ADENOSINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H13N5O4
Molecular Weight	267.2417
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C([C@]1([H])[C@]([H])([C@]([H])([C@]([H])(n2cnc3c(N)ncnc32)O1)O)O)O

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
Adenosine receptor 32 Target ID: CHEMBL2111329 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17438146	Agonist 2456	Paroxysmal supraventricular tachycardia
Human herpesvirus 1 DNA polymerase 16 Target ID: CHEMBL1872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24047739	Inhibitor 7701	Keratoconjunctivitis Epithelial keratitis Herpes simplex infection
Thymidine kinase 15 Target ID: CHEMBL1075062 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17438061	Substrate 609	Herpes simplex infection Epithelial keratitis Keratoconjunctivitis

Conditions

Condition	Modality	Targets	Highest Phase	Product
Paroxysmal supraventricular tachycardia 7 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019937s024lbl.pdf	Primary	Adenosine receptor	Approved 7997	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 625708800000
Keratoconjunctivitis 7 Sources: https://www.drugs.com/pro/vira-a.html	Curative	Human herpesvirus 1 DNA polymerase Thymidine kinase	Approved 7997	VIRA-A Launch Date 217814400000
Epithelial keratitis 5 Sources: https://www.drugs.com/pro/vira-a.html	Curative	Human herpesvirus 1 DNA polymerase Thymidine kinase	Approved 7997	VIRA-A Launch Date 217814400000
Herpes simplex infection 25 Sources: https://clinicaltrials.gov/ct2/show/NCT00000985	Primary	Human herpesvirus 1 DNA polymerase Thymidine kinase	Phase III 650	VIRA-A Launch Date 217814400000

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 547

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OAT1 551	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/21103968/	yes

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P003FEZ
1PlusChem LLC	1P003VRI
AA Blocks	AA00319I
AA Blocks	AA0034CX
AK Scientific	2793AH
AbovChem LLC	HY-B0277
Alfa Chemistry	ACM24356669
Alinda	IBS-L0126092
Ambeed	A153495
Angene	AGN-PC-0R7M86
Angene	AGN-PC-0SIZKY
AstaTech	A11530
AstaTech	HG1001
AstaTech	T72143
BLDpharm	BD42581
BOC Sciences	24356-66-9
Bide Pharmatech	BD42581
BioSynth	W-203087
BlocksMatrix Scientific	119439
Bosche Scientific	V6537
Cayman Chemical	18149
Chem Scene	CS-2267
Chem-Impex International	1750
ChemShuttle	151506
Combi-Blocks	QC-1734
Compound Cloud	21704
Compound Cloud	32326
Enamine	EN300-297292
Enamine	EN300-297293
Fluorochem	91487
Hairui	HR123665
Hairui	HR130668
Hairui	HR142060
KeyOrganics	AS-69806
KeyOrganics	DS-1755
Lab Network	LN00219929
Lab Network	LN00221150
Lab Network	LN01282073
Lab Seeker	SC-05540
Lab Seeker	SC-17048
Lan Pharmatech	LQT-B11908
MedChem Express	HY-B0277
MolPort	MolPort-001-785-903
MolPort	MolPort-003-666-308
MolPort	MolPort-003-986-948
Molnova	M15012
MuseChem	A000912
Nanjing Pope Bio-tech	NSTH-D11524
Norris Pharm	NSTH-D11524
Norris Pharm	NSZB-A080083
Oakwood	91487
Ryan Scientific	Chenodeoxycholic_acid
Ryan Scientific	Tiopronin
Scientific Exchange	POD_29/0640
Selleck Chemicals	S1784
Selleck Chemicals	S5297
ShangHai Biochempartner	BCP27778
Sigma Aldrich	1711508
Sigma Aldrich	1711508\|USP
Sigma Aldrich	A5762
Sigma Aldrich	A5762\|SIGMA
Sigma Aldrich	CDS020711
Sigma Aldrich	CDS020711\|ALDRICH
StruChem	SC-05540
StruChem	SC-17048
TargetMol	T0853
TargetMol	T1506
Toronto Research Chemicals	A280400
Toronto Research Chemicals	V305030
Toronto Research Chemicals	V305038
Vitas-M Laboratory	BBL007185
Vitas-M Laboratory	STK361815
Wonderchem	WD03AFC
Wonderchem	WD03P4V
Wonderchem	WD03RFK
Wonderchem	WD05P2W
ZINC	ZINC000000970363	http://zinc15.docking.org/substances/ZINC000000970363
eMolecules	206842881
eMolecules	299982187
eMolecules	474938
eMolecules	4927665
eMolecules	50377539
eMolecules	84832776
eNovation Chemicals	D582390
eNovation Chemicals	D589908
mcule	MCULE-4219451083
mcule	MCULE-7671875172

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
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
Adenosine as a neuromodulator and as a homeostatic regulator in the nervous system: different roles, different sources and different receptors.	2001 Feb	11137880
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
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
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
Pharmacokinetic-pharmacodynamic modeling of the antilipolytic effects of an adenosine receptor agonist in healthy volunteers.	2001 Jan	11144995
Influence of adduct position and sequence length on the ligation of oligonucleotides containing benzo[c]phenanthrene diol epoxide-deoxyadenosine adducts into M13mp7L2.	2001 Jan	11139600
P2 receptor agonists stimulate insulin release from human pancreatic islets.	2001 Jan	11138974
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
Nucleoside transport inhibition in ischemic myocardium results in enhanced taurine efflux.	2001 Jan 5	11137869
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:

Route of Administration: Intravenous

Name

Type

Language

ADENOSINE

Official Name

English

ADENOSINE [EP MONOGRAPH]

Common Name

English

9-.BETA.-D-RIBOFURANOSYLADENINE

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 [EP]

Common Name

English

ADENOSINE [HSDB]

Common Name

English

ADENOSINE [INCI]

Common Name

English

SR-96225

Code

English

ADENOSINE [USAN]

Common Name

English

Classification Tree Code System Code

DSLD

496 (Number of products:57)