Exhibits the transport characteristics of the nucleoside transport system cif or N1 subtype (N1/cif) (selective for purine nucleosides and uridine...
Gene Name
SLC28A2
Uniprot ID
O43868
Uniprot Name
Sodium/nucleoside cotransporter 2
Molecular Weight
71925.565 Da
References
  1. Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Signal transducer activity
Specific Function
Gap junction protein that acts as a regulator of bladder capacity. A gap junction consists of a cluster of closely packed pairs of transmembrane channels, the connexons, through which materials of ...
Gene Name
GJA1
Uniprot ID
P17302
Uniprot Name
Gap junction alpha-1 protein
Molecular Weight
43008.005 Da
References
  1. Boison D, Yegutkin GG: Adenosine Metabolism: Emerging Concepts for Cancer Therapy. Cancer Cell. 2019 Dec 9;36(6):582-596. doi: 10.1016/j.ccell.2019.10.007. [Article]
Kind
Protein
Organism
Humans
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. [Article]

Drug created on June 13, 2005 13:24 / Updated on October 22, 2021 23:18