Compounds > atevirdine
Page last updated: 2024-12-06

atevirdine

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

Description

Atevirdine is a non-nucleoside reverse transcriptase inhibitor (NNRTI) that was developed for the treatment of HIV infection. Its synthesis involves a complex multi-step process, starting with commercially available starting materials. Atevirdine exhibits potent antiviral activity against HIV-1, however, it has several limitations, including a short half-life, significant drug interactions, and a high incidence of adverse effects, such as hepatotoxicity and rash. Therefore, atevirdine was discontinued from the market. The study of atevirdine provided valuable insights into the development of other NNRTIs, and its synthesis remains a valuable example of organic chemistry techniques.'

atevirdine: inhibits replication of HIV-1; U 87201E is the methanesulfonate salt [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID60848
CHEMBL ID280527
SCHEMBL ID356038
MeSH IDM0206023

Synonyms (23)

Synonym
5-methoxyindole-2-carboxylic acid [n -[3-(aminoethyl)pyridin-2-yl]piperazide]
chembl280527 ,
n-ethyl-2-{4-[(5-methoxy-1h-indol-2-yl)carbonyl]piperazin-1-yl}pyridin-3-amine
bdbm1437
piperazine, 1-[3-(ethylamino)-2-pyridinyl]-4-[(5-methoxy-1h-indol-2-yl)carbonyl]-
[4-[3-(ethylamino)-2-pyridyl]piperazin-1-yl]-(5-methoxy-1h-indol-2-yl)methanone
1-[(5-methoxyindol-2-yl)carbonyl]-4-[3-(ethylamino)-2-pyridyl]piperazine
136816-75-6
atevirdine
atevirdine methanesulfonate
u-87201
[4-[3-(ethylamino)pyridin-2-yl]piperazin-1-yl]-(5-methoxy-1h-indol-2-yl)methanone
piperazine, 1-(3-(ethylamino)-2-pyridinyl)-4-((5-methoxy-1h-indol-2-yl)carbonyl)-
n24015wc6d ,
atevirdine [inn]
unii-n24015wc6d
atevirdine [who-dd]
atevirdine [mi]
SCHEMBL356038
methanone,[4-[3-(ethylamino)-2-pyridinyl]-1-piperazinyl](5-methoxy-1h-indol-2-yl)-
DTXSID40159940
DB12264
Q4813142

Research Excerpts

Overview

Atevirdine is a nonnucleoside reverse transcriptase inhibitor with in vitro activity against human immunodeficiency virus type 1. It is currently in phase II clinical trials.

ExcerptReferenceRelevance
"Atevirdine is a nonnucleoside reverse transcriptase inhibitor with in vitro activity against human immunodeficiency virus type 1 and is currently in phase II clinical trials. "( Didanosine reduces atevirdine absorption in subjects with human immunodeficiency virus infections.
Borin, MT; DeRemer, M; Driver, MR; Fischl, MA; Lee, K; Morse, GD; Shelton, MJ; Wajszczuk, CP, 1996)		2.07
"Atevirdine is a nonnucleoside reverse transcriptase inhibitor of human immunodeficiency virus type 1 (HIV-1). "( Safety, tolerance, and efficacy of atevirdine in asymptomatic human immunodeficiency virus-infected individuals.
Aldam, D; Been-Tiktak, AM; Borleffs, JC; Boucher, CA; Loveday, C; Richens, J; van Loon, AM; Vrehen, HM; Ward, P; Weller, IV; Williams, I, 1996)		2.01

Pharmacokinetics

Atevirdine was found to have relatively large intersubject Variabilities. The study had little power to detect dose-dependent changes in the values of the pharmacokinetic parameters.

ExcerptReferenceRelevance
" The values of the pharmacokinetic parameters for atevirdine were found to have relatively large intersubject variabilities, and consequently, the study had little power to detect dose-dependent changes in the values of the pharmacokinetic parameters."( Safety, tolerance, and pharmacokinetics of atevirdine mesylate (U-87201E) in asymptomatic human immunodeficiency virus-infected patients.
Been-Tiktak, AM; Borleffs, JC; Branger, T; Cox, SR; Harry, JD; Schneider, MM; van der Feltz, M; Vrehen, HM; Ward, P, 1995)		0.81
" Intensive pharmacokinetic studies were conducted prior to and at 4 and/or 8 weeks during atevirdine monotherapy in female patients."( Concentration-targeted phase I trials of atevirdine mesylate in patients with HIV infection: dosage requirements and pharmacokinetic studies. The ACTG 187 and 199 study teams.
Bassiakos, Y; Batts, D; Cox, S; Demeter, LM; Fischl, MA; Leedom, J; Morse, GD; Para, M; Powderly, W; Reichman, RC; Resnick, L; Timpone, J, 2000)		0.79

Compound-Compound Interactions

ExcerptReferenceRelevance
"Twenty patients were enrolled in a phase I clinical trial of atevirdine, a nonnucleoside reverse transcriptase inhibitor (NNRTI), given in combination with zidovudine for treatment of human immunodeficiency virus type 1 (HIV-1) infection."( Phase I study of atevirdine, a nonnucleoside reverse transcriptase inhibitor, in combination with zidovudine for human immunodeficiency virus type 1 infection. ACTG 199 Study Team.
Bassiakos, Y; Demeter, LM; Fischl, M; Greisberger, C; Leedom, J; Morse, GD; Para, M; Powderly, W; Reichman, RC; Resnick, L, 1995)		0.87

Bioavailability

ExcerptReferenceRelevance
" Good oral bioavailability was observed in rhesus monkeys upon oral dosing of 1 as a suspension in methocel."( 5-chloro-3-(phenylsulfonyl)indole-2-carboxamide: a novel, non-nucleoside inhibitor of HIV-1 reverse transcriptase.
Balani, SK; Ciccarone, TM; Condra, JH; Emini, EA; Goldman, ME; Greenlee, WJ; Kauffman, LR; MacTough, SC; Rooney, CS; Williams, TM, 1993)		0.29
" Nevertheless, one compound (13), PNU-103657, possessed oral bioavailability in rats approaching that of the structurally related NNRTI drug delavirdine which is currently on the market for the treatment of HIV infection."( Synthesis and structure-activity relationships of the (alkylamino)piperidine-containing BHAP class of non-nucleoside reverse transcriptase inhibitors: effect of 3-alkylpyridine ring substitution.
Adams, WJ; Friis, JM; Genin, MJ; Kopta, LA; May, PD; Olmsted, RA; Poel, TJ; Romero, DL; Thomas, RC; Voorman, RL; Yagi, Y, 1999)		0.3

Dosage Studied

Atevirdine was administered every 8 h with weekly dosage adjustments. Atevirdine metabolism did not appear to reach saturation during chronic dosing in many of our patients, as reflected by the pattern of N-ATV/ATV ratios.

ExcerptRelevanceReference
" Good oral bioavailability was observed in rhesus monkeys upon oral dosing of 1 as a suspension in methocel."( 5-chloro-3-(phenylsulfonyl)indole-2-carboxamide: a novel, non-nucleoside inhibitor of HIV-1 reverse transcriptase.
Balani, SK; Ciccarone, TM; Condra, JH; Emini, EA; Goldman, ME; Greenlee, WJ; Kauffman, LR; MacTough, SC; Rooney, CS; Williams, TM, 1993)		0.29
" Blood samples were collected before dosing and at intervals afterward for safety evaluation and estimation of atevirdine and metabolite levels."( Safety, tolerance, and pharmacokinetics of atevirdine mesylate (U-87201E) in asymptomatic human immunodeficiency virus-infected patients.
Been-Tiktak, AM; Borleffs, JC; Branger, T; Cox, SR; Harry, JD; Schneider, MM; van der Feltz, M; Vrehen, HM; Ward, P, 1995)		0.77
"To determine the dosage requirements and pharmacokinetics of atevirdine, a non-nucleoside reverse transcriptase inhibitor and its N-dealkylated metabolite (N-ATV) during phase I studies in patients receiving atevirdine alone or in combination with zidovudine."( Concentration-targeted phase I trials of atevirdine mesylate in patients with HIV infection: dosage requirements and pharmacokinetic studies. The ACTG 187 and 199 study teams.
Bassiakos, Y; Batts, D; Cox, S; Demeter, LM; Fischl, MA; Leedom, J; Morse, GD; Para, M; Powderly, W; Reichman, RC; Resnick, L; Timpone, J, 2000)		0.81
"Two open label, phase I studies conducted by the adult AIDS Clinical Trials Group (ACTG) in which atevirdine was administered every 8 h with weekly dosage adjustments to attain targeted trough plasma atevirdine concentrations."( Concentration-targeted phase I trials of atevirdine mesylate in patients with HIV infection: dosage requirements and pharmacokinetic studies. The ACTG 187 and 199 study teams.
Bassiakos, Y; Batts, D; Cox, S; Demeter, LM; Fischl, MA; Leedom, J; Morse, GD; Para, M; Powderly, W; Reichman, RC; Resnick, L; Timpone, J, 2000)		0.79
" Atevirdine metabolism did not appear to reach saturation during chronic dosing in many of our patients, as reflected by the pattern of N-ATV/ATV ratios in plasma and saturation was not an explanation for the variation in dosing requirements."( Concentration-targeted phase I trials of atevirdine mesylate in patients with HIV infection: dosage requirements and pharmacokinetic studies. The ACTG 187 and 199 study teams.
Bassiakos, Y; Batts, D; Cox, S; Demeter, LM; Fischl, MA; Leedom, J; Morse, GD; Para, M; Powderly, W; Reichman, RC; Resnick, L; Timpone, J, 2000)		1.48
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Gag-Pol polyproteinHIV-1 M:B_HXB2RIC50 (µMol)23.19430.00060.91418.3200AID1795311; AID1795349; AID1795381; AID1795382
Reverse transcriptase/RNaseH Human immunodeficiency virus 1IC50 (µMol)4.32800.00011.076810.0000AID197805; AID197807; AID197948; AID198396; AID353097
Protease Human immunodeficiency virus 1IC50 (µMol)34.97330.00010.22487.3200AID200169; AID200170; AID200171
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (2)

Processvia Protein(s)Taxonomy
viral life cycleGag-Pol polyproteinHIV-1 M:B_HXB2R
establishment of integrated proviral latencyGag-Pol polyproteinHIV-1 M:B_HXB2R
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
peptidase activityGag-Pol polyproteinHIV-1 M:B_HXB2R
integrase activityGag-Pol polyproteinHIV-1 M:B_HXB2R
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (47)

Assay IDTitleYearJournalArticle
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID200170Inhibition single mutant of HIV-1 RT (K103 N)1993Journal of medicinal chemistry, Apr-30, Volume: 36, Issue:9
5-chloro-3-(phenylsulfonyl)indole-2-carboxamide: a novel, non-nucleoside inhibitor of HIV-1 reverse transcriptase.
AID25384Half life upon microsomal incubation1996Journal of medicinal chemistry, Dec-20, Volume: 39, Issue:26
Synthesis and bioactivity of novel bis(heteroaryl)piperazine (BHAP) reverse transcriptase inhibitors: structure-activity relationships and increased metabolic stability of novel substituted pyridine analogs.
AID25643Half life of the parent compound upon microsomal incubation in the presence of hepatic microsomal cytochrome P450.1999Journal of medicinal chemistry, Oct-07, Volume: 42, Issue:20
Synthesis and structure-activity relationships of the (alkylamino)piperidine-containing BHAP class of non-nucleoside reverse transcriptase inhibitors: effect of 3-alkylpyridine ring substitution.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID198592In vitro inhibition of HIV-1 reverse transcriptase at 100 uM.1996Journal of medicinal chemistry, Dec-20, Volume: 39, Issue:26
Synthesis and bioactivity of novel bis(heteroaryl)piperazine (BHAP) reverse transcriptase inhibitors: structure-activity relationships and increased metabolic stability of novel substituted pyridine analogs.
AID153102Cytotoxic concentration against PBMC cells1993Journal of medicinal chemistry, May-14, Volume: 36, Issue:10
Bis(heteroaryl)piperazine (BHAP) reverse transcriptase inhibitors: structure-activity relationships of novel substituted indole analogues and the identification of 1-[(5-methanesulfonamido-1H-indol-2-yl)-carbonyl]-4-[3- [(1-methylethyl)amino]-pyridinyl]pi
AID105000Inhibitory concentration which prevents the spread of HIV-1 IIIB infection in MT2 T-lymphoid cells1993Journal of medicinal chemistry, Aug-20, Volume: 36, Issue:17
Selective non-nucleoside HIV-1 reverse transcriptase inhibitors. New 2,3-dihydrothiazolo[2,3-a]isoindol-5(9bH)-ones and related compounds with anti-HIV-1 activity.
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID106774Cell culture inhibitory concentration against spread of HIV-I infection in MT-4 cells was determined1993Journal of medicinal chemistry, Jan-22, Volume: 36, Issue:2
Synthesis and evaluation of 2-pyridinone derivatives as specific HIV-1 reverse transcriptase inhibitors. 3. Pyridyl and phenyl analogs of 3-aminopyridin-2(1H)-one.
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID353096Antiviral activity against HIV infected in human CEM-SS cells assessed as inhibition of virus induced cell killing by XTT assay2009Bioorganic & medicinal chemistry letters, May-01, Volume: 19, Issue:9
Synthesis of potent antitumor and antiviral benzofuran derivatives.
AID197807In vitro inhibition of HIV-1 reverse transcriptase1993Journal of medicinal chemistry, May-14, Volume: 36, Issue:10
Bis(heteroaryl)piperazine (BHAP) reverse transcriptase inhibitors: structure-activity relationships of novel substituted indole analogues and the identification of 1-[(5-methanesulfonamido-1H-indol-2-yl)-carbonyl]-4-[3- [(1-methylethyl)amino]-pyridinyl]pi
AID197948In vitro inhibitory concentration against HIV-1 reverse transcriptase using rC-dG template primer1993Journal of medicinal chemistry, Jan-22, Volume: 36, Issue:2
Synthesis and evaluation of 2-pyridinone derivatives as specific HIV-1 reverse transcriptase inhibitors. 3. Pyridyl and phenyl analogs of 3-aminopyridin-2(1H)-one.
AID155123In vitro inhibition of HIV-1 D34 replication in human peripheral blood mononuclear cells.1996Journal of medicinal chemistry, Dec-20, Volume: 39, Issue:26
Synthesis and bioactivity of novel bis(heteroaryl)piperazine (BHAP) reverse transcriptase inhibitors: structure-activity relationships and increased metabolic stability of novel substituted pyridine analogs.
AID106775Inhibition of cell culture in MT-4 cells1993Journal of medicinal chemistry, Apr-30, Volume: 36, Issue:9
5-chloro-3-(phenylsulfonyl)indole-2-carboxamide: a novel, non-nucleoside inhibitor of HIV-1 reverse transcriptase.
AID353098Therapeutic index, ratio of toxic dose of drug for 50% of the population TD50 to minimum effective dose ED50 of the population2009Bioorganic & medicinal chemistry letters, May-01, Volume: 19, Issue:9
Synthesis of potent antitumor and antiviral benzofuran derivatives.
AID198396Inhibitory activity against HIV-1 reverse transcriptase (HIV-RT)1993Journal of medicinal chemistry, Aug-20, Volume: 36, Issue:17
Selective non-nucleoside HIV-1 reverse transcriptase inhibitors. New 2,3-dihydrothiazolo[2,3-a]isoindol-5(9bH)-ones and related compounds with anti-HIV-1 activity.
AID81443Inhibition of HIV-1 IIIB replication in MT2 (human lymphocyte) cells.1993Journal of medicinal chemistry, May-14, Volume: 36, Issue:10
Bis(heteroaryl)piperazine (BHAP) reverse transcriptase inhibitors: structure-activity relationships of novel substituted indole analogues and the identification of 1-[(5-methanesulfonamido-1H-indol-2-yl)-carbonyl]-4-[3- [(1-methylethyl)amino]-pyridinyl]pi
AID1174470Cytotoxicity against human peripheral blood leukocyte cells at 100 uM2015European journal of medicinal chemistry, Jan-07, Volume: 89A review on recent developments of indole-containing antiviral agents.
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID104244Cytotoxic concentration against MT-2 cells1993Journal of medicinal chemistry, May-14, Volume: 36, Issue:10
Bis(heteroaryl)piperazine (BHAP) reverse transcriptase inhibitors: structure-activity relationships of novel substituted indole analogues and the identification of 1-[(5-methanesulfonamido-1H-indol-2-yl)-carbonyl]-4-[3- [(1-methylethyl)amino]-pyridinyl]pi
AID1174469Antiviral activity against HIV1 infected in human peripheral blood leukocyte cells assessed as inhibition of replication2015European journal of medicinal chemistry, Jan-07, Volume: 89A review on recent developments of indole-containing antiviral agents.
AID197805In vitro for inhibition of HIV-1 reverse transcriptase.1996Journal of medicinal chemistry, Dec-20, Volume: 39, Issue:26
Synthesis and bioactivity of novel bis(heteroaryl)piperazine (BHAP) reverse transcriptase inhibitors: structure-activity relationships and increased metabolic stability of novel substituted pyridine analogs.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID200171Inhibition single mutant of HIV-1 RT (Y181C)1993Journal of medicinal chemistry, Apr-30, Volume: 36, Issue:9
5-chloro-3-(phenylsulfonyl)indole-2-carboxamide: a novel, non-nucleoside inhibitor of HIV-1 reverse transcriptase.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID198593In vitro inhibition of HIV-1 reverse transcriptase at 100 uM1993Journal of medicinal chemistry, May-14, Volume: 36, Issue:10
Bis(heteroaryl)piperazine (BHAP) reverse transcriptase inhibitors: structure-activity relationships of novel substituted indole analogues and the identification of 1-[(5-methanesulfonamido-1H-indol-2-yl)-carbonyl]-4-[3- [(1-methylethyl)amino]-pyridinyl]pi
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID81442Inhibition of HIV-1 D34 replication in human peripheral blood mononuclear cells.1993Journal of medicinal chemistry, May-14, Volume: 36, Issue:10
Bis(heteroaryl)piperazine (BHAP) reverse transcriptase inhibitors: structure-activity relationships of novel substituted indole analogues and the identification of 1-[(5-methanesulfonamido-1H-indol-2-yl)-carbonyl]-4-[3- [(1-methylethyl)amino]-pyridinyl]pi
AID353097Inhibition of recombinant HIV1 reverse transcriptase in cell free Quan-T-RT by scintillation proximity assay2009Bioorganic & medicinal chemistry letters, May-01, Volume: 19, Issue:9
Synthesis of potent antitumor and antiviral benzofuran derivatives.
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID200169Inhibition of HIV-1 RT using rC-dG as template1993Journal of medicinal chemistry, Apr-30, Volume: 36, Issue:9
5-chloro-3-(phenylsulfonyl)indole-2-carboxamide: a novel, non-nucleoside inhibitor of HIV-1 reverse transcriptase.
AID1795349HIV-1 RT Assay from Article 10.1021/jm960158n: \\Targeting delavirdine/atevirdine resistant HIV-1: identification of (alkylamino)piperidine-containing bis(heteroaryl)piperazines as broad spectrum HIV-1 reverse transcriptase inhibitors.\\1996Journal of medicinal chemistry, Sep-13, Volume: 39, Issue:19
Targeting delavirdine/atevirdine resistant HIV-1: identification of (alkylamino)piperidine-containing bis(heteroaryl)piperazines as broad spectrum HIV-1 reverse transcriptase inhibitors.
AID1795382HIV-1 RT Assay from Article 10.1021/jm00062a027: \\Bis(heteroaryl)piperazine (BHAP) reverse transcriptase inhibitors: structure-activity relationships of novel substituted indole analogues and the identification of 1-[(5-methanesulfonamido-1H-indol-2-yl)-c1993Journal of medicinal chemistry, May-14, Volume: 36, Issue:10
Bis(heteroaryl)piperazine (BHAP) reverse transcriptase inhibitors: structure-activity relationships of novel substituted indole analogues and the identification of 1-[(5-methanesulfonamido-1H-indol-2-yl)-carbonyl]-4-[3- [(1-methylethyl)amino]-pyridinyl]pi
AID1795381HIV-1 RT Assay from Article 10.1021/jm00061a022: \\5-chloro-3-(phenylsulfonyl)indole-2-carboxamide: a novel, non-nucleoside inhibitor of HIV-1 reverse transcriptase.\\1993Journal of medicinal chemistry, Apr-30, Volume: 36, Issue:9
5-chloro-3-(phenylsulfonyl)indole-2-carboxamide: a novel, non-nucleoside inhibitor of HIV-1 reverse transcriptase.
AID1795311HIV-1 RT Assay from Article 10.1021/jm00069a011: \\Selective non-nucleoside HIV-1 reverse transcriptase inhibitors. New 2,3-dihydrothiazolo[2,3-a]isoindol-5(9bH)-ones and related compounds with anti-HIV-1 activity.\\1993Journal of medicinal chemistry, Aug-20, Volume: 36, Issue:17
Selective non-nucleoside HIV-1 reverse transcriptase inhibitors. New 2,3-dihydrothiazolo[2,3-a]isoindol-5(9bH)-ones and related compounds with anti-HIV-1 activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (28)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's25 (89.29)18.2507
2000's2 (7.14)29.6817
2010's1 (3.57)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: 18.35

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.

MetricThis Compound (vs All)
Research Demand Index18.35 (24.57)
Research Supply Index3.61 (2.92)
Research Growth Index4.33 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (18.35)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials7 (24.14%)5.53%
Reviews1 (3.45%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other21 (72.41%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (4)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
A Phase I Concentration-Controlled Trial to Assess the Safety, Tolerance, Pharmacokinetics and Development of Decreased HIV-1 Susceptibility to the Combination of Atevirdine Mesylate (U-87201E), Zidovudine (AZT), and Didanosine (ddI) [NCT00000742]Phase 115 participants InterventionalCompleted
A Phase I Concentration-Targeted Multidose Study of Atevirdine Mesylate ( U-87201E ), AZT, and ddI or ddC [NCT00000753]Phase 130 participants InterventionalCompleted
Prospective Open-Label Study of the Emergence of Drug Resistance in Patients Infected With HIV-1 Who Are Taking Oral U-87201E [NCT00002094]0 participants InterventionalCompleted
Randomized, Double-Blind, Placebo-Controlled Comparative Dose-Response Study of Two Doses of Atevirdine Mesylate (U-87201E) in Combination With Fixed Doses of Zidovudine (AZT) in HIV+ Patients [NCT00002322]Phase 20 participants InterventionalCompleted
[information is prepared from clinicaltrials.gov, extracted Sep-2024]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
fluorouracil
Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.		2.0510nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
nevirapine
Nevirapine: A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV INFECTIONS and AIDS.. nevirapine : A dipyridodiazepine that is 5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine which is substituted by methyl, oxo, and cyclopropyl groups at positions 4, 6, and 11, respectively. A non-nucleoside reverse transcriptase inhibitor with activity against HIV-1, it is used in combination with other antiretrovirals for the treatment of HIV infection.		3.2360cyclopropanes;
dipyridodiazepine		antiviral drug;
HIV-1 reverse transcriptase inhibitor
delavirdine
Delavirdine: A potent, non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1.. delavirdine : The amide resulting from the formal condensation of 5-[(methylsulfonyl)amino]-1H-indole-2-carboxylic acid and 4-amino group of 1-[3-(isopropylamino)pyridin-2-yl]piperazine, delavirdine is a non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. Viral resistance emerges rapidly when delavirdine is used alone, so it is therefore used (as the methanesulfonic acid salt) with other antiretrovirals for combination therapy of HIV infection.		8.3770aminopyridine;
indolecarboxamide;
N-acylpiperazine;
sulfonamide		antiviral drug;
HIV-1 reverse transcriptase inhibitor
cytarabine
[no description available]		2.0510beta-D-arabinoside;
monosaccharide derivative;
pyrimidine nucleoside		antimetabolite;
antineoplastic agent;
antiviral agent;
immunosuppressive agent
benzoxazoles
1,3-benzoxazole : A benzoxazole in which the benzene ring is fused to a 1,3-oxazole ring across positions 4 and 5.. benzoxazole : Compounds based on a fused 1,2- or 1,3-oxazole and benzene bicyclic ring skeleton.		1.98101,3-benzoxazoles;
mancude organic heterobicyclic parent
alpha-aminopyridine
alpha-aminopyridine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #485. aminopyridine : Compounds containing a pyridine skeleton substituted by one or more amine groups.		1.9810
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.		7.583azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
gemcitabine hydrochloride
[no description available]		2.0510hydrochloride;
organofluorine compound		anticoronaviral agent;
antimetabolite;
antineoplastic agent;
antiviral drug;
EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor;
immunosuppressive agent;
radiosensitizing agent
capecitabine
Capecitabine: A deoxycytidine derivative and fluorouracil PRODRUG that is used as an ANTINEOPLASTIC ANTIMETABOLITE in the treatment of COLON CANCER; BREAST CANCER and GASTRIC CANCER.. capecitabine : A carbamate ester that is cytidine in which the hydrogen at position 5 is replaced by fluorine and in which the amino group attached to position 4 is converted into its N-(penyloxy)carbonyl derivative. Capecitabine is a antineoplastic agent used in the treatment of cancers.		2.0510carbamate ester;
cytidines;
organofluorine compound		antimetabolite;
antineoplastic agent;
prodrug
5-ethyl-1-ethoxymethyl-6-(phenylthio)uracil
5-ethyl-1-ethoxymethyl-6-(phenylthio)uracil: inhibits human HIV-1; structure given in first source		1.9810
l-697661
L-697661: HIV-1 reverse transcriptase inhibitor		3.3770
u 88204
U 88204: structure given in first source		2.3820
l 734005
5-chloro-3-phenylthioindole-2-carboxamide: structure given in first source; an inhibitor of HIV-1 reverse transcriptase		1.9810
benzofurans
Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.		2.0510
delavirdine mesylate
delavirdine mesylate : The monomethanesulfonic acid salt of delavirdine, a non-nucleoside reverse transcriptase inhibitor with activity specific for HIV-1. Viral resistance emerges rapidly when delavirdine is used alone, so it is therefore used (as the methanesulfonic acid salt) with other antiretrovirals for combination therapy of HIV infection.		1.9910methanesulfonate saltantiviral drug;
HIV-1 reverse transcriptase inhibitor
l 737126
5-chloro-3-(phenylsulfonyl)indole-2-carboxamide: structure given in first source; an inhibitor of HIV-1 reverse transcriptase		1.9810
r 82150
R 82150: structure given in first source; inhibits HIV-1 replication		2.3820
r-82913
R-82913: antiviral target on reverse transcriptase of HIV-1		2.3820
telaprevir
[no description available]		2.0510cyclopentapyrrole;
cyclopropanes;
oligopeptide;
pyrazines		antiviral drug;
hepatitis C protease inhibitor;
peptidomimetic
technetium tc 99m exametazime
Technetium Tc 99m Exametazime: A gamma-emitting RADIONUCLIDE IMAGING agent used in the evaluation of regional cerebral blood flow and in non-invasive dynamic biodistribution studies and MYOCARDIAL PERFUSION IMAGING. It has also been used to label leukocytes in the investigation of INFLAMMATORY BOWEL DISEASES.		1.9910
chi 1043
[no description available]		3.2110
piperidines
Piperidines: A family of hexahydropyridines.		1.9910
neopterin
[no description available]		3.3711
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.		3.7721purine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor;
geroprotector;
HIV-1 reverse transcriptase inhibitor
trigonoliimine a
trigonoliimine A: from the leaves of Trigonostemon lii; structure in first source		3.2110
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.		01.9810
HIV Coinfection
[description not available]		09.22108
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).		111.22108
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.3920
AIDS Seroconversion
[description not available]		03.3711
Acquired-Immune Deficiency Syndrome Dementia Complex
[description not available]		03.7821
AIDS Dementia Complex
A neurologic condition associated with the ACQUIRED IMMUNODEFICIENCY SYNDROME and characterized by impaired concentration and memory, slowness of hand movements, ATAXIA, incontinence, apathy, and gait difficulties associated with HIV-1 viral infection of the central nervous system. Pathologic examination of the brain reveals white matter rarefaction, perivascular infiltrates of lymphocytes, foamy macrophages, and multinucleated giant cells. (From Adams et al., Principles of Neurology, 6th ed, pp760-1; N Engl J Med, 1995 Apr 6;332(14):934-40)		08.7821
Dermatitis Medicamentosa
[description not available]		04.311