adenosine 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: -2.16
  • 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 ┬ÁM/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
Drug hypersensitivity 113.82 24.14 89 1908 243736 46440329
Supraventricular tachycardia 81.92 24.14 28 1969 13242 46670823
Ventricular tachycardia 60.83 24.14 24 1973 16943 46667122
Bronchospasm 41.93 24.14 18 1979 15689 46668376
Atrial fibrillation 39.93 24.14 34 1963 103556 46580509
Arteriospasm coronary 36.08 24.14 11 1986 3610 46680455
Ventricular fibrillation 26.86 24.14 12 1985 11484 46672581
Exfoliative rash 26.35 24.14 8 1989 2587 46681478
Atrioventricular block 25.67 24.14 10 1987 6801 46677264
Tachycardia induced cardiomyopathy 25.62 24.14 4 1993 53 46684012
Toxic epidermal necrolysis 24.62 24.14 14 1983 22264 46661801

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 95.94 23.67 31 1506 10307 29940634
Supraventricular tachycardia 68.35 23.67 24 1513 10248 29940693
Oesophageal ulcer haemorrhage 66.42 23.67 11 1526 178 29950763
Mallory-Weiss syndrome 44.64 23.67 11 1526 1365 29949576
Cardiac arrest 37.86 23.67 34 1503 92816 29858125
Arteriospasm coronary 37.63 23.67 11 1526 2607 29948334
Ventricular tachycardia 34.42 23.67 19 1518 23843 29927098
Complex regional pain syndrome 32.37 23.67 7 1530 488 29950453
Gingival bleeding 31.55 23.67 12 1525 6392 29944549
Ventricular fibrillation 30.25 23.67 15 1522 15123 29935818
Myositis 29.12 23.67 13 1524 10364 29940577
Atrioventricular block complete 25.01 23.67 11 1526 8466 29942475
Procedural complication 24.23 23.67 9 1528 4488 29946453

Pharmacologic Action:

SourceCodeDescription
ATC C01EB10 CARDIOVASCULAR SYSTEM
CARDIAC THERAPY
OTHER CARDIAC PREPARATIONS
Other cardiac preparations
FDA MoA N0000175788 Adenosine Receptor Agonists
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
CHEBI has role CHEBI:35620 vasodilator
CHEBI has role CHEBI:38070 antiarrhythmic agent
CHEBI has role CHEBI:77746 h. sapiens metabolites
CHEBI has role CHEBI:78675 essential metabolite
FDA EPC N0000178375 Adenosine Receptor Agonist

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

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 A2a GPCR AGONIST EC50 6.15 WOMBAT-PK CHEMBL
Adenosine receptor A1 GPCR AGONIST EC50 6.51 WOMBAT-PK CHEMBL
Adenosine receptor A2b GPCR AGONIST EC50 4.62 WOMBAT-PK CHEMBL
Glyceraldehyde-3-phosphate dehydrogenase liver Enzyme IC50 4.46 CHEMBL
Adenosine deaminase Enzyme Kd 4.60 WOMBAT-PK
Adenosine kinase Kinase IC50 6 WOMBAT-PK
Adenosylhomocysteinase Enzyme Km 5.80 WOMBAT-PK
Adenosine receptor A3 GPCR AGONIST Ki 6.54 IUPHAR
Phosphatidylinositol 4-kinase type 2-alpha Kinase INHIBITOR IC50 5 IUPHAR
Phosphatidylinositol 4-kinase type 2-beta Kinase INHIBITOR IC50 5 IUPHAR
Adenosine kinase Kinase Ki 5.05 CHEMBL
Adenosine receptor A2a GPCR Ki 7.52 CHEMBL
Adenosine A2 receptor GPCR Ki 8.30 CHEMBL
Adenosine receptor A3 GPCR Ki 7 CHEMBL
Adenosine receptor A1 GPCR Ki 8.29 CHEMBL
cAMP-dependent protein kinase A Unclassified Ki 4.82 CHEMBL

External reference:

IDSource
K72T3FS567 UNII
4019507 VUID
N0000147627 NUI
D00045 KEGG_DRUG
C0718262 UMLSCUI
CHEBI:16335 CHEBI
ADN PDB_CHEM_ID
CHEMBL477 ChEMBL_ID
60961 PUBCHEM_CID
DB00640 DRUGBANK_ID
D000241 MESH_DESCRIPTOR_UI
2844 IUPHAR_LIGAND_ID
215025 RXNORM
1072 MMSL
4135 MMSL
57772 MMSL
d00164 MMSL
003603 NDDF
004537 NDDF
004813 NDDF
108502004 SNOMEDCT_US
35431001 SNOMEDCT_US
4019507 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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 17478-544 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 SNULLIL NUTRITION BBCREAM HUMAN OTC DRUG LABEL 5 49715-019 CREAM 0.02 g TOPICAL OTC monograph final 3 sections
Skin-ion HUMAN OTC DRUG LABEL 3 49742-1001 SPRAY 0.02 mL TOPICAL OTC monograph final 3 sections
Ra Sence Loe Cure Solu tion Aloe Mask HUMAN OTC DRUG LABEL 2 50410-100 PATCH 0.01 g TOPICAL unapproved drug other 8 sections