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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Adenosine
- Accession Number
- DB00640 (APRD00132, DB06639)
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Description
A nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. Adenosine itself is a neurotransmitter.
- Structure
Structure for DB00640 (Adenosine)
- 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
- Adenosinum
- Ado
- beta-D-Adenosine
- External IDs
- SR 96225 / SR-96225 / USAF CB-10
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Adenocard Solution 6 mg/2mL Intravenous Cardinal Health 1989-10-30 Not applicable US 
Adenocard Solution 3 mg/mL Intravenous Remedy Repack 2015-08-18 2017-09-05 US Adenocard Solution 3 mg/mL Intravenous Astellas Pharma Inc 1989-10-30 Not applicable US Adenocard Solution 3 mg/mL Intravenous Cardinal Health 1989-10-30 2018-05-11 US Adenocard - Liq Rapid Bolus IV 3mg/ml Solution 3 mg Intravenous Astellas Pharma Inc 1996-08-14 2014-12-05 Canada 
Adenocard Injection -pre-filled Syringe Solution 3 mg Intravenous Astellas Pharma Inc 1994-12-31 Not applicable Canada Adenocard Liq IV 3mg/ml Liquid 3 mg 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 3 mg Intravenous Fujisawa Pharmaceutical Co, Division Of Fujisawa Canada Inc. 1994-12-31 1996-09-09 Canada Adenoscan Solution 3 mg/mL Intravenous Remedy Repack 2013-06-27 2017-04-14 US Adenoscan Solution 3 mg/mL Intravenous Astellas Pharma Inc 1995-05-18 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Adenosine Injection 3 mg/mL Intravenous Wockhardt 2009-07-20 Not applicable US Adenosine Injection, solution 3 mg/mL Intravenous Remedy Repack 2016-06-07 2017-02-15 US Adenosine Injection, solution 3 mg/mL Intravenous Remedy Repack 2018-05-30 Not applicable US Adenosine Solution 3 mg/mL Intravenous Gland Pharma Limited 2017-01-13 Not applicable US Adenosine Injection, solution 3 mg/mL Intravenous Baxter Laboratories 2010-04-20 Not applicable US Adenosine Injection, solution 3 mg/mL Intravenous Heritage 2014-08-01 Not applicable US Adenosine Injection, solution 3 mg/mL Intravenous AGILA SPECIALTIES PRIVATE LIMITED 2014-03-22 2018-01-31 US Adenosine Injection, solution 3 mg/mL Intravenous Physicians Total Care, Inc. 2006-03-16 Not applicable US Adenosine Injection 3 mg/mL Intravenous Remedy Repack 2017-09-14 2018-03-08 US Adenosine Injection 3 mg/mL Intravenous West Ward Pharmaceutical 2004-06-16 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Absolute Total BB SPF37 PA 3Plus Adenosine (.016 g/40g) + Arbutin (.8 g/40g) + Titanium dioxide (3.6 g/40g) + Zinc oxide (2.52 g/40g) Cream Topical Wizcoz Corporation Ltd 2011-12-01 Not applicable US Aprilskin Magic Snow Fixing Foundation 22 Pink Beige Adenosine (.04 g/100g) + Nicotinamide (2 g/100g) + Titanium dioxide (12.00736 g/100g) Liquid Topical Aprilskin Co., Ltd. 2017-05-01 Not applicable US Aprilskin Magic Snow Fixing Foundation 23 Natural Beige Adenosine (.04 g/100g) + Nicotinamide (2 g/100g) + Titanium dioxide (12.00736 g/100g) Liquid Topical Aprilskin Co., Ltd. 2017-05-01 Not applicable US Derma First Duo Adenosine + Glycerin + Nicotinamide Kit Topical Cellalab 2018-03-01 Not applicable US Dr Deep Aqua Wrinklecream Adenosine (.04 mL/100mL) + Allantoin (1 mL/100mL) Cream Topical Mineral House Corporation 2012-01-01 2017-04-20 US Dr G deWrinkle BOOSTER ample by EGF Adenosine (.04 mL/10mL) + Glycerin (.5 mL/10mL) Solution / drops Topical The Doctor's Cosmetic Inc 2009-11-01 Not applicable US Dr G deWrinkle FORTIFIER by EGF Adenosine (.012 mL/30mL) + Glycerin (2.1 mL/30mL) Cream Topical The Doctor's Cosmetic Inc 2009-11-01 Not applicable US Dr G deWrinkle REFORMER by EGF Adenosine (.02 mL/50mL) + Dimethicone (.35 mL/50mL) Cream Topical The Doctor's Cosmetic Inc 2009-11-01 Not applicable US Lohasys Mayu Ultra Moisture Adenosine (.04 g/100mL) + Glycerin (8 g/100mL) Emulsion Topical Netcos Co., Ltd. 2017-09-13 Not applicable US Lohasys Mayu Ultra Moisture Care Adenosine (.04 g/100mL) + Glycerin (5 g/100mL) Cream Topical Netcos Co., Ltd. 2017-09-13 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End A.H.c Cotton 100 Mask Multi Peptide Adenosine (.01 g/25mL) + Allantoin (.025 g/25mL) + Nicotinamide (.05 g/25mL) Patch Topical Carver Korea Co.,Ltd. 2017-09-20 Not applicable US A.H.c Cotton 100 Mask Skin Ceramide Adenosine (.01 g/25mL) + Allantoin (.025 g/25mL) + Nicotinamide (.05 g/25mL) Patch Topical Carver Korea Co.,Ltd. 2017-09-05 Not applicable US A.H.c Cotton 100 Mask Soy Isoflavone Adenosine (.01 g/25mL) + Allantoin (.025 g/25mL) + Nicotinamide (.05 g/25mL) Patch Topical Carver Korea Co.,Ltd. 2017-09-14 Not applicable US A.H.c Cotton 100 Mask Triple Hyaluronic Adenosine (.01 g/25mL) + Allantoin (.025 g/25mL) + Nicotinamide (.05 g/25mL) Patch Topical Carver Korea Co.,Ltd. 2017-09-20 Not applicable US A.H.C Real Eye For Face Adenosine (.12 mg/30mL) Cream Topical Carver Korea Co.,Ltd. 2013-06-21 Not applicable US A.H.C. Collagen Cream Adenosine (20 mg/50mL) Cream Topical Carver Korea Co.,Ltd. 2013-08-15 Not applicable US A.H.C. Collagen Toner Adenosine (48 mg/120mL) Liquid Topical Carver Korea Co.,Ltd. 2013-08-15 Not applicable US Abalone Aqua Flood Water Adenosine (.04 g/100mL) + Nicotinamide (2 g/100mL) Cream Topical C&bcosmetic Co.,ltd. 2017-02-16 Not applicable US ABALONE CrystalDouble EX Adenosine (.04 g/100mL) + Nicotinamide (2 g/100mL) Cream Topical C&bcosmetic Co.,ltd. 2017-02-16 Not applicable US Abalone Crystaldouble EX Ampoule Adenosine (.044 g/100mL) + Arbutin (2.2 g/100mL) Liquid Topical C&bcosmetic Co.,ltd. 2017-03-10 Not applicable US - International/Other Brands
- Adenocard / Adenocor (Sanofi-Aventis) / Adenoject (Sun) / Adenoscan / Adenoz (Celon) / Adenozer (Purzer) / Adesin (Dae Han New Pharm) / Adrekar (Sanofi-Aventis) / Atépadène (Mayoly-Spindler) / Cardimax (AC Farma) / Cardiovert (Sanofi-Aventis) / Krenosin (Sanofi-Aventis) / Osiden (Square) / Pisdeno (Pisa)
- Categories
- Alkenes
- Analgesics
- Antiarrhythmic agents
- Antiarrhythmics, Class V
- Biological Factors
- Carbohydrates
- Cardiac Therapy
- Cardiovascular Agents
- Cardiovascular System
- Central Nervous System Agents
- Class IV Antiarrythmics
- Cyclohexanes
- Cyclohexenes
- Cycloparaffins
- Enzymes
- Enzymes and Coenzymes
- Glycosides
- Hydrocarbons, Acyclic
- Miscellaneous Cardiac Drugs
- Miscellaneous Therapeutic 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
- Ribonucleosides
- Sensory System Agents
- Terpenes
- Vasodilating Agents
- UNII
- K72T3FS567
- CAS number
- 58-61-7
- Weight
- Average: 267.2413
Monoisotopic: 267.096753929 - Chemical Formula
- C10H13N5O4
- InChI Key
- OIRDTQYFTABQOQ-KQYNXXCUSA-N
- InChI
- InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
- IUPAC Name
- (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
- SMILES
- NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1
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
- 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 agonistHuman AAdenosine receptor A2b agonistHuman AAdenosine receptor A3 agonistHuman AAdenosine receptor A1 agonistHuman - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
Intracellular adenosine is rapidly metabolized either via phosphorylation to adenosine monophosphate by adenosine kinase, or via deamination to inosine by adenosine deaminase in the cytosol.
- Route of elimination
- Not Available
- Half life
Less than 10 secs
- Clearance
- Not Available
- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction Drug group 3-isobutyl-1-methyl-7H-xanthine The therapeutic efficacy of Adenosine can be decreased when used in combination with 3-isobutyl-1-methyl-7H-xanthine. Experimental 6-O-benzylguanine The therapeutic efficacy of Adenosine can be decreased when used in combination with 6-O-benzylguanine. Investigational 7-Deazaguanine The therapeutic efficacy of Adenosine can be decreased when used in combination with 7-Deazaguanine. Experimental 7,9-Dimethylguanine The therapeutic efficacy of Adenosine can be decreased when used in combination with 7,9-Dimethylguanine. Experimental 8-azaguanine The therapeutic efficacy of Adenosine can be decreased when used in combination with 8-azaguanine. Experimental 8-chlorotheophylline The therapeutic efficacy of Adenosine can be decreased when used in combination with 8-chlorotheophylline. Approved 9-Deazaguanine The therapeutic efficacy of Adenosine can be decreased when used in combination with 9-Deazaguanine. Experimental 9-Methylguanine The therapeutic efficacy of Adenosine can be decreased when used in combination with 9-Methylguanine. Experimental Acefylline The therapeutic efficacy of Adenosine can be decreased when used in combination with Acefylline. Experimental Acyclovir The therapeutic efficacy of Adenosine can be decreased when used in combination with Acyclovir. Approved Azathioprine The therapeutic efficacy of Adenosine can be decreased when used in combination with Azathioprine. Approved Bamifylline The therapeutic efficacy of Adenosine can be decreased when used in combination with Bamifylline. Experimental Bromotheophylline The therapeutic efficacy of Adenosine can be decreased when used in combination with Bromotheophylline. Approved Bufylline The therapeutic efficacy of Adenosine can be decreased when used in combination with Bufylline. Experimental Cafedrine The therapeutic efficacy of Adenosine can be decreased when used in combination with Cafedrine. Investigational Caffeine The therapeutic efficacy of Adenosine can be decreased when used in combination with Caffeine. Approved Carbamazepine Carbamazepine may increase the atrioventricular blocking (AV block) activities of Adenosine. Approved, Investigational Digoxin The risk or severity of adverse effects can be increased when Digoxin is combined with Adenosine. Approved Dipyridamole The risk or severity of adverse effects can be increased when Dipyridamole is combined with Adenosine. Approved Doxofylline The therapeutic efficacy of Adenosine can be decreased when used in combination with Doxofylline. Approved, Investigational Entecavir The therapeutic efficacy of Adenosine can be decreased when used in combination with Entecavir. Approved, Investigational Etamiphylline The therapeutic efficacy of Adenosine can be decreased when used in combination with Etamiphylline. Experimental Fenethylline The therapeutic efficacy of Adenosine can be decreased when used in combination with Fenethylline. Approved Furafylline The therapeutic efficacy of Adenosine can be decreased when used in combination with Furafylline. Experimental Ganciclovir The therapeutic efficacy of Adenosine can be decreased when used in combination with Ganciclovir. Approved, Investigational Guanine The therapeutic efficacy of Adenosine can be decreased when used in combination with Guanine. Experimental Hypoxanthine The therapeutic efficacy of Adenosine can be decreased when used in combination with Hypoxanthine. Experimental Lisofylline The therapeutic efficacy of Adenosine can be decreased when used in combination with Lisofylline. Investigational Lobucavir The therapeutic efficacy of Adenosine can be decreased when used in combination with Lobucavir. Investigational Nicotine Nicotine may increase the atrioventricular blocking (AV block) activities of Adenosine. Approved Oxtriphylline The therapeutic efficacy of Adenosine can be decreased when used in combination with Oxtriphylline. Approved Patent Blue The therapeutic efficacy of Adenosine can be decreased when used in combination with Patent Blue. Approved Peldesine The therapeutic efficacy of Adenosine can be decreased when used in combination with Peldesine. Experimental, Investigational Pemetrexed The therapeutic efficacy of Adenosine can be decreased when used in combination with Pemetrexed. Approved, Investigational Penciclovir The therapeutic efficacy of Adenosine can be decreased when used in combination with Penciclovir. Approved Pentifylline The therapeutic efficacy of Adenosine can be decreased when used in combination with Pentifylline. Experimental Pentoxifylline The therapeutic efficacy of Adenosine can be decreased when used in combination with Pentoxifylline. Approved, Investigational Propentofylline The therapeutic efficacy of Adenosine can be decreased when used in combination with Propentofylline. Investigational Proxyphylline The therapeutic efficacy of Adenosine can be decreased when used in combination with Proxyphylline. Experimental Theobromine The therapeutic efficacy of Adenosine can be decreased when used in combination with Theobromine. Approved, Investigational Theodrenaline The therapeutic efficacy of Adenosine can be decreased when used in combination with Theodrenaline. Investigational Uric Acid The therapeutic efficacy of Adenosine can be decreased when used in combination with Uric Acid. Experimental, Investigational Valaciclovir The therapeutic efficacy of Adenosine can be decreased when used in combination with Valaciclovir. Approved, Investigational Valganciclovir The therapeutic efficacy of Adenosine can be decreased when used in combination with Valganciclovir. Approved, Investigational Valomaciclovir The therapeutic efficacy of Adenosine can be decreased when used in combination with Valomaciclovir. Investigational Vemurafenib The risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Adenosine. Approved Xanthine The therapeutic efficacy of Adenosine can be decreased when used in combination with Xanthine. Experimental - Food Interactions
- Avoid caffeine containing foods and drinks.
References
- Synthesis Reference
Giorgio Stramentinoli, Federico Gennari, "Process for preparing adenosine derivatives of anti-inflammatory and analgesic activity." U.S. Patent US4373097, issued October, 1965.
US4373097- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000050
- KEGG Drug
- D00045
- KEGG Compound
- C00212
- PubChem Compound
- 60961
- PubChem Substance
- 46508728
- ChemSpider
- 54923
- BindingDB
- 14487
- ChEBI
- 16335
- ChEMBL
- CHEMBL477
- Therapeutic Targets Database
- DAP000223
- PharmGKB
- PA448049
- HET
- ADN
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Adenosine
- ATC Codes
- C01EB10 — Adenosine
- AHFS Codes
- 24:04.04.24 — Class IV Antiarrythmics
- 24:04.92 — Miscellaneous Cardiac Drugs
- 92:00.00 — Miscellaneous Therapeutic Agents
- PDB Entries
- 1bx4 / 1d4f / 1dgm / 1fmo / 1ho5 / 1jdv / 1jg2 / 1jg3 / 1lii / 1lik … show 147 more
- FDA label
- Download (154 KB)
- MSDS
- Download (72.7 KB)
Clinical Trials
- Clinical Trials
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 .12 mg/30mL Liquid Topical 48 mg/120mL Solution Intravenous 6 mg/2mL Liquid Intravenous 3 mg Solution Intravenous 3 mg/mL Injection Intravenous 3 mg/mL Injection, solution Intravenous 3 mg/mL Injection, solution Intravenous 60 mg/20mL Injection, solution Intravenous 90 mg/30mL Cream Topical .04 mg/100mL Cream Topical .4 mg/mL Cream Topical 20 mg/50mL Liquid Topical 12.8 mg/32g Liquid Topical 12 mg/30mL Liquid Topical 54 mg/135mL Liquid Topical Liquid Topical 12 mg/30g Solution Topical .002 g/6mL Solution Topical 2.8 mg/7mL Liquid Topical .012 g/30mL Gel Topical Cream Topical .04 g/100mL Liquid Topical .05 g/130mL Cream Topical .01 g/45mL Cream Topical .02 g/50mL Cream Topical .01 g/30mL Solution Topical 1.2 mg/3mL Patch Topical .008 g/20g Emulsion Topical .04 g/120mL Emulsion Topical .0006 g/1.5mL Cream Topical .01 g/50mL Cream Topical .0003 g/1.5mL Liquid Topical .04 g/120mL Liquid Topical .0006 g/1.5mL Liquid Topical .6 mg/6mL Cream Topical .04 mL/100mL Cream Topical .004 g/10g Gel Topical .04 g/100g Cream Topical .03 g/95g Liquid Topical 20 mg/50mL Gel Topical .04 g/100mL Cream Topical .04 g/100g Patch Topical .0016 g/4g Cream Oral .04 g/100mL Liquid Topical 6 mg/15mL Liquid Topical .04 g/100mL Emulsion Topical .04 g/100g Patch Topical .001 g/2.8g Patch Topical .003 g/8g Solution / drops Topical Cream Topical Kit Topical Cream Topical .0428 g/100g Kit Topical Cream Topical .2 g/100g Liquid Topical 2 mg/5mL Liquid Topical .04 mL/100mL Liquid Topical 25 mg/50mL Liquid Topical .02 g/50mL Cream Topical .0004 mL/mL Cream Topical .0004 g/g Liquid Topical .0004 mL/mL Liquid Vaginal 15 g/100mL Emulsion Topical .04 g/100mL Kit Lotion Topical Aerosol, spray Topical Liquid Oral .0435 g/100mL Patch Topical .5 g/25g Patch Topical .012 g/30g Cream Topical 6 g/150g Cream Topical .004 mg/10g Cream Topical .08 mg/20mL Stick Topical Patch Topical .6 mg/3g Cream Topical .02 mg/50mL Liquid Topical .05 mg/125mL Patch Topical .014 g/35g Patch Topical 13.2 mg/33mL Cream Topical 10 mg/25mL Liquid Topical 16 mg/40mL Cream Topical .03 g/75mL Cream Topical .01 g/25mL Cream Topical .01 g/27g Liquid Topical .04 mg/100mL Lipstick Topical .001 g/3.5g Patch Topical Liquid Topical .00012 mg/.3mL Cream Topical .00012 mg/.3mL Cream Topical .011 mg/27mL Cream Topical .001 mg/2.5mL Patch Topical .01 g/25g Oil Topical .01 g/30mL Cream Topical .012 g/30g Liquid Topical .04 g/100g Solution Intravenous 3 mg Cream Topical .0004 1/100mL Liquid Topical .002 g/6mL Oil Topical Patch Topical .01 g/27g Solution Topical Cream Topical .01 g/25g Patch Topical 1 g/100g Spray Topical Cream Topical .018 g/45mL Cream Topical .012 g/30mL Cream Topical .4 mg/g Cream Topical .002 g/10g Cream Topical .01 g/50g Cream Topical .04 mL/mL Lotion Topical .05 g/100mL Cream Topical .05 g/100mL Liquid Topical .05 g/100mL Patch Topical .01 g/25mL Liquid Topical .001 g/3mL Patch Topical .009 g/24mL Patch Topical .008 g/20mL Liquid Topical .001 g/4mL Lotion Topical 1 mg/150mL Cream Topical .02 g/50g Cream Topical .024 g/60g Powder Topical Emulsion Topical Emulsion Topical .06 g/150mL Liquid Topical .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) US5731296 No 1995-03-24 2015-03-24 US
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
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
- Kingdom
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Class
- Purine nucleosides
- Sub Class
- Not Available
- Direct Parent
- Purine nucleosides
- Alternative Parents
- Glycosylamines / Pentoses / 6-aminopurines / Aminopyrimidines and derivatives / N-substituted imidazoles / Imidolactams / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Oxacyclic compounds show 5 more
- Substituents
- Purine nucleoside / Glycosyl compound / N-glycosyl compound / 6-aminopurine / Pentose monosaccharide / Imidazopyrimidine / Purine / Aminopyrimidine / Monosaccharide / N-substituted imidazole show 21 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- adenosines (CHEBI:16335) / Ribonucleosides (C00212)
Targets
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Identical protein binding
- Specific Function
- Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
- Gene Name
- ADORA2A
- Uniprot ID
- P29274
- Uniprot Name
- Adenosine receptor A2a
- Molecular Weight
- 44706.925 Da
References
- 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
- Human
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- G-protein coupled adenosine receptor activity
- Specific Function
- Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
- Gene Name
- ADORA2B
- Uniprot ID
- P29275
- Uniprot Name
- Adenosine receptor A2b
- Molecular Weight
- 36332.655 Da
References
- 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
- Human
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- G-protein coupled adenosine receptor activity
- Specific Function
- Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibits adenylyl cyclase. Possible role in reproduction.
- Gene Name
- ADORA3
- Uniprot ID
- P0DMS8
- Uniprot Name
- Adenosine receptor A3
- Molecular Weight
- 36184.175 Da
References
- 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
- Human
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Purine nucleoside binding
- Specific Function
- Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name
- ADORA1
- Uniprot ID
- P30542
- Uniprot Name
- Adenosine receptor A1
- Molecular Weight
- 36511.325 Da
References
- 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
- Human
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Zinc ion binding
- Specific Function
- Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, an...
- Gene Name
- ADA
- Uniprot ID
- P00813
- Uniprot Name
- Adenosine deaminase
- Molecular Weight
- 40764.13 Da
References
- Kopff M, Kopff A, Puczkowski S: [Adenosine deaminase: isoenzymes ADA1 and ADA2]. Pol Merkur Lekarski. 1997 Dec;3(18):288-90. [PubMed:9523470]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Poly(a) rna binding
- Specific Function
- ATP dependent phosphorylation of adenosine and other related nucleoside analogs to monophosphate derivatives. Serves as a potential regulator of concentrations of extracellular adenosine and intrac...
- Gene Name
- ADK
- Uniprot ID
- P55263
- Uniprot Name
- Adenosine kinase
- Molecular Weight
- 40545.075 Da
References
- Boison D: Adenosine kinase, epilepsy and stroke: mechanisms and therapies. Trends Pharmacol Sci. 2006 Dec;27(12):652-8. Epub 2006 Oct 23. [PubMed:17056128]
Transporters
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- General Function
- Pyrimidine- and adenine-specific:sodium symporter activity
- Specific Function
- Sodium-dependent, pyrimidine- and purine-selective. Involved in the homeostasis of endogenous nucleosides. Exhibits the transport characteristics of the nucleoside transport system cib or N3 subtyp...
- Gene Name
- SLC28A3
- Uniprot ID
- Q9HAS3
- Uniprot Name
- Solute carrier family 28 member 3
- Molecular Weight
- 76929.61 Da
References
- 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 15, 2018 09:42