ADENOSINE

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 Search

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019937s024lbl.pdfhttps://www.drugbank.ca/drugs/DB00194

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosine receptor 34 Target ID: CHEMBL2111329 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17438146	Agonist 2637
Human herpesvirus 1 DNA polymerase 17 Target ID: CHEMBL1872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24047739	Inhibitor 8146
Thymidine kinase 16 Target ID: CHEMBL1075062 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17438061	Substrate 643

Conditions

Condition	Modality	Highest Phase	Product
Paroxysmal supraventricular tachycardia 7 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019937s024lbl.pdf	Primary	Approved 8307	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 6.2570883E11
Keratoconjunctivitis 7 Sources: https://www.drugs.com/pro/vira-a.html	Curative	Approved 8307	VIRA-A Approved Use Unknown Launch Date 2.17814401E11
Epithelial keratitis 5 Sources: https://www.drugs.com/pro/vira-a.html	Curative	Approved 8307	VIRA-A Approved Use Unknown Launch Date 2.17814401E11
Herpes simplex infection 27 Sources: https://clinicaltrials.gov/ct2/show/NCT00000985	Primary	Phase III 651	VIRA-A Approved Use Unknown Launch Date 2.17814401E11

T_1/2

Value	Dose	Co-administered	Analyte	Population
3 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1348236	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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 584

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OAT1 588	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/21103968/	yes

PubMed

Title	Date	PubMed
Effect of 9-beta-D-arabinofuranosyladenine 5'-monophosphate and 9-beta-D-arabinofuranosylhypoxanthine 5'-monophosphate on experimental herpes simplex keratitis.	1976 Dec	1008546
[Preliminary clinical experiences with adenine arabinoside monophosphate (ARA-AMP) in encephalitis due to viruses of the herpes group and varicella/zoster infections (author's transl)].	1979 Nov	92592
Anti-herpesvirus activity of adenine arabinoside analogues in tissue culture and a genital infection of mice and guinea pigs.	1982 May	6179469
Effect of combinations of acyclovir with vidarabine or its 5'-monophosphate on herpes simplex viruses in cell culture and in mice.	1982 Sep	6182836
Comparison of the antiviral effects of 5-methoxymethyldeoxyuridine-5'-monophosphate with adenine arabinoside-5'-monophosphate.	1983 Sep	6197027
Inhibitory effects of 2'-fluorinated arabinosyl-pyrimidine nucleosides on woodchuck hepatitis virus replication in chronically infected woodchucks.	1990 Mar	2334160
Liver targeting of nucleoside analogues coupled to galactosyl terminating macromolecules: a new approach to the treatment of a chronic viral hepatitis.	1997 Jun	9646223
Regulation of platelet aggregation in vitro by plasma adenosine in preeclampsia.	2001	11150873
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	11159853
The effects of P2Y receptor agonists and adenosine on prostaglandin production by the guinea-pig uterus.	2001 Feb	11159724
Mechanism of prolonged vasorelaxation to ATP in the rat isolated mesenteric arterial bed.	2001 Feb	11159721
Regulation of G protein-coupled receptor-adenylyl cyclase responsiveness in human airway smooth muscle by exogenous and autocrine adenosine.	2001 Feb	11159049
Protein tyrosine phosphatase-dependent proteolysis of focal adhesion complexes in endothelial cell apoptosis.	2001 Feb	11159014
K(ATP)(+) channels, nitric oxide, and adenosine are not required for local metabolic coronary vasodilation.	2001 Feb	11158988
Regional differences in mechanisms of cerebral circulatory response to neuronal activation.	2001 Feb	11158982
Adenosine-enhanced ischemic preconditioning: adenosine receptor involvement during ischemia and reperfusion.	2001 Feb	11158956
Elevated interstitial adenosine concentrations do not activate the muscle reflex.	2001 Feb	11158950
New signaling pathways for hormones and cyclic adenosine 3',5'-monophosphate action in endocrine cells.	2001 Feb	11158328
Beta,gamma-methylene ATP-induced cAMP formation in C6Bu-1 cells: involvement of local metabolism and subsequent stimulation of adenosine A2B receptor.	2001 Feb	11158259
Protein kinase C and G(i/o) proteins are involved in adenosine- and ischemic preconditioning-mediated renal protection.	2001 Feb	11158213
Construction of gene therapy vectors targeting thyroid cells: enhancement of activity and specificity with histone deacetylase inhibitors and agents modulating the cyclic adenosine 3',5'-monophosphate pathway and demonstration of activity in follicular and anaplastic thyroid carcinoma cells.	2001 Feb	11158054
Adenosine triphosphate-evoked cytosolic calcium oscillations in human granulosa-luteal cells: role of protein kinase C.	2001 Feb	11158045
Leptin-induced lipolysis opposes the tonic inhibition of endogenous adenosine in white adipocytes.	2001 Feb	11156949
Dysregulation of extracellular adenosine levels by vascular smooth muscle cells from spontaneously hypertensive rats.	2001 Feb	11156861
Distinct modulation of evoked and spontaneous EPSCs by purinoceptors in the nucleus tractus solitarii of the rat.	2001 Feb 1	11158277
Full hematopoietic engraftment after allogeneic bone marrow transplantation without cytoreduction in a child with severe combined immunodeficiency.	2001 Feb 1	11157502
Melphalan and purine analog-containing preparative regimens: reduced-intensity conditioning for patients with hematologic malignancies undergoing allogeneic progenitor cell transplantation.	2001 Feb 1	11157478
Adenosine-mediated presynaptic modulation of glutamatergic transmission in the laterodorsal tegmentum.	2001 Feb 1	11157094
Effects of extracellular nucleotides and nucleosides on prostate carcinoma cells.	2001 Jan	11159704
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	11159696
Two subtypes of G protein-coupled nucleotide receptors, P2Y(1) and P2Y(2) are involved in calcium signalling in glioma C6 cells.	2001 Jan	11159687
Nitrogen-dependent accumulation of cytokinins in root and the translocation to leaf: implication of cytokinin species that induces gene expression of maize response regulator.	2001 Jan	11158447
Activity of adenosine diphosphates and triphosphates on a P2Y(T) -type receptor in brain capillary endothelial cells.	2001 Jan	11156575
Potentiation of cytokine induction of group IIA phospholipase A(2) in rat mesangial cells by ATP and adenosine via the A2A adenosine receptor.	2001 Jan	11156559
Quantitative relationship between the chemical structure of antisense nucleosides and their capacity to interact with cyclomalto-octaose.	2001 Jan	11154902
Sildenafil citrate (Viagra) does not exacerbate myocardial ischemia in canine models of coronary artery stenosis.	2001 Jan	11153753
Quantitative assessment of myocardial perfusion during graded coronary stenosis by real-time myocardial contrast echo refilling curves.	2001 Jan	11153750
Myocardial perfusion in patients with permanent ventricular pacing and normal coronary arteries.	2001 Jan	11153726
Hoechst 33342-induced apoptosis is associated with intracellular accumulation of E2F-1 protein in BC3H-1 myocytes and HL-60 cells.	2001 Jan	11151061
Extracellular ATP formation on vascular endothelial cells is mediated by ecto-nucleotide kinase activities via phosphotransfer reactions.	2001 Jan	11149913
Purines inhibit poly(ADP-ribose) polymerase activation and modulate oxidant-induced cell death.	2001 Jan	11149897
Differential effect of adenosine on tumor and normal cell growth: focus on the A3 adenosine receptor.	2001 Jan	11147810
Paroxysmal supraventricular tachycardia: outcome after ED care.	2001 Jan	11146016
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	11145997
Cellular distribution of constitutively active mutant parathyroid hormone (PTH)/PTH-related protein receptors and regulation of cyclic adenosine 3',5'-monophosphate signaling by beta-arrestin2.	2001 Jan	11145746
Effects of neuroprotective cocktails on hippocampal neuron death in an in vitro model of cerebral ischemia.	2001 Jan	11145473
Motivational effects of ethanol in DARPP-32 knock-out mice.	2001 Jan 1	11150351
Nucleotide-dependent single- to double-headed binding of kinesin.	2001 Jan 26	11158681
Estrogen modulates norepinephrine-induced accumulation of adenosine cyclic monophosphate in a subpopulation of immortalized luteinizing hormone-releasing hormone secreting neurons from the mouse hypothalamus.	2001 Jan 26	11154836
Differential patterns of sympathetic responses to selective stimulation of nucleus tractus solitarius purinergic receptor subtypes.	2001 Jan-Feb	11153527

Patents

Sample Use Guides

In Vivo Use Guide

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

ADENOSINE

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

ADENOCARD

Brand 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

ADENOSINE [INCI]

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)

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LOINC

75136-2

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WHO-ATC

C01EB10

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FDA ORPHAN DRUG

32388

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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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CHEBI

16335

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PRIMARY

MESH

D000241

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EVMPD

SUB00297MIG

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WIKIPEDIA

ADENOSINE

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DAILYMED

K72T3FS567

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PRIMARY

IUPHAR

2844

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PRIMARY

FDA UNII

K72T3FS567

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PRIMARY

MERCK INDEX

M1411

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Merck Index

HSDB

7774

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PRIMARY

PUBCHEM

60961

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PRIMARY

ChEMBL

CHEMBL477

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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

ACTIVE MOIETY


					K72T3FS567

ADENOSINE

METABOLITE (PARENT)


					5A614L51CT

INOSINE

Details

SMILES

InChI

DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019937s024lbl.pdfhttps://www.drugbank.ca/drugs/DB00194

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

T1/2

Overview

OverviewOther

Drug as perpetrator​

PubMed

Patents

Sample Use Guides

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019937s024lbl.pdfhttps://www.drugbank.ca/drugs/DB00194

T_1/2

Drug as perpetrator