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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
Use of a standardized cell culture assay to assess activities of nucleoside analogs against hepatitis B virus replication.
1992 Jul 1
Synthesis and anti-HIV activity of isonucleosides.
1992 Jun 26
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 Aug
A facile synthetic method for 3'-alpha-fluoro-2',3'-dideoxyadenosine.
2003 May-Aug
An industrial process for synthesizing Lodenosine (FddA).
2003 May-Aug
Structure of the N-terminal domain of GRP94. Basis for ligand specificity and regulation.
2003 Nov 28
Phosphoramidate protides of 2',3'-dideoxy-3'-fluoroadenosine and related nucleosides with potent activity against HIV and HBV.
2003 Oct
Evidence for multiple distinctly localized adenylyl cyclase isoforms in mammalian spermatozoa.
2003 Oct
Decreased adenylyl cyclase and cAMP-dependent protein kinase activities inhibit the cytotoxic function of human natural killer cells.
2003 Sep
Anti-HIV-1 activity of 3-deaza-adenosine analogs. Inhibition of S-adenosylhomocysteine hydrolase and nucleotide congeners.
2003 Sep
Atrial natriuretic peptide-C receptor-induced attenuation of adenylyl cyclase signaling activates phosphatidylinositol turnover in A10 vascular smooth muscle cells.
2004 Apr
Mu-opioid receptor trafficking on inhibitory synapses in the rat brainstem.
2004 Aug 18
Nicotine and epibatidine triggered prolonged rise in calcium and TH gene transcription in PC12 cells.
2004 Dec 3
Determination of carrier-mediated transport of 2',3'-dideoxypurine nucleosides in the rat ileum using a bidirectional perfusion technique.
2004 Feb
Synthesis of 2',5'-dideoxy-2-fluoroadenosine and 2',5'-dideoxy-2,5'-difluoroadenosine: potent P-site inhibitors of adenylyl cyclase.
2004 Feb 26
Inhibition of severe acute respiratory syndrome-associated coronavirus (SARSCoV) by calpain inhibitors and beta-D-N4-hydroxycytidine.
2004 Jan
PGE2 induces IL-1beta gene expression in mouse osteoblasts through a cAMP-PKA signaling pathway.
2004 Jun
Human chorionic gonadotropin decreases proliferation and invasion of breast cancer MCF-7 cells by inhibiting NF-kappaB and AP-1 activation.
2004 Jun 11
[Heterogeneity of olfactory transduction mechanisms in the frog Rana temporaria].
2004 Mar-Apr
Enhanced inhibition of the EDHF phenomenon by a phenyl methoxyalaninyl phosphoramidate derivative of dideoxyadenosine.
2004 May
Effects of primer-template sequence on ATP-dependent removal of chain-terminating nucleotide analogues by HIV-1 reverse transcriptase.
2004 Oct 29
Glucagon-like peptide-2: divergent signaling pathways.
2004 Sep
Phosphoramidate derivatives of 2',5'-dideoxyadenosine as potential inhibitors of the EDHF phenomenon.
2005
Relaxant effect of adrenomedullin on bovine isolated iris sphincter muscle under resting conditions.
2005 Aug
Short chain fatty acids regulate tyrosine hydroxylase gene expression through a cAMP-dependent signaling pathway.
2005 Dec 7
Mechanisms of action of angiotensin II on mammalian sperm function.
2005 Feb
Enhancement of cellular adenosine triphosphate levels in PC12 cells by 2,5-dideoxyadenosine, a P-site inhibitor of adenylate cyclase.
2005 Feb
cAMP and protein kinase A contribute to the downregulation of spinal glutamate transporters after chronic morphine.
2005 Mar 7
[Synthesis of a novel L-nucleoside, beta-L-D4A and its inhibition on the replication of hepatitis B virus in vitro].
2005 Sep
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
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 Aug
Short chain fatty acids induce TH gene expression via ERK-dependent phosphorylation of CREB protein.
2006 Aug 30
Multiple signalling pathways involved in beta2-adrenoceptor-mediated glucose uptake in rat skeletal muscle cells.
2006 Feb
Calcitonin gene-related peptide activates different signaling pathways in mesenteric lymphatics of guinea pigs.
2006 Feb
Cyclooxygenase-2 induction by bradykinin in aortic vascular smooth muscle cells.
2006 Jan
Adenylate cyclase 5 and KCa1.1 channel are required for EGFR up-regulation of PCNA in native contractile rat basilar artery smooth muscle.
2006 Jan 1
Impaired complement-mediated phagocytosis by HIV type-1-infected human monocyte-derived macrophages involves a cAMP-dependent mechanism.
2006 Jul
Effects of adenylyl cyclase and protein kinase A inhibition on signaling enzymes in natural killer cells: comparison to tributyltin.
2006 Jun
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 Mar
Signaling pathways for modulation of mouse sperm motility by adenosine and catecholamine agonists.
2006 Mar
Angiotensin II subtype AT1 and AT2 receptors regulate microvascular hydraulic permeability via cAMP and cGMP.
2006 Mar
Effects of estrogenic xenobiotics on human and mouse spermatozoa.
2006 May
Phosphorylation of paracellin-1 at Ser217 by protein kinase A is essential for localization in tight junctions.
2006 May 1
C-phycocyanin transcriptionally regulates uPA mRNA through cAMP mediated PKA pathway in human fibroblast WI-38 cells.
2006 Nov
Salbutamol inhibits trypsin-mediated production of CXCL8 by keratinocytes.
2006 Oct
Butyrate differentially regulates cytokines and proliferation in porcine peripheral blood mononuclear cells.
2006 Sep 15
Angiotensin II type 2 receptor decreases ischemia reperfusion induced fluid leak.
2007 Apr
Prostaglandin E(2) protects human lung fibroblasts from cigarette smoke extract-induced apoptosis via EP(2) receptor activation.
2007 Jan
Protein kinase signalling requirements for metabotropic action of kainate receptors in rat CA1 pyramidal neurones.
2007 Mar 1
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 Sat Dec 16 03:31:14 UTC 2023
Edited
by admin
on Sat Dec 16 03:31:14 UTC 2023
Record UNII
4Q86AH641A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIDEOXYADENOSINE
MART.   MI  
Systematic Name English
DIDANOSINE IMPURITY G
EP   WHO-IP  
Common 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 Sat Dec 16 03:31:14 UTC 2023 , Edited by admin on Sat Dec 16 03:31:14 UTC 2023
NCI_THESAURUS C707
Created by admin on Sat Dec 16 03:31:14 UTC 2023 , Edited by admin on Sat Dec 16 03:31:14 UTC 2023
NCI_THESAURUS C97452
Created by admin on Sat Dec 16 03:31:14 UTC 2023 , Edited by admin on Sat Dec 16 03:31:14 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
223-853-2
Created by admin on Sat Dec 16 03:31:14 UTC 2023 , Edited by admin on Sat Dec 16 03:31:14 UTC 2023
PRIMARY
CAS
4097-22-7
Created by admin on Sat Dec 16 03:31:14 UTC 2023 , Edited by admin on Sat Dec 16 03:31:14 UTC 2023
PRIMARY
NCI_THESAURUS
C429
Created by admin on Sat Dec 16 03:31:14 UTC 2023 , Edited by admin on Sat Dec 16 03:31:14 UTC 2023
PRIMARY
RS_ITEM_NUM
1191237
Created by admin on Sat Dec 16 03:31:14 UTC 2023 , Edited by admin on Sat Dec 16 03:31:14 UTC 2023
PRIMARY
PUBCHEM
20039
Created by admin on Sat Dec 16 03:31:14 UTC 2023 , Edited by admin on Sat Dec 16 03:31:14 UTC 2023
PRIMARY
FDA UNII
4Q86AH641A
Created by admin on Sat Dec 16 03:31:14 UTC 2023 , Edited by admin on Sat Dec 16 03:31:14 UTC 2023
PRIMARY
CHEBI
91207
Created by admin on Sat Dec 16 03:31:14 UTC 2023 , Edited by admin on Sat Dec 16 03:31:14 UTC 2023
PRIMARY
NSC
98700
Created by admin on Sat Dec 16 03:31:14 UTC 2023 , Edited by admin on Sat Dec 16 03:31:14 UTC 2023
PRIMARY
EPA CompTox
DTXSID2023771
Created by admin on Sat Dec 16 03:31:14 UTC 2023 , Edited by admin on Sat Dec 16 03:31:14 UTC 2023
PRIMARY
MERCK INDEX
m4382
Created by admin on Sat Dec 16 03:31:14 UTC 2023 , Edited by admin on Sat Dec 16 03:31:14 UTC 2023
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