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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 of VIDARABINE ANHYDROUS

SMILES

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

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

HIDE SMILES / InChI
Adenosine is a nucleoside that is composed of adenine and d-ribose, occurring in all cells of the body and play many important biological roles in addition to being components of DNA and RNA. Adenosine itself is a neurotransmitter. Adenocard (adenosine injection) is used as an initial treatment for the termination of paroxysmal supraventricular tachycardia (PVST), including that associated with accessory bypass tracts (Wolff-Parkinson-White Syndrome). When clinically advisable, appropriate vagal maneuvers. Adenocard does not convert atrial flutter, atrial fibrillation, or ventricular tachycardia to normal sinus rhythm. In the presence of atrial flutter or atrial fibrillation, a transient modest slowing of ventricular response may occur immediately following Adenocard administration. Adenosine slows conduction time through the A-V node, can interrupt the reentry pathways through the A-V node, and can restore normal sinus rhythm. This effect may be mediated through the drug's activation of cell-surface A1 and A2 adenosine receptors. Adenocard is antagonized competitively by methylxanthines such as caffeine and theophylline, and potentiated by blockers of nucleoside transport such as dipyridamole. Adenocard is not blocked by atropine. Adenosine also inhibits the slow inward calcium current and activation of adenylate cyclase in smooth muscle cells, thereby causing relaxation of vascular smooth muscle. By increasing blood flow in normal coronary arteries with little or no increase in stenotic arteries, adenosine produces a relative difference in thallous (thallium) chloride TI 201 uptake in myocardium supplied by normal verus stenotic coronary arteries.

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

6.2570883E11
Curative
VIRA-A

Approved Use

Unknown

Launch Date

2.17814401E11
Curative
VIRA-A

Approved Use

Unknown

Launch Date

2.17814401E11
Primary
VIRA-A

Approved Use

Unknown

Launch Date

2.17814401E11
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Autoimmune thrombocytopenia associated with the first cycle of fludarabine therapy in the treatment of relapsed non-Hodgkin's lymphoma.
2001
A systematic overview of chemotherapy effects in B-cell chronic lymphocytic leukaemia.
2001
Successful treatment of angioimmunoblastic lymphadenopathy with dysproteinemia-type T-cell lymphoma with fludarabine.
2001
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
Fludarabine and cytarabine as a sequential infusion regimen for treatment of adults with recurrent, refractory or poor prognosis acute leukemia.
2001 Apr
Recombinant bacterial cells as efficient biocatalysts for the production of nucleosides.
2001 Apr-Jul
Mito-flag as salvage therapy for relapsed and refractory acute myeloid leukemia.
2001 Aug
Fludarabine plus cyclophosphamide is an efficient treatment for advanced chronic lymphocytic leukaemia (CLL): results of a phase II study of the German CLL Study Group.
2001 Aug
Dose-reduced conditioning and allogeneic hematopoietic stem cell transplantation from unrelated donors in 42 patients.
2001 Aug
Erythroleukaemia in the north of England: a population based study.
2001 Aug
Impact of therapy With chlorambucil, fludarabine, or fludarabine plus chlorambucil on infections in patients with chronic lymphocytic leukemia: Intergroup Study Cancer and Leukemia Group B 9011.
2001 Aug 15
Molecular remission following high-dose hydroxyurea and fludarabine plus cytarabine in a patient with simultaneous acute myeloid leukemia and low-grade lymphoma.
2001 Feb
Mitoxantrone and fludarabine in the treatment of patients with non-Hodgkin's lymphoma failing primary therapy with a doxorubicinor mitoxantrone-containing regimen.
2001 Jan
First line therapy with fludarabine combinations in 42 patients with either post myelodysplastic syndrome or therapy related acute myeloid leukaemia.
2001 Jan
Treatment of "poor risk" acute myeloid leukemia with fludarabine, cytarabine and G-CSF (flag regimen): a single center study.
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
Lethal adenovirus infection in a patient who had undergone nonmyeloablative stem cell transplantation.
2001 Jul
Failure of sustained engraftment after non-myeloablative conditioning with low-dose TBI and T cell-reduced allogeneic peripheral stem cell transplantation.
2001 Jul
Unrelated cord blood transplantation in a Fanconi anemia patient using fludarabine-based conditioning.
2001 Jul
Acute left ventricular failure following melphalan and fludarabine conditioning.
2001 Jul
Successful HLA-identical bone marrow transplantation in a patient with PNP deficiency using busulfan and fludarabine for conditioning.
2001 Jul
Flavopiridol circumvents Bcl-2 family mediated inhibition of apoptosis and drug resistance in B-cell chronic lymphocytic leukaemia.
2001 Jul
Evaluating treatment strategies in chronic lymphocytic leukemia: use of quality-adjusted survival analysis.
2001 Jul
Imbalanced DNA synthesis induced by cytosine arabinoside and fludarabine in human leukemia cells.
2001 Jul 1
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
Combination chemotherapy and rituximab.
2001 Jun
Non-myeloablative hematopoietic stem cell transplantation.
2001 Jun
Cost of de novo acute myeloid leukemia induction therapy in adults: analysis of EORTC-GIMEMA AML10 and FLANG regimens.
2001 Jun
Efficacy of fludarabine, intermittent sequential high-dose cytosine arabinoside, and mitoxantrone (FIS-HAM) salvage therapy in highly resistant acute leukemias.
2001 Jun
Nonmyeloablative hematopoietic cell transplantation. Replacing high-dose cytotoxic therapy by the graft-versus-tumor effect.
2001 Jun
Paraneoplastic pemphigus: an association with fludarabine?
2001 Jun
Nucleoside analogues: mechanisms of drug resistance and reversal strategies.
2001 Jun
UCN-01 induces cytotoxicity toward human CLL cells through a p53-independent mechanism.
2001 Jun
[Chronic lymphatic leukemia. 3. The concrete case].
2001 Jun 8
[Chronic lymphocytic leukemia. 2. Therapy].
2001 Jun 8
Vidarabine therapy for severe chronic active Epstein-Barr virus infection.
2001 Jun-Jul
Retrospective study of the prognostic role of serum thymidine kinase level in CLL patients with active disease treated with fludarabine.
2001 May
A trial of fludarabine and cyclophosphamide combination chemotherapy in the treatment of advanced refractory primary cutaneous T-cell lymphoma.
2001 May
Early full donor myeloid chimerism after reduced-intensity stem cell transplantation using a combination of fludarabine and busulfan.
2001 Oct
Phosphodiesterase type 4 inhibitor suppresses expression of anti-apoptotic members of the Bcl-2 family in B-CLL cells and induces caspase-dependent apoptosis.
2001 Oct
Cyclosporin A for the treatment of cytopenia associated with chronic lymphocytic leukemia.
2001 Oct 15
High-dose chemotherapy in high-risk myelodysplastic syndrome: covariate-adjusted comparison of five regimens.
2001 Oct 15
Synergism between fludarabine and rituximab revealed in a follicular lymphoma cell line resistant to the cytotoxic activity of either drug alone.
2001 Sep
Cathepsins are upregulated by IFN-gamma/STAT1 in human muscle culture: a possible active factor in dermatomyositis.
2001 Sep
Non-myeloablative conditioning regimen of fludarabine, busulfan, anti-thymocyte globulin, and methylprednisolone for allogeneic peripheral blood hematopoietic cell transplantation.
2001 Sep
Evaluating treatment strategies in advanced Waldenström macroglobulinemia: use of quality-adjusted survival analysis.
2001 Sep
Therapeutic options for acute myelogenous leukemia.
2001 Sep 1
Patents

Sample Use Guides

In Vivo Use Guide
Administer approximately one-half inch of Vira-A Ophthalmic Ointment (Vidarabine), 3%, into the lower conjunctival sac five times daily at three-hour intervals.
Route of Administration: Topical
Confluent monolayers of Vero cells in 12-well microplates were infected with approximately 200 PFU of virus and incubated at 37°C with twofold serial dilutions of antiviral drug. After 1 h, the inoculum was removed and replaced with medium containing 1% methylcellulose and Vidarabine. Control wells did not contain antiviral drugs. The cells were fixed in 100% methanol 40 h after infection and were stained with Giemsa stain. Plaques were visually inspected and counted using a dissecting microscope. The number of plaques at each drug concentration was plotted versus the log of the drug concentration, and the slope of the regression line in the linear range was determined. The amount of Vidarabine required to reduce the number of plaques by 50% from those in the control wells (EC50) was calculated from the equation of the regression line. Vidarabine was tested against each isolate at least twice in replicate wells, and the EC50 was calculated as an average value. Cytotoxicity in Vero cells for all the compounds was determined previously using a 3-(4,5- dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay.
Name Type Language
VIDARABINE ANHYDROUS
Common Name English
VIDARABINE [WHO-DD]
Common Name English
NSC-404241
Code English
NSC-247519
Code English
ARASENA-A
Brand Name English
VIDARABINE [HSDB]
Common Name English
9-.BETA.-D-ARABINOFURANOSYL-9H-PURIN-6-AMINE
Common Name English
VIDARABINE [MI]
Common Name English
VIDARABINE, ANHYDROUS
Common Name English
VIDARABINE [INN]
Common Name English
9H-PURIN-6-AMINE, 9-.BETA.-D-ARABINOFURANOSYL-
Common Name English
CI-673
Code English
VIRA-A
Brand Name English
Classification Tree Code System Code
WHO-ATC J05AB03
Created by admin on Sat Jun 26 06:40:25 UTC 2021 , Edited by admin on Sat Jun 26 06:40:25 UTC 2021
NCI_THESAURUS C29575
Created by admin on Sat Jun 26 06:40:25 UTC 2021 , Edited by admin on Sat Jun 26 06:40:25 UTC 2021
NCI_THESAURUS C1556
Created by admin on Sat Jun 26 06:40:25 UTC 2021 , Edited by admin on Sat Jun 26 06:40:25 UTC 2021
WHO-ATC S01AD06
Created by admin on Sat Jun 26 06:40:25 UTC 2021 , Edited by admin on Sat Jun 26 06:40:25 UTC 2021
NCI_THESAURUS C281
Created by admin on Sat Jun 26 06:40:25 UTC 2021 , Edited by admin on Sat Jun 26 06:40:25 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
226-893-9
Created by admin on Sat Jun 26 06:40:25 UTC 2021 , Edited by admin on Sat Jun 26 06:40:25 UTC 2021
PRIMARY
FDA UNII
3XQD2MEW34
Created by admin on Sat Jun 26 06:40:25 UTC 2021 , Edited by admin on Sat Jun 26 06:40:25 UTC 2021
PRIMARY
NCI_THESAURUS
C77393
Created by admin on Sat Jun 26 06:40:25 UTC 2021 , Edited by admin on Sat Jun 26 06:40:25 UTC 2021
PRIMARY
MERCK INDEX
M11443
Created by admin on Sat Jun 26 06:40:25 UTC 2021 , Edited by admin on Sat Jun 26 06:40:25 UTC 2021
PRIMARY Merck Index
CAS
5536-17-4
Created by admin on Sat Jun 26 06:40:25 UTC 2021 , Edited by admin on Sat Jun 26 06:40:25 UTC 2021
PRIMARY
RXCUI
2108659
Created by admin on Sat Jun 26 06:40:25 UTC 2021 , Edited by admin on Sat Jun 26 06:40:25 UTC 2021
PRIMARY
PUBCHEM
21704
Created by admin on Sat Jun 26 06:40:25 UTC 2021 , Edited by admin on Sat Jun 26 06:40:25 UTC 2021
PRIMARY
EVMPD
SUB00047MIG
Created by admin on Sat Jun 26 06:40:25 UTC 2021 , Edited by admin on Sat Jun 26 06:40:25 UTC 2021
PRIMARY
INN
2842
Created by admin on Sat Jun 26 06:40:25 UTC 2021 , Edited by admin on Sat Jun 26 06:40:25 UTC 2021
PRIMARY
HSDB
6514
Created by admin on Sat Jun 26 06:40:25 UTC 2021 , Edited by admin on Sat Jun 26 06:40:25 UTC 2021
PRIMARY