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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 of VIDARABINE ANHYDROUS

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

HIDE SMILES / InChI

Molecular Formula C10H13N5O4
Molecular Weight 267.2413
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Effect of 9-beta-D-arabinofuranosyladenine 5'-monophosphate and 9-beta-D-arabinofuranosylhypoxanthine 5'-monophosphate on experimental herpes simplex keratitis.
1976 Dec
[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
Anti-herpesvirus activity of adenine arabinoside analogues in tissue culture and a genital infection of mice and guinea pigs.
1982 May
Effect of combinations of acyclovir with vidarabine or its 5'-monophosphate on herpes simplex viruses in cell culture and in mice.
1982 Sep
Comparison of the antiviral effects of 5-methoxymethyldeoxyuridine-5'-monophosphate with adenine arabinoside-5'-monophosphate.
1983 Sep
Inhibitory effects of 2'-fluorinated arabinosyl-pyrimidine nucleosides on woodchuck hepatitis virus replication in chronically infected woodchucks.
1990 Mar
Liver targeting of nucleoside analogues coupled to galactosyl terminating macromolecules: a new approach to the treatment of a chronic viral hepatitis.
1997 Jun
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
Salvage chemotherapy with mitoxantrone, fludarabine, cytarabine, and cisplatin (MIFAP) in relapsing and refractory lymphoma.
2001
Successful treatment of angioimmunoblastic lymphadenopathy with dysproteinemia-type T-cell lymphoma with fludarabine.
2001
Allogeneic cell therapy for patients who relapse after autologous stem cell transplantation.
2001
Successful salvage of RAEB/AML relapsing early post allograft with FLAG-Ida conditioned mini-allograft: a report of two cases.
2001 Apr
Double reinforcement with fludarabine/high-dose cytarabine enhances the impact of autologous stem cell transplantation in acute myeloid leukemia patients.
2001 Apr
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
Immune reconstitution following allogeneic stem cell transplantation in recipients conditioned by low intensity vs myeloablative regimen.
2001 Aug
Erythroleukaemia in the north of England: a population based study.
2001 Aug
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
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
Prognostic factors and response to fludarabine therapy in patients with Waldenström macroglobulinemia: results of United States intergroup trial (Southwest Oncology Group S9003).
2001 Jul 1
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
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
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
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
A trial of fludarabine and cyclophosphamide combination chemotherapy in the treatment of advanced refractory primary cutaneous T-cell lymphoma.
2001 May
Fludarabine pharmacokinetics after subcutaneous and intravenous administration in patients with lupus nephritis.
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
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.
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:20:00 UTC 2023
Edited
by admin
on Wed Jul 05 23:20:00 UTC 2023
Record UNII
3XQD2MEW34
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VIDARABINE ANHYDROUS
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
Vidarabine [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC J05AB03
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
NCI_THESAURUS C29575
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
NCI_THESAURUS C1556
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
WHO-ATC S01AD06
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
NCI_THESAURUS C281
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
Code System Code Type Description
NSC
247519
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
ECHA (EC/EINECS)
226-893-9
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
FDA UNII
3XQD2MEW34
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
NCI_THESAURUS
C77393
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
MERCK INDEX
M11443
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY Merck Index
CAS
5536-17-4
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
RXCUI
2108659
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
PUBCHEM
21704
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
EPA CompTox
DTXSID80873976
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
DAILYMED
3XQD2MEW34
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
EVMPD
SUB00047MIG
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
INN
2842
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
NSC
404241
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
HSDB
6514
Created by admin on Wed Jul 05 23:20:00 UTC 2023 , Edited by admin on Wed Jul 05 23:20:00 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SOLVATE->ANHYDROUS
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY