adenosine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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) 2.67 mg/mL Bocci G, Oprea TI, Benet LZ
EoM (Fraction excreted unchanged in urine) 0 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 7.48 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 -0.693 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 28.119 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 1.742 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 1.722 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 86.070 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 90.970 % High 1
herg hERG pIC50 3.626 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 1.161 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 3.342 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 75.040 % High 1
kinase-safety-class ACVR2B,AURKA,AXL,BRAF,CAMK2D,CDK5,CDK9,CLK2,DDR1,DYRK1B,EIF2AK3,ERBB2,FLT3,GRK2,IRAK1,ITK,MAP2K6,MAP3K21,MAPK7,NTRK1,NTRK2,PDK1,PDK2,PDK4,PIK3CD,PRKDC,SIK2 27
kinase-selectivity-class MAP2K6,MAP3K21 2
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 4.753 High 1
mh-clint Mouse hepatocyte intrinsic clearance 1.045 High 1
mppb Mouse plasma protein binding (% unbound) 92.220 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 2.636 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pld-class Phospholipidosis risk class (1 = positive, 0 = negative) 0 Moderate 0.68
pppb Pig plasma protein binding (% unbound) 89.910 % High 1
rh-clint Rat hepatocyte intrinsic clearance 1.945 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 94.770 % High 1
rppb Rat plasma protein binding (% unbound) 88.680 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 864.968 uM High 1

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 ineffective 133.60 22.09 189 2704 1384109 89241445
Pneumonia aspiration 59.24 22.09 28 2865 40912 90584642
Supraventricular tachycardia 57.20 22.09 21 2872 16315 90609239
Pemphigoid 52.66 22.09 17 2876 9009 90616545
Alcohol use disorder 52.45 22.09 7 2886 38 90625516
Coma 46.71 22.09 29 2864 72603 90552951
Underdose 41.01 22.09 24 2869 53993 90571561
Ventricular tachycardia 36.03 22.09 17 2876 24691 90600863
Gastric ulcer haemorrhage 35.09 22.09 11 2882 5300 90620254
Gastrooesophageal reflux disease 34.59 22.09 34 2859 166303 90459251
Product use in unapproved indication 31.89 22.09 46 2847 336190 90289364
Arteriospasm coronary 31.46 22.09 10 2883 5040 90620514
Exfoliative rash 31.45 22.09 9 2884 3183 90622371
Atrial fibrillation 30.96 22.09 29 2864 133582 90491972
Bronchospasm 29.43 22.09 14 2879 20695 90604859
Ventricular fibrillation 27.92 22.09 12 2881 14032 90611522
Drug ineffective for unapproved indication 27 22.09 20 2873 66624 90558930
Peptic ulcer 26.66 22.09 9 2884 5466 90620088
Sinus arrest 25.46 22.09 7 2886 2139 90623415
Somnolence 24.95 22.09 32 2861 209052 90416502
Hypotension 24.47 22.09 40 2853 325357 90300197
Tachycardia induced cardiomyopathy 24.27 22.09 4 2889 103 90625451
Toxic epidermal necrolysis 23.49 22.09 14 2879 32514 90593040
Tachycardia 23.47 22.09 27 2866 157646 90467908
Off label use 22.95 22.09 82 2811 1102170 89523384
Cardiac arrest 22.82 22.09 22 2871 104913 90520641

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
Drug ineffective 132.60 23.30 164 2123 630033 41989015
Bronchospasm 87.79 23.30 31 2256 12854 42606194
Oesophageal ulcer haemorrhage 58.16 23.30 11 2276 372 42618676
Ventricular fibrillation 56.51 23.30 29 2258 30094 42588954
Ventricular tachycardia 53.59 23.30 28 2259 30132 42588916
Drug ineffective for unapproved indication 52.55 23.30 32 2255 46131 42572917
Coronary steal syndrome 48.85 23.30 6 2281 6 42619042
Cardiac arrest 46.83 23.30 42 2245 109278 42509770
Mallory-Weiss syndrome 43.05 23.30 11 2276 1510 42617538
Arteriospasm coronary 42.42 23.30 14 2273 4724 42614324
Supraventricular tachycardia 42.08 23.30 18 2269 12390 42606658
Complex regional pain syndrome 30.21 23.30 7 2280 638 42618410
Rebound tachycardia 28.52 23.30 4 2283 18 42619030
Electrocardiogram QRS complex prolonged 28.51 23.30 11 2276 5812 42613236
Benign soft tissue neoplasm 28.04 23.30 5 2282 121 42618927
Gingival bleeding 27.75 23.30 12 2275 8473 42610575
Atrioventricular block complete 27.42 23.30 13 2274 11351 42607697
Myositis 26.95 23.30 14 2273 14852 42604196
Intracardiac mass 25.54 23.30 5 2282 203 42618845
Treatment failure 24.69 23.30 23 2264 62601 42556447
Immune effector cell-associated neurotoxicity syndrome 23.37 23.30 11 2276 9450 42609598

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
Drug ineffective 234.62 19.30 305 4483 1520235 109064276
Bronchospasm 112.15 19.30 44 4744 30195 110554316
Supraventricular tachycardia 92.18 19.30 36 4752 24386 110560125
Ventricular fibrillation 86.24 19.30 40 4748 41273 110543238
Ventricular tachycardia 76.06 19.30 39 4749 49970 110534541
Arteriospasm coronary 75.08 19.30 24 4764 9076 110575435
Drug ineffective for unapproved indication 63.72 19.30 45 4743 102793 110481718
Cardiac arrest 60.11 19.30 57 4731 196696 110387815
Oesophageal ulcer haemorrhage 50.51 19.30 11 4777 941 110583570
Coronary steal syndrome 49.65 19.30 6 4782 7 110584504
Atrial fibrillation 44.16 19.30 52 4736 229590 110354921
Product use in unapproved indication 39.58 19.30 70 4718 447307 110137204
Mallory-Weiss syndrome 37.40 19.30 11 4777 3150 110581361
Pneumonia aspiration 35.77 19.30 29 4759 81204 110503307
Exfoliative rash 33.40 19.30 11 4777 4563 110579948
Cardiogenic shock 32.98 19.30 24 4764 57314 110527197
Tachycardia induced cardiomyopathy 32.37 19.30 6 4782 226 110584285
Atrioventricular block complete 31.49 19.30 16 4772 20066 110564445
Underdose 30.78 19.30 24 4764 63530 110520981
Sinus arrest 30.17 19.30 10 4778 4232 110580279
Pemphigoid 28.88 19.30 15 4773 19692 110564819
Benign soft tissue neoplasm 28.69 19.30 5 4783 132 110584379
Off label use 28.50 19.30 134 4654 1500051 109084460
Gastric ulcer haemorrhage 28.20 19.30 12 4776 10082 110574429
Coma 26.55 19.30 29 4759 117840 110466671
Bradycardia 26.26 19.30 33 4755 155484 110429027
Hypotension 25.25 19.30 64 4724 523785 110060726
Drug interaction 25.04 19.30 62 4726 500121 110084390
Intracardiac mass 24.77 19.30 5 4783 296 110584215
Gingival bleeding 23.20 19.30 13 4775 19826 110564685
Complex regional pain syndrome 22.57 19.30 7 4781 2398 110582113
Immune effector cell-associated neurotoxicity syndrome 20.94 19.30 11 4777 14771 110569740
Hyperthyroidism 20.92 19.30 14 4774 29247 110555264
Myositis 20.14 19.30 14 4774 31102 110553409
Gastrooesophageal reflux disease 19.66 19.30 31 4757 179945 110404566
Pulseless electrical activity 19.64 19.30 11 4777 16746 110567765
Atrioventricular block 19.57 19.30 11 4777 16866 110567645

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 D014665 Vasodilator Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018689 Sensory System Agents
MeSH PA D058906 Purinergic P1 Receptor Agonists
FDA MoA N0000175788 Adenosine Receptor Agonists
FDA EPC N0000178375 Adenosine Receptor Agonist
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:35554 cardiovascular drug
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:35620 vasodilator agent
CHEBI has role CHEBI:38070 anti-arrhythmia drug
CHEBI has role CHEBI:67079 anti-inflammatory agent
CHEBI has role CHEBI:77746 human metabolite
CHEBI has role CHEBI:78675 fundamental metabolite

Related Drugs by ATC class:

C01EB Other cardiac preparations 15 drugs
acadesineacoramidiscamphorcreatinolfosfateibuprofenindomethacinivabradinemavacamtenmeldoniumphosphocreatineranolazineregadenoson show all 15 →

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

None

🐶 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 A2a GPCR AGONIST EC50 6.16 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
Adenosine receptor A3 GPCR AGONIST Ki 6.54 IUPHAR
Adenosine kinase Kinase IC50 6 WOMBAT-PK
Adenosine deaminase Enzyme Kd 4.60 WOMBAT-PK
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
Histone-lysine N-methyltransferase, H3 lysine-79 specific Enzyme IC50 4 CHEMBL
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
4019507 VANDF
003603 NDDF
004537 NDDF
004813 NDDF
108502004 SNOMEDCT_US
35431001 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
ADENOSINE HUMAN PRESCRIPTION DRUG LABEL 1 0404-9993 INJECTION, SOLUTION 3 mg INTRAVENOUS ANDA 13 sections
ADENOSINE HUMAN PRESCRIPTION DRUG LABEL 1 0404-9993 INJECTION, SOLUTION 3 mg INTRAVENOUS ANDA 13 sections
Adenosine HUMAN PRESCRIPTION DRUG LABEL 1 0641-6113 INJECTION 3 mg INTRAVENOUS ANDA 21 sections
Adenosine HUMAN PRESCRIPTION DRUG LABEL 1 16714-556 INJECTION, SOLUTION 3 mg INTRAVENOUS ANDA 25 sections
Adenosine HUMAN PRESCRIPTION DRUG LABEL 1 16714-997 INJECTION, SOLUTION 3 mg INTRAVENOUS ANDA 25 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
adenosine HUMAN PRESCRIPTION DRUG LABEL 1 25021-301 INJECTION 3 mg INTRAVENOUS ANDA 23 sections
Adenosine HUMAN PRESCRIPTION DRUG LABEL 1 25021-318 INJECTION 3 mg INTRAVENOUS ANDA 22 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
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
U-max Wrinkle Serum HUMAN OTC DRUG LABEL 1 50795-1001 LIQUID 0.04 mL TOPICAL unapproved drug other 8 sections
NATURAL SUN AQ TOTAL ANTI-AGING ESSENCE SUN HUMAN OTC DRUG LABEL 7 51523-102 CREAM 0.40 mL TOPICAL OTC monograph not final 7 sections
Adenosine Injection, 6mg/2mL (3mg/mL) Vial HUMAN PRESCRIPTION DRUG LABEL 1 51662-1201 INJECTION, SOLUTION 3 mg INTRAVENOUS ANDA 13 sections
ADENOSINE HUMAN PRESCRIPTION DRUG LABEL 1 51662-1345 INJECTION, SOLUTION 3 mg INTRAVENOUS ANDA 18 sections