U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 ADENOSINE

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

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

1989
Curative
VIRA-A

Approved Use

Unknown

Launch Date

1976
Curative
VIRA-A

Approved Use

Unknown

Launch Date

1976
Primary
VIRA-A

Approved Use

Unknown

Launch Date

1976
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
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
Management of neonatal herpes simplex virus infection.
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
Fludarabine and cytarabine as a sequential infusion regimen for treatment of adults with recurrent, refractory or poor prognosis acute leukemia.
2001 Apr
Fludarabine for chronic lymphocytic leukemia.
2001 Apr 12
Immune reconstitution following allogeneic stem cell transplantation in recipients conditioned by low intensity vs myeloablative regimen.
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
Second primary tumors and immune phenomena after fludarabine or 2-chloro-2'-deoxyadenosine treatment.
2001 Feb
Reactivation of hepatitis B virus infection during cytotoxic chemotherapy.
2001 Feb
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
The effects of P2Y receptor agonists and adenosine on prostaglandin production by the guinea-pig uterus.
2001 Feb
Protein tyrosine phosphatase-dependent proteolysis of focal adhesion complexes in endothelial cell apoptosis.
2001 Feb
New signaling pathways for hormones and cyclic adenosine 3',5'-monophosphate action in endocrine cells.
2001 Feb
Distinct modulation of evoked and spontaneous EPSCs by purinoceptors in the nucleus tractus solitarii of the rat.
2001 Feb 1
Antiviral drugs in chronic hepatitis B: review and meta-analysis.
2001 Jan
A multicentre, open, non-comparative phase II study of a combination of fludarabine phosphate, cytarabine and granulocyte colony-stimulating factor in relapsed and refractory acute myeloid leukaemia and de novo refractory anaemia with excess of blasts in transformation.
2001 Jan
Red swollen nail folds and nail deformity as presenting findings in chronic lymphocytic leukaemia.
2001 Jan
Fludarabine, cytarabine and topotecan (FLAT) as induction therapy for acute myeloid leukemia in the elderly: a preliminary report.
2001 Jan
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
Nucleotide-dependent single- to double-headed binding of kinesin.
2001 Jan 26
Results of IDA-FLAG programme in the treatment of recurrent acute myeloblastic leukaemia--preliminary report.
2001 Jan-Feb
Lethal adenovirus infection in a patient who had undergone nonmyeloablative 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
Evaluating treatment strategies in chronic lymphocytic leukemia: use of quality-adjusted survival analysis.
2001 Jul
Herpes simplex virus dermatitis in patients using latanoprost.
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
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
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
Early allogeneic blood stem cell transplantation after modified conditioning therapy during marrow aplasia: stable remission in high-risk acute myeloid leukemia.
2001 Mar
Fludarabine in combination with cyclophosphamide or with cyclophosphamide plus mitoxantrone for relapsed or refractory low-grade non-Hodgkin's lymphoma.
2001 Mar
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
Fatal legionella pneumonia after fludarabine treatment in chronic lymphocytic leukaemia.
2001 May
Contact dermatitis from topical antiviral drugs.
2001 May
Treatment of adenovirus infections in patients undergoing allogeneic hematopoietic stem cell transplantation.
2001 May 1
Early full donor myeloid chimerism after reduced-intensity stem cell transplantation using a combination of fludarabine and busulfan.
2001 Oct
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
ADENOSINE
EP   HSDB   INCI   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INCI   USAN  
Official Name English
ADENOSINE [EP MONOGRAPH]
Common Name English
9-.BETA.-D-RIBOFURANOSYLADENINE
Common Name English
ADENOSINE [EP IMPURITY]
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 [HSDB]
Common Name English
ADENOSINE [INCI]
Common Name English
SR-96225
Code English
ADENOSINE [USAN]
Common Name English
Adenosine [WHO-DD]
Common Name English
Classification Tree Code System Code
DSLD 496 (Number of products:57)
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
LOINC 75136-2
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
WHO-ATC C01EB10
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
FDA ORPHAN DRUG 32388
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
NCI_THESAURUS C707
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
LOINC 75142-0
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
WHO-VATC QC01EB10
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
NDF-RT N0000178375
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
NDF-RT N0000175788
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
LOINC 75160-2
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID1022558
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY
RXCUI
296
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB00640
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY
CHEBI
16335
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY
MESH
D000241
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY
EVMPD
SUB00297MIG
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY
WIKIPEDIA
ADENOSINE
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY
DAILYMED
K72T3FS567
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY
IUPHAR
2844
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY
SMS_ID
100000078834
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY
FDA UNII
K72T3FS567
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY
MERCK INDEX
m1411
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY Merck Index
HSDB
7774
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY
PUBCHEM
60961
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY
ChEMBL
CHEMBL477
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY
DRUG CENTRAL
90
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-389-9
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY
RS_ITEM_NUM
1012123
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY
NCI_THESAURUS
C207
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY
NSC
7652
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY
CAS
58-61-7
Created by admin on Fri Dec 15 15:17:31 GMT 2023 , Edited by admin on Fri Dec 15 15:17:31 GMT 2023
PRIMARY