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-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
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 |
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Target ID: CHEMBL2111329 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17438146 |
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Target ID: CHEMBL1872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24047739 |
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Target ID: CHEMBL1075062 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17438061 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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 Date1989 |
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Curative | VIRA-A Approved UseUnknown Launch Date1976 |
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Curative | VIRA-A Approved UseUnknown Launch Date1976 |
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Primary | VIRA-A Approved UseUnknown Launch Date1976 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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0.17 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8359193/ |
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 |
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0.48 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8359193/ |
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 |
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0.78 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8359193/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
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0.92 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8359193/ |
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 |
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1.24 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8359193/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8359193/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8359193/ |
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 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 |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
PubMed
Title | Date | PubMed |
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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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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 |
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Adenosine-induced cardiac pause for endovascular embolization of cerebral arteriovenous malformations: technical case report. | 1999 Apr |
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Adenosine conversion of supraventricular tachycardia associated with high-dose epinephrine therapy for cardiac arrest. | 1999 Apr-Jun |
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Lipolysis is an important determinant of isoproterenol-induced myocardial necrosis. | 1999 Sep-Oct |
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N-cycloalkyl derivatives of adenosine and 1-deazaadenosine as agonists and partial agonists of the A(1) adenosine receptor. | 2000 Jan 27 |
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Adenine-induced selective apoptosis toward HIV chronically infected cells in vitro. | 2000 Jul 14 |
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Adenosine inhibits IL-12 and TNF-[alpha] production via adenosine A2a receptor-dependent and independent mechanisms. | 2000 Oct |
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ATP induces dephosphorylation of myosin light chain in endothelial cells. | 2000 Sep |
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Successful salvage of RAEB/AML relapsing early post allograft with FLAG-Ida conditioned mini-allograft: a report of two cases. | 2001 Apr |
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Double reinforcement with fludarabine/high-dose cytarabine enhances the impact of autologous stem cell transplantation in acute myeloid leukemia patients. | 2001 Apr |
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Treatment of aggressive, or progressing indolent peripheral T- and NK-cell neoplasias by combination of fludarabine, cyclophosphamide and doxorubicine. | 2001 Apr |
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[Mantle cell lymphoma]. | 2001 Apr |
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[Molecular biology examination in chronic lymphocytic leukemia]. | 2001 Apr 22 |
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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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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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Interactions between 2-fluoroadenine 9-beta-D-arabinofuranoside and the kinase inhibitor UCN-01 in human leukemia and lymphoma cells. | 2001 Feb |
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Reactivation of hepatitis B virus infection during cytotoxic chemotherapy. | 2001 Feb |
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Bilateral breast relapse in acute myelogenous leukemia. | 2001 Feb |
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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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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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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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Perioperative activation of hemostasis in vascular surgery patients. | 2001 Jan |
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Mechanism-based design of a protein kinase inhibitor. | 2001 Jan |
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Adenosine A2B receptors behave as an alternative anchoring protein for cell surface adenosine deaminase in lymphocytes and cultured cells. | 2001 Jan |
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A3 adenosine receptor activation triggers phosphorylation of protein kinase B and protects rat basophilic leukemia 2H3 mast cells from apoptosis. | 2001 Jan |
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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 |
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Short-term hibernation in adult cardiomyocytes is PO(2) dependent and Ca(2+) mediated. | 2001 Jan |
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Interleukin-6 enhances expression of adenosine A(1) receptor mRNA and signaling in cultured rat cortical astrocytes and brain slices. | 2001 Jan |
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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 |
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Modulation of ara-CTP levels by fludarabine and hydroxyurea in leukemic cells. | 2001 Jan |
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Cyclic GMP-dependent relaxation of isolated rat renal glomeruli induced by extracellular ATP. | 2001 Jan 1 |
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Differential patterns of sympathetic responses to selective stimulation of nucleus tractus solitarius purinergic receptor subtypes. | 2001 Jan-Feb |
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Evaluating treatment strategies in chronic lymphocytic leukemia: use of quality-adjusted survival analysis. | 2001 Jul |
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Will mixed chimerism cure autoimmune diseases after a nonmyeloablative stem cell transplant? | 2001 Jul 27 |
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Treatment options in Waldenström's macroglobulinaemia: the role of the purine analogues. | 2001 Jun |
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Nucleoside analogues in the treatment of haematological malignancies. | 2001 Jun |
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UCN-01 induces cytotoxicity toward human CLL cells through a p53-independent mechanism. | 2001 Jun |
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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 |
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Fludarabine in alkylator-resistant follicular non-Hodgkin's lymphoma. | 2001 Mar |
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Fludarabine in combination with cyclophosphamide or with cyclophosphamide plus mitoxantrone for relapsed or refractory low-grade non-Hodgkin's lymphoma. | 2001 Mar |
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Control of CYP11B2 gene expression through differential regulation of its promoter by atypical and conventional protein kinase C isoforms. | 2001 Mar 16 |
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Cystic fibrosis transmembrane conductance regulator gating requires cytosolic electrolytes. | 2001 Mar 2 |
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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
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496 (Number of products:57)
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75160-2
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ACTIVE MOIETY
METABOLITE (PARENT)