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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/019937s024lbl.pdfhttps://www.drugbank.ca/drugs/DB00194

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
Adenosine receptor 35 Target ID: CHEMBL2111329 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17438146	Agonist 2752
Human herpesvirus 1 DNA polymerase 24 Target ID: CHEMBL1872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24047739	Inhibitor 8504
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 8583	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 8583	VIRA-A Approved Use Unknown Launch Date 1976
Epithelial keratitis 5 Sources: https://www.drugs.com/pro/vira-a.html	Curative	Approved 8583	VIRA-A Approved Use Unknown Launch Date 1976
Herpes simplex infection 28 Sources: https://clinicaltrials.gov/ct2/show/NCT00000985	Primary	Phase III 665	VIRA-A Approved Use Unknown Launch Date 1976

C_max

Value	Dose	Analyte	Population
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
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
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

T_1/2

Value	Dose	Analyte	Population
10 s DRUG LABEL https://nctr-crs.fda.gov/fdalabel/services/spl/set-ids/fecdce1e-4233-f44c-e053-6294a90a714f/spl-doc?hl=adenosine	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
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
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.017% EXPERIMENT https://pubs.acs.org/doi/epdf/10.1021/acs.jmedchem.6b00866	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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 725

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/21103968/	yes

PubMed

Title	Date	PubMed
Comparison of the antiviral effects of 5-methoxymethyldeoxyuridine-5'-monophosphate with adenine arabinoside-5'-monophosphate.	1983 Sep	6197027
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	10087507
Adenosine-induced cardiac pause for endovascular embolization of cerebral arteriovenous malformations: technical case report.	1999 Apr	10201317
Adenosine conversion of supraventricular tachycardia associated with high-dose epinephrine therapy for cardiac arrest.	1999 Apr-Jun	10558324
Lipolysis is an important determinant of isoproterenol-induced myocardial necrosis.	1999 Sep-Oct	10533957
N-cycloalkyl derivatives of adenosine and 1-deazaadenosine as agonists and partial agonists of the A(1) adenosine receptor.	2000 Jan 27	10649980
Adenine-induced selective apoptosis toward HIV chronically infected cells in vitro.	2000 Jul 14	10891366
Adenosine inhibits IL-12 and TNF-[alpha] production via adenosine A2a receptor-dependent and independent mechanisms.	2000 Oct	11023991
ATP induces dephosphorylation of myosin light chain in endothelial cells.	2000 Sep	10942722
Successful salvage of RAEB/AML relapsing early post allograft with FLAG-Ida conditioned mini-allograft: a report of two cases.	2001 Apr	11488854
Double reinforcement with fludarabine/high-dose cytarabine enhances the impact of autologous stem cell transplantation in acute myeloid leukemia patients.	2001 Apr	11477440
Treatment of aggressive, or progressing indolent peripheral T- and NK-cell neoplasias by combination of fludarabine, cyclophosphamide and doxorubicine.	2001 Apr	11441297
[Mantle cell lymphoma].	2001 Apr	11400298
[Molecular biology examination in chronic lymphocytic leukemia].	2001 Apr 22	11340945
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	11159853
The effects of P2Y receptor agonists and adenosine on prostaglandin production by the guinea-pig uterus.	2001 Feb	11159724
Mechanism of prolonged vasorelaxation to ATP in the rat isolated mesenteric arterial bed.	2001 Feb	11159721
Adenosine triphosphate-evoked cytosolic calcium oscillations in human granulosa-luteal cells: role of protein kinase C.	2001 Feb	11158045
Leptin-induced lipolysis opposes the tonic inhibition of endogenous adenosine in white adipocytes.	2001 Feb	11156949
Dysregulation of extracellular adenosine levels by vascular smooth muscle cells from spontaneously hypertensive rats.	2001 Feb	11156861
Interactions between 2-fluoroadenine 9-beta-D-arabinofuranoside and the kinase inhibitor UCN-01 in human leukemia and lymphoma cells.	2001 Feb	11234887
Reactivation of hepatitis B virus infection during cytotoxic chemotherapy.	2001 Feb	11232724
Bilateral breast relapse in acute myelogenous leukemia.	2001 Feb	11216705
Effects of extracellular nucleotides and nucleosides on prostate carcinoma cells.	2001 Jan	11159704
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	11159696
Myocardial perfusion in patients with permanent ventricular pacing and normal coronary arteries.	2001 Jan	11153726
Hoechst 33342-induced apoptosis is associated with intracellular accumulation of E2F-1 protein in BC3H-1 myocytes and HL-60 cells.	2001 Jan	11151061
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	11145997
Perioperative activation of hemostasis in vascular surgery patients.	2001 Jan	11135724
Mechanism-based design of a protein kinase inhibitor.	2001 Jan	11135668
Adenosine A2B receptors behave as an alternative anchoring protein for cell surface adenosine deaminase in lymphocytes and cultured cells.	2001 Jan	11125033
A3 adenosine receptor activation triggers phosphorylation of protein kinase B and protects rat basophilic leukemia 2H3 mast cells from apoptosis.	2001 Jan	11125027
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	11123369
Short-term hibernation in adult cardiomyocytes is PO(2) dependent and Ca(2+) mediated.	2001 Jan	11123216
Interleukin-6 enhances expression of adenosine A(1) receptor mRNA and signaling in cultured rat cortical astrocytes and brain slices.	2001 Jan	11106879
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	11372748
Modulation of ara-CTP levels by fludarabine and hydroxyurea in leukemic cells.	2001 Jan	11243402
Cyclic GMP-dependent relaxation of isolated rat renal glomeruli induced by extracellular ATP.	2001 Jan 1	11136864
Differential patterns of sympathetic responses to selective stimulation of nucleus tractus solitarius purinergic receptor subtypes.	2001 Jan-Feb	11153527
Evaluating treatment strategies in chronic lymphocytic leukemia: use of quality-adjusted survival analysis.	2001 Jul	11438417
Will mixed chimerism cure autoimmune diseases after a nonmyeloablative stem cell transplant?	2001 Jul 27	11477365
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
UCN-01 induces cytotoxicity toward human CLL cells through a p53-independent mechanism.	2001 Jun	11378265
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	11342377
Fludarabine in alkylator-resistant follicular non-Hodgkin's lymphoma.	2001 Mar	11342365
Fludarabine in combination with cyclophosphamide or with cyclophosphamide plus mitoxantrone for relapsed or refractory low-grade non-Hodgkin's lymphoma.	2001 Mar	11255275
Control of CYP11B2 gene expression through differential regulation of its promoter by atypical and conventional protein kinase C isoforms.	2001 Mar 16	11115506
Cystic fibrosis transmembrane conductance regulator gating requires cytosolic electrolytes.	2001 Mar 2	11112782
Rotavirus nonstructural protein NSP2 self-assembles into octamers that undergo ligand-induced conformational changes.	2001 Mar 30	11121414

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

Unknown

Name

Type

Language

ADENOCARD

Preferred Name

English

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

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

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)