ADENOSINE

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 Search

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

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

Description
Sources: https://www.drugbank.ca/drugs/DB00194http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019937s024lbl.pdf

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosine receptor 34 Target ID: CHEMBL2111329 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17438146	Agonist 2678
Human herpesvirus 1 DNA polymerase 19 Target ID: CHEMBL1872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24047739	Inhibitor 8297
Thymidine kinase 17 Target ID: CHEMBL1075062 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17438061	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Paroxysmal supraventricular tachycardia 7 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019937s024lbl.pdf	Primary	Approved 8429	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
Keratoconjunctivitis 7 Sources: https://www.drugs.com/pro/vira-a.html	Curative	Approved 8429	VIRA-A Approved Use Unknown Launch Date 1976
Epithelial keratitis 5 Sources: https://www.drugs.com/pro/vira-a.html	Curative	Approved 8429	VIRA-A Approved Use Unknown Launch Date 1976
Herpes simplex infection 28 Sources: https://clinicaltrials.gov/ct2/show/NCT00000985	Primary	Phase III 656	VIRA-A Approved Use Unknown Launch Date 1976

T_1/2

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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 599

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OAT1 603	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/21103968/	yes

PubMed

Title	Date	PubMed
Autoimmune thrombocytopenia associated with the first cycle of fludarabine therapy in the treatment of relapsed non-Hodgkin's lymphoma.	2001	11554624
Management of neonatal herpes simplex virus infection.	2001	11269641
Successful salvage of RAEB/AML relapsing early post allograft with FLAG-Ida conditioned mini-allograft: a report of two cases.	2001 Apr	11488854
Results of an outpatient-based stem cell allotransplant program using nonmyeloablative conditioning regimens.	2001 Apr	11279633
Fludarabine for chronic lymphocytic leukemia.	2001 Apr 12	11302142
Recombinant bacterial cells as efficient biocatalysts for the production of nucleosides.	2001 Apr-Jul	11563158
Mito-flag as salvage therapy for relapsed and refractory acute myeloid leukemia.	2001 Aug	11574763
Immune reconstitution following allogeneic stem cell transplantation in recipients conditioned by low intensity vs myeloablative regimen.	2001 Aug	11535991
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	11529853
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	11504743
Molecular remission following high-dose hydroxyurea and fludarabine plus cytarabine in a patient with simultaneous acute myeloid leukemia and low-grade lymphoma.	2001 Feb	11426540
Second primary tumors and immune phenomena after fludarabine or 2-chloro-2'-deoxyadenosine treatment.	2001 Feb	11426527
Fludarabine-based stem cell transplantation protocol for Fanconi's anaemia in myelodysplastic transformation.	2001 Feb	11167843
Protein tyrosine phosphatase-dependent proteolysis of focal adhesion complexes in endothelial cell apoptosis.	2001 Feb	11159014
Regional differences in mechanisms of cerebral circulatory response to neuronal activation.	2001 Feb	11158982
Adenosine-enhanced ischemic preconditioning: adenosine receptor involvement during ischemia and reperfusion.	2001 Feb	11158956
Elevated interstitial adenosine concentrations do not activate the muscle reflex.	2001 Feb	11158950
Protein kinase C and G(i/o) proteins are involved in adenosine- and ischemic preconditioning-mediated renal protection.	2001 Feb	11158213
Dysregulation of extracellular adenosine levels by vascular smooth muscle cells from spontaneously hypertensive rats.	2001 Feb	11156861
Adenosine-mediated presynaptic modulation of glutamatergic transmission in the laterodorsal tegmentum.	2001 Feb 1	11157094
Mitoxantrone and fludarabine in the treatment of patients with non-Hodgkin's lymphoma failing primary therapy with a doxorubicinor mitoxantrone-containing regimen.	2001 Jan	11426553
Fludarabine, cytarabine and topotecan (FLAT) as induction therapy for acute myeloid leukemia in the elderly: a preliminary report.	2001 Jan	11146581
Effects of extracellular nucleotides and nucleosides on prostate carcinoma cells.	2001 Jan	11159704
Two subtypes of G protein-coupled nucleotide receptors, P2Y(1) and P2Y(2) are involved in calcium signalling in glioma C6 cells.	2001 Jan	11159687
Lethal adenovirus infection in a patient who had undergone nonmyeloablative stem cell transplantation.	2001 Jul	11530814
Failure of sustained engraftment after non-myeloablative conditioning with low-dose TBI and T cell-reduced allogeneic peripheral stem cell transplantation.	2001 Jul	11509933
Unrelated cord blood transplantation in a Fanconi anemia patient using fludarabine-based conditioning.	2001 Jul	11498756
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	11418461
Treatment options in Waldenström's macroglobulinaemia: the role of the purine analogues.	2001 Jun	11585010
Nucleoside analogues in the treatment of haematological malignancies.	2001 Jun	11585009
Combination chemotherapy and rituximab.	2001 Jun	11508932
Non-myeloablative hematopoietic stem cell transplantation.	2001 Jun	11499966
Nonmyeloablative hematopoietic cell transplantation. Replacing high-dose cytotoxic therapy by the graft-versus-tumor effect.	2001 Jun	11458521
Paraneoplastic pemphigus: an association with fludarabine?	2001 Jun	11422053
Vidarabine therapy for severe chronic active Epstein-Barr virus infection.	2001 Jun-Jul	11464986
Fludarabine in alkylator-resistant follicular non-Hodgkin's lymphoma.	2001 Mar	11342365
Indolent aspergillus arthritis complicating fludarabine-based non-myeloablative stem cell transplantation.	2001 Mar	11319599
New drug combinations for the treatment of murine AIDS and macrophage protection.	2001 Mar	11264653
Fatal legionella pneumonia after fludarabine treatment in chronic lymphocytic leukaemia.	2001 May	11328847
Contact dermatitis from topical antiviral drugs.	2001 May	11298689
Novel treatment strategies in chronic lymphocytic leukemia.	2001 May	11296131
Early full donor myeloid chimerism after reduced-intensity stem cell transplantation using a combination of fludarabine and busulfan.	2001 Oct	11602413
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	11587214
Cyclosporin A for the treatment of cytopenia associated with chronic lymphocytic leukemia.	2001 Oct 15	11596014
High-dose chemotherapy in high-risk myelodysplastic syndrome: covariate-adjusted comparison of five regimens.	2001 Oct 15	11596013
Synergism between fludarabine and rituximab revealed in a follicular lymphoma cell line resistant to the cytotoxic activity of either drug alone.	2001 Sep	11564066
Cathepsins are upregulated by IFN-gamma/STAT1 in human muscle culture: a possible active factor in dermatomyositis.	2001 Sep	11556541
Non-myeloablative conditioning regimen of fludarabine, busulfan, anti-thymocyte globulin, and methylprednisolone for allogeneic peripheral blood hematopoietic cell transplantation.	2001 Sep	11532635
Evaluating treatment strategies in advanced Waldenström macroglobulinemia: use of quality-adjusted survival analysis.	2001 Sep	11516109
Therapeutic options for acute myelogenous leukemia.	2001 Sep 1	11571716

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

In Vitro Use Guide

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 `Fri Dec 15 15:17:31 GMT 2023` Edited by `admin` on `Fri Dec 15 15:17:31 GMT 2023`
Record UNII	K72T3FS567
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ADENOSINE

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)