Page last updated: 2024-12-04

2'-deoxyadenosine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

2'-deoxyformycin A: RN not in Chemline 9/85; RN and structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID13730
CHEMBL ID449329
CHEBI ID17256
SCHEMBL ID19877
MeSH IDM0162235

Synonyms (96)

Synonym
p582c98ulc ,
4-26-00-03589 (beilstein handbook reference)
unii-p582c98ulc
brn 0091015
nsc 141848
einecs 213-488-7
nsc 83258
nsc 143510
adenosine, 2'-deoxy-
2-deoxyadenosine
adenine deoxyribose
nsc-141848
adenyldeoxyriboside
desoxyadenosine
adenine deoxy nucleoside
adenine deoxyribonucleoside
9-(2-deoxy-beta-d-ribofuranosyl)-9h-purin-6-amine
9-(2-deoxy-beta-d-erythro-pentofuranosyl)adenine
(2r,3s,5r)-5-(6-amino-9h-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol
CHEBI:17256 ,
5-(6-amino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-ol
ACON0_001347
9-(2'-deoxy-.beta.-d-erythro-pentofuranosyl)adenine
(2r,3s,5r)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol
nsc-83258
beta-d-ribofuranose, 1-(6-amino-9h-purin-9-yl)-1,2-dideoxy-
adenosine, 2'-deoxy- (6ci,7ci,8ci,9ci)
9h-purin-6-amine, 9-(2-deoxy-beta-d-ribofuranosyl)-
3D1 ,
beta-d-erythro-pentofuranoside, adenine-9 2-deoxy-
ai3-52383
(2r,3s,5r)-5-(6-amino-9h-purin-9-yl)-tetrahydro-2-(hydroxymethyl)furan-3-ol
ccris 1782
9h-purin-6-amine, 9-(2-deoxy-beta-d-erythro-pentofuranosyl)-
2'-deoxyadenosine ,
deoxyadenosine ,
958-09-8
C00559
2-deoxy-adenosine
nsc-143510
2'-deoxyadenosine monohydrate, powder, bioreagent, suitable for cell culture
2'-deoxyadenosine monohydrate, >=99%
(2r,3s,5r)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
NCGC00161970-01
D2DF2A54-B4A8-4727-A05C-3D1123687898
D0046
CHEMBL449329
(2r,3s,5r)-5-(6-amino-9h-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
40627-14-3
(r)-1-c-(7-amino-1h-pyrazolo(4,3-d)pyrimidin-3-yl)-1,4-anhydro-2-deoxy-d-erythro-pentitol
d-erythro-pentitol, 1-c-(7-amino-1h-pyrazolo(4,3-d)pyrimidin-3-yl)-1,4-anhydro-2-deoxy-, (r)-
2'-deoxyformycin a
2 inverted exclamation marka-deoxyadenosine ,
2-deoxyadenosine monohydrate
AKOS015896793
gtpl5109
SCHEMBL19877
.beta.-d-ribofuranose, 1-(6-amino-9h-purin-9-yl)-1,2-dideoxy-
9-(2-deoxy-.beta.-d-erythro-pentofuranosyl)adenine
2'-deoxyadenosine [inci]
2'-deoxyadenosine [usp impurity]
663188-78-1
bdbm50453912
2''''-deoxyadenosine
OLXZPDWKRNYJJZ-RRKCRQDMSA-N
2'-deoxy-d-adenosine
mfcd00005754
desoxyadenosin
CS-W021069
9-(2-deoxy-b-d-erythro-pentofuranosyl)-9h-purin-6-amine
9-(2-deoxy-b-d-ribofuranosyl)-9h-purin-6-amine
9-(2-deoxy-beta-delta-erythro-pentofuranosyl)adenine
adenine-9 2-deoxy-b-d-erythro-pentofuranoside
adenine-9 2-deoxy-beta-d-erythro-pentofuranoside
1-(6-amino-9h-purin-9-yl)-1,2-dideoxy-beta-delta-ribofuranose
1-(6-amino-9h-purin-9-yl)-1,2-dideoxy-b-d-ribofuranose
9-(2-deoxy-beta-d-erythro-pentofuranosyl)-9h-purin-6-amine
9-(2-deoxy-b-d-erythro-pentofuranosyl)adenine
9-(2-deoxy-beta-delta-ribofuranosyl)-9h-purin-6-amine
adenine-9 2-deoxy-beta-delta-erythro-pentofuranoside
9-(2-deoxy-beta-delta-erythro-pentofuranosyl)-9h-purin-6-amine
1-(6-amino-9h-purin-9-yl)-1,2-dideoxy-beta-d-ribofuranose
HY-W040329
7005-15-4
Q422457
AS-14314
BCP11997
EN300-108104
AMY31025
dna nucleoside a
DTXSID10883624
adenosine, 2'-deoxy,
CS-0674964
HY-154058
9-(2-deoxy-|a-d-threo-pentofuranosyl)-9h-purin-6-amine
Z1416201984

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
" The drug induced functional and morphologic differentiation of myeloid leukemia cells in combination with 2'-deoxyadenosine (dAd), but not dCF alone."( Induction of differentiation of human myeloid leukemia cells by 2'-deoxycoformycin in combination with 2'-deoxyadenosine.
Honma, Y; Niitsu, N; Umeda, M, 1997
)
0.3

Dosage Studied

ExcerptRelevanceReference
" Dosage experiments on E6 1/2 embryos showed that adenosine was less toxic than 2'-dAdo and that 2'-dAdo in sublethal doses was teratogenic."( 2'-Deoxyadenosine causes cell death in embryonic chicken sympathetic ganglia and brain.
Crossland, WJ; Kulkarni, JS; Wakade, AR; Wakade, TD; Zhao, Z, 1999
)
0.3
" We found that adduct formation at the exocyclic amino groups of deoxyguanosine and deoxyadenosine in epidermal DNA followed a linear dose-response within 6--100 nmol/cm(2) with both chemicals."( Trans- and cis-DNA adduct concentration in epidermis from mouse and rat skin treated ex vivo with benzo[a]pyrene diol epoxide and its corresponding chlorohydrin.
Meehan, T; Vock, EH; Wolfe, AR, 2001
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Saccharomyces cerevisiae metaboliteAny fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae).
Escherichia coli metaboliteAny bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
purine 2'-deoxyribonucleosideA 2'-deoxyribonucleoside that has a purine moiety as the nucleobase (the R group in the illustration).
purines 2'-deoxy-D-ribonucleoside
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (30)

PathwayProteinsCompounds
Purine Metabolism3766
Adenosine Deaminase Deficiency3766
Adenylosuccinate Lyase Deficiency3766
Gout or Kelley-Seegmiller Syndrome3766
Lesch-Nyhan Syndrome (LNS)3766
Molybdenum Cofactor Deficiency3766
Xanthine Dehydrogenase Deficiency (Xanthinuria)3766
Purine Nucleoside Phosphorylase Deficiency3766
AICA-Ribosiduria3766
Azathioprine Action Pathway4782
Mercaptopurine Action Pathway4780
Thioguanine Action Pathway4781
Xanthinuria Type I3766
Xanthinuria Type II3766
Adenine Phosphoribosyltransferase Deficiency (APRT)3766
Mitochondrial DNA Depletion Syndrome-33766
Myoadenylate Deaminase Deficiency3766
Purine Deoxyribonucleosides Degradation414
Mitochondrial DNA Depletion Syndrome3566
purine deoxyribonucleosides salvage411
Purine nucleotides and Nucleosides metabolism ( Purine nucleotides and Nucleosides metabolism )10577
Deoxy-adenosine + Orthophosphate = 2-Deoxy-D-ribose 1-phosphate + Adenine ( Purine nucleotides and Nucleosides metabolism )14
Purine metabolism1336
The impact of Nsp14 on metabolism (COVID-19 Disease Map)084
Genetic causes of porto-sinusoidal vascular disease09
purine deoxyribonucleosides degradation210
purine deoxyribonucleosides degradation II210
purine deoxyribonucleosides degradation I212
superpathway of purine deoxyribonucleosides degradation637
purine deoxyribonucleosides salvage1212
salvage pathways of adenine, hypoxanthine, and their nucleosides023
Biochemical pathways: part I0466
Purine metabolism and related disorders2353

Protein Targets (7)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TDP1 proteinHomo sapiens (human)Potency13.51610.000811.382244.6684AID686978; AID686979
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency25.92900.00419.984825.9290AID504444
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A1Rattus norvegicus (Norway rat)Ki23.30000.00011.20929.9700AID32353
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Thymidine kinase, cytosolicHomo sapiens (human)ID501,000.00002.00002.00002.0000AID210695
Deoxycytidine kinaseHomo sapiens (human)Km61.75000.40003.57908.5000AID344442; AID344443
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (15)

Processvia Protein(s)Taxonomy
nucleobase-containing compound metabolic processThymidine kinase, cytosolicHomo sapiens (human)
deoxyribonucleoside monophosphate biosynthetic processThymidine kinase, cytosolicHomo sapiens (human)
thymidine metabolic processThymidine kinase, cytosolicHomo sapiens (human)
thymidine biosynthetic processThymidine kinase, cytosolicHomo sapiens (human)
protein homotetramerizationThymidine kinase, cytosolicHomo sapiens (human)
DNA synthesis involved in mitotic DNA replicationThymidine kinase, cytosolicHomo sapiens (human)
pyrimidine nucleotide metabolic processDeoxycytidine kinaseHomo sapiens (human)
CMP biosynthetic processDeoxycytidine kinaseHomo sapiens (human)
dAMP salvageDeoxycytidine kinaseHomo sapiens (human)
nucleoside phosphate biosynthetic processDeoxycytidine kinaseHomo sapiens (human)
adenosine catabolic processAdenosine deaminase Bos taurus (cattle)
cell adhesionAdenosine deaminase Bos taurus (cattle)
nucleotide metabolic processAdenosine deaminase Bos taurus (cattle)
purine ribonucleoside monophosphate biosynthetic processAdenosine deaminase Bos taurus (cattle)
inosine biosynthetic processAdenosine deaminase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
thymidine kinase activityThymidine kinase, cytosolicHomo sapiens (human)
protein bindingThymidine kinase, cytosolicHomo sapiens (human)
ATP bindingThymidine kinase, cytosolicHomo sapiens (human)
zinc ion bindingThymidine kinase, cytosolicHomo sapiens (human)
identical protein bindingThymidine kinase, cytosolicHomo sapiens (human)
deoxyadenosine kinase activityDeoxycytidine kinaseHomo sapiens (human)
deoxycytidine kinase activityDeoxycytidine kinaseHomo sapiens (human)
deoxyguanosine kinase activityDeoxycytidine kinaseHomo sapiens (human)
ATP bindingDeoxycytidine kinaseHomo sapiens (human)
protein homodimerization activityDeoxycytidine kinaseHomo sapiens (human)
cytidine kinase activityDeoxycytidine kinaseHomo sapiens (human)
adenosine deaminase activityAdenosine deaminase Bos taurus (cattle)
protein bindingAdenosine deaminase Bos taurus (cattle)
zinc ion bindingAdenosine deaminase Bos taurus (cattle)
2'-deoxyadenosine deaminase activityAdenosine deaminase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
nucleusThymidine kinase, cytosolicHomo sapiens (human)
cytosolThymidine kinase, cytosolicHomo sapiens (human)
nucleoplasmDeoxycytidine kinaseHomo sapiens (human)
cytosolDeoxycytidine kinaseHomo sapiens (human)
mitochondrionDeoxycytidine kinaseHomo sapiens (human)
cytoplasmDeoxycytidine kinaseHomo sapiens (human)
lysosomeAdenosine deaminase Bos taurus (cattle)
cytoplasmic vesicle lumenAdenosine deaminase Bos taurus (cattle)
anchoring junctionAdenosine deaminase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (80)

Assay IDTitleYearJournalArticle
AID105766Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 5 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID84402Antiviral activity against HSV-1(KOS) strain in primary rabbit kidney (PRK) / embryonic skin-muscle (E6SM) fibroblast culture lines1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives.
AID369218Antiviral activity against woodchuck hepatitis virus infected woodchucks assessed as log reduction of serum viral DNA per ml of serum after 4 weeks2007Antimicrobial agents and chemotherapy, Sep, Volume: 51, Issue:9
Antiviral effect of orally administered (-)-beta-D-2-aminopurine dioxolane in woodchucks with chronic woodchuck hepatitis virus infection.
AID68253Minimum inhibitory concentration required for antiviral activity to reduce HSV-2 (G) induced cytopathicity in human embryonic skin-muscle cells (ESM)1994Journal of medicinal chemistry, Apr-29, Volume: 37, Issue:9
Synthesis and antiviral activities of 8-alkynyl-, 8-alkenyl-, and 8-alkyl-2'-deoxyadenosine analogues.
AID344444Ratio of Kcat for human wild type deoxycytidine kinase to Km for human wild type deoxycytidine kinase in presence of ATP2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Elucidation of different binding modes of purine nucleosides to human deoxycytidine kinase.
AID210718Compound was tested for inhibit phosphorylation of [3H]-D-T catalyzed by human thymidine kinase; Inactive at 1 uM concentration1992Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22
L-thymidine is phosphorylated by herpes simplex virus type 1 thymidine kinase and inhibits viral growth.
AID33205Binding affinity determined by displacement of specific binding of [125I]N-(4-amino-3-iodophenethyl)-adenosine in membranes of CHO cells stably transfected with the rat Adenosine A3 receptor1995Journal of medicinal chemistry, Mar-31, Volume: 38, Issue:7
Search for new purine- and ribose-modified adenosine analogues as selective agonists and antagonists at adenosine receptors.
AID68254Minimum inhibitory concentration required for antiviral activity to reduce TK-HSV-1 (B2006) induced cytopathicity in human embryonic skin-muscle cells (ESM)1994Journal of medicinal chemistry, Apr-29, Volume: 37, Issue:9
Synthesis and antiviral activities of 8-alkynyl-, 8-alkenyl-, and 8-alkyl-2'-deoxyadenosine analogues.
AID202931Compound evaluated for the inhibitory concentration of S49 Mouse Lymphoma T-cells1985Journal of medicinal chemistry, Aug, Volume: 28, Issue:8
Improved synthesis of 2'-deoxyformycin A and studies of its in vitro activity against mouse lymphoma of T-cell origin.
AID68256Minimum inhibitory concentration required for antiviral activity to reduce Vesicular stomatitis virus (VSV) induced cytopathicity in human embryonic skin-muscle cells (ESM)1994Journal of medicinal chemistry, Apr-29, Volume: 37, Issue:9
Synthesis and antiviral activities of 8-alkynyl-, 8-alkenyl-, and 8-alkyl-2'-deoxyadenosine analogues.
AID342012Activity of Staphylococcus aureus CCM 885 recombinant deoxyadenosine kinase2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Deoxyribonucleoside kinases activate nucleoside antibiotics in severely pathogenic bacteria.
AID226341Antiviral activity against sindbis virus in Vero cell culture lines1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives.
AID28386Partition coefficient in 1-octanol and 10 mM aqueous potassium phosphate buffer at pH 7.41989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
Nucleic acid related compounds. 57. Synthesis, x-ray crystal structure, lipophilic partition properties, and antiretroviral activities of anomeric 3'-azido-2',3'-dideoxy-2,6-diaminopurine ribosides.
AID445471Displacement of [3H]adenine from adenine 1 receptor in HEK293 cells by liquid scintillation counting2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family.
AID86485Minimum inhibitory concentration required for antiviral activity to reduce Respiratory syncytial virus (RSV) (Long) induced cytopathicity in human carcinoma cells (HeLa)1994Journal of medicinal chemistry, Apr-29, Volume: 37, Issue:9
Synthesis and antiviral activities of 8-alkynyl-, 8-alkenyl-, and 8-alkyl-2'-deoxyadenosine analogues.
AID353131Inhibition of penicillin-resistant Streptococcus pneumoniae 159 recombinant MurM at 1 mM by liquid scintillation counting2009Bioorganic & medicinal chemistry, May-01, Volume: 17, Issue:9
Inhibition of tRNA-dependent ligase MurM from Streptococcus pneumoniae by phosphonate and sulfonamide inhibitors.
AID85279Antiviral activity against HSV-2(G) strain in primary rabbit kidney (PRK) / embryonic skin-muscle (E6SM) fibroblast culture lines1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives.
AID229234Antiviral activity against vesicular stomatitis virus (VSV) in HeLa cell culture lines,1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives.
AID344442Activity of human wild type deoxycytidine kinase in presence of ATP2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Elucidation of different binding modes of purine nucleosides to human deoxycytidine kinase.
AID105780Minimum inhibitory concentration required for antiviral activity to reduce influenza B virus (Singapore) induced cytopathicity in Madin-Darby canine kidney cells (MDCK)1994Journal of medicinal chemistry, Apr-29, Volume: 37, Issue:9
Synthesis and antiviral activities of 8-alkynyl-, 8-alkenyl-, and 8-alkyl-2'-deoxyadenosine analogues.
AID68257Minimum inhibitory concentration to reduce cytopathicity by 50% in morphology of human embryonic skin-muscle cells (ESM)1994Journal of medicinal chemistry, Apr-29, Volume: 37, Issue:9
Synthesis and antiviral activities of 8-alkynyl-, 8-alkenyl-, and 8-alkyl-2'-deoxyadenosine analogues.
AID344445Ratio of Kcat for human wild type deoxycytidine kinase to Km for human wild type deoxycytidine kinase in presence of UTP2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Elucidation of different binding modes of purine nucleosides to human deoxycytidine kinase.
AID445467Displacement of [3H]adenine from adenine 1 receptor in rat brain cortical membrane by liquid scintillation counting2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family.
AID83199Minimum inhibitory concentration required for antiviral activity to reduce Varicella Zoster virus (VZV) (Oka) induced cytopathicity in human embryonic lung cells (HEL)1994Journal of medicinal chemistry, Apr-29, Volume: 37, Issue:9
Synthesis and antiviral activities of 8-alkynyl-, 8-alkenyl-, and 8-alkyl-2'-deoxyadenosine analogues.
AID372436Inhibition of Trypanosoma brucei brucei 427 P2 transporter-mediated [3H]adenosine uptake by fluid scintillation counting in presence of 100 uM inosine2007Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11
2,N6-disubstituted adenosine analogs with antitrypanosomal and antimalarial activities.
AID344443Activity of human wild type deoxycytidine kinase in presence of UTP2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Elucidation of different binding modes of purine nucleosides to human deoxycytidine kinase.
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID105750Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.2 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID344446Activity of human deoxycytidine kinase C4S mutant in presence of ATP2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Elucidation of different binding modes of purine nucleosides to human deoxycytidine kinase.
AID31247Binding affinity determined on Adenosine A1 receptor in rat brain membranes by measuring displacement of specific [3H]PIA as radioligand.1995Journal of medicinal chemistry, Mar-31, Volume: 38, Issue:7
Search for new purine- and ribose-modified adenosine analogues as selective agonists and antagonists at adenosine receptors.
AID83198Minimum inhibitory concentration required for antiviral activity to reduce TK Varicella Zoster virus (VZV) (07/1) induced cytopathicity in human embryonic lung cells (HEL)1994Journal of medicinal chemistry, Apr-29, Volume: 37, Issue:9
Synthesis and antiviral activities of 8-alkynyl-, 8-alkenyl-, and 8-alkyl-2'-deoxyadenosine analogues.
AID220034Antiviral activity against coxsackie B4 virus in HeLa cell culture lines1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives.
AID105779Minimum inhibitory concentration required for antiviral activity to reduce Influenza A virus (Ishikawa) induced cytopathicity in Madin-Darby canine kidney cells (MDCK)1994Journal of medicinal chemistry, Apr-29, Volume: 37, Issue:9
Synthesis and antiviral activities of 8-alkynyl-, 8-alkenyl-, and 8-alkyl-2'-deoxyadenosine analogues.
AID220033Antiviral activity against coxsackie B4 in Vero cell culture lines1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives.
AID83197Minimum inhibitory concentration required for antiviral activity to reduce Cytomegalovirus (CMV) (Davis) induced cytopathicity in human embryonic lung cells (HEL)1994Journal of medicinal chemistry, Apr-29, Volume: 37, Issue:9
Synthesis and antiviral activities of 8-alkynyl-, 8-alkenyl-, and 8-alkyl-2'-deoxyadenosine analogues.
AID33836Kinetic constant (Vmax) for the deamination of compound by adenosine deaminase2000Bioorganic & medicinal chemistry letters, Jan-17, Volume: 10, Issue:2
3'-Beta-ethynyl and 2'-deoxy-3'-beta-ethynyl adenosines: first 3'-beta-branched-adenosines substrates of adenosine deaminase.
AID1769623Displacement of [3H]ZM241385 from human adenosine A2A receptor expressed in HeLa cell membrane ay 10 uM incubated for 30 mins by microplate beta scintillation counting based radioligand inhibition assay relative to control2021European journal of medicinal chemistry, Nov-05, Volume: 223Synthesis and evaluation of adenosine derivatives as A
AID344449Ratio of Kcat for human deoxycytidine kinase C4S mutant to Km for deoxycytidine kinase C4S mutant in presence of UTP2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Elucidation of different binding modes of purine nucleosides to human deoxycytidine kinase.
AID445473Selectivity ratio of Ki for adenine 1 receptor in HEK293 cells to Ki for adenine 1 receptor in rat brain cortical membrane2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family.
AID81438Dose required to inhibit cytopathic effect of human immunodeficiency virus replication in MT-4 cells.1988Journal of medicinal chemistry, Oct, Volume: 31, Issue:10
Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides.
AID105753Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 125 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID33765Binding affinity determined on Adenosine A2A receptor in rat striatal membranes by measuring displacement of specific [3H]-CGS- 21680 as radioligand.1995Journal of medicinal chemistry, Mar-31, Volume: 38, Issue:7
Search for new purine- and ribose-modified adenosine analogues as selective agonists and antagonists at adenosine receptors.
AID344447Activity of human deoxycytidine kinase C4S mutant in presence of UTP2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Elucidation of different binding modes of purine nucleosides to human deoxycytidine kinase.
AID32065Protection of ATH8 cells against the cytopathic effect of HIV.1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID225768Antiviral activity against polio virus type 1 in HeLa cell culture lines1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives.
AID68252Minimum inhibitory concentration required for antiviral activity to reduce HSV-1 (KOS) induced cytopathicity in human embryonic skin-muscle cells (ESM)1994Journal of medicinal chemistry, Apr-29, Volume: 37, Issue:9
Synthesis and antiviral activities of 8-alkynyl-, 8-alkenyl-, and 8-alkyl-2'-deoxyadenosine analogues.
AID105782Minimum inhibitory concentration to reduce cytopathicity by 50% in morphology of Madin-Darby canine kidney cells (MDCK)1994Journal of medicinal chemistry, Apr-29, Volume: 37, Issue:9
Synthesis and antiviral activities of 8-alkynyl-, 8-alkenyl-, and 8-alkyl-2'-deoxyadenosine analogues.
AID445472Inhibition of [3H]adenine binding to adenine 1 receptor in HEK293 cells at 100 uM by liquid scintillation counting2009Journal of medicinal chemistry, Oct-08, Volume: 52, Issue:19
Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family.
AID517826Antiviral activity against DHBV infected in duck hepatocytes assessed as inhibition of viral DNA replication at 10 ug/ml2010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
Antiviral activity of various 1-(2'-deoxy-β-D-lyxofuranosyl), 1-(2'-fluoro-β-D-xylofuranosyl), 1-(3'-fluoro-β-D-arabinofuranosyl), and 2'-fluoro-2',3'-didehydro-2',3'-dideoxyribose pyrimidine nucleoside analogues against duck hepatitis B virus (DHBV) and
AID83196Minimum inhibitory concentration required for antiviral activity to reduce Cytomegalovirus (CMV) (AD-169) induced cytopathicity in human embryonic lung cells (HEL)1994Journal of medicinal chemistry, Apr-29, Volume: 37, Issue:9
Synthesis and antiviral activities of 8-alkynyl-, 8-alkenyl-, and 8-alkyl-2'-deoxyadenosine analogues.
AID229236Antiviral activity against vesicular stomatitis virus (VSV) in primary rabbit kidney (PRK) / embryonic skin-muscle (E6SM) fibroblast culture lines1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives.
AID229026Antiviral activity against vaccinia virus (VV) in primary rabbit kidney (PRK) / embryonic skin-muscle (E6SM) fibroblast culture lines1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives.
AID517842Cytotoxicity against HuH7 cells2010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
Antiviral activity of various 1-(2'-deoxy-β-D-lyxofuranosyl), 1-(2'-fluoro-β-D-xylofuranosyl), 1-(3'-fluoro-β-D-arabinofuranosyl), and 2'-fluoro-2',3'-didehydro-2',3'-dideoxyribose pyrimidine nucleoside analogues against duck hepatitis B virus (DHBV) and
AID342013Ratio of kcat to Km for Staphylococcus aureus CCM 885 recombinant deoxyadenosine kinase2007Antimicrobial agents and chemotherapy, Aug, Volume: 51, Issue:8
Deoxyribonucleoside kinases activate nucleoside antibiotics in severely pathogenic bacteria.
AID105765Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 125 uM concentration; Range is 10-401987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID372435Inhibition of Trypanosoma brucei brucei 427 P1 transporter-mediated [3H]adenosine uptake by fluid scintillation counting in presence of 100 uM adenine2007Antimicrobial agents and chemotherapy, Nov, Volume: 51, Issue:11
2,N6-disubstituted adenosine analogs with antitrypanosomal and antimalarial activities.
AID32066Required dose to reduce viability of normal uninfected ATH8 cells.1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID1769622Displacement of [3H]NECA from human adenosine A3 receptor expressed in HeLa cell membrane at 10 uM incubated for 180 mins by microplate beta scintillation counting based radioligand inhibition assay relative to control2021European journal of medicinal chemistry, Nov-05, Volume: 223Synthesis and evaluation of adenosine derivatives as A
AID33830Ratio of kinetic constant (Vmax/Km) for the deamination of compound by adenosine deaminase2000Bioorganic & medicinal chemistry letters, Jan-17, Volume: 10, Issue:2
3'-Beta-ethynyl and 2'-deoxy-3'-beta-ethynyl adenosines: first 3'-beta-branched-adenosines substrates of adenosine deaminase.
AID517832Antiviral activity against HBV assessed as inhibition of viral DNA replication at 10 ug/mL2010Journal of medicinal chemistry, Oct-14, Volume: 53, Issue:19
Antiviral activity of various 1-(2'-deoxy-β-D-lyxofuranosyl), 1-(2'-fluoro-β-D-xylofuranosyl), 1-(3'-fluoro-β-D-arabinofuranosyl), and 2'-fluoro-2',3'-didehydro-2',3'-dideoxyribose pyrimidine nucleoside analogues against duck hepatitis B virus (DHBV) and
AID228985Antiviral activity against semliki forest virus (SFV) in Vero cell culture lines1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives.
AID33813Kinetic constant (Km) for the deamination of compound by adenosine deaminase2000Bioorganic & medicinal chemistry letters, Jan-17, Volume: 10, Issue:2
3'-Beta-ethynyl and 2'-deoxy-3'-beta-ethynyl adenosines: first 3'-beta-branched-adenosines substrates of adenosine deaminase.
AID210695Compound was tested for inhibit phosphorylation of [3H]-D-T catalyzed by HSV 1 thymidine kinase1992Journal of medicinal chemistry, Oct-30, Volume: 35, Issue:22
L-thymidine is phosphorylated by herpes simplex virus type 1 thymidine kinase and inhibits viral growth.
AID33834Kinetic constant (relative Vmax) for the deamination of compound by adenosine deaminase2000Bioorganic & medicinal chemistry letters, Jan-17, Volume: 10, Issue:2
3'-Beta-ethynyl and 2'-deoxy-3'-beta-ethynyl adenosines: first 3'-beta-branched-adenosines substrates of adenosine deaminase.
AID228408Antiviral activity against reovirus type 1 in Vero cell culture lines1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives.
AID1769631Displacement of [3H]DPCPX from human adenosine A2B receptor expressed in HEK cell membrane at 10 uM incubated for 30 mins by microplate beta scintillation counting based radioligand inhibition assay relative to control2021European journal of medicinal chemistry, Nov-05, Volume: 223Synthesis and evaluation of adenosine derivatives as A
AID344448Ratio of Kcat for human deoxycytidine kinase C4S mutant to Km for deoxycytidine kinase C4S mutant in presence of ATP2008Journal of medicinal chemistry, Jul-24, Volume: 51, Issue:14
Elucidation of different binding modes of purine nucleosides to human deoxycytidine kinase.
AID81802Antiviral activity against (HIV-1) in MT-4 cells Value in parentheses is inhibitory concentration for cell growth (MT-4)1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives.
AID202930Compound along with 10 uM of erythro-9-(2-hydroxy-3-nonyl)adenine (EHNA) was tested against mouse lymphoma T-cells1985Journal of medicinal chemistry, Aug, Volume: 28, Issue:8
Improved synthesis of 2'-deoxyformycin A and studies of its in vitro activity against mouse lymphoma of T-cell origin.
AID32353Affinity for the Adenosine A1 receptor in the presence of GTP (A1+GTP) by using [3H]-DPCPX as radioligand1995Journal of medicinal chemistry, Sep-29, Volume: 38, Issue:20
Ribose-modified adenosine analogues as potential partial agonists for the adenosine receptor.
AID105756Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 5 uM concentration.1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID86488Minimum inhibitory concentration to reduce cytopathicity by 50% in morphology of human carcinoma cells (HeLa)1994Journal of medicinal chemistry, Apr-29, Volume: 37, Issue:9
Synthesis and antiviral activities of 8-alkynyl-, 8-alkenyl-, and 8-alkyl-2'-deoxyadenosine analogues.
AID224916Antiviral activity against parainfluenza virus type 3 in Vero cell culture lines1992Journal of medicinal chemistry, Nov-27, Volume: 35, Issue:24
Synthesis and antiviral activity of some new S-adenosyl-L-homocysteine derivatives.
AID662565Growth inhibition of Trichomonas vaginalis T1 at 100 uM after 24 hrs by hemocytometry2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
S-Adenosylhomocysteine hydrolase of the protozoan parasite Trichomonas vaginalis: potent inhibitory activity of 9-(2-deoxy-2-fluoro-β,D-arabinofuranosyl)adenine.
AID1769624Displacement [3H]DPCPX from human adenosine A1 receptor expressed in CHO cell membrane at 10 uM incubated for 60 mins by microplate beta scintillation counting based radioligand inhibition assay relative to control2021European journal of medicinal chemistry, Nov-05, Volume: 223Synthesis and evaluation of adenosine derivatives as A
AID34585Compound was evaluated for inhibition of adenylate cyclase from rat brain2004Journal of medicinal chemistry, Feb-26, Volume: 47, Issue:5
Synthesis of 2',5'-dideoxy-2-fluoroadenosine and 2',5'-dideoxy-2,5'-difluoroadenosine: potent P-site inhibitors of adenylyl cyclase.
AID81069Cytotoxic dose required to reduce the viability of normal uninfected MT-4 cells.1988Journal of medicinal chemistry, Oct, Volume: 31, Issue:10
Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides.
AID105762Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.2 uM concentration1987Journal of medicinal chemistry, Aug, Volume: 30, Issue:8
3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID68255Minimum inhibitory concentration required for antiviral activity to reduce Vaccinia virus (VV) induced cytopathicity in human embryonic skin-muscle cells (ESM)1994Journal of medicinal chemistry, Apr-29, Volume: 37, Issue:9
Synthesis and antiviral activities of 8-alkynyl-, 8-alkenyl-, and 8-alkyl-2'-deoxyadenosine analogues.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (284)

TimeframeStudies, This Drug (%)All Drugs %
pre-199022 (7.75)18.7374
1990's66 (23.24)18.2507
2000's76 (26.76)29.6817
2010's105 (36.97)24.3611
2020's15 (5.28)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (1.35%)5.53%
Reviews4 (1.35%)6.00%
Case Studies2 (0.68%)4.05%
Observational0 (0.00%)0.25%
Other286 (96.62%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (1)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
An Investigator Sponsored Phase I/II Study of CLAG + Selinexor in Relapsed or Refractory Acute Myeloid Leukemia [NCT02416908]Phase 1/Phase 240 participants (Actual)Interventional2015-06-16Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial Outcomes

TrialOutcome
NCT02416908 (9) [back to overview]Complete Remission Rate (CR + CRi)
NCT02416908 (9) [back to overview]Duration of Remission
NCT02416908 (9) [back to overview]Event-free Survival
NCT02416908 (9) [back to overview]Number of Participants Who Were Able to Undergo Hematopoietic Stem Cell Transplantation
NCT02416908 (9) [back to overview]Overall Survival
NCT02416908 (9) [back to overview]Relapse-free Survival
NCT02416908 (9) [back to overview]Time to Neutrophil Engraftment
NCT02416908 (9) [back to overview]Time to Platelet Engraftment
NCT02416908 (9) [back to overview]Safety and Tolerability of Treatment as Measured by Incidence of Grade 3-4 Adverse Events Occurring in >5% of Participants

Complete Remission Rate (CR + CRi)

"Morphologic complete remission (CR): neutrophil count > 1.0 x 109 /L, platelet count ≥ 100 x 109/L, < 5% bone marrow blasts by morphologic review, no Auer rods, no evidence of extramedullary disease. (No requirements for marrow cellularity, hemoglobin concentration).~Morphologic complete remission with incomplete blood count recovery (CRi): same as CR but ANC may be <1000/mcl or platelet count <100,000/mcl~Participants in the phase I portion of the study, treated at the MTD will count towards the phase II accrual goal for evaluation of the primary endpoint." (NCT02416908)
Timeframe: Median follow-up of 34 days

InterventionParticipants (Count of Participants)
Phase I Schedule A and Phase II18

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Duration of Remission

-Duration of remission (DOR): Defined as the interval from the date complete remission is documented to the date of recurrence. (NCT02416908)
Timeframe: Up to 2 years

Interventionmonths (Median)
Phase I Schedule A and Phase II9.1

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Event-free Survival

Event-free survival (EFS): Defined as the interval from the date of first dose of study drug to date of treatment failure including progressive disease, recurrence, or discontinuation for any reason (including toxicity, patient preference, initiation of new treatment without documented progression, or death due to any cause). (NCT02416908)
Timeframe: Up to 2 years (median follow-up of 307 days)

Interventionmonths (Median)
Phase I Schedule A and Phase II6.1

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Number of Participants Who Were Able to Undergo Hematopoietic Stem Cell Transplantation

Allogeneic stem cell transplant utilization: the number of patients proceeding to allogeneic transplant within 2 months following end of study without any additional salvage therapy following study treatment. (NCT02416908)
Timeframe: Up to 2 years (median follow-up of 307 days)

InterventionParticipants (Count of Participants)
Phase I Schedule A and Phase II24

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Overall Survival

Overall survival (OS): Defined as the date of first dose of study drug to the date of death from any cause. OS will be evaluated at 3 month intervals for at least 12 months and up to a maximum of 2 years. (NCT02416908)
Timeframe: Up to 2 years (median follow-up of 307 days)

Interventionmonths (Median)
Phase I Schedule A and Phase II7.8

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Relapse-free Survival

Relapse-free survival (RFS): For patients achieving a complete remission, defined as the interval from the date of first documentation of a leukemia free state to date of recurrence or death due to any cause. (NCT02416908)
Timeframe: Median follow-up of 307 days

Interventiondays (Median)
Phase I Schedule A and Phase II152

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Time to Neutrophil Engraftment

-Time to neutrophil engraftment: Defined as the date of the first dose of study drug to the date that the absolute neutrophil count is >1,000/mm3 (NCT02416908)
Timeframe: Up to 2 years

Interventiondays (Median)
Phase I Schedule A and Phase II28

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Time to Platelet Engraftment

-Time to platelet engraftment: Defined as the date of the first dose of study drug to the date that the platelet count is >100,000/mm^3 in the absence of platelet transfusions. (NCT02416908)
Timeframe: 56 days

Interventiondays (Median)
Phase I Schedule A and Phase II38

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Safety and Tolerability of Treatment as Measured by Incidence of Grade 3-4 Adverse Events Occurring in >5% of Participants

-All adverse events will be classified using the descriptions and grading scales found in the revised NCI Common Terminology Criteria for Adverse Events (CTCAE) v4.0 (NCT02416908)
Timeframe: From start of treatment until 30 days following last day of study treatment or until the start of a subsequent treatment for AML, whichever came first (41 days)

InterventionParticipants (Count of Participants)
Lymphocyte count decreasedWhite blood cell decreasedHypophosphatemiaPlatelet count decreasedNeutrophil count decreasedHyponatremiaAnemiaHyperglycemiaSkin infectionFebrile neutropeniaSepsisHypokalemiaLung infectionAlanine aminotransferase increasedOral thrushHypoxiaHypertensionDiarrheaNauseaEdema limbsCatheter-related infectionHematuriaRespiratory failure
Phase I Schedule A and Phase II32282622211814111088875444333333

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