adenosine ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
90 58-61-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • adenosine
  • adenine riboside
  • riboadenosine
  • beta-Adenosine
  • beta-D-Adenosine
  • adenoscan
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.
  • Molecular weight: 267.25
  • Formula: C10H13N5O4
  • CLOGP: -1.36
  • LIPINSKI: 0
  • HAC: 9
  • HDO: 4
  • TPSA: 139.54
  • ALOGS: -1.28
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
15 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 5 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 7.48 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
Oct. 30, 1989 FDA ASTELLAS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Supraventricular tachycardia 45.50 24.06 17 1737 12784 50590586
Atrial fibrillation 44.57 24.06 33 1721 101712 50501658
Pneumonia aspiration 42.61 24.06 21 1733 30983 50572387
Ventricular tachycardia 42.00 24.06 17 1737 15804 50587566
Coma 33.16 24.06 22 1732 56857 50546513
Exfoliative rash 32.79 24.06 9 1745 2521 50600849
Underdose 31.67 24.06 15 1739 20263 50583107
Ventricular fibrillation 30.29 24.06 12 1742 10547 50592823
Drug ineffective 29.93 24.06 78 1676 819255 49784115
Bronchospasm 29.53 24.06 13 1741 14841 50588529
Gastrooesophageal reflux disease 29.48 24.06 23 1731 76405 50526965
Toxic epidermal necrolysis 28.18 24.06 14 1740 20978 50582392
Tachycardia induced cardiomyopathy 26.32 24.06 4 1750 55 50603315
Tachycardia 26.08 24.06 24 1730 99739 50503631
Arteriospasm coronary 25.87 24.06 8 1746 3394 50599976
Cardiogenic shock 25.78 24.06 12 1742 15587 50587783
Ventricular asystole 25.26 24.06 4 1750 73 50603297

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Bronchospasm 94.60 23.82 30 1459 9579 29563459
Oesophageal ulcer haemorrhage 66.87 23.82 11 1478 174 29572864
Ventricular tachycardia 53.60 23.82 25 1464 22549 29550489
Drug ineffective 45.96 23.82 72 1417 363098 29209940
Mallory-Weiss syndrome 45.67 23.82 11 1478 1266 29571772
Supraventricular tachycardia 36.66 23.82 15 1474 9869 29563169
Myositis 32.74 23.82 14 1475 10269 29562769
Complex regional pain syndrome 32.56 23.82 7 1482 484 29572554
Gingival bleeding 31.68 23.82 12 1477 6441 29566597
Ventricular fibrillation 29.89 23.82 15 1474 15818 29557220
Rebound tachycardia 28.77 23.82 4 1485 18 29573020

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Bronchospasm 115.59 21.68 42 2982 21640 64474068
Ventricular tachycardia 80.88 21.68 37 2987 34228 64461480
Supraventricular tachycardia 73.17 21.68 29 2995 18878 64476830
Ventricular fibrillation 57.02 21.68 26 2998 23834 64471874
Drug ineffective 55.30 21.68 121 2903 840126 63655582
Oesophageal ulcer haemorrhage 54.93 21.68 11 3013 577 64495131
Atrial fibrillation 49.81 21.68 50 2974 171039 64324669
Arteriospasm coronary 46.34 21.68 15 3009 5450 64490258
Mallory-Weiss syndrome 38.74 21.68 11 3013 2572 64493136
Exfoliative rash 35.30 21.68 11 3013 3535 64492173
Tachycardia induced cardiomyopathy 34.96 21.68 6 3018 133 64495575
Cardiac arrest 34.16 21.68 39 2985 154025 64341683
Cardiogenic shock 30.56 21.68 19 3005 32408 64463300
Myositis 27.44 21.68 14 3010 16363 64479345
Drug ineffective for unapproved indication 26.24 21.68 17 3007 31116 64464592
Gingival bleeding 25.77 21.68 13 3011 14841 64480867
Complex regional pain syndrome 24.43 21.68 7 3017 1689 64494019
Pneumonia aspiration 24.31 21.68 21 3003 59250 64436458
Underdose 23.99 21.68 15 3009 25814 64469894

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC C01EB10 CARDIOVASCULAR SYSTEM
CARDIAC THERAPY
OTHER CARDIAC PREPARATIONS
Other cardiac preparations
MeSH PA D000700 Analgesics
MeSH PA D000889 Anti-Arrhythmia Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D058913 Purinergic Agonists
MeSH PA D058906 Purinergic P1 Receptor Agonists
MeSH PA D018689 Sensory System Agents
MeSH PA D014665 Vasodilator Agents
FDA MoA N0000175788 Adenosine Receptor Agonists
FDA EPC N0000178375 Adenosine Receptor Agonist
CHEBI has role CHEBI:35620 vasodilator agents
CHEBI has role CHEBI:38070 antiarrhythmic agent
CHEBI has role CHEBI:77746 Homo sapiens metabolite
CHEBI has role CHEBI:78675 fundamental metabolites

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Paroxysmal supraventricular tachycardia indication 67198005
Myocardial Perfusion Imaging Adjunct indication
Supraventricular tachycardia off-label use 6456007
Pericarditis contraindication 3238004 DOID:1787
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Disorder of autonomic nervous system contraindication 15241006
Complete atrioventricular block contraindication 27885002
Hypovolemia contraindication 28560003
Acute cerebrovascular insufficiency contraindication 29322000
Transplantation of heart contraindication 32413006
Sick sinus syndrome contraindication 36083008 DOID:13884
Low blood pressure contraindication 45007003
Aortic valve stenosis contraindication 60573004 DOID:1712
Left to right cardiovascular shunt contraindication 66130006
Mitral valve stenosis contraindication 79619009 DOID:1754
Pulmonary emphysema contraindication 87433001
Respiratory alkalosis contraindication 111378004
Second degree atrioventricular block contraindication 195042002
Asthma contraindication 195967001 DOID:2841
Left main coronary artery disease contraindication 371804009
Acute coronary syndrome contraindication 394659003
Respiratory insufficiency contraindication 409623005
Syncope due to Bradycardia contraindication




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.67 acidic
pKa2 12.33 acidic
pKa3 13.34 acidic
pKa4 3.95 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Adenosine receptor A2b GPCR AGONIST EC50 4.62 WOMBAT-PK CHEMBL
Adenosine receptor A2a GPCR AGONIST EC50 6.16 WOMBAT-PK CHEMBL
Adenosine receptor A1 GPCR AGONIST EC50 6.51 WOMBAT-PK CHEMBL
Mitogen-activated protein kinase kinase kinase 7 Kinase Kd 5.36 CHEMBL
Adenosylhomocysteinase Enzyme Km 5.80 WOMBAT-PK
Phosphatidylinositol 4-kinase type 2-alpha Kinase INHIBITOR IC50 5 IUPHAR
Phosphatidylinositol 4-kinase type 2-beta Kinase INHIBITOR IC50 5 IUPHAR
Glyceraldehyde-3-phosphate dehydrogenase liver Enzyme IC50 4.46 CHEMBL
Adenosine deaminase Enzyme Kd 4.60 WOMBAT-PK
Histone-lysine N-methyltransferase, H3 lysine-79 specific Enzyme IC50 4 CHEMBL
Adenosine receptor A3 GPCR AGONIST Ki 6.54 IUPHAR
Adenosine kinase Kinase IC50 6 WOMBAT-PK
Adenosine receptor A1 GPCR Ki 8.29 CHEMBL
Adenosine receptor A2a GPCR Ki 7.52 CHEMBL
Adenosine receptor A3 GPCR Ki 7 CHEMBL
Adenosine kinase Kinase Ki 5.05 CHEMBL
Adenosine A2 receptor GPCR Ki 8.30 CHEMBL
cAMP-dependent protein kinase A Kinase Ki 4.82 CHEMBL

External reference:

IDSource
4019507 VUID
N0000147627 NUI
D00045 KEGG_DRUG
215025 RXNORM
C0001443 UMLSCUI
CHEBI:16335 CHEBI
ADN PDB_CHEM_ID
CHEMBL477 ChEMBL_ID
DB00640 DRUGBANK_ID
D000241 MESH_DESCRIPTOR_UI
60961 PUBCHEM_CID
2844 IUPHAR_LIGAND_ID
K72T3FS567 UNII
1072 MMSL
4135 MMSL
57772 MMSL
d00164 MMSL
003603 NDDF
004537 NDDF
004813 NDDF
4019507 VANDF
108502004 SNOMEDCT_US
35431001 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Adenosine HUMAN PRESCRIPTION DRUG LABEL 1 0404-9809 INJECTION, SOLUTION 3 mg INTRAVENOUS ANDA 20 sections
Adenosine HUMAN PRESCRIPTION DRUG LABEL 1 0409-1932 INJECTION, SOLUTION 3 mg INTRAVENOUS ANDA 25 sections
Adenocard HUMAN PRESCRIPTION DRUG LABEL 1 0469-8234 SOLUTION 3 mg INTRAVENOUS NDA 17 sections
Adenosine HUMAN PRESCRIPTION DRUG LABEL 1 0641-6113 INJECTION 3 mg INTRAVENOUS ANDA 21 sections
Adenosine HUMAN PRESCRIPTION DRUG LABEL 1 0703-8776 INJECTION, SOLUTION 3 mg INTRAVENOUS ANDA 27 sections
Adenosine HUMAN PRESCRIPTION DRUG LABEL 1 0703-8777 INJECTION, SOLUTION 3 mg INTRAVENOUS ANDA 27 sections
Adenosine HUMAN PRESCRIPTION DRUG LABEL 1 16714-180 INJECTION, SOLUTION 3 mg INTRAVENOUS ANDA 27 sections
Adenosine HUMAN PRESCRIPTION DRUG LABEL 1 16714-972 INJECTION, SOLUTION 3 mg INTRAVENOUS ANDA 27 sections
Adenosine HUMAN PRESCRIPTION DRUG LABEL 1 17478-542 INJECTION, SOLUTION 3 mg INTRAVENOUS ANDA 21 sections
Adenosine HUMAN PRESCRIPTION DRUG LABEL 1 17478-542 INJECTION, SOLUTION 3 mg INTRAVENOUS ANDA 21 sections
Adenosine HUMAN PRESCRIPTION DRUG LABEL 1 17478-544 INJECTION, SOLUTION 3 mg INTRAVENOUS ANDA 26 sections
Adenosine HUMAN PRESCRIPTION DRUG LABEL 1 17478-953 INJECTION, SOLUTION 3 mg INTRAVENOUS ANDA 20 sections
Adenosine HUMAN PRESCRIPTION DRUG LABEL 1 23155-258 INJECTION, SOLUTION 3 mg INTRAVENOUS ANDA 25 sections
Too im Cell ALL IN ONE HUMAN OTC DRUG LABEL 3 24765-124 LOTION 0.40 mg TOPICAL OTC monograph not final 8 sections
adenosine HUMAN PRESCRIPTION DRUG LABEL 1 25021-301 INJECTION 3 mg INTRAVENOUS ANDA 23 sections
Tissen NF 10 HUMAN OTC DRUG LABEL 1 42491-1100 LIQUID 0.01 g TOPICAL unapproved drug other 8 sections
Tissen ICM 10 HUMAN OTC DRUG LABEL 1 42491-1200 LIQUID 0.01 g TOPICAL unapproved drug other 8 sections
Dr G deWrinkle BOOSTER ample by EGF HUMAN OTC DRUG LABEL 2 43948-3001 SOLUTION/ DROPS 0.04 mL TOPICAL OTC monograph final 4 sections
Dr G deWrinkle FORTIFIER by EGF HUMAN OTC DRUG LABEL 2 43948-3002 CREAM 0.01 mL TOPICAL OTC monograph final 4 sections
Dr G deWrinkle REFORMER by EGF HUMAN OTC DRUG LABEL 2 43948-3003 CREAM 0.02 mL TOPICAL OTC monograph final 4 sections
Super Plus Beblesh Balm Triple Functions SPF50 Plus PA 3Plus (40g) HUMAN OTC DRUG LABEL 6 49715-007 CREAM 0.02 g TOPICAL OTC monograph final 10 sections
The Prestige BB SPF25 PA 2Plus HUMAN OTC DRUG LABEL 4 49715-008 CREAM 0.02 g TOPICAL OTC monograph final 10 sections
The Oriental Gold BB SPF25 PA 2Plus HUMAN OTC DRUG LABEL 4 49715-010 CREAM 0.02 g TOPICAL OTC monograph final 10 sections
Absolute Total BB SPF37 PA 3Plus HUMAN OTC DRUG LABEL 4 49715-011 CREAM 0.02 g TOPICAL OTC monograph final 10 sections
SuperPlus Beblesh Balm Triple Functions SPF25 PA 2Plus HUMAN OTC DRUG LABEL 6 49715-014 CREAM 0.02 g TOPICAL OTC monograph final 10 sections
SuperPlus Beblesh Balm Gold SPF25 PA 2Plus HUMAN OTC DRUG LABEL 4 49715-015 CREAM 0.01 g TOPICAL OTC monograph final 10 sections
SuperPlus Beblesh Balm Gold SPF25 PA 2Plus HUMAN OTC DRUG LABEL 6 49715-016 CREAM 0.02 g TOPICAL OTC monograph final 10 sections
SuperPlus Beblesh Balm SPF25 PA 2Plus HUMAN OTC DRUG LABEL 4 49715-017 CREAM 0.01 g TOPICAL OTC monograph final 10 sections
SuperPlus Beblesh Balm SPF25 PA 2Plus HUMAN OTC DRUG LABEL 6 49715-018 CREAM 0.02 g TOPICAL OTC monograph final 10 sections
SKIN79 SNAIL NUTRITION BBCREAM HUMAN OTC DRUG LABEL 5 49715-019 CREAM 0.02 g TOPICAL OTC monograph final 3 sections