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Identification
- Name
- Adenosine
- Accession Number
- DB00640
- 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.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Adenosine (DB00640)
- 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
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.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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.
Target Actions Organism AAdenosine receptor A2a agonistHumans AAdenosine receptor A2b agonistHumans AAdenosine receptor A3 agonistHumans AAdenosine receptor A1 agonistHumans - 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.
Hover over products below to view reaction partners
- Route of elimination
- Not Available
- Half-life
Less than 10 secs
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
- 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.
Drug Interaction Unlock Additional DataAcebutolol Adenosine may increase the arrhythmogenic activities of Acebutolol. Acetyldigitoxin Acetyldigitoxin may increase the arrhythmogenic activities of Adenosine. Aclidinium The risk or severity of Tachycardia can be increased when Adenosine is combined with Aclidinium. Acrivastine The risk or severity of QTc prolongation can be increased when Acrivastine is combined with Adenosine. Ajmaline Ajmaline may increase the arrhythmogenic activities of Adenosine. Alfuzosin The risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Adenosine. Alimemazine The risk or severity of QTc prolongation can be increased when Alimemazine is combined with Adenosine. Amantadine The risk or severity of QTc prolongation can be increased when Amantadine is combined with Adenosine. Amifampridine The risk or severity of QTc prolongation can be increased when Adenosine is combined with Amifampridine. Aminophylline The therapeutic efficacy of Adenosine can be decreased when used in combination with Aminophylline. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Avoid caffeine.
Products
- 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
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataAdenocard Solution 3 mg/1mL Intravenous Cardinal Health 1989-10-30 2018-01-31 US 
Adenocard Solution 3 mg/1mL Intravenous Astellas Pharma US, Inc. 1989-10-30 Not applicable US Adenocard Solution 3 mg/1mL Intravenous Remedy Repack 2015-08-18 2016-08-18 US Adenocard Solution 6 mg/2mL Intravenous Cardinal Health 1989-10-30 2019-01-31 US Adenocard - Liq Rapid Bolus IV 3mg/ml Solution Intravenous Astellas Pharma Inc 1996-08-14 2014-12-05 Canada 
Adenocard Injection -pre-filled Syringe Solution Intravenous Astellas Pharma Inc 1994-12-31 Not applicable Canada Adenocard Liq IV 3mg/ml Liquid Intravenous Fujisawa Pharmaceutical Co, Division Of Fujisawa Canada Inc. 1993-12-31 1996-09-09 Canada Adenocard Liq IV 3mg/ml (pre-filled Syringe) Liquid Intravenous Fujisawa Pharmaceutical Co, Division Of Fujisawa Canada Inc. 1994-12-31 1996-09-09 Canada Adenoscan Solution 3 mg/1mL Intravenous Remedy Repack 2010-07-31 2012-08-31 US Adenoscan Solution 3 mg/1mL Intravenous Physicians Total Care, Inc. 2007-10-17 2012-06-30 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataAdenosine Injection, solution 90 mg/30mL Intravenous Mylan Institutional LLC 2019-08-22 Not applicable US Adenosine Injection, solution 3 mg/1mL Intravenous Baxter Healthcare Corporation 2010-04-20 2010-09-30 US Adenosine Injection, solution 3 mg/1mL Intravenous Bedford Pharmaceuticals 2004-06-17 2012-02-29 US Adenosine Injection, solution 60 mg/20mL Intravenous AuroMedics Pharma LLC 2017-11-02 Not applicable US Adenosine Injection 3 mg/1mL Intravenous Wockhardt 2009-07-20 Not applicable US Adenosine Injection, solution 3 mg/1mL Intravenous Remedy Repack 2016-06-07 2016-06-09 US Adenosine Injection 3 mg/1mL Intravenous Remedy Repack 2018-03-06 2018-03-06 US Adenosine Injection 3 mg/1mL Intravenous Gland Pharma Limited 2013-04-01 Not applicable US Adenosine Injection 3 mg/1mL Intravenous Remedy Repack 2018-03-05 2018-03-05 US Adenosine Injection, solution 3 mg/1mL Intravenous REMEDYREPACK INC. 2014-09-30 2015-09-30 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional Data9tails Premium Wrinkle Power Lifting Liquid 0.04 g/100g Topical ELUO.CO.,Ltd. 2019-10-28 Not applicable US A.H.C Real Eye For Face Cream 0.12 mg/30mL Topical Carver Korea Co Ltd 2013-06-21 2018-12-01 US A.H.C. Collagen Cream Cream 20 mg/50mL Topical Carver Korea Co.,Ltd 2013-08-15 2018-12-01 US A.H.C. Collagen Toner Liquid 48 mg/120mL Topical Carver Korea Co.,Ltd 2013-08-15 2018-12-01 US Advanced Snail 92 All in One Cream Cream 0.04 mg/100mL Topical Cosrx Inc. 2016-05-24 2017-06-28 US AHC Collagen Serum Liquid 12 mg/30mL Topical Carver Korea Co.,Ltd 2013-08-15 2018-12-01 US AHC Complex Choice EGF Booster Cream 0.4 mg/1mL Topical Carver Korea Co.,Ltd. 2013-08-15 2017-11-20 US AHC Complex Choice EGF Booster Cream 0.4 mg/1mL Topical Carver Korea Co.,Ltd. 2013-08-15 2017-11-20 US AHC Hydration Special Gen Cream Cream 20 mg/50mL Topical Carver Korea Co.,Ltd. 2013-07-15 2017-11-04 US AHC Hydration Special Gen Mask Liquid 12.8 mg/32g Topical Carver Korea Co.,Ltd. 2013-07-15 2017-11-04 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image A.H.c Cotton 100 Mask Multi Peptide Adenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL) Patch Topical Carver Korea Co.,Ltd. 2017-09-20 2018-12-01 US A.H.c Cotton 100 Mask Skin Ceramide Adenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL) Patch Topical Carver Korea Co.,Ltd. 2017-09-05 2018-12-01 US A.H.c Cotton 100 Mask Soy Isoflavone Adenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL) Patch Topical Carver Korea Co.,Ltd. 2017-09-14 2018-12-01 US A.H.c Cotton 100 Mask Triple Hyaluronic Adenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL) Patch Topical Carver Korea Co.,Ltd. 2017-09-20 2018-12-01 US A.H.c Cotton 100 Mask Triple Hyaluronic Adenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL) Patch Topical Carver Korea Co.,Ltd. 2017-09-20 2017-09-21 US AAPE Continuous Renewal Adenosine (0.02 g/50mL) + Nicotinamide (1.00 g/50mL) Cream Topical Prostemics Co., Ltd. 2019-08-01 Not applicable US AAPE Continuous Renewal Eye Adenosine (0.008 g/20mL) + Nicotinamide (0.40 g/20mL) Cream Topical Prostemics Co., Ltd. 2019-08-01 Not applicable US AAPE Continuous Renewal Serum Adenosine (0.01 g/40mL) + Nicotinamide (0.80 g/40mL) Liquid Topical Prostemics Co., Ltd. 2019-08-01 Not applicable US Abalone Aqua Flood Water Adenosine (0.04 g/100mL) + Nicotinamide (2 g/100mL) Cream Topical C&bcosmetic Co.,ltd. 2017-02-16 Not applicable US ABALONE CrystalDouble EX Adenosine (0.04 g/100mL) + Nicotinamide (2 g/100mL) Cream Topical C&bcosmetic Co.,ltd. 2017-02-16 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 9tails Premium Wrinkle Power Lifting Adenosine (0.04 g/100g) Liquid Topical ELUO.CO.,Ltd. 2019-10-28 Not applicable US A.H.c Cotton 100 Mask Multi Peptide Adenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL) Patch Topical Carver Korea Co.,Ltd. 2017-09-20 2018-12-01 US A.H.c Cotton 100 Mask Skin Ceramide Adenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL) Patch Topical Carver Korea Co.,Ltd. 2017-09-05 2018-12-01 US A.H.c Cotton 100 Mask Soy Isoflavone Adenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL) Patch Topical Carver Korea Co.,Ltd. 2017-09-14 2018-12-01 US A.H.c Cotton 100 Mask Triple Hyaluronic Adenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL) Patch Topical Carver Korea Co.,Ltd. 2017-09-20 2017-09-21 US A.H.c Cotton 100 Mask Triple Hyaluronic Adenosine (0.01 g/25mL) + Allantoin (0.025 g/25mL) + Nicotinamide (0.05 g/25mL) Patch Topical Carver Korea Co.,Ltd. 2017-09-20 2018-12-01 US A.H.C Real Eye For Face Adenosine (0.12 mg/30mL) Cream Topical Carver Korea Co Ltd 2013-06-21 2018-12-01 US A.H.C. Collagen Cream Adenosine (20 mg/50mL) Cream Topical Carver Korea Co.,Ltd 2013-08-15 2018-12-01 US A.H.C. Collagen Toner Adenosine (48 mg/120mL) Liquid Topical Carver Korea Co.,Ltd 2013-08-15 2018-12-01 US AAPE Continuous Renewal Adenosine (0.02 g/50mL) + Nicotinamide (1.00 g/50mL) Cream Topical Prostemics Co., Ltd. 2019-08-01 Not applicable US
Categories
- ATC Codes
- C01EB10 — Adenosine
- Drug Categories
- Adenosine, antagonists & inhibitors
- Agents producing tachycardia
- Alkenes
- Analgesics
- Antiarrhythmic agents
- Antiarrhythmics, Class V
- Biological Factors
- Carbohydrates
- Cardiac Therapy
- Cardiovascular Agents
- Central Nervous System Agents
- Class IV Antiarrythmics
- Cyclohexanes
- Cyclohexenes
- Cycloparaffins
- Enzymes
- Enzymes and Coenzymes
- Glycosides
- Heterocyclic Compounds, Fused-Ring
- Hydrocarbons, Acyclic
- Miscellaneous Cardiac Drugs
- Miscellaneous Therapeutic Agents
- Moderate Risk QTc-Prolonging Agents
- Neurotransmitter Agents
- Nucleic Acids, Nucleotides, and Nucleosides
- Nucleosides
- Oxidoreductases
- Peripheral Nervous System Agents
- Pigments, Biological
- Polyenes
- Purine Nucleosides
- Purinergic Agents
- Purinergic Agonists
- Purinergic P1 Receptor Agonists
- Purines
- QTc Prolonging Agents
- Ribonucleosides
- Sensory System Agents
- Terpenes
- Vasodilating Agents
- 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)
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
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000050
- KEGG Drug
- D00045
- KEGG Compound
- C00212
- PubChem Compound
- 60961
- PubChem Substance
- 46508728
- ChemSpider
- 54923
- BindingDB
- 14487
- 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
- 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 162 more
- FDA label
- Download (154 KB)
- MSDS
- Download (72.7 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Basic Science Hypertrophic Cardiomyopathy (HCM) / Microvascular Ischaemia of Myocardium / Non-ischemic Dilated Cardiomyopathy 1 4 Completed Treatment Tachycardia, Supraventricular 1 4 Recruiting Diagnostic Percutaneous Coronary Intervention (PCI) 1 4 Recruiting Diagnostic Premature Ventricular Contraction (PVC) 1 4 Terminated Treatment Resistant Hypertension 1 3 Completed Diagnostic Coronary Artery Disease (CAD) 6 3 Completed Diagnostic Orthotopic Heart Transplant 1 3 Completed Prevention Coronary Angioplasty 1 3 Completed Treatment Acute Myocardial Infarction (AMI) 1 3 Completed Treatment Atrial Fibrillation (AF) / Persistent Common Pulmonary Vein 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
Form Route Strength Cream Topical 0.12 mg/30mL Liquid Topical 48 mg/120mL Soap Topical Solution Intravenous 6 mg/2mL Liquid Intravenous Solution Intravenous 3 mg/1mL Injection Intravenous 3 mg/1mL Injection, solution Intravenous 3 mg/1mL Injection, solution Intravenous 60 mg/20mL Injection, solution Intravenous 90 mg/30mL Cream Topical 0.04 mg/100mL Cream Topical 0.4 mg/1mL Cream Topical 20 mg/50mL Liquid Topical 12.8 mg/32g Liquid Topical 12 mg/30mL Liquid Topical 54 mg/135mL Liquid Topical 12 mg/30g Solution Topical 0.002 g/6mL Solution Topical 2.8 mg/7mL Cream Topical 0.012 g/30mL Liquid Topical 0.012 g/30mL Gel Topical Liquid Topical 0.05 g/130mL Cream Topical 0.01 g/45mL Cream Topical 0.02 g/50mL Cream Topical 0.01 g/30mL Solution Topical 1.2 mg/3mL Emulsion Topical 0.04 g/120mL Emulsion Topical 0.0006 g/1.5mL Cream Topical 0.01 g/50mL Cream Topical 0.0003 g/1.5mL Liquid Topical 0.04 g/120mL Liquid Topical 0.0006 g/1.5mL Liquid Topical 0.6 mg/6mL Cream Topical 0.04 mL/100mL Cream Topical 0.004 g/10g Liquid Topical 0.04 g/100mL Gel Topical 0.04 g/100g Patch Topical 0.01 g/25mL Cream Topical 0.03 g/95g Patch Topical 0.008 g/20g Solution Topical Liquid Topical 20 mg/50mL Gel Topical 0.04 g/100mL Cream Topical 0.04 g/100g Patch Topical 0.0016 g/4g Liquid Topical 0.002 g/6mL Liquid Topical 0.001 g/3mL Cream Oral 0.04 g/100mL Liquid Topical 6 mg/15mL Emulsion Topical 0.04 g/100g Cream Topical 0.04 g/100mL Patch Topical 0.001 g/2.8g Patch Topical 0.014 g/35g Patch Topical 0.003 g/8g Liquid Topical 0.04 g/100g Solution / drops Topical Cream Topical 0.0428 g/100g Cream Topical 0.2 g/100g Liquid Topical 2.0 mg/5mL Liquid Topical 25 mg/50mL Patch Topical 0.005 g/0.55g Kit Topical Emulsion Topical Cream Topical 0.0004 g/1g Cream Topical 0.0004 g/1mL Liquid Topical 0.0004 g/1mL Liquid Vaginal 15 g/100mL Emulsion Topical 0.05 g/130mL Cream Topical 0.04 g/120mL Lotion Topical Aerosol, spray Topical Liquid Oral 0.0435 g/100mL Patch Topical 0.5 g/25g Patch Topical 0.012 g/30g Cream Topical 6 g/150g Cream Topical 0.004 mg/10g Cream Topical 0.08 mg/20mL Stick Topical Patch Topical 0.6 mg/3g Cream Topical 0.02 mg/50mL Liquid Topical 0.05 mg/125mL Patch Topical 13.2 mg/33mL Cream Topical 10 mg/25mL Liquid Topical 16 mg/40mL Cream Topical 0.03 g/75mL Cream Topical 0.01 g/25mL Cream Topical 0.018 g/45mL Cream Topical Cream Topical 0.01 g/27g Liquid Topical 0.04 mg/100mL Lipstick Topical 0.001 g/3.5g Liquid Topical 0.00012 mg/0.3mL Cream Topical 0.00012 mg/0.3mL Cream Topical 0.011 mg/27mL Cream Topical 0.001 mg/2.5mL Patch Topical 0.01 g/25g Oil Topical 0.01 g/30mL Patch Topical Liquid Topical Cream Topical 0.012 g/30g Solution Intravenous Cream Topical 0.0004 1/100mL Oil Topical Liquid Topical 0.02 g/50mL Patch Topical 0.01 g/27g Liquid Topical 0.02 g/50g Patch Topical 0.008 g/20mL Cream Topical 0.01 g/25g Patch Topical 1 g/100g Spray Topical Cream Topical 0.4 mg/1g Cream Topical 0.002 g/10g Cream Topical 0.01 g/50g Cream Topical 0.04 mL/1mL Liquid Topical 0.0004 mL/1mL Lotion Topical 0.05 g/100mL Cream Topical 0.05 g/100mL Liquid Topical 0.05 g/100mL Liquid Topical 0.001 g/4mL Patch Topical 0.009 g/24mL Emulsion Topical 0.04 g/100mL Liquid Topical 0.005 g/13mL Lotion Topical 1 mg/150mL Liquid Topical 0.04 mL/100mL Cream Topical 0.02 g/50g Cream Topical 0.024 g/60g Powder Topical Emulsion Topical 0.06 g/150mL Liquid Topical 0.06 g/150mL - Prices
Unit description Cost Unit Adenosine-5 monophosphate 19.74USD g Adenosine powder 15.86USD g Adenoscan 3 mg/ml vial 10.09USD ml Adenosine 12 mg/4 ml vial 8.44USD ml Adenosine 6 mg/2 ml vial 8.1USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS5731296 No 1998-03-24 2015-03-24 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 235.5 °C PhysProp water solubility 8230 mg/L Not Available logP -1.05 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 14.0 mg/mL ALOGPS logP -1.2 ALOGPS logP -2.1 ChemAxon logS -1.3 ALOGPS pKa (Strongest Acidic) 12.45 ChemAxon pKa (Strongest Basic) 3.94 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 139.54 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 63.2 m3·mol-1 ChemAxon Polarizability 25.28 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9227 Blood Brain Barrier + 0.9383 Caco-2 permeable - 0.8957 P-glycoprotein substrate Non-substrate 0.7026 P-glycoprotein inhibitor I Non-inhibitor 0.966 P-glycoprotein inhibitor II Non-inhibitor 0.9533 Renal organic cation transporter Non-inhibitor 0.9444 CYP450 2C9 substrate Non-substrate 0.8639 CYP450 2D6 substrate Non-substrate 0.8349 CYP450 3A4 substrate Non-substrate 0.5866 CYP450 1A2 substrate Non-inhibitor 0.9667 CYP450 2C9 inhibitor Non-inhibitor 0.9595 CYP450 2D6 inhibitor Non-inhibitor 0.977 CYP450 2C19 inhibitor Non-inhibitor 0.9514 CYP450 3A4 inhibitor Non-inhibitor 0.962 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9701 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.9182 Biodegradation Not ready biodegradable 0.9738 Rat acute toxicity 1.9715 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.989 hERG inhibition (predictor II) Non-inhibitor 0.9102
Spectra
- Mass Spec (NIST)
- Download (9.12 KB)
- Spectra
Targets
- 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
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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
- 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]
- 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]
- 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]
- 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]
- 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]
- 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
- 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
- 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
- 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
- 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
- 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
- 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 August 10, 2020 08:11
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