Tox | Related Drugs | BioActivity |

Stem definition	Drug id	CAS RN
	90	58-61-7

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
15	mg	P

ADMET properties:

Property	Value	Reference
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):

Property	Description	Value	Unit	Confidence	Similarity
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
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:

Date	Agency	Company	Orphan
Oct. 30, 1989	FDA	ASTELLAS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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:

Source	Code	Description
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

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Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
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 level	Dissociation constant	Type (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:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Adenosine receptor A2a	GPCR	P29274	AA2AR_HUMAN	AGONIST	EC50	6.16	WOMBAT-PK	CHEMBL
Adenosine receptor A1	GPCR	P30542	AA1R_HUMAN	AGONIST	EC50	6.51	WOMBAT-PK	CHEMBL
Adenosine receptor A2b	GPCR	P29275	AA2BR_HUMAN	AGONIST	EC50	4.62	WOMBAT-PK	CHEMBL
Adenosine receptor A3	GPCR	P0DMS8	AA3R_HUMAN	AGONIST	Ki	6.54	IUPHAR
Adenosine kinase	Kinase	P55263	ADK_HUMAN		IC50	6	WOMBAT-PK
Adenosine deaminase	Enzyme	P00813	ADA_HUMAN		Kd	4.60	WOMBAT-PK
Mitogen-activated protein kinase kinase kinase 7	Kinase	O43318	M3K7_HUMAN		Kd	5.36	CHEMBL
Adenosylhomocysteinase	Enzyme	P23526	SAHH_HUMAN		Km	5.80	WOMBAT-PK
Phosphatidylinositol 4-kinase type 2-alpha	Kinase	Q9BTU6	P4K2A_HUMAN	INHIBITOR	IC50	5	IUPHAR
Phosphatidylinositol 4-kinase type 2-beta	Kinase	Q8TCG2	P4K2B_HUMAN	INHIBITOR	IC50	5	IUPHAR
Glyceraldehyde-3-phosphate dehydrogenase liver	Enzyme	P04406	G3P_HUMAN		IC50	4.46	CHEMBL
Histone-lysine N-methyltransferase, H3 lysine-79 specific	Enzyme	Q8TEK3	DOT1L_HUMAN		IC50	4	CHEMBL
Adenosine receptor A1	GPCR		AA1R_RAT		Ki	8.29	CHEMBL
Adenosine receptor A2a	GPCR		AA2AR_RAT		Ki	7.52	CHEMBL
Adenosine receptor A3	GPCR		AA3R_RAT		Ki	7	CHEMBL
Adenosine kinase	Kinase		ADK_TOXGO		Ki	5.05	CHEMBL
Adenosine A2 receptor	GPCR		AA2BR_RAT AA2AR_RAT		Ki	8.30	CHEMBL
cAMP-dependent protein kinase A	Kinase		KAP2_BOVIN KAPCA_BOVIN KAPCB_BOVIN KAP3_BOVIN		Ki	4.82	CHEMBL

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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