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
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O
InChI
InChIKey=OIRDTQYFTABQOQ-UHTZMRCNSA-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
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 |
|---|---|---|---|
Target ID: CHEMBL2111329 |
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Target ID: CHEMBL1872 |
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Target ID: CHEMBL1075062 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | ADENOCARD Approved UseIntravenous 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 Date6.2570883E11 |
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| Curative | VIRA-A Approved UseUnknown Launch Date2.17814401E11 |
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| Curative | VIRA-A Approved UseUnknown Launch Date2.17814401E11 |
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| Primary | VIRA-A Approved UseUnknown Launch Date2.17814401E11 |
T1/2
| 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 |
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 |
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| [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 |
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| Anti-herpesvirus activity of adenine arabinoside analogues in tissue culture and a genital infection of mice and guinea pigs. | 1982 May |
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| Effect of combinations of acyclovir with vidarabine or its 5'-monophosphate on herpes simplex viruses in cell culture and in mice. | 1982 Sep |
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| Comparison of the antiviral effects of 5-methoxymethyldeoxyuridine-5'-monophosphate with adenine arabinoside-5'-monophosphate. | 1983 Sep |
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| Inhibitory effects of 2'-fluorinated arabinosyl-pyrimidine nucleosides on woodchuck hepatitis virus replication in chronically infected woodchucks. | 1990 Mar |
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| Liver targeting of nucleoside analogues coupled to galactosyl terminating macromolecules: a new approach to the treatment of a chronic viral hepatitis. | 1997 Jun |
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| Regulation of platelet aggregation in vitro by plasma adenosine in preeclampsia. | 2001 |
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| 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 |
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| The effects of P2Y receptor agonists and adenosine on prostaglandin production by the guinea-pig uterus. | 2001 Feb |
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| Mechanism of prolonged vasorelaxation to ATP in the rat isolated mesenteric arterial bed. | 2001 Feb |
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| Regulation of G protein-coupled receptor-adenylyl cyclase responsiveness in human airway smooth muscle by exogenous and autocrine adenosine. | 2001 Feb |
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| Protein tyrosine phosphatase-dependent proteolysis of focal adhesion complexes in endothelial cell apoptosis. | 2001 Feb |
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| K(ATP)(+) channels, nitric oxide, and adenosine are not required for local metabolic coronary vasodilation. | 2001 Feb |
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| Regional differences in mechanisms of cerebral circulatory response to neuronal activation. | 2001 Feb |
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| Adenosine-enhanced ischemic preconditioning: adenosine receptor involvement during ischemia and reperfusion. | 2001 Feb |
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| Elevated interstitial adenosine concentrations do not activate the muscle reflex. | 2001 Feb |
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| New signaling pathways for hormones and cyclic adenosine 3',5'-monophosphate action in endocrine cells. | 2001 Feb |
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| Beta,gamma-methylene ATP-induced cAMP formation in C6Bu-1 cells: involvement of local metabolism and subsequent stimulation of adenosine A2B receptor. | 2001 Feb |
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| Protein kinase C and G(i/o) proteins are involved in adenosine- and ischemic preconditioning-mediated renal protection. | 2001 Feb |
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| 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 |
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| Adenosine triphosphate-evoked cytosolic calcium oscillations in human granulosa-luteal cells: role of protein kinase C. | 2001 Feb |
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| Leptin-induced lipolysis opposes the tonic inhibition of endogenous adenosine in white adipocytes. | 2001 Feb |
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| Dysregulation of extracellular adenosine levels by vascular smooth muscle cells from spontaneously hypertensive rats. | 2001 Feb |
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| Distinct modulation of evoked and spontaneous EPSCs by purinoceptors in the nucleus tractus solitarii of the rat. | 2001 Feb 1 |
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| Full hematopoietic engraftment after allogeneic bone marrow transplantation without cytoreduction in a child with severe combined immunodeficiency. | 2001 Feb 1 |
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| Melphalan and purine analog-containing preparative regimens: reduced-intensity conditioning for patients with hematologic malignancies undergoing allogeneic progenitor cell transplantation. | 2001 Feb 1 |
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| Adenosine-mediated presynaptic modulation of glutamatergic transmission in the laterodorsal tegmentum. | 2001 Feb 1 |
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| Effects of extracellular nucleotides and nucleosides on prostate carcinoma cells. | 2001 Jan |
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| 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 |
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| Two subtypes of G protein-coupled nucleotide receptors, P2Y(1) and P2Y(2) are involved in calcium signalling in glioma C6 cells. | 2001 Jan |
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| 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 |
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| Activity of adenosine diphosphates and triphosphates on a P2Y(T) -type receptor in brain capillary endothelial cells. | 2001 Jan |
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| 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 |
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| Quantitative relationship between the chemical structure of antisense nucleosides and their capacity to interact with cyclomalto-octaose. | 2001 Jan |
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| Sildenafil citrate (Viagra) does not exacerbate myocardial ischemia in canine models of coronary artery stenosis. | 2001 Jan |
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| Quantitative assessment of myocardial perfusion during graded coronary stenosis by real-time myocardial contrast echo refilling curves. | 2001 Jan |
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| Myocardial perfusion in patients with permanent ventricular pacing and normal coronary arteries. | 2001 Jan |
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| Hoechst 33342-induced apoptosis is associated with intracellular accumulation of E2F-1 protein in BC3H-1 myocytes and HL-60 cells. | 2001 Jan |
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| Extracellular ATP formation on vascular endothelial cells is mediated by ecto-nucleotide kinase activities via phosphotransfer reactions. | 2001 Jan |
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| Purines inhibit poly(ADP-ribose) polymerase activation and modulate oxidant-induced cell death. | 2001 Jan |
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| Differential effect of adenosine on tumor and normal cell growth: focus on the A3 adenosine receptor. | 2001 Jan |
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| Paroxysmal supraventricular tachycardia: outcome after ED care. | 2001 Jan |
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| 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 |
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| 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 |
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| Effects of neuroprotective cocktails on hippocampal neuron death in an in vitro model of cerebral ischemia. | 2001 Jan |
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| Motivational effects of ethanol in DARPP-32 knock-out mice. | 2001 Jan 1 |
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| Nucleotide-dependent single- to double-headed binding of kinesin. | 2001 Jan 26 |
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| 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 |
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| Differential patterns of sympathetic responses to selective stimulation of nucleus tractus solitarius purinergic receptor subtypes. | 2001 Jan-Feb |
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
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WHO-ATC |
J05AB03
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NCI_THESAURUS |
C29575
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NCI_THESAURUS |
C1556
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S01AD06
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NCI_THESAURUS |
C281
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247519
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226-893-9
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3XQD2MEW34
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C77393
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M11443
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5536-17-4
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2108659
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SUB00047MIG
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2842
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404241
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6514
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
