Page last updated: 2024-11-07

bromotubercidin

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

Bromotubercidin is a synthetic nucleoside analog of tubercidin. It is a potent inhibitor of adenosine deaminase (ADA), an enzyme that breaks down adenosine. This property makes bromotubercidin a potential therapeutic agent for the treatment of diseases that involve ADA deficiency, such as severe combined immunodeficiency (SCID). Bromotubercidin has also been shown to have anti-inflammatory and anti-cancer activity. Its synthesis involves the bromination of tubercidin, which can be obtained from natural sources. Research on bromotubercidin focuses on its potential as a drug candidate, studying its pharmacokinetic properties, efficacy in various models of disease, and safety in preclinical studies.'

Cross-References

ID SourceID
PubMed CID97186
CHEMBL ID62099
SCHEMBL ID2786440
MeSH IDM0040419

Synonyms (27)

Synonym
5-bromo-7-pentofuranosyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine
(2r,3r,4s,5r)-2-(4-amino-5-bromo-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
5-bromotubercidin
7h-pyrrolo(2,3-d)pyrimidin-4-amine, 5-bromo-7-beta-d-ribofuranosyl-
bromotubercidin
21193-80-6
tubercidin, 5-bromo-
CHEMBL62099 ,
(2r,3r,4s,5r)-2-(4-amino-5-bromopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
(2r,3r,4s,5r)-2-(4-amino-5-bromo-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
bdbm50000300
(2r,3r,4s,5r)-2-(4-amino-5-bromo-7h-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-tetrahydrofuran-3,4-diol
2-(4-amino-5-bromo-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol (br-tub)
2-(4-amino-5-bromo-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol(5-bromotubercidin)
2-(4-amino-5-bromo-pyrrolo[2,3-d]pyrimidin-7-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
5-bromotubericidin
nsc 103802
bromotubercidin; nsc 103802; ac1l6fwl; ac1q26l1; ar-1g7497;(2r,3r,4s,5r)-2-(4-amino-5-bromo-7h-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-tetrahydrofuran-3,4-diol
SCHEMBL2786440
AKOS030228349
CS-0188232
mfcd22124434
(2r,3r,4s,5r)-2-(4-amino-5-bromo-7h-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
5-bromo-7-beta-d-ribofuranosyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine
5-bromo-7-ss-d-ribofuranosyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine
AS-77775
(2r,3r,4s,5r)-2-{4-amino-5-bromo-7h-pyrrolo[2,3-d]pyrimidin-7-yl}-5-(hydroxymethyl)oxolane-3,4-diol
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A1Rattus norvegicus (Norway rat)IC50 (µMol)8,317,640.00000.00020.552110.0000AID34006
Adenosine receptor A3Rattus norvegicus (Norway rat)IC50 (µMol)8,317,640.00000.00070.03740.0957AID34006
Adenosine receptor A2bRattus norvegicus (Norway rat)IC50 (µMol)8,317,640.00000.00240.68169.0000AID34006
Adenosine receptor A2aRattus norvegicus (Norway rat)IC50 (µMol)8,317,640.00000.00120.48289.0000AID34006
Adenosine kinaseHomo sapiens (human)IC50 (µMol)4,163,612.56000.00050.605210.0000AID33985; AID33990; AID33993; AID34006
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (7)

Processvia Protein(s)Taxonomy
purine ribonucleoside salvageAdenosine kinaseHomo sapiens (human)
dATP biosynthetic processAdenosine kinaseHomo sapiens (human)
ribonucleoside monophosphate biosynthetic processAdenosine kinaseHomo sapiens (human)
GMP salvageAdenosine kinaseHomo sapiens (human)
AMP salvageAdenosine kinaseHomo sapiens (human)
dAMP salvageAdenosine kinaseHomo sapiens (human)
purine nucleobase metabolic processAdenosine kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
G protein-coupled adenosine receptor activityAdenosine receptor A2aRattus norvegicus (Norway rat)
RNA bindingAdenosine kinaseHomo sapiens (human)
deoxyadenosine kinase activityAdenosine kinaseHomo sapiens (human)
ATP bindingAdenosine kinaseHomo sapiens (human)
metal ion bindingAdenosine kinaseHomo sapiens (human)
adenosine kinase activityAdenosine kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
Golgi membraneAdenosine receptor A2aRattus norvegicus (Norway rat)
nucleoplasmAdenosine kinaseHomo sapiens (human)
cytosolAdenosine kinaseHomo sapiens (human)
plasma membraneAdenosine kinaseHomo sapiens (human)
nucleusAdenosine kinaseHomo sapiens (human)
cytosolAdenosine kinaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (41)

Assay IDTitleYearJournalArticle
AID83889Concentration required to reduce HSV-1 (KOS) induced cytopathogenicity by 50% in primary rabbit kidney cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID225769Concentration required to reduce polio virus type 1 induced cytopathogenicity by 50% in HeLa cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID90952Cytotoxicity of compound was determined visually in human diploid fibroblasts (HFF).1992Journal of medicinal chemistry, Feb-07, Volume: 35, Issue:3
Synthesis, antiproliferative, and antiviral activity of certain 4-aminopyrrolo[2,3-d]pyridazine nucleosides: an entry into a novel series of adenosine analogues.
AID97510In vitro antiproliferative effect against growth rate of L1210 cells at 100 uM concentration1992Journal of medicinal chemistry, Feb-07, Volume: 35, Issue:3
Synthesis, antiproliferative, and antiviral activity of certain 4-aminopyrrolo[2,3-d]pyridazine nucleosides: an entry into a novel series of adenosine analogues.
AID80106Tested for antiviral activity against human cytomegalovirus by plaque assay1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
Synthesis, antiproliferative, and antiviral activity of 4-amino-1-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyridazin-7(6H)-one and related derivatives.
AID228410Concentration required to reduce reovirus type 1 induced cytopathogenicity by 50% in vero cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID229059Concentration required to cause a microscopically detectable alteration in cell morphology in vero cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID96214Cytotoxicity against human neoplastic cell line(KB cells)1988Journal of medicinal chemistry, Nov, Volume: 31, Issue:11
Synthesis and antiviral activity of certain 4- and 4,5-disubstituted 7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidines.
AID229230Concentration required to reduce vesicular stomatitis virus induced cytopathogenicity by 50% in HeLa cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID33985Inhibition of recombinant human adenosine kinase2000Journal of medicinal chemistry, Jul-27, Volume: 43, Issue:15
Adenosine kinase inhibitors. 1. Synthesis, enzyme inhibition, and antiseizure activity of 5-iodotubercidin analogues.
AID224918Concentration required to reduce parainfluenza virus type 3 induced cytopathogenicity by 50% in vero cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID90612Inhibition of human cytomegalovirus (HCMV) in plaque reduction assay1990Journal of medicinal chemistry, Jul, Volume: 33, Issue:7
Synthesis, antiproliferative, and antiviral activity of certain 4-substituted and 4,5-disubstituted 7-[(1,3-dihydroxy-2-propoxy)methyl]pyrrolo[2,3-d]pyrimidines.
AID229022Concentration required to reduce vaccinia virus induced cytopathogenicity by 50% in primary rabbit kidney cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID34006Concentration required for 50% inhibition of the adenosine kinase (AK) activity.2004Bioorganic & medicinal chemistry letters, Jun-21, Volume: 14, Issue:12
A TOPS-MODE approach to predict adenosine kinase inhibition.
AID98751In vitro inhibition of L1210 cell growth to half of the control rate1990Journal of medicinal chemistry, Jul, Volume: 33, Issue:7
Synthesis, antiproliferative, and antiviral activity of certain 4-substituted and 4,5-disubstituted 7-[(1,3-dihydroxy-2-propoxy)methyl]pyrrolo[2,3-d]pyrimidines.
AID84959Concentration required to reduce HSV-2 (G) induced cytopathogenicity by 50% in primary rabbit kidney cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID90616Concentration required to decrease the growth rate to 50% of control was evaluated against HCMV by using plaque reduction assay.1992Journal of medicinal chemistry, Feb-07, Volume: 35, Issue:3
Synthesis, antiproliferative, and antiviral activity of certain 4-aminopyrrolo[2,3-d]pyridazine nucleosides: an entry into a novel series of adenosine analogues.
AID91311Cytotoxic activity against HFF cells.1990Journal of medicinal chemistry, Jul, Volume: 33, Issue:7
Synthesis, antiproliferative, and antiviral activity of certain 4-substituted and 4,5-disubstituted 7-[(1,3-dihydroxy-2-propoxy)methyl]pyrrolo[2,3-d]pyrimidines.
AID90982Cytotoxic activity against KB cells.1990Journal of medicinal chemistry, Jul, Volume: 33, Issue:7
Synthesis, antiproliferative, and antiviral activity of certain 4-substituted and 4,5-disubstituted 7-[(1,3-dihydroxy-2-propoxy)methyl]pyrrolo[2,3-d]pyrimidines.
AID90613Inhibitory concentration against human cytomegalovirus (HCMV) in plaque reduction assay1988Journal of medicinal chemistry, Nov, Volume: 31, Issue:11
Synthesis and antiviral activity of certain 4- and 4,5-disubstituted 7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidines.
AID91293Cytotoxicity against uninfected human foreskin fibroblast(HFF cells)1988Journal of medicinal chemistry, Nov, Volume: 31, Issue:11
Synthesis and antiviral activity of certain 4- and 4,5-disubstituted 7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidines.
AID220038Concentration required to reduce coxsackie virus B4 induced cytopathogenicity by 50% in vero cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID226343Concentration required to reduce sindbis virus induced cytopathogenicity by 50% in vero cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID96381Tested for the inhibition of KB cell growth1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
Synthesis, antiproliferative, and antiviral activity of 4-amino-1-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyridazin-7(6H)-one and related derivatives.
AID220035Concentration required to reduce coxsackie virus 4 induced cytopathogenicity by 50% in HeLa cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID87343Concentration required to decrease the growth rate to 50% of control was evaluated against HSV-1 by using plaque reduction assay.1992Journal of medicinal chemistry, Feb-07, Volume: 35, Issue:3
Synthesis, antiproliferative, and antiviral activity of certain 4-aminopyrrolo[2,3-d]pyridazine nucleosides: an entry into a novel series of adenosine analogues.
AID98500Tested for in vitro cell growth inhibition of L1210 cells1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
Synthesis, antiproliferative, and antiviral activity of 4-amino-1-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyridazin-7(6H)-one and related derivatives.
AID229232Concentration required to reduce vesicular stomatitis virus induced cytopathogenicity by 50% in primary rabbit kidney cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID98167Concentration required to decrease the growth rate to 50% of control was evaluated by determining their ability to inhibit growth of L1210 cells in vitro.1992Journal of medicinal chemistry, Feb-07, Volume: 35, Issue:3
Synthesis, antiproliferative, and antiviral activity of certain 4-aminopyrrolo[2,3-d]pyridazine nucleosides: an entry into a novel series of adenosine analogues.
AID87304Concentration required to cause a microscopically detectable alteration in cell morphology in HeLa cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID97385In vitro inhibition of L1210 cell growth.1990Journal of medicinal chemistry, Jul, Volume: 33, Issue:7
Synthesis, antiproliferative, and antiviral activity of certain 4-substituted and 4,5-disubstituted 7-[(1,3-dihydroxy-2-propoxy)methyl]pyrrolo[2,3-d]pyrimidines.
AID96660Dose required to inhibit proliferation of L-1210 Cells by 50%1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID80113Tested for antiviral activity against human cytomegalovirus by yield reduction assay1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
Synthesis, antiproliferative, and antiviral activity of 4-amino-1-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyridazin-7(6H)-one and related derivatives.
AID85868Tested for antiviral activity against Herpes simplex virus type-1 using plaque assay1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
Synthesis, antiproliferative, and antiviral activity of 4-amino-1-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyridazin-7(6H)-one and related derivatives.
AID90618Concentration required to decrease the growth rate to 50% of control was evaluated against HCMV by using yield reduction assay.1992Journal of medicinal chemistry, Feb-07, Volume: 35, Issue:3
Synthesis, antiproliferative, and antiviral activity of certain 4-aminopyrrolo[2,3-d]pyridazine nucleosides: an entry into a novel series of adenosine analogues.
AID167327Concentration required to cause a microscopically detectable alteration in cell morphology in primary rabbit kidney cell cultures.1984Journal of medicinal chemistry, Mar, Volume: 27, Issue:3
Antiviral activity of C-5 substituted tubercidin analogues.
AID82420Tested for cytotoxicity in human foreskin fibroblasts at time of HCMV plaque enumeration1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
Synthesis, antiproliferative, and antiviral activity of 4-amino-1-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyridazin-7(6H)-one and related derivatives.
AID33993Inhibition concentration against human adenosine kinase2002Bioorganic & medicinal chemistry letters, Mar-25, Volume: 12, Issue:6
QSAR study on adenosine kinase inhibition of pyrrolo[2,3-d]pyrimidine nucleoside analogues using the hansch approach.
AID382097Inhibition of adenosine kinase2008Bioorganic & medicinal chemistry, May-01, Volume: 16, Issue:9
A CoMSIA study on the adenosine kinase inhibition of pyrrolo[2,3-d]pyrimidine nucleoside analogues.
AID90979Cytotoxicity of compound was determined by assaying cell growth in human neoplastic cell line(KB).1992Journal of medicinal chemistry, Feb-07, Volume: 35, Issue:3
Synthesis, antiproliferative, and antiviral activity of certain 4-aminopyrrolo[2,3-d]pyridazine nucleosides: an entry into a novel series of adenosine analogues.
AID33990Inhibition of human adenosine kinase activity2002Bioorganic & medicinal chemistry letters, Mar-25, Volume: 12, Issue:6
QSAR study on adenosine kinase inhibition of pyrrolo[2,3-d]pyrimidine nucleoside analogues using the hansch approach.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (23.08)18.7374
1990's5 (38.46)18.2507
2000's5 (38.46)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.84

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.84 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.48 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.84)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]