Page last updated: 2024-12-07

amdoxovir

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

Description

amdoxovir: structure in first source; RN given refers to (2R-cis)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	124088
CHEMBL ID	458876
SCHEMBL ID	141228
MeSH ID	M0476128

Synonyms (33)

Synonym
(-)-dapd
amdoxovir (usan/inn)
D02890
dapd
(-)-.beta.-d-2,6-diaminopurine dioxolane
145514-04-1
[(2r,4r)-4-(2,6-diaminopurin-9-yl)-1,3-dioxolan-2-yl]methanol
amdoxovir
(-)-(2r,4r)-2-amino-[2-(hydroxymethyl)-1,3-dioxolan-4-yl]adenine
1,3-dioxolane-2-methanol, 4-(2,6-diamino-9h-purin-9-yl)-, (2r-cis)-
1,3-dioxolane-2-methanol, 4-(2,6-diamino-9h-purin-9-yl)-, (2r,4r)-
dapd cpd
(2r,4r)-4-(2,6-diamino-9h-purin-9-yl)-1,3-dioxolane-2-methanol
beta-d-2,6-diaminopurine-dioxolane
(2r-cis)-4-(2,6-diamino-9h-purin-9-yl)-1,3-dioxolane-2-methanol
amdoxovir [usan]
(-)-(2r,4r)-2-amino-(2-(hydroxymethyl)-1,3-dioxolan-4-yl)adenine
CHEMBL458876
unii-54i81h0m9c
54i81h0m9c ,
((-))-dapd
amdoxovir [usan:inn]
amdoxovir [inn]
RLAHNGKRJJEIJL-RFZPGFLSSA-N
(2r,4r)-[4-(2,6-diamino-9h-purin-9-yl)-1,3-dioxolan-2-yl]methanol
SCHEMBL141228
AKOS027326607
Q460478
DB06619
((2r,4r)-4-(2,6-diamino-9h-purin-9-yl)-1,3-dioxolan-2-yl)methanol
[(2r,4r)-4-(2,6-diamino-9h-purin-9-yl)-1,3-dioxolan-2-yl]methanol
153611-19-9
DTXSID801027435

Research Excerpts

Toxicity

Excerpt	Reference	Relevance
" Safety and tolerability was analyzed by incidence of grade 1 to 4 clinical and laboratory adverse events."	( Short-term safety and pharmacodynamics of amdoxovir in HIV-infected patients. Adda, N; Eron, JJ; Harris, J; Jacobson, JM; Kessler, HA; Moxham, C; Rousseau, FS; Shen, G; Thompson, MA; Zong, J, 2005)	0.59
" The incidence of adverse events was similar across groups with the majority of adverse events reported as mild or moderate in severity."	( Short-term safety and pharmacodynamics of amdoxovir in HIV-infected patients. Adda, N; Eron, JJ; Harris, J; Jacobson, JM; Kessler, HA; Moxham, C; Rousseau, FS; Shen, G; Thompson, MA; Zong, J, 2005)	0.59

Pharmacokinetics

Excerpt	Reference	Relevance
" The pharmacokinetic profiles of D-DOT in serum and urine were adequately described by a two-compartment open pharmacokinetic model."	( Pharmacokinetics of the anti-human immunodeficiency virus agent 1-(beta-D-dioxolane)thymine in rhesus monkeys. Asif, G; Chu, CK; Delinsky, D; Hurwitz, SJ; McClure, HM; Narayanasamy, J; Obikhod, A; Schinazi, RF, 2007)	0.34
" A recent in silico pharmacokinetic (PK)/enzyme kinetic study suggested that ZDV at 200 mg twice a day (b."	( Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals. Asif, G; Fromentin, E; Hurwitz, SJ; Schinazi, RF; Tharnish, PM, 2010)	0.62

Bioavailability

Excerpt	Reference	Relevance
" Oral bioavailability of DAPD was estimated to be approximately 30%."	( Pharmacokinetics of (-)-beta-D-dioxolane guanine and prodrug (-)-beta-D-2,6-diaminopurine dioxolane in rats and monkeys. Boudinot, FD; Chen, H; Chu, CK; Gao, Z; McClure, HM; Rajagopalan, P; Schinazi, RF, 1999)	0.3

Dosage Studied

Excerpt	Relevance	Reference
" Peak concentrations of DXGTP were obtained 8 h after dosing and were measurable through 48 h postdose."	( Enzymatic assay for measurement of intracellular DXG triphosphate concentrations in peripheral blood mononuclear cells from human immunodeficiency virus type 1-infected patients. Back, DJ; Hart, R; Hoggard, PG; Kewn, S; Khoo, SH; MacNeela, JP; Rousseau, F; Wang, LH, 2003)	0.32

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

Bioassays (40)

Assay ID	Title	Year	Journal	Article
AID760341	Cytotoxicity against human HuH7 cells after 2 to 4 days by MTT assay	2013	ACS medicinal chemistry letters, Aug-08, Volume: 4, Issue:8	Adenosine Dioxolane Nucleoside Phosphoramidates as Antiviral Agents for Human Immunodeficiency and Hepatitis B Viruses.
AID1174088	Cytotoxicity against human HepG2 cells	2014	Bioorganic & medicinal chemistry, Dec-01, Volume: 22, Issue:23	Synthesis and antiviral evaluation of 2-amino-6-carbamoylpurine dioxolane nucleoside derivatives and their phosphoramidates prodrugs.
AID1174084	Antiviral activity against Hepatitis B virus	2014	Bioorganic & medicinal chemistry, Dec-01, Volume: 22, Issue:23	Synthesis and antiviral evaluation of 2-amino-6-carbamoylpurine dioxolane nucleoside derivatives and their phosphoramidates prodrugs.
AID572111	Ratio of AUC (0 to 12 hrs) in HIV-1 infected patient at 500 mg, po bid on day 10 to AUC (0 to 12 hrs) in HIV-1 infected patient at 500 mg, po bid on day 1	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID369220	Antiviral activity against Duck hepatitis B virus infected ip dosed ducklings assessed as log reduction of serum viral DNA copies per ml of serum after 4 weeks	2007	Antimicrobial 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.
AID572106	Tmax in HIV-1 infected patient at 500 mg, po bid on day 10 by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID369222	Antiviral activity against Duck hepatitis B virus chronically infected ducklings assessed as log reduction of serum viral DNA copies per ml of serum at 40 mg/kg, ip after 4 weeks	2007	Antimicrobial 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.
AID572100	Tmax in HIV-1 infected patient at 500 mg, po bid on day 10 coadministered with 300 mg, po bid zidovudine by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID760344	Cytotoxicity against human PBMC after 2 to 4 days by MTT assay	2013	ACS medicinal chemistry letters, Aug-08, Volume: 4, Issue:8	Adenosine Dioxolane Nucleoside Phosphoramidates as Antiviral Agents for Human Immunodeficiency and Hepatitis B Viruses.
AID572102	AUC (0 to 12 hrs) in HIV-1 infected patient at 500 mg, po bid on day 10 coadministered with 300 mg, po bid zidovudine by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID406049	Oral bioavailability in rhesus monkey	2007	Antimicrobial agents and chemotherapy, Jul, Volume: 51, Issue:7	Pharmacokinetics of the anti-human immunodeficiency virus agent 1-(beta-D-dioxolane)thymine in rhesus monkeys.
AID572103	Apparent oral clearance in HIV-1 infected patient at 500 mg, po bid on day 10 coadministered with 300 mg, po bid zidovudine by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID571606	Tmax in HIV-1 infected patient at 500 mg, po bid on day 1 by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID760342	Cytotoxicity against human HepG2 cells after 2 to 4 days by neutral red dye uptake assay	2013	ACS medicinal chemistry letters, Aug-08, Volume: 4, Issue:8	Adenosine Dioxolane Nucleoside Phosphoramidates as Antiviral Agents for Human Immunodeficiency and Hepatitis B Viruses.
AID406056	Terminal phase half life in rhesus monkey	2007	Antimicrobial agents and chemotherapy, Jul, Volume: 51, Issue:7	Pharmacokinetics of the anti-human immunodeficiency virus agent 1-(beta-D-dioxolane)thymine in rhesus monkeys.
AID572109	Apparent oral clearance in HIV-1 infected patient at 500 mg, po bid on day 10 by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID760346	Antiviral activity against Hepatitis B virus infected in human HepAD38 cells after 5 days	2013	ACS medicinal chemistry letters, Aug-08, Volume: 4, Issue:8	Adenosine Dioxolane Nucleoside Phosphoramidates as Antiviral Agents for Human Immunodeficiency and Hepatitis B Viruses.
AID572099	Ratio of AUC (0 to 12 hrs) in HIV-1 infected patient at 500 mg, po bid on day 10 coadministered with 200 mg, po bid zidovudine to AUC (0 to 12 hrs) in HIV-1 infected patient at 500 mg, po bid on day 1 coadministered with 200 mg, po bid zidovudine	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID572098	Half life in HIV-1 infected patient at 500 mg, po bid on day 10 coadministered with 200 mg, po bid zidovudine by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID572108	AUC (0 to 12 hrs) in HIV-1 infected patient at 500 mg, po bid on day 10 by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID1174086	Cytotoxicity against human CEM cell	2014	Bioorganic & medicinal chemistry, Dec-01, Volume: 22, Issue:23	Synthesis and antiviral evaluation of 2-amino-6-carbamoylpurine dioxolane nucleoside derivatives and their phosphoramidates prodrugs.
AID571610	Half life in HIV-1 infected patient at 500 mg, po bid on day 1 by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID572110	Half life in HIV-1 infected patient at 500 mg, po bid on day 10 by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID572095	Cmax in HIV-1 infected patient at 500 mg, po bid on day 10 coadministered with 200 mg, po bid zidovudine by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID760340	Cytotoxicity against human CEM cells after 2 to 4 days by MTT assay	2013	ACS medicinal chemistry letters, Aug-08, Volume: 4, Issue:8	Adenosine Dioxolane Nucleoside Phosphoramidates as Antiviral Agents for Human Immunodeficiency and Hepatitis B Viruses.
AID572104	Half life in HIV-1 infected patient at 500 mg, po bid on day 10 coadministered with 300 mg, po bid zidovudine by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID1174083	Antiviral activity against HIV1	2014	Bioorganic & medicinal chemistry, Dec-01, Volume: 22, Issue:23	Synthesis and antiviral evaluation of 2-amino-6-carbamoylpurine dioxolane nucleoside derivatives and their phosphoramidates prodrugs.
AID1174087	Cytotoxicity against african green monkey Vero cells	2014	Bioorganic & medicinal chemistry, Dec-01, Volume: 22, Issue:23	Synthesis and antiviral evaluation of 2-amino-6-carbamoylpurine dioxolane nucleoside derivatives and their phosphoramidates prodrugs.
AID369221	Antiviral activity against Duck hepatitis B virus chronically infected ducklings assessed as log reduction of serum viral DNA copies per ml of serum at 20 mg/kg, ip after 4 weeks	2007	Antimicrobial 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.
AID572096	AUC (0 to 12 hrs) in HIV-1 infected patient at 500 mg, po bid on day 10 coadministered with 200 mg, po bid zidovudine by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID572101	Cmax in HIV-1 infected patient at 500 mg, po bid on day 10 coadministered with 300 mg, po bid zidovudine by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID571608	Cmax in HIV-1 infected patient at 500 mg, po bid on day 1 by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID572107	Cmax in HIV-1 infected patient at 500 mg, po bid on day 10 by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID571607	Tmax in HIV-1 infected patient assessed as beta-D-dioxolane guanosine level at 500 mg, po bid on day 1 by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID572105	Ratio of AUC (0 to 12 hrs) in HIV-1 infected patient at 500 mg, po bid on day 10 coadministered with 300 mg, po bid zidovudine to AUC (0 to 12 hrs) in HIV-1 infected patient at 500 mg, po bid on day 1 coadministered with 300 mg, po bid zidovudine	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID1174085	Cytotoxicity against human PBMC	2014	Bioorganic & medicinal chemistry, Dec-01, Volume: 22, Issue:23	Synthesis and antiviral evaluation of 2-amino-6-carbamoylpurine dioxolane nucleoside derivatives and their phosphoramidates prodrugs.
AID760343	Cytotoxicity against African green monkey Vero cells after 2 to 4 days by MTT assay	2013	ACS medicinal chemistry letters, Aug-08, Volume: 4, Issue:8	Adenosine Dioxolane Nucleoside Phosphoramidates as Antiviral Agents for Human Immunodeficiency and Hepatitis B Viruses.
AID572097	Apparent oral clearance in HIV-1 infected patient at 500 mg, po bid on day 10 coadministered with 200 mg, po bid zidovudine by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
AID760345	Antiviral activity against Human immunodeficiency virus 1 LAI infected in PHA-stimulated human PBMC	2013	ACS medicinal chemistry letters, Aug-08, Volume: 4, Issue:8	Adenosine Dioxolane Nucleoside Phosphoramidates as Antiviral Agents for Human Immunodeficiency and Hepatitis B Viruses.
AID572094	Tmax in HIV-1 infected patient at 500 mg, po bid on day 10 coadministered with 200 mg, po bid zidovudine by LC-MS/MS analysis	2010	Antimicrobial agents and chemotherapy, Mar, Volume: 54, Issue:3	Lack of pharmacokinetic interaction between amdoxovir and reduced- and standard-dose zidovudine in HIV-1-infected individuals.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (32)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	2 (6.25)	18.2507
2000's	26 (81.25)	29.6817
2010's	4 (12.50)	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: 18.84

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 moderate demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	18.84 (24.57)
Research Supply Index	3.66 (2.92)
Research Growth Index	4.88 (4.65)
Search Engine Demand Index	15.26 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (18.84)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	5 (15.15%)	5.53%
Reviews	4 (12.12%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	24 (72.73%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
adenine [no description available]	4.72	5	0	6-aminopurines; purine nucleobase	Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
cytosine [no description available]	3.13	1	0	aminopyrimidine; pyrimidine nucleobase; pyrimidone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	2	1	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
phenol [no description available]	2.08	1	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
ag-1549 capravirine: a non-nucleoside reverse transcriptase inhibitor	2	1	0
brl 42810 [no description available]	2.03	1	0	2-aminopurines; acetate ester	antiviral drug; prodrug
cytidine triphosphate Cytidine Triphosphate: Cytidine 5'-(tetrahydrogen triphosphate). A cytosine nucleotide containing three phosphate groups esterified to the sugar moiety.	4.32	3	0	cytidine 5'-phosphate; pyrimidine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2.01	1	0	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
deoxycytidine [no description available]	4.54	4	0	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	2.03	1	0	purine 2'-deoxyribonucleoside; purines 2'-deoxy-D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
deoxycytidine monophosphate Deoxycytidine Monophosphate: Deoxycytidine (dihydrogen phosphate). A deoxycytosine nucleotide containing one phosphate group esterified to the deoxyribose moiety in the 2'-,3'- or 5- positions.. 2'-deoxycytosine 5'-monophosphate : A pyrimidine 2'-deoxyribonucleoside 5'-monophosphate having cytosine as the nucleobase.	3.12	1	0	2'-deoxycytidine phosphate; pyrimidine 2'-deoxyribonucleoside 5'-monophosphate	Escherichia coli 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	2.03	1	0	dihydrofuran; nucleoside analogue; organic molecular entity	antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) 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.	4.03	2	0	pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
arabinofuranosylcytosine triphosphate Arabinofuranosylcytosine Triphosphate: A triphosphate nucleotide analog which is the biologically active form of CYTARABINE. It inhibits nuclear DNA synthesis.	2.41	2	0
alovudine [no description available]	3.12	1	0	pyrimidine 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.	6.16	6	2	azide; pyrimidine 2',3'-dideoxyribonucleoside	antimetabolite; antiviral drug; HIV-1 reverse transcriptase inhibitor
ribavirin Rebetron: Rebetron is tradename	7.02	1	0	1-ribosyltriazole; aromatic amide; monocarboxylic acid amide; primary carboxamide	anticoronaviral agent; antiinfective agent; antimetabolite; antiviral agent; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
adefovir adefovir: inhibitor of African swine fever virus. adefovir(1-) : A organophosphonate oxoanion obtained by removal of a proton from the phosphonate group of adefovir, a nucleoside reverse transcriptase inhibitor. It is the major microspecies at pH 7.3 (according to Marvin v 6.2.0.).. adefovir : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(t-butoxycarbonyloxymethyl) ester (dipivoxil ester) prodrug is used to treat chronic hepatitis B viral infection.	2.41	2	0	6-aminopurines; ether; phosphonic acids	antiviral drug; DNA synthesis inhibitor; drug metabolite; HIV-1 reverse transcriptase inhibitor; nephrotoxic agent
cidofovir anhydrous Cidofovir: An acyclic nucleoside phosphonate that acts as a competitive inhibitor of viral DNA polymerases. It is used in the treatment of RETINITIS caused by CYTOMEGALOVIRUS INFECTIONS and may also be useful for treating HERPESVIRUS INFECTIONS.. cidofovir anhydrous : Cytosine substituted at the 1 position by a 3-hydroxy-2-(phosphonomethoxy)propyl group (S configuration). A nucleoside analogue, it is an injectable antiviral used for the treatment of cytomegalovirus (CMV) retinitis in AIDS patients.	3.13	1	0	phosphonic acids; pyrimidone	anti-HIV agent; antineoplastic agent; antiviral drug; photosensitizing agent
lamivudine [no description available]	2.93	4	0	monothioacetal; nucleoside analogue; oxacycle; primary alcohol	allergen; anti-HBV agent; antiviral drug; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor; HIV-1 reverse transcriptase inhibitor; prodrug
adefovir dipivoxil bis(pivaloyloxymethyl)-9-(2-phosphonylmethoxyethyl)adenine: structure given in first source. adefovir pivoxil : An organic phosphonate that is the dipivoxil ester of adefovir. A prodrug for adefovir, an HIV-1 reverse transcriptase inhibitor, adefovir pivoxil is used to treat chronic hepatitis B viral infection.	2.03	1	0	6-aminopurines; carbonate ester; ether; organic phosphonate	antiviral drug; DNA synthesis inhibitor; HIV-1 reverse transcriptase inhibitor; nephrotoxic agent; prodrug
emtricitabine Emtricitabine: A deoxycytidine analog and REVERSE TRANSCRIPTASE INHIBITOR with antiviral activity against HIV-1 and HEPATITIS B viruses. It is used to treat HIV INFECTIONS.. emtricitabine : An organofluorine compound that is 5-fluorocytosine substituted at the 1 position by a 2-(hydroxymethyl)-1,3-oxathiolan-5-yl group (2R,5S configuration). It is used in combination therapy for the treatment of HIV-1 infection.	4.54	4	0	monothioacetal; nucleoside analogue; organofluorine compound; pyrimidone	antiviral drug; HIV-1 reverse transcriptase inhibitor
efavirenz efavirenz: HIV-1 reverse transcriptase inhibitor. efavirenz : 1,4-Dihydro-2H-3,1-benzoxazin-2-one substituted at the 4 position by cyclopropylethynyl and trifluoromethyl groups (S configuration) and at the 6 position by chlorine. A non-nucleoside reverse transcriptase inhibitor with activity against HIV, it is used with other antiretrovirals for combination therapy of HIV infection.	2	1	0	acetylenic compound; benzoxazine; cyclopropanes; organochlorine compound; organofluorine compound	antiviral drug; HIV-1 reverse transcriptase inhibitor
dexelvucitabine dexelvucitabine: inhibits human hepatitis B virus (HBV) and human immunodeficiency virus (HIV) in vitro	4.03	2	0
lopinavir [no description available]	2	1	0	amphetamines; dicarboxylic acid diamide	anticoronaviral agent; antiviral drug; HIV protease inhibitor
1-(2'-deoxy-2'-fluoro-beta-arabinofuranosyl)-5-methylcytosine triphosphate 1-(2'-deoxy-2'-fluoro-beta-arabinofuranosyl)-5-methylcytosine triphosphate: RN given refers to (D)-isomer	2.41	2	0
atazanavir sulfate Atazanavir Sulfate: An azapeptide and HIV-PROTEASE INHIBITOR that is used in the treatment of HIV INFECTIONS and AIDS in combination with other ANTI-HIV AGENTS.	2	1	0	organic sulfate salt
telbivudine [no description available]	2.03	1	0	pyrimidine 2'-deoxyribonucleoside	antiviral drug; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	4.72	5	0	divalent inorganic anion; phosphite ion
2'-fluorothymidine [no description available]	4.03	4	0
mycophenolic acid Mycophenolic Acid: Compound derived from Penicillium stoloniferum and related species. It blocks de novo biosynthesis of purine nucleotides by inhibition of the enzyme inosine monophosphate dehydrogenase (IMP DEHYDROGENASE). Mycophenolic acid exerts selective effects on the immune system in which it prevents the proliferation of T-CELLS, LYMPHOCYTES, and the formation of antibodies from B-CELLS. It may also inhibit recruitment of LEUKOCYTES to sites of INFLAMMATION.. mycophenolate : A monocarboxylic acid anion resulting from the removal of a proton from the carboxy group of mycophenolic acid.. mycophenolic acid : A member of the class of 2-benzofurans that is 2-benzofuran-1(3H)-one which is substituted at positions 4, 5, 6, and 7 by methyl, methoxy, (2E)-5-carboxy-3-methylpent-2-en-1-yl, and hydroxy groups, respectively. It is an antibiotic produced by Penicillium brevi-compactum, P. stoloniferum, P. echinulatum and related species. An immunosuppressant, it is widely used (partiularly as its sodium salt and as the 2-(morpholin-4-yl)ethyl ester prodrug, mycophenolate mofetil) to prevent tissue rejection following organ transplants and for the treatment of certain autoimmune diseases.	8.82	2	1	2-benzofurans; gamma-lactone; monocarboxylic acid; phenols	anticoronaviral agent; antimicrobial agent; antineoplastic agent; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; environmental contaminant; immunosuppressive agent; mycotoxin; Penicillium metabolite; xenobiotic
dioxolane-thymine dioxolane-thymine: structure in first source	2.03	1	0
tenofovir tenofovir (anhydrous) : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.	4.54	4	0	nucleoside analogue; phosphonic acids	antiviral drug; drug metabolite; HIV-1 reverse transcriptase inhibitor
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	2	1	0	chalcogen; nonmetal atom	macronutrient
tenofovir disoproxil fumarate tenofovir disoproxil fumarate : A fumarate salt prepared from equimolar amounts of tenofovir disoproxil and fumaric acid. It is used in combination therapy for the treatment of HIV infection.	2.03	1	0	fumarate salt	antiviral drug; HIV-1 reverse transcriptase inhibitor; prodrug
racivir [no description available]	3.12	1	0
arabinofuranosyluracil Arabinofuranosyluracil: A pyrimidine nucleoside formed in the body by the deamination of CYTARABINE.	4.03	4	0
enfuvirtide Enfuvirtide: A synthetic 36-amino acid peptide that corresponds to the heptad repeat sequence of HIV-1 gp41. It blocks HIV cell fusion and viral entry and is used with other anti-retrovirals for combination therapy of HIV INFECTIONS and AIDS.. enfuvirtide : A synthetic 36-amino acid peptide consisting of N-acetyltyrosyl, threonyl, seryl, leucyl, isoleucyl, histidyl, seryl, leucyl, isoleucyl, alpha-glutamyl, alpha-glutamyl, seryl, glutaminyl, asparaginyl, glutaminyl, glutaminyl, alpha-glutamyl, lysyl, asparaginyl, alpha-glutamyl, alpha-glutamyl, alpha-glutamyl, leucyl, leucyl, alpha-glutamyl, leucyl, alpha-aspartyl, lysyl, tryptophyl, alanyl, seryl, leucyl, tryptophyl, asparaginyl, tryptophyl, and phenylalaninamide residues joined in sequence. An HIV fusion inhibitor, it was the first of a novel class of antiretroviral drugs used in combination therapy for the treatment of HIV-1 infection. It interferes with entry of HIV into cells by binding to the gp41 sub-unit of the viral envelope glycoprotein, so inhibiting fusion of viral and cellular membranes.	9.73	2	1
tipranavir tipranavir: inhibits HIV-1 protease. tipranavir : A pyridine-2-sulfonamide substituted at C-5 by a trifluoromethyl group and at the sulfonamide nitrogen by a dihydropyrone-containing m-tolyl substituent. It is an HIV-1 protease inhibitor.	2	1	0	sulfonamide	antiviral drug; HIV protease inhibitor
entecavir entecavir (anhydrous) : Guanine substituted at the 9 position by a 4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl group. A synthetic analogue of 2'-deoxyguanosine, it is a nucleoside reverse transcriptase inhibitor with selective antiviral activity against hepatitis B virus. Entecavir is phosphorylated intracellularly to the active triphosphate form, which competes with deoxyguanosine triphosphate, the natural substrate of hepatitis B virus reverse transcriptase, inhibiting every stage of the enzyme's activity, although it has no activity against HIV. It is used for the treatment of chronic hepatitis B.	2.03	1	0	2-aminopurines; oxopurine; primary alcohol; secondary alcohol	antiviral drug; EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
acyclovir Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.	2	1	0	2-aminopurines; oxopurine	antimetabolite; antiviral drug
guanosine triphosphate Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.	2.02	1	0	guanosine 5'-phosphate; purine ribonucleoside 5'-triphosphate	Escherichia coli metabolite; mouse metabolite; uncoupling protein inhibitor
guanine [no description available]	7.42	2	0	2-aminopurines; oxopurine; purine nucleobase	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
guanosine ribonucleoside : Any nucleoside where the sugar component is D-ribose.	3.62	9	0	guanosines; purines D-ribonucleoside	fundamental metabolite
penciclovir penciclovir : A member of the class of 2-aminopurines that is guanine in which the hydrogen at position 9 is substituted by a 4-hydroxy-3-(hydroxymethyl)but-1-yl group. An antiviral drug, it is administered topically for treatment of herpes labialis. A prodrug, famciclovir, is used for oral administration.	2	1	0	2-aminopurines; propane-1,3-diols	antiviral drug
2-aminopurine dioxolane (4-2-aminopurin-9-yl)-1,3-dioxolane-2-methanol: structure in first source	5.19	11	1
lobucavir lobucavir: inhibits the replication of HIV virus in T cells, monocytes & macrophages in vitro by inhibiting DNA polymerase and viral DNA synthesis	2	1	0
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	2	1	0

Condition	Indicated	Relationship Strength	Studies	Trials
Chronic Hepatitis B [description not available]	0	2.43	2	0
Hepatitis B, Chronic INFLAMMATION of the LIVER in humans caused by HEPATITIS B VIRUS lasting six months or more. It is primarily transmitted by parenteral exposure, such as transfusion of contaminated blood or blood products, but can also be transmitted via sexual or intimate personal contact.	0	2.43	2	0
HIV Coinfection [description not available]	0	9.68	11	5
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).	1	11.68	11	5
Hepatocellular Carcinoma [description not available]	0	2.01	1	0
Cancer of Liver [description not available]	0	2.01	1	0
Hepatitis, Viral, Animal INFLAMMATION of the LIVER in animals due to viral infection.	0	2.42	2	0
Infections, Hepadnaviridae [description not available]	0	2.42	2	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	0	2.01	1	0
Liver Neoplasms Tumors or cancer of the LIVER.	0	2.01	1	0
Hepadnaviridae Infections Virus diseases caused by the HEPADNAVIRIDAE.	0	2.42	2	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	0	2.01	1	0
Hepatitis B Virus Infection [description not available]	0	2.93	1	0
Hepatitis B INFLAMMATION of the LIVER in humans caused by a member of the ORTHOHEPADNAVIRUS genus, HEPATITIS B VIRUS. It is primarily transmitted by parenteral exposure, such as transfusion of contaminated blood or blood products, but can also be transmitted via sexual or intimate personal contact.	0	2.93	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	7.03	1	0
Lipodystrophy A collection of heterogenous conditions resulting from defective LIPID METABOLISM and characterized by ADIPOSE TISSUE atrophy. Often there is redistribution of body fat resulting in peripheral fat wasting and central adiposity. They include generalized, localized, congenital, and acquired lipodystrophy.	0	2	1	0

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