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
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
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.
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1908444
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3262616
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
Edited
Sat Dec 16 03:31:14 UTC 2023
by
admin
on
Sat Dec 16 03:31:14 UTC 2023
|
Record UNII |
4Q86AH641A
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |