3'-azido-2',3'-dideoxy-5-methylcytidine

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

Description

3'-azido-2',3'-dideoxy-5-methylcytidine, also known as AZT, is a nucleoside analog that inhibits the reverse transcriptase enzyme of HIV. It was the first drug approved for the treatment of HIV infection. AZT is synthesized by replacing the hydroxyl group at the 3' position of thymidine with an azido group. This structural modification prevents the incorporation of AZT into the growing DNA chain by reverse transcriptase, leading to the termination of viral DNA synthesis. AZT has been shown to be effective in reducing viral load and delaying the progression of HIV infection. However, it can cause significant side effects, including bone marrow suppression, anemia, and gastrointestinal problems. Despite the development of newer and more effective antiretroviral drugs, AZT remains an important part of HIV treatment regimens, especially in resource-limited settings. It is studied to understand its mechanisms of action, explore its potential in combination therapies, and identify strategies to minimize its adverse effects.'

3'-azido-2',3'-dideoxy-5-methylcytidine: inhibits reproduction of AIDS virus in cultured cells [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	64986
CHEMBL ID	1791027
SCHEMBL ID	15531809
MeSH ID	M0161204

Synonyms (21)

Synonym
nsc687371
2(1h)-pyrimidinone, 4-amino-1-(3-azido-2,3-dideoxy-.beta.-d-erythro-pentofuranosyl)-5-methyl-
3'-n3-5-me-ddc
3'-azido-2',3'-dideoxy-5-methylcytidine
cytidine, 3'-azido-2',3'-dideoxy-5-methyl-
azddmec
az-5mec
87190-79-2
cs-92
4-amino-1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidin-2-one
4-amino-1-[(2r,4s,5s)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one
CHEMBL1791027
az-dcme
DTXSID40236164
SCHEMBL15531809
MS-23757
4-amino-1-((2r,4s,5s)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidin-2(1h)-one
CS-0025552
HY-105268
A900569
AKOS040747903

Research Excerpts

Bioavailability

Excerpt	Reference	Relevance
"74 h after intravenous and oral administration, respectively, and the oral bioavailability was about 21 percent."	( Antiretroviral activity, biochemistry, and pharmacokinetics of 3'-azido-2',3'-dideoxy-5-methylcytidine. Boudinot, FD; Chu, CK; Doshi, KJ; Eriksson, BF; McClure, HM; Oswald, B; Schinazi, RF; Sommadossi, JP, 1990)	0.52

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (19)

Assay ID	Title	Year	Journal	Article
AID125177	In vitro inhibitory activity against Moloney murine leukemia virus (M-MULV) replication, a mammalian T-lymphotropic retrovirus	1987	Journal of medicinal chemistry, Feb, Volume: 30, Issue:2	Synthesis and antiviral activity of various 3'-azido, 3'-amino, 2',3'-unsaturated, and 2',3'-dideoxy analogues of pyrimidine deoxyribonucleosides against retroviruses.
AID235875	Ratio of CD50 to ED50 rvaluated for inhibition of HIV replication in MT-4 cells	1988	Journal of medicinal chemistry, Oct, Volume: 31, Issue:10	Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides.
AID81438	Dose required to inhibit cytopathic effect of human immunodeficiency virus replication in MT-4 cells.	1988	Journal of medicinal chemistry, Oct, Volume: 31, Issue:10	Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides.
AID105758	Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 5 uM concentration; Range is 40-60	1987	Journal of medicinal chemistry, Aug, Volume: 30, Issue:8	3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID201886	In vitro inhibition against replication of Sarcoma-80 cells; inactive	1983	Journal of medicinal chemistry, Dec, Volume: 26, Issue:12	Synthesis and biological activity of various 3'-azido and 3'-amino analogues of 5-substituted pyrimidine deoxyribonucleosides.
AID210869	Inhibitory activity against thymidine kinase (TK) from L1210 cells	1983	Journal of medicinal chemistry, Dec, Volume: 26, Issue:12	Synthesis and biological activity of various 3'-azido and 3'-amino analogues of 5-substituted pyrimidine deoxyribonucleosides.
AID56582	Inhibitory activity against deoxycytidine kinase from L1210 cells	1983	Journal of medicinal chemistry, Dec, Volume: 26, Issue:12	Synthesis and biological activity of various 3'-azido and 3'-amino analogues of 5-substituted pyrimidine deoxyribonucleosides.
AID105766	Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 5 uM concentration	1987	Journal of medicinal chemistry, Aug, Volume: 30, Issue:8	3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID105751	Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.2 uM concentration; Range is 10-40	1987	Journal of medicinal chemistry, Aug, Volume: 30, Issue:8	3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID105762	Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 0.2 uM concentration	1987	Journal of medicinal chemistry, Aug, Volume: 30, Issue:8	3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID154963	Antiviral activity against HIV I strain (LAV) in human peripheral blood mononuclear (PBM) cells; Range is 0.081 - 0.22	1989	Journal of medicinal chemistry, Mar, Volume: 32, Issue:3	Structure-activity relationships of pyrimidine nucleosides as antiviral agents for human immunodeficiency virus type 1 in peripheral blood mononuclear cells.
AID81069	Cytotoxic dose required to reduce the viability of normal uninfected MT-4 cells.	1988	Journal of medicinal chemistry, Oct, Volume: 31, Issue:10	Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides.
AID105753	Protection was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 125 uM concentration	1987	Journal of medicinal chemistry, Aug, Volume: 30, Issue:8	3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID98047	In vitro inhibition against replication of L1210 murine cells; inactive	1983	Journal of medicinal chemistry, Dec, Volume: 26, Issue:12	Synthesis and biological activity of various 3'-azido and 3'-amino analogues of 5-substituted pyrimidine deoxyribonucleosides.
AID105765	Toxicity was determined by evaluation of cluster morphology and reclustering properties in mock infected MT-4 cells at 125 uM concentration; Range is 10-40	1987	Journal of medicinal chemistry, Aug, Volume: 30, Issue:8	3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID81411	Inhibition of HIV-1 replication in human peripheral blood mononuclear cells.	1988	Journal of medicinal chemistry, Feb, Volume: 31, Issue:2	Synthesis and antiviral activity of various 3'-azido analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1, HTLV-III/LAV).
AID32065	Protection of ATH8 cells against the cytopathic effect of HIV.	1987	Journal of medicinal chemistry, Aug, Volume: 30, Issue:8	3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
AID152642	Cytotoxic effect in uninfected human peripheral blood mononuclear (PBM) cells	1989	Journal of medicinal chemistry, Mar, Volume: 32, Issue:3	Structure-activity relationships of pyrimidine nucleosides as antiviral agents for human immunodeficiency virus type 1 in peripheral blood mononuclear cells.
AID32066	Required dose to reduce viability of normal uninfected ATH8 cells.	1987	Journal of medicinal chemistry, Aug, Volume: 30, Issue:8	3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	6 (75.00)	18.7374
1990's	2 (25.00)	18.2507
2000's	0 (0.00)	29.6817
2010's	0 (0.00)	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]

Market Indicators

Research Demand Index: 11.92

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.

Metric	This Compound (vs All)
Research Demand Index	11.92 (24.57)
Research Supply Index	2.40 (2.92)
Research Growth Index	4.32 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (11.92)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (10.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	9 (90.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
thymidine [no description available]	1.97	1	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite
idoxuridine [no description available]	1.96	1	organoiodine compound; pyrimidine 2'-deoxyribonucleoside	antiviral drug; DNA synthesis inhibitor
cordycepin [no description available]	1.97	1	3'-deoxyribonucleoside; adenosines	antimetabolite; nucleoside antibiotic
deoxycytidine [no description available]	1.97	1	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
deoxyuridine [no description available]	2.37	2	pyrimidine 2'-deoxyribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
2'-deoxyadenosine 2'-deoxyformycin A: RN not in Chemline 9/85; RN and structure given in first source	2.37	2	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
uridine diphosphate glucuronic acid Uridine Diphosphate Glucuronic Acid: A nucleoside diphosphate sugar which serves as a source of glucuronic acid for polysaccharide biosynthesis. It may also be epimerized to UDP iduronic acid, which donates iduronic acid to polysaccharides. In animals, UDP glucuronic acid is used for formation of many glucosiduronides with various aglycones.. UDP-alpha-D-glucuronic acid : A UDP-sugar having alpha-D-glucuronic acid as the sugar component.	1.98	1	UDP-D-glucuronic acid	Escherichia coli metabolite; human metabolite; mouse metabolite
stavudine Stavudine: A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.. stavudine : A nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase	2.66	3	dihydrofuran; nucleoside analogue; organic molecular entity	antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
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.	1.97	1	adenosines; purine 2',3'-dideoxyribonucleoside	EC 3.5.4.4 (adenosine deaminase) inhibitor; EC 4.6.1.1 (adenylate cyclase) inhibitor
zalcitabine Zalcitabine: 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 a potent inhibitor of HIV replication at low concentrations, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal toxic side effect is axonal degeneration resulting in peripheral neuropathy.. zalcitabine : A pyrimidine 2',3'-dideoxyribonucleoside compound having cytosine as the nucleobase.	3.98	4	pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
alovudine [no description available]	2.37	2	pyrimidine 2',3'-dideoxyribonucleoside
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	3.48	2	pseudohalide anion	mitochondrial respiratory-chain 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.	3.35	7	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
3'-azido-2',3'-dideoxyuridine [no description available]	3.06	5
2',3'-dideoxycytidinene 2',3'-dideoxycytidinene: 2',3'-unsaturated derivative of 2',3'-dideoxycytidine; potent inhibitor of HTLV-III in vitro; structure given in first source	2.37	2
2'3'-didehydro-2'3'-dideoxyadenosine 2'3'-didehydro-2'3'-dideoxyadenosine: structure given in first source	1.97	1
3'-azido-2',3'-dideoxy-5-bromouridine 3'-azido-2',3'-dideoxy-5-bromouridine: a potent, selective inhibitor of HIV replication; a weak competitive inhibitor of thymidylate kinase	2.66	3
2',3'-dideoxythymidine [no description available]	2.66	3
2',3'-didehydro-2',3'-dideoxyuridine [no description available]	2.66	3
2',3'-dideoxyuridine [no description available]	2.37	2	pyrimidine 2',3'-dideoxyribonucleoside
5'-amino-2',5'-dideoxythymidine 5'-amino-5'-deoxythymidine: RN given refers to parent cpd	2.37	2
adenosine 2',3'-ribo-epoxide adenosine 2',3'-ribo-epoxide: structure	1.97	1
3'-amino-2',3'-dideoxycytidine [no description available]	1.96	1
3'-amino-2',3'-dideoxythymidine [no description available]	2.66	3
3'-amino-2',3'-dideoxyuridine 3'-amino-2',3'-dideoxyuridine: structure given in first source; a major metabolite of the antiviral agent, 3'-azido-2',3'-dideoxyuridine	2.66	3
3'-fluoro-2',3'-dideoxyuridine [no description available]	1.97	1
3'-azido-2',3'-dideoxyadenosine [no description available]	2.37	2
3'-azido-2',3'-dideoxycytidine [no description available]	3.06	5
5-bromo-2',3'-dideoxyuridine 5-bromo-2',3'-dideoxyuridine: structure given in first source	1.97	1
(2R,3S,5S)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)-3-oxolanol [no description available]	1.97	1	3'-deoxyribonucleoside; purines
nadp [no description available]	1.98	1
3'-azido-2',3'-dideoxyuridine 3'-azido-2',3'-dideoxyuridine: structure given in first source	1.98	1
deoxyguanosine [no description available]	1.97	1	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite

Condition	Relationship Strength	Studies
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.	2.88	4
Leukemia L 1210 [description not available]	1.96	1
Sarcoma 180 An experimental sarcoma of mice.	1.96	1

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