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

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H13N5O2
Molecular Weight 235.2425
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIDEOXYADENOSINE

SMILES

NC1=NC=NC2=C1N=CN2[C@H]3CC[C@@H](CO)O3

InChI

InChIKey=WVXRAFOPTSTNLL-NKWVEPMBSA-N
InChI=1S/C10H13N5O2/c11-9-8-10(13-4-12-9)15(5-14-8)7-2-1-6(3-16)17-7/h4-7,16H,1-3H2,(H2,11,12,13)/t6-,7+/m0/s1

HIDE SMILES / InChI

Molecular Formula C10H13N5O2
Molecular Weight 235.2425
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Dideoxyadenosine (2′,3′-dideoxyadenosine) is a prodrug form of didanosine (2',3'-dideoxyinosine), a nucleoside reverse transcriptase inhibitor analog of adenosine. 2',3'-Dideoxyadenosine and 2',3'-dideoxyinosine were shown to be equally effective in the inhibition of HIV proliferation in human T cells. Dideoxyadenosine competitively inhibits adenylyl cyclase, thereby reducing levels of cyclic adenosine monophosphate (cAMP). By inhibiting cAMP-mediated gene activation in tumor cells, this agent may retard tumor cell proliferation. 2',3'-dideoxyadenosine inhibits retroviral DNA synthesis and mRNA expression in T cells exposed to the virus that causes acquired immunodeficiency syndrome, and affords such cells long-term protection in vitro under conditions of substantial viral excess. 2',3'-dideoxyadenosine appears to completely block reverse transcription from viral RNA to viral DNA. 2',3'-dideoxyadenosine was also shown not only to possess antibacterial activity in vitro against a variety of Enterobacteriaceae, but also to be effective in vivo, dideoxyadenosine was active in experimental mouse infections by the oral route against 5 Salmonella strains, 2 of 3 Arizona strains, 5 of 7 Citrobacter strains, 3 of 8 Klebsiella strains, 3 of 5 Escherichia strains, 1 of 3 Shigella strains, and 3 of 15 Serratia strains at concentrations generally well below the toxic level.

Originator

Curator's Comment: Dideoxyadenosine (2′,3′-dideoxyadenosine) was initially synthesized by Morris J. Robins (professor of Organic Chemistry at Brigham Young University) and R.K. Robins in 1964.

Approval Year

PubMed

PubMed

TitleDatePubMed
Angiotensin II type 2 receptor decreases ischemia reperfusion induced fluid leak.
2007-04
Protein kinase signalling requirements for metabotropic action of kainate receptors in rat CA1 pyramidal neurones.
2007-03-01
Prostaglandin E(2) protects human lung fibroblasts from cigarette smoke extract-induced apoptosis via EP(2) receptor activation.
2007-01
C-phycocyanin transcriptionally regulates uPA mRNA through cAMP mediated PKA pathway in human fibroblast WI-38 cells.
2006-11
Salbutamol inhibits trypsin-mediated production of CXCL8 by keratinocytes.
2006-10
Butyrate differentially regulates cytokines and proliferation in porcine peripheral blood mononuclear cells.
2006-09-15
Short chain fatty acids induce TH gene expression via ERK-dependent phosphorylation of CREB protein.
2006-08-30
Lipoteichoic acid-induced nitric oxide synthase expression in RAW 264.7 macrophages is mediated by cyclooxygenase-2, prostaglandin E2, protein kinase A, p38 MAPK, and nuclear factor-kappaB pathways.
2006-08
Impaired complement-mediated phagocytosis by HIV type-1-infected human monocyte-derived macrophages involves a cAMP-dependent mechanism.
2006-07
Effects of adenylyl cyclase and protein kinase A inhibition on signaling enzymes in natural killer cells: comparison to tributyltin.
2006-06
Phosphorylation of paracellin-1 at Ser217 by protein kinase A is essential for localization in tight junctions.
2006-05-01
Effects of estrogenic xenobiotics on human and mouse spermatozoa.
2006-05
Ethanol induces apoptotic death of developing beta-endorphin neurons via suppression of cyclic adenosine monophosphate production and activation of transforming growth factor-beta1-linked apoptotic signaling.
2006-03
Signaling pathways for modulation of mouse sperm motility by adenosine and catecholamine agonists.
2006-03
Angiotensin II subtype AT1 and AT2 receptors regulate microvascular hydraulic permeability via cAMP and cGMP.
2006-03
Multiple signalling pathways involved in beta2-adrenoceptor-mediated glucose uptake in rat skeletal muscle cells.
2006-02
Calcitonin gene-related peptide activates different signaling pathways in mesenteric lymphatics of guinea pigs.
2006-02
Adenylate cyclase 5 and KCa1.1 channel are required for EGFR up-regulation of PCNA in native contractile rat basilar artery smooth muscle.
2006-01-01
Cyclooxygenase-2 induction by bradykinin in aortic vascular smooth muscle cells.
2006-01
Influence of dipeptidyl peptidase IV on enzymatic properties of adenosine deaminase.
2006
2'-deoxy-4'-C-ethynyl-2-fluoroadenosine, a nucleoside reverse transcriptase inhibitor, is highly potent against all human immunodeficiency viruses type 1 and has low toxicity.
2006
Short chain fatty acids regulate tyrosine hydroxylase gene expression through a cAMP-dependent signaling pathway.
2005-12-07
[Synthesis of a novel L-nucleoside, beta-L-D4A and its inhibition on the replication of hepatitis B virus in vitro].
2005-09
Relaxant effect of adrenomedullin on bovine isolated iris sphincter muscle under resting conditions.
2005-08
cAMP and protein kinase A contribute to the downregulation of spinal glutamate transporters after chronic morphine.
2005-03-07
Mechanisms of action of angiotensin II on mammalian sperm function.
2005-02
Enhancement of cellular adenosine triphosphate levels in PC12 cells by 2,5-dideoxyadenosine, a P-site inhibitor of adenylate cyclase.
2005-02
Phosphoramidate derivatives of 2',5'-dideoxyadenosine as potential inhibitors of the EDHF phenomenon.
2005
Nicotine and epibatidine triggered prolonged rise in calcium and TH gene transcription in PC12 cells.
2004-12-03
Effects of primer-template sequence on ATP-dependent removal of chain-terminating nucleotide analogues by HIV-1 reverse transcriptase.
2004-10-29
Glucagon-like peptide-2: divergent signaling pathways.
2004-09
Mu-opioid receptor trafficking on inhibitory synapses in the rat brainstem.
2004-08-18
[Heterogeneity of olfactory transduction mechanisms in the frog Rana temporaria].
2004-07-29
Human chorionic gonadotropin decreases proliferation and invasion of breast cancer MCF-7 cells by inhibiting NF-kappaB and AP-1 activation.
2004-06-11
PGE2 induces IL-1beta gene expression in mouse osteoblasts through a cAMP-PKA signaling pathway.
2004-06
Enhanced inhibition of the EDHF phenomenon by a phenyl methoxyalaninyl phosphoramidate derivative of dideoxyadenosine.
2004-05
Atrial natriuretic peptide-C receptor-induced attenuation of adenylyl cyclase signaling activates phosphatidylinositol turnover in A10 vascular smooth muscle cells.
2004-04
Synthesis of 2',5'-dideoxy-2-fluoroadenosine and 2',5'-dideoxy-2,5'-difluoroadenosine: potent P-site inhibitors of adenylyl cyclase.
2004-02-26
Determination of carrier-mediated transport of 2',3'-dideoxypurine nucleosides in the rat ileum using a bidirectional perfusion technique.
2004-02
Inhibition of severe acute respiratory syndrome-associated coronavirus (SARSCoV) by calpain inhibitors and beta-D-N4-hydroxycytidine.
2004-01
Structure of the N-terminal domain of GRP94. Basis for ligand specificity and regulation.
2003-11-28
A facile synthetic method for 3'-alpha-fluoro-2',3'-dideoxyadenosine.
2003-10-21
An industrial process for synthesizing Lodenosine (FddA).
2003-10-21
Phosphoramidate protides of 2',3'-dideoxy-3'-fluoroadenosine and related nucleosides with potent activity against HIV and HBV.
2003-10
Evidence for multiple distinctly localized adenylyl cyclase isoforms in mammalian spermatozoa.
2003-10
Decreased adenylyl cyclase and cAMP-dependent protein kinase activities inhibit the cytotoxic function of human natural killer cells.
2003-09
Anti-HIV-1 activity of 3-deaza-adenosine analogs. Inhibition of S-adenosylhomocysteine hydrolase and nucleotide congeners.
2003-09
A strategy for liquid chromatography/tandem mass spectrometric assays of intracellular drugs: application to the validation of the triphosphorylated anabolite of antiretrovirals in peripheral blood mononuclear cells.
2003-08
Use of a standardized cell culture assay to assess activities of nucleoside analogs against hepatitis B virus replication.
1992-07-01
Synthesis and anti-HIV activity of isonucleosides.
1992-06-26
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Oral route: oral dosage solutions contained ddAdo (25 mg/mL) in a 0.1 M acetate buffer (pH 7.0).
The pharmacokinetics of 2',3'-dideoxyadenosine (ddAdo) and 2',3'-dideoxyinosine (ddIno) were determined after intravenous administration of 100 mg/kg ddAdo, by bolus administration in four dogs and 500 rng/kg in two dogs. Intravenous doses of 500 mg/kg were administered in a volume of 20 mL/kg of physiologic saline at a rate of 15- 18 mL/min. Intravenous doses of 100 mg/kg were given at a volume of 4 mL/kg.
Route of Administration: Intravenous
In Vitro Use Guide
Curator's Comment: 2',3'-dideoxyadenosine (ddAdo) and 2',3'-dideoxyinosine (ddIno) are equally effective in the inhibition of HIV proliferation in human T cells, and minimal viral inhibitory concentrations are approximately 10 uM or 2.4 ug/ml. https://www.ncbi.nlm.nih.gov/pubmed/1908444
At an extracellular concentration of 10 uM, which blocks the cytopathic effect of human immunodeficiency virus in vitro, 2',3'-dideoxyadenosine (ddAdo) was found to be metabolized to its mono-, di-, and triphosphates and to dideoxyinosine monophosphate (ddIMP).
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:19:08 GMT 2025
Edited
by admin
on Mon Mar 31 21:19:08 GMT 2025
Record UNII
4Q86AH641A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIDANOSINE IMPURITY G
EP   WHO-IP  
Preferred Name English
DIDEOXYADENOSINE
MART.   MI  
Systematic Name English
2'-3'-DIDEOXYADENOSINE
Common Name English
DIDEOXYADENOSINE [MART.]
Common Name English
DIDANOSINE IMPURITY G [EP IMPURITY]
Common Name English
2',3'-DIDEOXYADENOSINE [WHO-IP]
Common Name English
DIDANOSINE RELATED COMPOUND B [USP-RS]
Common Name English
6-AMINO-9-(2',3'-DIDEOXY-.BETA.-D-GLYCERO-PENTOFURANOSYL)PURINE
Common Name English
DIDANOSINE RELATED COMPOUND B [USP IMPURITY]
Common Name English
NSC-98700
Code English
2',3'-DIDEOXYADENOSINE
WHO-IP  
Systematic Name English
DIDEOXYADENOSINE [MI]
Common Name English
9-(2,3-DIDEOXY-.BETA.-D-GLYCERO-PENTOFURANOSYL)-9H-PURIN-6-AMINE [WHO-IP]
Systematic Name English
DIDANOSINE RELATED COMPOUND B
USP   USP-RS  
Common Name English
DIDANOSINE IMPURITY G [WHO-IP]
Common Name English
DDA
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 20587
Created by admin on Mon Mar 31 21:19:08 GMT 2025 , Edited by admin on Mon Mar 31 21:19:08 GMT 2025
NCI_THESAURUS C707
Created by admin on Mon Mar 31 21:19:08 GMT 2025 , Edited by admin on Mon Mar 31 21:19:08 GMT 2025
NCI_THESAURUS C97452
Created by admin on Mon Mar 31 21:19:08 GMT 2025 , Edited by admin on Mon Mar 31 21:19:08 GMT 2025
Code System Code Type Description
ECHA (EC/EINECS)
223-853-2
Created by admin on Mon Mar 31 21:19:08 GMT 2025 , Edited by admin on Mon Mar 31 21:19:08 GMT 2025
PRIMARY
CAS
4097-22-7
Created by admin on Mon Mar 31 21:19:08 GMT 2025 , Edited by admin on Mon Mar 31 21:19:08 GMT 2025
PRIMARY
NCI_THESAURUS
C429
Created by admin on Mon Mar 31 21:19:08 GMT 2025 , Edited by admin on Mon Mar 31 21:19:08 GMT 2025
PRIMARY
RS_ITEM_NUM
1191237
Created by admin on Mon Mar 31 21:19:08 GMT 2025 , Edited by admin on Mon Mar 31 21:19:08 GMT 2025
PRIMARY
PUBCHEM
20039
Created by admin on Mon Mar 31 21:19:08 GMT 2025 , Edited by admin on Mon Mar 31 21:19:08 GMT 2025
PRIMARY
FDA UNII
4Q86AH641A
Created by admin on Mon Mar 31 21:19:08 GMT 2025 , Edited by admin on Mon Mar 31 21:19:08 GMT 2025
PRIMARY
CHEBI
91207
Created by admin on Mon Mar 31 21:19:08 GMT 2025 , Edited by admin on Mon Mar 31 21:19:08 GMT 2025
PRIMARY
NSC
98700
Created by admin on Mon Mar 31 21:19:08 GMT 2025 , Edited by admin on Mon Mar 31 21:19:08 GMT 2025
PRIMARY
EPA CompTox
DTXSID2023771
Created by admin on Mon Mar 31 21:19:08 GMT 2025 , Edited by admin on Mon Mar 31 21:19:08 GMT 2025
PRIMARY
MERCK INDEX
m4382
Created by admin on Mon Mar 31 21:19:08 GMT 2025 , Edited by admin on Mon Mar 31 21:19:08 GMT 2025
PRIMARY Merck Index
Related Record Type Details
PARENT -> IMPURITY
In the chromatogram obtained with solution (2), the following peaks are eluted at the following relative retention with reference to didanosine (retention time about 13-15 min): impurity G about 1.6. The area of any individual peak corresponding to impurity G is not greater than 0.2 times the area of the principal peak obtained with solution (4) (0.2%).
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY