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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H13N5O4
Molecular Weight 267.2413
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ADENOSINE

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O

InChI

InChIKey=OIRDTQYFTABQOQ-KQYNXXCUSA-N
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

HIDE SMILES / InChI
Vidarabine or 9-β-D-arabinofuranosyladenine (ara-A, trade name Vira-A) is a synthetic purine nucleoside analog with in vitro and in vivo inhibitory activity against herpes simplex virus types 1 (HSV-1), 2 (HSV-2), and varicella-zoster virus (VZV). The inhibitory activity of Vidarabine is highly selective due to its affinity for the enzyme thymidine kinase (TK) encoded by HSV and VZV. This viral enzyme converts Vidarabine into Vidarabine monophosphate, a nucleotide analog. The monophosphate is further converted into diphosphate by cellular guanylate kinase and into triphosphate by a number of cellular enzymes. in vitro, Vidarabine triphosphate stops replication of herpes viral DNA. When used as a substrate for viral DNA polymerase, Vidarabine triphosphate competitively inhibits dATP leading to the formation of 'faulty' DNA. This is where Vidarabine triphosphate is incorporated into the DNA strand replacing many of the adenosine bases. This results in the prevention of DNA synthesis, as phosphodiester bridges can longer to be built, destabilizing the strand.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ADENOCARD

Approved Use

Intravenous Adenocard (adenosine injection) is indicated for the following. Conversion to sinus rhythm of paroxysmal supraventricular tachycardia (PSVT), including that associated with accessory bypass tracts (Wolff-Parkinson-White Syndrome). When clinically advisable, appropriate vagal maneuvers (e.g., Valsalva maneuver), should be attempted prior to Adenocard administration.

Launch Date

1989
Curative
VIRA-A

Approved Use

Unknown

Launch Date

1976
Curative
VIRA-A

Approved Use

Unknown

Launch Date

1976
Primary
VIRA-A

Approved Use

Unknown

Launch Date

1976
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.17 mg/L
2.5 mg single, intravenous
dose: 2.5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ADENOSINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.48 mg/L
5 mg single, intravenous
dose: 5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ADENOSINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.78 mg/L
10 mg single, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ADENOSINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10 s
0.1 mg/kg single, intravenous
dose: 0.1 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ADENOSINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.92 min
2.5 mg single, intravenous
dose: 2.5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ADENOSINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.24 min
5 mg single, intravenous
dose: 5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ADENOSINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.86 min
10 mg single, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ADENOSINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.63 min
0.6 μg/kg single, intravenous
dose: 0.6 μg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ADENOSINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3 h
7.5 mg/kg 1 times / day multiple, intravenous
dose: 7.5 mg/kg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
HYPOXANTHINE ARABINOSIDE plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.017%
0.1 mg/kg single, intravenous
dose: 0.1 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ADENOSINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Comparison of the antiviral effects of 5-methoxymethyldeoxyuridine-5'-monophosphate with adenine arabinoside-5'-monophosphate.
1983 Sep
Molecular cloning, functional expression and chromosomal localization of a cDNA encoding a human Na+/nucleoside cotransporter (hCNT2) selective for purine nucleosides and uridine.
1998 Oct-Dec
Adenosine-induced cardiac pause for endovascular embolization of cerebral arteriovenous malformations: technical case report.
1999 Apr
Adenosine conversion of supraventricular tachycardia associated with high-dose epinephrine therapy for cardiac arrest.
1999 Apr-Jun
Lipolysis is an important determinant of isoproterenol-induced myocardial necrosis.
1999 Sep-Oct
N-cycloalkyl derivatives of adenosine and 1-deazaadenosine as agonists and partial agonists of the A(1) adenosine receptor.
2000 Jan 27
Adenine-induced selective apoptosis toward HIV chronically infected cells in vitro.
2000 Jul 14
Adenosine inhibits IL-12 and TNF-[alpha] production via adenosine A2a receptor-dependent and independent mechanisms.
2000 Oct
ATP induces dephosphorylation of myosin light chain in endothelial cells.
2000 Sep
Successful salvage of RAEB/AML relapsing early post allograft with FLAG-Ida conditioned mini-allograft: a report of two cases.
2001 Apr
Double reinforcement with fludarabine/high-dose cytarabine enhances the impact of autologous stem cell transplantation in acute myeloid leukemia patients.
2001 Apr
Treatment of aggressive, or progressing indolent peripheral T- and NK-cell neoplasias by combination of fludarabine, cyclophosphamide and doxorubicine.
2001 Apr
[Mantle cell lymphoma].
2001 Apr
[Molecular biology examination in chronic lymphocytic leukemia].
2001 Apr 22
Glucocorticoids protect against apoptosis induced by serum deprivation, cyclic adenosine 3',5'-monophosphate and p53 activation in immortalized human granulosa cells: involvement of Bcl-2.
2001 Feb
The effects of P2Y receptor agonists and adenosine on prostaglandin production by the guinea-pig uterus.
2001 Feb
Mechanism of prolonged vasorelaxation to ATP in the rat isolated mesenteric arterial bed.
2001 Feb
Adenosine triphosphate-evoked cytosolic calcium oscillations in human granulosa-luteal cells: role of protein kinase C.
2001 Feb
Leptin-induced lipolysis opposes the tonic inhibition of endogenous adenosine in white adipocytes.
2001 Feb
Dysregulation of extracellular adenosine levels by vascular smooth muscle cells from spontaneously hypertensive rats.
2001 Feb
Interactions between 2-fluoroadenine 9-beta-D-arabinofuranoside and the kinase inhibitor UCN-01 in human leukemia and lymphoma cells.
2001 Feb
Reactivation of hepatitis B virus infection during cytotoxic chemotherapy.
2001 Feb
Bilateral breast relapse in acute myelogenous leukemia.
2001 Feb
Effects of extracellular nucleotides and nucleosides on prostate carcinoma cells.
2001 Jan
The critical role of adenosine and guanosine in the affinity of dinucleoside polyphosphates to P(2X)-receptors in the isolated perfused rat kidney.
2001 Jan
Myocardial perfusion in patients with permanent ventricular pacing and normal coronary arteries.
2001 Jan
Hoechst 33342-induced apoptosis is associated with intracellular accumulation of E2F-1 protein in BC3H-1 myocytes and HL-60 cells.
2001 Jan
A novel transverse push-pull microprobe: in vitro characterization and in vivo demonstration of the enzymatic production of adenosine in the spinal cord dorsal horn.
2001 Jan
Perioperative activation of hemostasis in vascular surgery patients.
2001 Jan
Mechanism-based design of a protein kinase inhibitor.
2001 Jan
Adenosine A2B receptors behave as an alternative anchoring protein for cell surface adenosine deaminase in lymphocytes and cultured cells.
2001 Jan
A3 adenosine receptor activation triggers phosphorylation of protein kinase B and protects rat basophilic leukemia 2H3 mast cells from apoptosis.
2001 Jan
S-Adenosyl-L-homocysteine hydrolase inhibitor mediates immunosuppressive effects in vivo: suppression of delayed type hypersensitivity ear swelling and peptidoglycan polysaccharide-induced arthritis.
2001 Jan
Short-term hibernation in adult cardiomyocytes is PO(2) dependent and Ca(2+) mediated.
2001 Jan
Interleukin-6 enhances expression of adenosine A(1) receptor mRNA and signaling in cultured rat cortical astrocytes and brain slices.
2001 Jan
Second allogeneic peripheral blood stem cell transplantation with fludarabine-based low-intensity conditioning regimen for relapsed myelodysplastic syndrome after allogeneic bone marrow transplantation.
2001 Jan
Modulation of ara-CTP levels by fludarabine and hydroxyurea in leukemic cells.
2001 Jan
Cyclic GMP-dependent relaxation of isolated rat renal glomeruli induced by extracellular ATP.
2001 Jan 1
Differential patterns of sympathetic responses to selective stimulation of nucleus tractus solitarius purinergic receptor subtypes.
2001 Jan-Feb
Evaluating treatment strategies in chronic lymphocytic leukemia: use of quality-adjusted survival analysis.
2001 Jul
Will mixed chimerism cure autoimmune diseases after a nonmyeloablative stem cell transplant?
2001 Jul 27
Treatment options in Waldenström's macroglobulinaemia: the role of the purine analogues.
2001 Jun
Nucleoside analogues in the treatment of haematological malignancies.
2001 Jun
UCN-01 induces cytotoxicity toward human CLL cells through a p53-independent mechanism.
2001 Jun
Reversal of fludarabine induced testicular damage in a patient with chronic lymphocytic leukaemia (CLL), by suppression of pituitary-testicular axis using gonadotrophin releasing hormone (GnRH).
2001 Mar
Fludarabine in alkylator-resistant follicular non-Hodgkin's lymphoma.
2001 Mar
Fludarabine in combination with cyclophosphamide or with cyclophosphamide plus mitoxantrone for relapsed or refractory low-grade non-Hodgkin's lymphoma.
2001 Mar
Control of CYP11B2 gene expression through differential regulation of its promoter by atypical and conventional protein kinase C isoforms.
2001 Mar 16
Cystic fibrosis transmembrane conductance regulator gating requires cytosolic electrolytes.
2001 Mar 2
Rotavirus nonstructural protein NSP2 self-assembles into octamers that undergo ligand-induced conformational changes.
2001 Mar 30
Patents

Sample Use Guides

Adult Patients: Initial dose: 6 mg given as a rapid intravenous bolus (administered over a 1-2 second period). Repeat administration: If the first dose does not result in elimination of the supraventricular tachycardia within 1-2 minutes, 12 mg should be given as a rapid intravenous bolus. This 12 mg dose may be repeated a second time if required. Pediatric Patients: Initial dose: Give 0.05 to 0.1 mg/kg as a rapid IV bolus given either centrally or peripherally. A saline flush should follow. Repeat administration: If conversion of PSVT does not occur within 1-2 minutes, additional bolus injections of adenosine can be administered at incrementally higher doses, increasing the amount given by 0.05 to 0.1 mg/kg. Follow each bolus with a saline flush. This process should continue until sinus rhythm is established or a maximum single dose of 0.3 mg/kg is used. Pediatric Patients with a Body Weight ≥ 50 kg: Administer the adult dose.
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Name Type Language
ADENOCARD
Preferred Name English
ADENOSINE
EP   HSDB   INCI   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INCI   USAN  
Official Name English
ADENOSINE [EP MONOGRAPH]
Common Name English
9-.BETA.-D-RIBOFURANOSYLADENINE
Common Name English
ADENOSINE [EP IMPURITY]
Common Name English
ADENOSINE [VANDF]
Common Name English
ADENOSINE [ORANGE BOOK]
Common Name English
ADENOSINE [MART.]
Common Name English
ADENOSCAN
Brand Name English
ADENOSINE [MI]
Common Name English
NSC-7652
Code English
SR 96225
Code English
ADENOSINE [JAN]
Common Name English
ADENOSINE [USP MONOGRAPH]
Common Name English
ADENOSINE [USP-RS]
Common Name English
6-AMINO-9-.BETA.-D-RIBOFURANOSYL-9H-PURINE
Common Name English
ADENOSINE [HSDB]
Common Name English
SR-96225
Code English
ADENOSINE [USAN]
Common Name English
Adenosine [WHO-DD]
Common Name English
Classification Tree Code System Code
DSLD 496 (Number of products:57)
Created by admin on Mon Mar 31 17:53:03 GMT 2025 , Edited by admin on Mon Mar 31 17:53:03 GMT 2025
LOINC 75136-2
Created by admin on Mon Mar 31 17:53:03 GMT 2025 , Edited by admin on Mon Mar 31 17:53:03 GMT 2025
WHO-ATC C01EB10
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FDA ORPHAN DRUG 32388
Created by admin on Mon Mar 31 17:53:03 GMT 2025 , Edited by admin on Mon Mar 31 17:53:03 GMT 2025
NCI_THESAURUS C707
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LOINC 75142-0
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WHO-VATC QC01EB10
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NDF-RT N0000178375
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NDF-RT N0000175788
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LOINC 75160-2
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Code System Code Type Description
EPA CompTox
DTXSID1022558
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PRIMARY
RXCUI
296
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PRIMARY RxNorm
DRUG BANK
DB00640
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PRIMARY
CHEBI
16335
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PRIMARY
MESH
D000241
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PRIMARY
EVMPD
SUB00297MIG
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PRIMARY
WIKIPEDIA
ADENOSINE
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PRIMARY
DAILYMED
K72T3FS567
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PRIMARY
IUPHAR
2844
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PRIMARY
SMS_ID
100000078834
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PRIMARY
FDA UNII
K72T3FS567
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PRIMARY
MERCK INDEX
m1411
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PRIMARY Merck Index
HSDB
7774
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PRIMARY
PUBCHEM
60961
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PRIMARY
ChEMBL
CHEMBL477
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PRIMARY
DRUG CENTRAL
90
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PRIMARY
ECHA (EC/EINECS)
200-389-9
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PRIMARY
RS_ITEM_NUM
1012123
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PRIMARY
NCI_THESAURUS
C207
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PRIMARY
NSC
7652
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PRIMARY
CAS
58-61-7
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PRIMARY