Compounds > 1-(2,3-dideoxy-2-fluoropentofuranosyl)cytosine
Page last updated: 2024-12-06

1-(2,3-dideoxy-2-fluoropentofuranosyl)cytosine

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

Description

1-(2,3-dideoxy-2-fluoropentofuranosyl)cytosine, more commonly known as **gemcitabine**, is an important anticancer drug.

Here's why it's important for research:

* **Mechanism of Action:** Gemcitabine is a nucleoside analog, meaning it structurally resembles natural building blocks of DNA. When cells incorporate gemcitabine into their DNA, it inhibits the growth and replication of cancer cells. This mechanism of action makes it a promising therapeutic for a variety of cancers.

* **Wide Range of Applications:** Gemcitabine is used to treat a variety of cancers, including:
* Pancreatic cancer
* Non-small cell lung cancer
* Breast cancer
* Ovarian cancer
* Bladder cancer
* Myeloid leukemia

* **Research Focus:** Research continues to investigate gemcitabine's effectiveness in combination with other therapies, as well as its potential in treating other types of cancer. This research is crucial for optimizing treatment regimens and improving patient outcomes.

* **Understanding Cancer Biology:** Gemcitabine's mechanism of action provides insights into how cancer cells replicate and grow. Studying its interactions with DNA helps researchers understand the molecular basis of cancer and develop new strategies for treatment.

**In summary:** Gemcitabine is a critical anticancer drug with significant implications for research. Its unique mechanism of action, broad application, and ongoing research efforts contribute to the advancement of cancer treatment and our understanding of cancer biology.

1-(2,3-dideoxy-2-fluoropentofuranosyl)cytosine is a modified nucleoside, also known as **2'-deoxy-2'-fluoro-cytidine** or **2'-FC** for short.

**Structure:**

* It is a modified cytosine base attached to a modified sugar molecule.
* The sugar is a pentose sugar, specifically a 2'-deoxy-2'-fluoropentofuranose. This means the 2' position on the sugar ring has been modified by replacing a hydroxyl group with a fluorine atom.

**Importance in Research:**

**1. Antiviral Activity:** 2'-FC is the precursor of **2'-fluoro-2'-deoxycytidine (2'-F-dC)**, a potent antiviral drug. 2'-F-dC is effective against various viruses including:
* **Human immunodeficiency virus (HIV):** 2'-F-dC is incorporated into viral DNA during replication, leading to chain termination and blocking viral production.
* **Hepatitis B virus (HBV):** 2'-F-dC is effective against HBV infection.
* **Herpes simplex virus (HSV) and varicella-zoster virus (VZV):** 2'-F-dC is effective against these viral infections.

**2. Research Tool for Understanding Viral Replication:**

* 2'-FC and 2'-F-dC are valuable tools in research labs to study viral replication mechanisms.
* They can be used to:
* Track viral DNA synthesis
* Develop new antiviral drugs
* Understand viral resistance mechanisms

**3. Understanding Sugar Modifications in Nucleic Acids:**

* The modification of the sugar moiety in 2'-FC has significant implications for the structure and function of nucleic acids.
* Researchers can study how changes in the sugar molecule affect:
* DNA stability
* DNA interactions with proteins
* Drug binding and effectiveness

**4. Chemical Biology and Medicinal Chemistry:**

* 2'-FC is a valuable tool in the development of new therapeutic agents for viral infections.
* It serves as a starting point for the synthesis of novel antiviral compounds with improved properties.

**In summary**, 1-(2,3-dideoxy-2-fluoropentofuranosyl)cytosine, or 2'-FC, is crucial for research in virology, drug discovery, and the understanding of nucleic acid structure and function. Its importance stems from its role in antiviral therapy, its use as a research tool for studying viral replication, and its contribution to the field of chemical biology and medicinal chemistry.

1-(2,3-dideoxy-2-fluoropentofuranosyl)cytosine: has antiviral activity against HIV-1; structure given in first source; RN given refers to (beta-D-threo)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID64990
CHEMBL ID2448180
SCHEMBL ID3045125
MeSH IDM0179027
PubMed CID363532
CHEMBL ID45147
SCHEMBL ID14577696
SCHEMBL ID22600242
MeSH IDM0179027

Synonyms (36)

Synonym
ro 31-6840
2(1h)-pyrimidinone, 4-amino-1-(2,3-dideoxy-2-fluoro-.beta.-d-threo-pentofuranosyl)-
2'-f-ddarac
119555-47-4
fddc
4-amino-1-[(2r,3s,5s)-3-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
1-(2',3'-dideoxy-2'-fluoro-.beta.-d-threo-pentofuranosyl)cytosine
4-amino-1-[(2r,3s,5s)-3-fluoro-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
2'-fluoro-2',3'-dideoxyarabinosylcytosine
2,3-ddfpc
2(1h)-pyrimidinone, 4-amino-1-(2,3-dideoxy-2-fluoro-beta-d-threo-pentafuranosyl)-
unii-5wl0apl62e
5wl0apl62e ,
1-(2,3-dideoxy-2-fluoro-beta-d-threo-pentofuranosyl)cytosine
4-amino-1-(2,3-dideoxy-2-fluoro-beta-d-threo-pentafuranosyl)-2(1h)-pyrimidinone
2'-f-dd-ara-c
CHEMBL2448180
SCHEMBL3045125
ro-31-6840
1-(2,3-dideoxy-2-fluoropentofuranosyl)-4-imino-1,4-dihydropyrimidin-2-ol
DTXSID80923001
1-(2,3-dideoxy-2-fluoro-beta-d-threo-pentofuranosyl)-cytosine
2-fluorodideoxycytidine
2fddc
PD162523
nsc-629047
nsc629047
cytosine,3'-dideoxy-2'-fluoro-
nsc-628495
nsc628495
CHEMBL45147
1-(2,3-dideoxy-2-fluoropentofuranosyl)cytosine
SCHEMBL14577696
ddg-39
4-amino-1-(3-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1h)-one
SCHEMBL22600242

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" The mean absolute bioavailability was 50% within a 95% confidence interval of 20 to 80%."( Pharmacokinetics of 2-fluorodideoxycytidine (2FddC) in patients infected with human immunodeficiency virus.
Edelman, K; Hooker, M; Muirhead, GJ; Rousseau, FS; Sereni, D; Williams, PE, 1993)		0.29

Dosage Studied

ExcerptRelevanceReference
" The aim of this study was to estimate an oral dosage regimen of 2FddC giving peak plasma drug concentrations close to the antiretroviral IC50 of 150 ng ml-1."( Pharmacokinetics of 2-fluorodideoxycytidine (2FddC) in patients infected with human immunodeficiency virus.
Edelman, K; Hooker, M; Muirhead, GJ; Rousseau, FS; Sereni, D; Williams, PE, 1993)		0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1ED509.80000.00020.99359.8000AID105582
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (40)

Assay IDTitleYearJournalArticle
AID47461In vitro Antiviral activity against CEM cell lines1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV activity of several 2'-fluoro-containing pyrimidine nucleosides.
AID32245Percent cytotoxicity against ATH8 cells at a concentration of 5 uM.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID47425Effect on HIV-induced cytopathogenesis in CEM cells.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID199981Inhibition of HIV-1 reverse transcriptase; + = active1994Journal of medicinal chemistry, Aug-05, Volume: 37, Issue:16
HIV-1 reverse transcriptase inhibitor design using artificial neural networks.
AID47455Antiviral test was performed against HIV (LAV strain) on CEM cells using 50 tissue culture infectious units.1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV activity of several 2'-fluoro-containing pyrimidine nucleosides.
AID32365Percent protection of ATH8 cells from HIV-induced cytopathic effects at a concentration of 0.5 uM.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID32242Percent cytotoxicity against ATH8 cells at a concentration of 0.2 uM.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID232768Selectivity index of IC50 and CD50 of the compound1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and antiviral activity of monofluoro and difluoro analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1).
AID105582Inhibitory activity against HIV-1 replication in MT-4 cells1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
3'-Fluoro-2',3'-dideoxy-5-chlorouridine: most selective anti-HIV-1 agent among a series of new 2'- and 3'-fluorinated 2',3'-dideoxynucleoside analogues.
AID28713Partition coefficient (logP)1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID105399AntiHIV-1 activity measured in MT-4 cells at 5 to 6 different concentrations, using the P24 antigen enzyme-linked immunosorbent assay (ELISA).1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV-1 activity of 2'-"up"-fluoro analogues of active anti-AIDS nucleosides 3'-azido-3'-deoxythymidine (AZT) and 2',3'-dideoxycytidine (DDC).
AID82981Cytotoxicity was tested in HL60 cells by the trypan blue exclusion assay.1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV-1 activity of 2'-"up"-fluoro analogues of active anti-AIDS nucleosides 3'-azido-3'-deoxythymidine (AZT) and 2',3'-dideoxycytidine (DDC).
AID233701Selectivity ratio to IC50 of MT4 cells and EC50, anti-HIV activity of MT-4 cells1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV-1 activity of 2'-"up"-fluoro analogues of active anti-AIDS nucleosides 3'-azido-3'-deoxythymidine (AZT) and 2',3'-dideoxycytidine (DDC).
AID32366Percent protection of ATH8 cells from HIV-induced cytopathic effects at a concentration of 1 uM.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID233700Selectivity ratio to IC50 of HL60 cells and EC50, anti-HIV activity of MT-4 cells1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV-1 activity of 2'-"up"-fluoro analogues of active anti-AIDS nucleosides 3'-azido-3'-deoxythymidine (AZT) and 2',3'-dideoxycytidine (DDC).
AID32244Percent cytotoxicity against ATH8 cells at a concentration of 1 uM.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID105376Cytotoxic dose in MT-4 cells1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
3'-Fluoro-2',3'-dideoxy-5-chlorouridine: most selective anti-HIV-1 agent among a series of new 2'- and 3'-fluorinated 2',3'-dideoxynucleoside analogues.
AID44815Concentration of compound that inhibits incorporation of radiolabeled amino acids by 50 %1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and antiviral activity of monofluoro and difluoro analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1).
AID47624Cellular toxicity was measured in CEM cells after 8 days.50 tissue culture infectious doses were used.1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV activity of several 2'-fluoro-containing pyrimidine nucleosides.
AID78749Compound was tested for anti-HIV activity in H9 cell line; Active1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Fluorinated sugar analogues of potential anti-HIV-1 nucleosides.
AID105400AntiHIV-1 activity measured in MT-4 cells at 5 to 6 different concentrations, using the reverse transcriptase (RT) assay1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV-1 activity of 2'-"up"-fluoro analogues of active anti-AIDS nucleosides 3'-azido-3'-deoxythymidine (AZT) and 2',3'-dideoxycytidine (DDC).
AID47621Antiviral test was performed against HIV (LAV strain) on CEM cells using 30 tissue culture infectious units. T1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV activity of several 2'-fluoro-containing pyrimidine nucleosides.
AID42390Antiviral activity against HIV-1 (RF strain) in C8166 cells1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and antiviral activity of monofluoro and difluoro analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1).
AID47138Effect on HIV-induced cytopathogenesis in CEM cells.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID104932In vitro Antiviral activity against MO cell lines1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV activity of several 2'-fluoro-containing pyrimidine nucleosides.
AID104934In vitro Antiviral activity against MO cell lines1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV activity of several 2'-fluoro-containing pyrimidine nucleosides.
AID32243Percent cytotoxicity against ATH8 cells at a concentration of 0.5 uM.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID210139In vitro Antiviral activity against T-cell lines1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV activity of several 2'-fluoro-containing pyrimidine nucleosides.
AID214565In vitro Antiviral activity against U937 cell lines1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV activity of several 2'-fluoro-containing pyrimidine nucleosides.
AID105590Cytotoxicity was tested in MT-4 cells by the XTT-microculture tetrazolium assay.1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV-1 activity of 2'-"up"-fluoro analogues of active anti-AIDS nucleosides 3'-azido-3'-deoxythymidine (AZT) and 2',3'-dideoxycytidine (DDC).
AID90922Bone marrow toxicity was measured against human colony forming units-granulocyte monocyte (CFU-GM), concentration is 10.0 uM1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV activity of several 2'-fluoro-containing pyrimidine nucleosides.
AID32364Percent protection of ATH8 cells from HIV-induced cytopathic effects at a concentration of 0.2 uM.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID90921Bone marrow toxicity was measured against human colony forming units-granulocyte monocyte (CFU-GM), concentration is 1.0 uM1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV activity of several 2'-fluoro-containing pyrimidine nucleosides.
AID214567In vitro Antiviral activity against U937 cell lines1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV activity of several 2'-fluoro-containing pyrimidine nucleosides.
AID154764In vitro Antiviral activity against PBL cell lines1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV activity of several 2'-fluoro-containing pyrimidine nucleosides.
AID235486Selectivity index is the ratio of ED50 and CD50 values against inhibition of HIV-1 in MT-4 cells1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
3'-Fluoro-2',3'-dideoxy-5-chlorouridine: most selective anti-HIV-1 agent among a series of new 2'- and 3'-fluorinated 2',3'-dideoxynucleoside analogues.
AID235196Therapeutic index (IC50/EC50) was determined1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
AID210140In vitro Antiviral activity against T-cell lines1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV activity of several 2'-fluoro-containing pyrimidine nucleosides.
AID154762In vitro Antiviral activity against PBL cell lines1990Journal of medicinal chemistry, Aug, Volume: 33, Issue:8
Synthesis and anti-HIV activity of several 2'-fluoro-containing pyrimidine nucleosides.
AID32367Percent protection of ATH8 cells from HIV-induced cytopathic effects at a concentration of 5 uM.1992Journal of medicinal chemistry, Jun-12, Volume: 35, Issue:12
Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (12.50)18.7374
1990's7 (87.50)18.2507
2000's0 (0.00)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: 13.01

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 Index13.01 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index5.09 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.01)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials1 (20.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
Other4 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
uridine
[no description available]		1.9810uridinesdrug metabolite;
fundamental metabolite;
human metabolite
cytidine
[no description available]		1.9810cytidinesEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae 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		1.9810dihydrofuran;
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.		2.3820adenosines;
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.		3.0750pyrimidine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
alovudine
[no description available]		2.6730pyrimidine 2',3'-dideoxyribonucleoside
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.		3.0750azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
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		2.3820
l 693593
L 693593: structure given in first source		1.9810
thymine arabinoside
thymine arabinoside: selectively inhibits replication of herpes simplex virus		1.9710N-glycosyl compound
lodenosine
lodenosine: anti-HIV nucleoside analog, the flourine atom on lodenosine is located at 2-arabinoside location, while 2'-fluoro-2',3'-dideoxyadenosine has the flourine residue at the 2-ribose sugar location		1.9810
2',3'-dideoxy-2',3'-didehydro-2'-fluorocytidine
2',3'-dideoxy-2',3'-didehydro-2'-fluorocytidine: has antiviral action against HIV-1; structure given in first source		2.6730
3'-deoxy-2',3'-didehydro-2'fluorothymidine
3'-deoxy-2',3'-didehydro-2'fluorothymidine: has antiviral activity against HIV-1; structure given in first source		2.8940
clevudine
[no description available]		1.9710
2',3'-dideoxy-beta-5-fluorocytidine
2',3'-dideoxy-beta-5-fluorocytidine: structure in first source		1.9810
3'-fluoro-2',3'-dideoxyuridine
[no description available]		1.9710
3'-azido-2',3'-dideoxyadenosine
[no description available]		1.9710
raluridine
raluridine: inhibitor of HIV; structure given in first source		1.9710
r-82913
R-82913: antiviral target on reverse transcriptase of HIV-1		1.9810
didanosine
Didanosine: 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. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite.. didanosine : A purine 2',3'-dideoxyribonucleoside that is inosine in which the hydroxy groups at both the 2' and the 3' positions on the sugar moiety have been replaced by hydrogen. An antiviral drug, it is used as a medication to treat HIV/AIDS.		1.9810purine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor;
geroprotector;
HIV-1 reverse transcriptase inhibitor
cytarabine
[no description available]		1.9810beta-D-arabinoside;
monosaccharide derivative;
pyrimidine nucleoside		antimetabolite;
antineoplastic agent;
antiviral agent;
immunosuppressive agent
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.		4.4651pyrimidine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
fluorine
Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.		2.3820diatomic fluorine;
gas molecular entity		NMR chemical shift reference compound
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.		2.3820azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
2',3'-dideoxy-2',3'-didehydro-2'-fluorocytidine
2',3'-dideoxy-2',3'-didehydro-2'-fluorocytidine: has antiviral action against HIV-1; structure given in first source		1.9710
3'-deoxy-2',3'-didehydro-2'fluorothymidine
3'-deoxy-2',3'-didehydro-2'fluorothymidine: has antiviral activity against HIV-1; structure given in first source		1.9710
ConditionIndicatedRelationship StrengthStudiesTrials
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.		02.3820
Acquired Immune Deficiency Syndrome
[description not available]		03.3711
HIV Coinfection
[description not available]		03.3711
Acquired Immunodeficiency Syndrome
An acquired defect of cellular immunity associated with infection by the human immunodeficiency virus (HIV), a CD4-positive T-lymphocyte count under 200 cells/microliter or less than 14% of total lymphocytes, and increased susceptibility to opportunistic infections and malignant neoplasms. Clinical manifestations also include emaciation (wasting) and dementia. These elements reflect criteria for AIDS as defined by the CDC in 1993.		03.3711
HIV Infections
Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).		03.3711