3'-azido-2,6-diaminopurine-2',3'-dideoxyriboside profile

3'-azido-2,6-diaminopurine-2',3'-dideoxyriboside, also known as AZT, is a nucleoside reverse transcriptase inhibitor (NRTI) used in the treatment of HIV/AIDS. It was the first drug approved by the FDA for the treatment of AIDS. AZT works by inhibiting the activity of reverse transcriptase, an enzyme that HIV uses to convert its RNA into DNA. By blocking reverse transcriptase, AZT prevents HIV from replicating and spreading. AZT is typically administered orally, but it can also be given intravenously. Common side effects of AZT include nausea, vomiting, headache, and anemia. AZT can also cause liver problems and bone marrow suppression. However, the benefits of AZT in treating HIV/AIDS outweigh its potential risks.'

3'-azido-2,6-diaminopurine-2',3'-dideoxyriboside: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	72182
CHEMBL ID	589391
MeSH ID	M0155808

Synonym
3'-n3dddapr
[(2s,3s,5r)-3-azido-5-(2,6-diaminopurin-9-yl)tetrahydrofuran-2-yl]methanol
2,6-diaminopurine-3'-azido-2',3'-dideoxyriboside
adenosine, 2-amino-3'-azido-2',3'-dideoxy-
114753-52-5
azdddapr
[(2s,3s,5r)-3-azido-5-(2,6-diaminopurin-9-yl)oxolan-2-yl]methanol
CHEMBL589391
3'-azido-2',3'-dideoxy-2-aminoadenosine
3'-azido-2-amino-2',3'-dideoxyadenosine
3'-azido-2,6-diaminopurine-2',3'-dideoxyriboside
BFTAFRDMRHNFKO-KVQBGUIXSA-N
((2s,3s,5r)-3-azido-5-(2,6-diamino-9h-purin-9-yl)tetrahydrofuran-2-yl)methanol
DTXSID90150846
3/'-azido-2,6-diaminopurine-2/',3/'-dideoxyriboside

Assay ID	Title	Year	Journal	Article
AID232359	Ratio of CD50 and ED50 values against inhibition of HIV in MT-4 cells	1989	Journal 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.
AID452273	Ratio of compound EC50 to AZG EC50 for HIV1 LAI infected in human PBM cells after 5 days	2010	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 20, Issue:1	Synthesis and evaluation of 3'-azido-2',3'-dideoxypurine nucleosides as inhibitors of human immunodeficiency virus.
AID141915	Toxic dose required to cause an alteration of normal C3H cell morphology	1989	Journal 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.
AID141914	Effective dose required to inhibit MSV-induced transformation in murine C3H cells	1989	Journal 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.
AID28386	Partition coefficient in 1-octanol and 10 mM aqueous potassium phosphate buffer at pH 7.4	1989	Journal 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.
AID452272	Cytotoxicity against african green monkey Vero cells after 5 days	2010	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 20, Issue:1	Synthesis and evaluation of 3'-azido-2',3'-dideoxypurine nucleosides as inhibitors of human immunodeficiency virus.
AID452274	Ratio of compound EC90 to AZG EC90 for HIV1 LAI infected in human PBM cells after 5 days	2010	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 20, Issue:1	Synthesis and evaluation of 3'-azido-2',3'-dideoxypurine nucleosides as inhibitors of human immunodeficiency virus.
AID89115	Cytotoxic dose required to inhibit HIV-induced cytopathogenicity in human MT-4 cells	1989	Journal 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.
AID452269	Antiviral activity against HIV1 LAI infected in human PBM cells after 5 days	2010	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 20, Issue:1	Synthesis and evaluation of 3'-azido-2',3'-dideoxypurine nucleosides as inhibitors of human immunodeficiency virus.
AID452271	Cytotoxicity against human CEM cells after 5 days	2010	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 20, Issue:1	Synthesis and evaluation of 3'-azido-2',3'-dideoxypurine nucleosides as inhibitors of human immunodeficiency virus.
AID89116	Effective dose required to inhibit HIV-induced cytopathogenicity in human MT-4 cells	1989	Journal 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.
AID452270	Cytotoxicity against human PBMC after 5 days	2010	Bioorganic & medicinal chemistry letters, Jan-01, Volume: 20, Issue:1	Synthesis and evaluation of 3'-azido-2',3'-dideoxypurine nucleosides as inhibitors of human immunodeficiency virus.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	3 (50.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	2 (33.33)	29.6817
2010's	1 (16.67)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	7 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
2'-deoxyadenosine 2'-deoxyformycin A: RN not in Chemline 9/85; RN and structure given in first source	1.97	1	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
dideoxyadenosine Dideoxyadenosine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is an inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal side effect is nephrotoxicity. In vivo, dideoxyadenosine is rapidly metabolized to DIDANOSINE (ddI) by enzymatic deamination; ddI is then converted to dideoxyinosine monophosphate and ultimately to dideoxyadenosine triphosphate, the putative active metabolite.	3.09	5	adenosines; purine 2',3'-dideoxyribonucleoside	EC 3.5.4.4 (adenosine deaminase) inhibitor; EC 4.6.1.1 (adenylate cyclase) inhibitor
vidarabine adenine arabinoside : A purine nucleoside in which adenine is attached to arabinofuranose via a beta-N(9)-glycosidic bond.	1.97	1	beta-D-arabinoside; purine nucleoside	antineoplastic agent; bacterial metabolite; nucleoside antibiotic
coformycin [no description available]	1.97	1	coformycins	EC 3.5.4.4 (adenosine deaminase) inhibitor
zidovudine Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.	2.45	2	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
3'-azido-2',3'-dideoxyuridine [no description available]	2.05	1
2'3'-didehydro-2'3'-dideoxyadenosine 2'3'-didehydro-2'3'-dideoxyadenosine: structure given in first source	1.97	1
2,6-diaminopurine 2',3'-dideoxyriboside 2,6-diaminopurine 2',3'-dideoxyriboside: selectively inhibits HIV virus replication in vitro; structure given in first source	2.66	3
pentostatin Pentostatin: A potent inhibitor of ADENOSINE DEAMINASE. The drug induces APOPTOSIS of LYMPHOCYTES, and is used in the treatment of many lymphoproliferative malignancies, particularly HAIRY CELL LEUKEMIA. It is also synergistic with some other antineoplastic agents and has immunosuppressive activity.. pentostatin : A member of the class of coformycins that is coformycin in which the hydroxy group at position 2' is replaced with a hydrogen. It is a drug used for the treatment of hairy cell leukaemia.	1.97	1	coformycins	antimetabolite; antineoplastic agent; Aspergillus metabolite; bacterial metabolite; EC 3.5.4.4 (adenosine deaminase) inhibitor
3'-azido-2',3'-dideoxyadenosine [no description available]	2.4	2
deoxyguanosine [no description available]	7.37	2	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
3'-fluoro-2',3'-dideoxyguanosine 3'-fluoro-2',3'-dideoxyguanosine: structure given in first source	6.97	1
3'-azido-2',3'-dideoxyguanosine [no description available]	2.45	2

Condition	Indicated	Relationship Strength	Studies	Trials
Cell Transformation, Viral An inheritable change in cells manifested by changes in cell division and growth and alterations in cell surface properties. It is induced by infection with a transforming virus.	0	1.97	1	0
HIV Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.	0	1.97	1	0

3'-azido-2,6-diaminopurine-2',3'-dideoxyriboside

Description

Cross-References

Synonyms (15)

Bioassays (12)

Research

Studies (6)

Market Indicators

Research Demand Index: 12.06

Study Types