Page last updated: 2024-12-08

delavirdine mesylate

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Description

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. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID441386
CHEMBL ID929
CHEBI ID4379
SCHEMBL ID40522
MeSH IDM0329069

Synonyms (69)

Synonym
u-90152s
rescriptor
C08087
147221-93-0
delavirdine mesylate
delavirdine mesilate
delavirdine mesilate (jan)
D00895
delavirdine mesylate (usan)
rescriptor (tn)
u 90152s
delavirdine mesylate [usan]
delavirdine monomethanesulfonate
u 90152e
hsdb 7162
piperazine, 1-(3-((1-methylethyl)amino)-2-pyridinyl)-4-((5-((methylsulfonyl)amino)-1h-indol-2-yl)carbonyl)-, monomethanesulfonate
drg-0166
1-(3-(isopropylamino)-2-pyridyl)-4-((5-methanesulfonamidoindol-2-yl)carbonyl)piperazine monomethanesulfonate
u 90152t
mesylate, delavirdine
u-90152t
CHEMBL929
delavirdine methanesulfonate
CHEBI:4379 ,
n-{2-[4-(3-isopropylamino-pyridin-2-yl)-piperazine-1-carbonyl]-1h-indol-5-yl}-methanesulfonamide; compound with methanesulfonic acid
n-[2-({4-[3-(propan-2-ylamino)pyridin-2-yl]piperazin-1-yl}carbonyl)-1h-indol-5-yl]methanesulfonamide methanesulfonate
unii-421105krqe
421105krqe ,
FT-0603116
delavirdine mesylate [vandf]
delavirdine mesylate [who-dd]
delavirdine mesilate [mart.]
piperazine, 1-(3-((1-methylethyl)amino)-2-pyridinyl)-4-((5-((methylsulphonyl)amino)-1h-indol-2-yl)carbonyl)-, monomethanesulphonate
delavirdine methanesulfonate [mi]
delavirdine mesilate [jan]
delavirdine mesylate [hsdb]
1-(3-(isopropylamino)-2-pyridyl)-4-((5-methanesulphonamidoindol-2-yl)carbonyl)piperazine monomethanesulphonate
1-[3-(isopropylamino)-2-pyridyl]-4-[(5-methanesulfonamidoindol-2-yl)carbonyl]piperazine monomethanesulfonate
delavirdine mesylate [orange book]
S6452
CS-1661
HY-10571A
delavirdine (mesylate)
SCHEMBL40522
1-[3-[(1-methylethyl)amino]-2-pyridinyl]-4-[[5-[(methylsulfonyl)amino]-1h-indol-2-yl]carbonyl]-piperazine monomethanesulfonate
n-(2-(4-(3-(isopropylamino)pyridin-2-yl)piperazine-1-carbonyl)-1h-indol-5-yl)methanesulfonamide methanesulfonate
AKOS024458004
sr-05000001471
SR-05000001471-2
AT12830
delavirdine mesylate, >=98% (hplc)
J-008332
BS-15144
Q27068164
u 90152 (mesylate);bhap-u 90152 (mesylate)
BCP09460
DTXSID701017136
methanesulfonic acid;n-[2-[4-[3-(propan-2-ylamino)pyridin-2-yl]piperazine-1-carbonyl]-1h-indol-5-yl]methanesulfonamide
u 90152 (mesylate)
bhap-u 90152 (mesylate)
methanesulfonamide, n-[2-[[4-[3-[(1-methylethyl)amino]-2-pyridinyl]-1-piperazinyl]carbonyl]-1h-indol-5-yl]-, methanesulfonate (1:1)
?delavirdine
n-[2-(4-{3-[(propan-2-yl)amino]pyridin-2-yl}piperazine-1-carbonyl)-1h-indol-5-yl]methanesulfonamide; methanesulfonic acid
EN300-19767275
u-90
n-(2-((4-(3-(propan-2-ylamino)pyridin-2-yl)piperazin-1-yl)carbonyl)-1h-indol-5-yl)methanesulfonamide methanesulfonate
delavirdine mesilate (mart.)
n-(2-(4-(3-(isopropylamino)pyridin-2-yl)piperazine-1-carbonyl)-1h-indol-5-yl)methanesulfonamidemethanesulfonate
Z3243811539
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
antiviral drugA substance used in the prophylaxis or therapy of virus diseases.
HIV-1 reverse transcriptase inhibitorAn entity which inhibits the activity of HIV-1 reverse transcriptase.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
methanesulfonate salt
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Replicase polyprotein 1abBetacoronavirus England 1IC50 (µMol)10.00000.00403.43889.5100AID1640022
Replicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2IC50 (µMol)3.99000.00022.45859.9600AID1640021
CruzipainTrypanosoma cruziIC50 (µMol)161.00000.00022.04508.0000AID484274; AID484275
Reverse transcriptase/RNaseH Human immunodeficiency virus 1IC50 (µMol)19.13750.00011.076810.0000AID143390; AID143391; AID197787; AID197788; AID197941; AID197943; AID197944; AID198563
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
3'-5'-RNA exonuclease activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
RNA-dependent RNA polymerase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
cysteine-type endopeptidase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
mRNA 5'-cap (guanine-N7-)-methyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
mRNA (nucleoside-2'-O-)-methyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
mRNA guanylyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
RNA endonuclease activity, producing 3'-phosphomonoestersReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
ISG15-specific peptidase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
5'-3' RNA helicase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
protein guanylyltransferase activityReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
double membrane vesicle viral factory outer membraneReplicase polyprotein 1abSevere acute respiratory syndrome coronavirus 2
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (104)

Assay IDTitleYearJournalArticle
AID1197829Antiviral activity against HIV1 3B infected in human MT4 cells assessed as reduction in virus-induced cytopathic effect after 5 days by MTT assay2015European journal of medicinal chemistry, Mar-06, Volume: 92Fused heterocycles bearing bridgehead nitrogen as potent HIV-1 NNRTIs. Part 3: optimization of [1,2,4]triazolo[1,5-a]pyrimidine core via structure-based and physicochemical property-driven approaches.
AID197943In vitro inhibition of mutant Y181C recombinant reverse transcriptase of HIV-1 IIIB1996Journal 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.
AID1446816Antiviral activity against HIV1 harboring K103N mutant infected in human MT4 cells assessed as protection against virus-induced cytopathic effect measured at 5 days post infection by MTT assay2017European journal of medicinal chemistry, Apr-21, Volume: 130Discovery of uracil-bearing DAPYs derivatives as novel HIV-1 NNRTIs via crystallographic overlay-based molecular hybridization.
AID1200844Antiviral activity against HIV1 RES056 expressing reverse transcriptase K103N/Y181C double mutant infected in human MT4 cells assessed as reduction in virus-induced cytopathic effect after 5 days by MTT assay2015European journal of medicinal chemistry, Mar-26, Volume: 93Fused heterocycles bearing bridgehead nitrogen as potent HIV-1 NNRTIs. Part 4: design, synthesis and biological evaluation of novel imidazo[1,2-a]pyrazines.
AID1292013Selectivity index, ratio of CC50 for mock infected human MT4 cells to EC50 for HIV1 RES056 harboring reverse transcriptase K103N/YI81C double mutant infected in human MT4 cells2016European journal of medicinal chemistry, Jun-10, Volume: 115Design, synthesis and evaluation of novel HIV-1 NNRTIs with dual structural conformations targeting the entrance channel of the NNRTI binding pocket.
AID484294Colloidal aggregation in fed state simulated intestinal fluid at 700 uM by transmission electron microscopy in presence of 3% DMSO2010Journal of medicinal chemistry, May-27, Volume: 53, Issue:10
Colloid formation by drugs in simulated intestinal fluid.
AID648424Antiviral activity against HIV1 expressing reverse transcriptase K103N/Y181C mutant infected in human MT4 cells assessed as protection against virus-induced cytotoxicity after 5 days by MTT assay2012European journal of medicinal chemistry, May, Volume: 51Synthesis and biological evaluation of piperidine-substituted triazine derivatives as HIV-1 non-nucleoside reverse transcriptase inhibitors.
AID619634Antiviral activity against HIV-1 3B harboring RT E138K mutant infected in human MT4 cells assessed as inhibition of virus-induced syncytium formation after 5 days by MTT assay2011European journal of medicinal chemistry, Oct, Volume: 46, Issue:10
Arylazolylthioacetanilide. Part 8: Design, synthesis and biological evaluation of novel 2-(2-(2,4-dichlorophenyl)-2H-1,2,4-triazol-3-ylthio)-N-arylacetamides as potent HIV-1 inhibitors.
AID619635Antiviral activity against HIV-1 3B harboring RT K103N mutant infected in human MT4 cells assessed as inhibition of virus-induced syncytium formation after 5 days by MTT assay2011European journal of medicinal chemistry, Oct, Volume: 46, Issue:10
Arylazolylthioacetanilide. Part 8: Design, synthesis and biological evaluation of novel 2-(2-(2,4-dichlorophenyl)-2H-1,2,4-triazol-3-ylthio)-N-arylacetamides as potent HIV-1 inhibitors.
AID1059145Antiviral activity against drug-resistant HIV1 RES056 harboring reverse transcriptase K103N/Y181C double mutant infected in human MT-4 cells assessed as protection against virus-induced cytopathicity after 5 days by MTT assay2013Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24
Novel piperidinylamino-diarylpyrimidine derivatives with dual structural conformations as potent HIV-1 non-nucleoside reverse transcriptase inhibitors.
AID143391Inhibitory activity against non-nucleoside reverse transcriptase inhibitors (NNRTI) -resistant HIV-1 strain A17 with a Y181C mutation in RT (reverse transcriptase)2001Bioorganic & medicinal chemistry letters, Feb-26, Volume: 11, Issue:4
Anti-HIV activity of aromatic and heterocyclic thiazolyl thiourea compounds.
AID197944In vitro inhibition of recombinant reverse transcriptase (WT) of HIV-1 IIIB1996Journal 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.
AID82141Effective concentration required to achieve 50% inhibition of HIV-1 multiplication in MT-4-infected K103N strain2002Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26
Synthesis of novel N-1 (allyloxymethyl) analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (MKC-442, emivirine) with improved activity against HIV-1 and its mutants.
AID235444Selective index as the ratio of CD50 to that of ED50 against HIV-1 HxB2 strain.2002Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26
Synthesis of novel N-1 (allyloxymethyl) analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (MKC-442, emivirine) with improved activity against HIV-1 and its mutants.
AID1165077Cytotoxicity against mock-infected human MT4 cells after 5 days by MTT assay2014European journal of medicinal chemistry, Nov-24, Volume: 87Design, synthesis and anti-HIV evaluation of novel diarylnicotinamide derivatives (DANAs) targeting the entrance channel of the NNRTI binding pocket through structure-guided molecular hybridization.
AID484282Colloidal aggregation in fed state simulated intestinal fluid by dynamic light scattering assay in presence of 3% DMSO2010Journal of medicinal chemistry, May-27, Volume: 53, Issue:10
Colloid formation by drugs in simulated intestinal fluid.
AID484275Inhibition of Trypanosoma cruzi cruzaine preincubated for 5 mins before substrate addition by fluorescence assay in presence of 0.01% Triton X-1002010Journal of medicinal chemistry, May-27, Volume: 53, Issue:10
Colloid formation by drugs in simulated intestinal fluid.
AID665551Antiviral activity against HIV1 RES056 harboring reverse transcriptase K103N/Y181C mutant infected in human MT4 cells assessed as inhibition of virus-induced cytopathic effect after 5 days by MTT assay2012Bioorganic & medicinal chemistry, Jun-15, Volume: 20, Issue:12
Design, synthesis, anti-HIV evaluation and molecular modeling of piperidine-linked amino-triazine derivatives as potent non-nucleoside reverse transcriptase inhibitors.
AID1292011Cytotoxicity against mock infected human MT4 cells after 4 days by MTT assay2016European journal of medicinal chemistry, Jun-10, Volume: 115Design, synthesis and evaluation of novel HIV-1 NNRTIs with dual structural conformations targeting the entrance channel of the NNRTI binding pocket.
AID1446819Antiviral activity against HIV1 harboring E138K mutant infected in human MT4 cells assessed as protection against virus-induced cytopathic effect measured at 5 days post infection by MTT assay2017European journal of medicinal chemistry, Apr-21, Volume: 130Discovery of uracil-bearing DAPYs derivatives as novel HIV-1 NNRTIs via crystallographic overlay-based molecular hybridization.
AID1197833Resistance index, ratio of EC50 for HIV1 RES056 expressing reverse transcriptase K103N + Y181C double mutant to EC50 for wild type HIV1 3B2015European journal of medicinal chemistry, Mar-06, Volume: 92Fused heterocycles bearing bridgehead nitrogen as potent HIV-1 NNRTIs. Part 3: optimization of [1,2,4]triazolo[1,5-a]pyrimidine core via structure-based and physicochemical property-driven approaches.
AID227244The compound was evaluated for antiviral activity using whole cell assay2000Bioorganic & medicinal chemistry letters, Jan-17, Volume: 10, Issue:2
Novel 2,2-dioxide-4,4-disubstituted-1,3-H-2,1,3-benzothiadiazines as non-nucleoside reverse transcriptase inhibitors.
AID619643Ratio of EC50 for HIV-1 3B harboring RT L100I mutant infected in human MT4 cells to EC50 for wild type HIV-1 3B infected in human MT4 cells2011European journal of medicinal chemistry, Oct, Volume: 46, Issue:10
Arylazolylthioacetanilide. Part 8: Design, synthesis and biological evaluation of novel 2-(2-(2,4-dichlorophenyl)-2H-1,2,4-triazol-3-ylthio)-N-arylacetamides as potent HIV-1 inhibitors.
AID1446811Antiviral activity against HIV1 RES056 harboring K103N/Y181C double mutant infected in human MT4 cells assessed as protection against virus-induced cytopathic effect measured at 5 days post infection by MTT assay2017European journal of medicinal chemistry, Apr-21, Volume: 130Discovery of uracil-bearing DAPYs derivatives as novel HIV-1 NNRTIs via crystallographic overlay-based molecular hybridization.
AID105859Compound was tested for potency to achieve protection of MT-4 cells from 101E strain of HIV-1 virus2001Bioorganic & medicinal chemistry letters, Sep-03, Volume: 11, Issue:17
Evolution of anti-HIV drug candidates. Part 1: From alpha-anilinophenylacetamide (alpha-APA) to imidoyl thiourea (ITU).
AID105860Compound was tested for potency to achieve protection of MT-4 cells from 103N strain of HIV-1 virus2001Bioorganic & medicinal chemistry letters, Sep-03, Volume: 11, Issue:17
Evolution of anti-HIV drug candidates. Part 1: From alpha-anilinophenylacetamide (alpha-APA) to imidoyl thiourea (ITU).
AID1446820Antiviral activity against HIV1 harboring F227L/V106A double mutant infected in human MT4 cells assessed as protection against virus-induced cytopathic effect measured at 5 days post infection by MTT assay2017European journal of medicinal chemistry, Apr-21, Volume: 130Discovery of uracil-bearing DAPYs derivatives as novel HIV-1 NNRTIs via crystallographic overlay-based molecular hybridization.
AID197788In vitro ability to inhibit wild type resistant (WT) reverse transcriptase2000Journal of medicinal chemistry, Mar-09, Volume: 43, Issue:5
Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: lead identification and SAR of 3- and 4-substituted derivatives.
AID484394Colloidal aggregation in fed state simulated intestinal fluid assessed as colloid radius at 600 uM by dynamic light scattering assay in presence of 3% DMSO2010Journal of medicinal chemistry, May-27, Volume: 53, Issue:10
Colloid formation by drugs in simulated intestinal fluid.
AID1446814Selectivity index, ratio of CC50 for human MT4 cells to EC50 for wild-type HIV1 3B infected in human MT4 cells2017European journal of medicinal chemistry, Apr-21, Volume: 130Discovery of uracil-bearing DAPYs derivatives as novel HIV-1 NNRTIs via crystallographic overlay-based molecular hybridization.
AID105862Compound was tested for potency to achieve protection of MT-4 cells from 181C strain of HIV-1 virus2001Bioorganic & medicinal chemistry letters, Sep-03, Volume: 11, Issue:17
Evolution of anti-HIV drug candidates. Part 1: From alpha-anilinophenylacetamide (alpha-APA) to imidoyl thiourea (ITU).
AID484274Inhibition of Trypanosoma cruzi cruzaine preincubated for 5 mins before substrate addition by fluorescence assay in absence of Triton X-1002010Journal of medicinal chemistry, May-27, Volume: 53, Issue:10
Colloid formation by drugs in simulated intestinal fluid.
AID82275Effective concentration required to achieve 50% inhibition of HIV-1 multiplication in MT-4-infected Y181C strain2002Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26
Synthesis of novel N-1 (allyloxymethyl) analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (MKC-442, emivirine) with improved activity against HIV-1 and its mutants.
AID619638Antiviral activity against HIV-1 3B harboring RT Y188L mutant infected in human MT4 cells assessed as inhibition of virus-induced syncytium formation after 5 days by MTT assay2011European journal of medicinal chemistry, Oct, Volume: 46, Issue:10
Arylazolylthioacetanilide. Part 8: Design, synthesis and biological evaluation of novel 2-(2-(2,4-dichlorophenyl)-2H-1,2,4-triazol-3-ylthio)-N-arylacetamides as potent HIV-1 inhibitors.
AID665552Selectivity index, ratio of CC50 for human MT4 cells to EC50 for HIV1 RES056 harboring reverse transcriptase K103N/Y181C RT mutant2012Bioorganic & medicinal chemistry, Jun-15, Volume: 20, Issue:12
Design, synthesis, anti-HIV evaluation and molecular modeling of piperidine-linked amino-triazine derivatives as potent non-nucleoside reverse transcriptase inhibitors.
AID484288Aggregation-based binding affinity to beta-lactamase AmpC at 700 uM in fed state simulated intestinal fluid after 30 mins by silver staining in presence of 3% DMSO2010Journal of medicinal chemistry, May-27, Volume: 53, Issue:10
Colloid formation by drugs in simulated intestinal fluid.
AID619641Ratio of EC50 for HIV-1 3B harboring RT K103N mutant infected in human MT4 cells to EC50 for wild type HIV-1 3B infected in human MT4 cells2011European journal of medicinal chemistry, Oct, Volume: 46, Issue:10
Arylazolylthioacetanilide. Part 8: Design, synthesis and biological evaluation of novel 2-(2-(2,4-dichlorophenyl)-2H-1,2,4-triazol-3-ylthio)-N-arylacetamides as potent HIV-1 inhibitors.
AID354464Antiviral activity against HIV1 3B infected in human CEM-SS cells assessed as inhibition of virus-induced cytopathic effect after 6 days by MTS assay2004Journal of natural products, Jun, Volume: 67, Issue:6
New 3-O-acyl betulinic acids from Strychnos vanprukii Craib.
AID11497Bioavailability at an iv dose of 14 mg/Kg and po dose of 28 mg/Kg1996Journal 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.
AID619636Antiviral activity against HIV-1 3B harboring RT L100I mutant infected in human MT4 cells assessed as inhibition of virus-induced syncytium formation after 5 days by MTT assay2011European journal of medicinal chemistry, Oct, Volume: 46, Issue:10
Arylazolylthioacetanilide. Part 8: Design, synthesis and biological evaluation of novel 2-(2-(2,4-dichlorophenyl)-2H-1,2,4-triazol-3-ylthio)-N-arylacetamides as potent HIV-1 inhibitors.
AID1197830Cytotoxicity against mock-infected human MT4 cells assessed as reduction in cell viability after 4 days by MTT assay2015European journal of medicinal chemistry, Mar-06, Volume: 92Fused heterocycles bearing bridgehead nitrogen as potent HIV-1 NNRTIs. Part 3: optimization of [1,2,4]triazolo[1,5-a]pyrimidine core via structure-based and physicochemical property-driven approaches.
AID619639Antiviral activity against HIV-1 3B harboring RT F227L and V106A mutant infected in human MT4 cells assessed as inhibition of virus-induced syncytium formation after 5 days by MTT assay2011European journal of medicinal chemistry, Oct, Volume: 46, Issue:10
Arylazolylthioacetanilide. Part 8: Design, synthesis and biological evaluation of novel 2-(2-(2,4-dichlorophenyl)-2H-1,2,4-triazol-3-ylthio)-N-arylacetamides as potent HIV-1 inhibitors.
AID82277Inhibition of HIV-1 IIIB replication in MT-4-infected wild type cells.2002Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26
Synthesis of novel N-1 (allyloxymethyl) analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (MKC-442, emivirine) with improved activity against HIV-1 and its mutants.
AID105863Compound was tested for potency to achieve protection of MT-4 cells from 188L strain of HIV-1 virus2001Bioorganic & medicinal chemistry letters, Sep-03, Volume: 11, Issue:17
Evolution of anti-HIV drug candidates. Part 1: From alpha-anilinophenylacetamide (alpha-APA) to imidoyl thiourea (ITU).
AID235446Selective index (CD50 compared to ED50 against HIV-1 IIIB strain).2002Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26
Synthesis of novel N-1 (allyloxymethyl) analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (MKC-442, emivirine) with improved activity against HIV-1 and its mutants.
AID82276Effective concentration required to achieve 50% inhibition of HIV-1 multiplication in MT-4-infected Y181C+K103N strain2002Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26
Synthesis of novel N-1 (allyloxymethyl) analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (MKC-442, emivirine) with improved activity against HIV-1 and its mutants.
AID198563The compound was evaluated for the inhibition of HIV-1 reverse transcriptase2000Bioorganic & medicinal chemistry letters, Jan-17, Volume: 10, Issue:2
Novel 2,2-dioxide-4,4-disubstituted-1,3-H-2,1,3-benzothiadiazines as non-nucleoside reverse transcriptase inhibitors.
AID152788Tested for the ability to inhibit the replication of HIV-1 strain HTLV IIIB in human peripheral blood mononuclear cells (PBMC)2001Bioorganic & medicinal chemistry letters, Feb-26, Volume: 11, Issue:4
Anti-HIV activity of aromatic and heterocyclic thiazolyl thiourea compounds.
AID1446813Cytotoxicity against human MT4 cells after 5 days by MTT assay2017European journal of medicinal chemistry, Apr-21, Volume: 130Discovery of uracil-bearing DAPYs derivatives as novel HIV-1 NNRTIs via crystallographic overlay-based molecular hybridization.
AID153129Cytotoxic concentration was determined2000Journal of medicinal chemistry, Mar-09, Volume: 43, Issue:5
Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: lead identification and SAR of 3- and 4-substituted derivatives.
AID1059141Selectivity index, ratio of CC50 for human MT4 cells to EC50 for drug-resistant HIV1 RES056 harboring reverse transcriptase K103N/Y181C double mutant2013Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24
Novel piperidinylamino-diarylpyrimidine derivatives with dual structural conformations as potent HIV-1 non-nucleoside reverse transcriptase inhibitors.
AID106769Cytotoxic dose required to reduce the viability of normal uninfected MT-4 cells by 50%2002Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26
Synthesis of novel N-1 (allyloxymethyl) analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (MKC-442, emivirine) with improved activity against HIV-1 and its mutants.
AID484280Colloidal aggregation in fed state simulated intestinal fluid by dynamic light scattering assay in presence of 0.5% DMSO2010Journal of medicinal chemistry, May-27, Volume: 53, Issue:10
Colloid formation by drugs in simulated intestinal fluid.
AID105866Compound was tested for potency to achieve protection of MT-4 cells from LAI strain of HIV-1 virus2001Bioorganic & medicinal chemistry letters, Sep-03, Volume: 11, Issue:17
Evolution of anti-HIV drug candidates. Part 1: From alpha-anilinophenylacetamide (alpha-APA) to imidoyl thiourea (ITU).
AID484286Colloidal aggregation in fed state simulated intestinal fluid assessed as critical aggregation concentration by UV-visible spectrophotometry in presence of 0.35% DMSO2010Journal of medicinal chemistry, May-27, Volume: 53, Issue:10
Colloid formation by drugs in simulated intestinal fluid.
AID354455Antiviral activity against HIV1 3B infected in human HOG.R5 cells after 4 days2004Journal of natural products, Jun, Volume: 67, Issue:6
New 3-O-acyl betulinic acids from Strychnos vanprukii Craib.
AID1446815Antiviral activity against HIV1 harboring L100I mutant infected in human MT4 cells assessed as protection against virus-induced cytopathic effect measured at 5 days post infection by MTT assay2017European journal of medicinal chemistry, Apr-21, Volume: 130Discovery of uracil-bearing DAPYs derivatives as novel HIV-1 NNRTIs via crystallographic overlay-based molecular hybridization.
AID1292012Selectivity index, ratio of CC50 for mock infected human MT4 cells to EC50 for HIV1 3B infected in human MT4 cells2016European journal of medicinal chemistry, Jun-10, Volume: 115Design, synthesis and evaluation of novel HIV-1 NNRTIs with dual structural conformations targeting the entrance channel of the NNRTI binding pocket.
AID484385Colloidal aggregation in fed state simulated intestinal fluid assessed as colloid radius at 100 uM by dynamic light scattering assay in presence of 1% DMSO2010Journal of medicinal chemistry, May-27, Volume: 53, Issue:10
Colloid formation by drugs in simulated intestinal fluid.
AID1200845Cytotoxicity against mock-infected human MT4 cells assessed as reduction in cell viability after 4 days by MTT assay2015European journal of medicinal chemistry, Mar-26, Volume: 93Fused heterocycles bearing bridgehead nitrogen as potent HIV-1 NNRTIs. Part 4: design, synthesis and biological evaluation of novel imidazo[1,2-a]pyrazines.
AID1165075Antiviral activity against HIV2 ROD infected in human MT4 cells assessed as inhibition of virus-induced syncytium formation after 5 days by MTT assay2014European journal of medicinal chemistry, Nov-24, Volume: 87Design, synthesis and anti-HIV evaluation of novel diarylnicotinamide derivatives (DANAs) targeting the entrance channel of the NNRTI binding pocket through structure-guided molecular hybridization.
AID82272Effective concentration required to achieve 50% inhibition of HIV-1 multiplication in MT-4-infected wild type cells2002Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26
Synthesis of novel N-1 (allyloxymethyl) analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (MKC-442, emivirine) with improved activity against HIV-1 and its mutants.
AID11496Bioavailability at an iv dose of 14 mg/Kg and po dose of 15 mg/Kg1996Journal 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.
AID648422Selectivity index, ratio of CC50 for human MT4 cells to EC50 for HIV1 3B2012European journal of medicinal chemistry, May, Volume: 51Synthesis and biological evaluation of piperidine-substituted triazine derivatives as HIV-1 non-nucleoside reverse transcriptase inhibitors.
AID619640Antiviral activity against HIV-1 3B harboring RT K103N and Y181C mutant infected in human MT4 cells assessed as inhibition of virus-induced syncytium formation after 5 days by MTT assay2011European journal of medicinal chemistry, Oct, Volume: 46, Issue:10
Arylazolylthioacetanilide. Part 8: Design, synthesis and biological evaluation of novel 2-(2-(2,4-dichlorophenyl)-2H-1,2,4-triazol-3-ylthio)-N-arylacetamides as potent HIV-1 inhibitors.
AID1197831Selectivity index, ratio of CC50 for mock-infected human MT4 cells to EC50 for HIV1 3B infected in human MT4 cells2015European journal of medicinal chemistry, Mar-06, Volume: 92Fused heterocycles bearing bridgehead nitrogen as potent HIV-1 NNRTIs. Part 3: optimization of [1,2,4]triazolo[1,5-a]pyrimidine core via structure-based and physicochemical property-driven approaches.
AID665553Fold resistance, ratio of EC50 for HIV1 RES056 harboring reverse transcriptase K103N/Y181C RT mutant to EC50 for wild type HIV1 3B2012Bioorganic & medicinal chemistry, Jun-15, Volume: 20, Issue:12
Design, synthesis, anti-HIV evaluation and molecular modeling of piperidine-linked amino-triazine derivatives as potent non-nucleoside reverse transcriptase inhibitors.
AID1200846Selectivity index, ratio of CC50 for mock-infected human MT4 cells to EC50 for HIV1 3B infected in human MT4 cells2015European journal of medicinal chemistry, Mar-26, Volume: 93Fused heterocycles bearing bridgehead nitrogen as potent HIV-1 NNRTIs. Part 4: design, synthesis and biological evaluation of novel imidazo[1,2-a]pyrazines.
AID1292009Antiviral activity against wild type HIV1 3B infected in human MT4 cells assessed as cell viability after 4 days by MTT assay2016European journal of medicinal chemistry, Jun-10, Volume: 115Design, synthesis and evaluation of novel HIV-1 NNRTIs with dual structural conformations targeting the entrance channel of the NNRTI binding pocket.
AID1059146Antiviral activity against HIV1 3B infected in human MT-4 cells assessed as protection against virus-induced cytopathicity after 5 days by MTT assay2013Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24
Novel piperidinylamino-diarylpyrimidine derivatives with dual structural conformations as potent HIV-1 non-nucleoside reverse transcriptase inhibitors.
AID1059144Selectivity index, ratio of CC50 for human MT4 cells to EC50 for HIV1 3B2013Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24
Novel piperidinylamino-diarylpyrimidine derivatives with dual structural conformations as potent HIV-1 non-nucleoside reverse transcriptase inhibitors.
AID1165074Antiviral activity against HIV1 3B infected in human MT4 cells assessed as inhibition of virus-induced syncytium formation after 5 days by MTT assay2014European journal of medicinal chemistry, Nov-24, Volume: 87Design, synthesis and anti-HIV evaluation of novel diarylnicotinamide derivatives (DANAs) targeting the entrance channel of the NNRTI binding pocket through structure-guided molecular hybridization.
AID484295Colloidal aggregation in phosphate buffer at 200 uM by transmission electron microscopy in presence of 0.2% DMSO2010Journal of medicinal chemistry, May-27, Volume: 53, Issue:10
Colloid formation by drugs in simulated intestinal fluid.
AID1200847Selectivity index, ratio of CC50 for mock-infected human MT4 cells to EC50 for HIV1 RES056 expressing reverse transcriptase K103N/Y181C double mutant2015European journal of medicinal chemistry, Mar-26, Volume: 93Fused heterocycles bearing bridgehead nitrogen as potent HIV-1 NNRTIs. Part 4: design, synthesis and biological evaluation of novel imidazo[1,2-a]pyrazines.
AID1446812Antiviral activity against HIV-2 ROD infected in human MT4 cells assessed as protection against virus-induced cytopathic effect measured at 5 days post infection by MTT assay2017European journal of medicinal chemistry, Apr-21, Volume: 130Discovery of uracil-bearing DAPYs derivatives as novel HIV-1 NNRTIs via crystallographic overlay-based molecular hybridization.
AID153130Effective dose for inhibition of viral replication in cell culture of 0.1 uM2000Journal of medicinal chemistry, Mar-09, Volume: 43, Issue:5
Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: lead identification and SAR of 3- and 4-substituted derivatives.
AID11014Clearance at an iv dose of 14 mg/Kg and po dose of 15 mg/Kg1996Journal 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.
AID354458Cytotoxicity against human CEM-SS cells at 40 ug/ml after 6 days by MTS assay2004Journal of natural products, Jun, Volume: 67, Issue:6
New 3-O-acyl betulinic acids from Strychnos vanprukii Craib.
AID105864Compound was tested for potency to achieve protection of MT-4 cells from 190A strain of HIV-1 virus2001Bioorganic & medicinal chemistry letters, Sep-03, Volume: 11, Issue:17
Evolution of anti-HIV drug candidates. Part 1: From alpha-anilinophenylacetamide (alpha-APA) to imidoyl thiourea (ITU).
AID484390Colloidal aggregation in fed state simulated intestinal fluid by dynamic light scattering-based beads autocorrelation assay in presence of 1% DMSO2010Journal of medicinal chemistry, May-27, Volume: 53, Issue:10
Colloid formation by drugs in simulated intestinal fluid.
AID665547Antiviral activity against HIV1 3B infected in human MT4 cells assessed as inhibition of virus-induced cytopathic effect after 5 days by MTT assay2012Bioorganic & medicinal chemistry, Jun-15, Volume: 20, Issue:12
Design, synthesis, anti-HIV evaluation and molecular modeling of piperidine-linked amino-triazine derivatives as potent non-nucleoside reverse transcriptase inhibitors.
AID1197834Selectivity index, ratio of CC50 for mock-infected human MT4 cells to EC50 for HIV1 RES056 expressing reverse transcriptase K103N + Y181C double mutant2015European journal of medicinal chemistry, Mar-06, Volume: 92Fused heterocycles bearing bridgehead nitrogen as potent HIV-1 NNRTIs. Part 3: optimization of [1,2,4]triazolo[1,5-a]pyrimidine core via structure-based and physicochemical property-driven approaches.
AID354454Cytotoxicity against human HOG.R5 cells at 40 ug/ml after 4 days2004Journal of natural products, Jun, Volume: 67, Issue:6
New 3-O-acyl betulinic acids from Strychnos vanprukii Craib.
AID105858Compound was tested for potency to achieve protection of MT-4 cells from 100I strain of HIV-1 virus2001Bioorganic & medicinal chemistry letters, Sep-03, Volume: 11, Issue:17
Evolution of anti-HIV drug candidates. Part 1: From alpha-anilinophenylacetamide (alpha-APA) to imidoyl thiourea (ITU).
AID197941In vitro inhibition of mutant P236L recombinant reverse transcriptase of HIV-1 IIIB1996Journal 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.
AID1446818Antiviral activity against HIV1 harboring Y188L mutant infected in human MT4 cells assessed as protection against virus-induced cytopathic effect measured at 5 days post infection by MTT assay2017European journal of medicinal chemistry, Apr-21, Volume: 130Discovery of uracil-bearing DAPYs derivatives as novel HIV-1 NNRTIs via crystallographic overlay-based molecular hybridization.
AID82271Effective concentration required to achieve 50% inhibition of HIV-1 multiplication in MT-4-infected Y181C strain2002Journal of medicinal chemistry, Dec-19, Volume: 45, Issue:26
Synthesis of novel N-1 (allyloxymethyl) analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (MKC-442, emivirine) with improved activity against HIV-1 and its mutants.
AID1059143Cytotoxicity against human MT4 cells after 5 days by MTT assay2013Bioorganic & medicinal chemistry letters, Dec-15, Volume: 23, Issue:24
Novel piperidinylamino-diarylpyrimidine derivatives with dual structural conformations as potent HIV-1 non-nucleoside reverse transcriptase inhibitors.
AID665550Selectivity index, ratio of CC50 for human MT4 cells to EC50 for wild type HIV1 3B2012Bioorganic & medicinal chemistry, Jun-15, Volume: 20, Issue:12
Design, synthesis, anti-HIV evaluation and molecular modeling of piperidine-linked amino-triazine derivatives as potent non-nucleoside reverse transcriptase inhibitors.
AID619642Ratio of EC50 for HIV-1 3B harboring RT E138K mutant infected in human MT4 cells to EC50 for wild type HIV-1 3B infected in human MT4 cells2011European journal of medicinal chemistry, Oct, Volume: 46, Issue:10
Arylazolylthioacetanilide. Part 8: Design, synthesis and biological evaluation of novel 2-(2-(2,4-dichlorophenyl)-2H-1,2,4-triazol-3-ylthio)-N-arylacetamides as potent HIV-1 inhibitors.
AID665549Cytotoxicity against human MT4 cells after 5 days by MTT assay2012Bioorganic & medicinal chemistry, Jun-15, Volume: 20, Issue:12
Design, synthesis, anti-HIV evaluation and molecular modeling of piperidine-linked amino-triazine derivatives as potent non-nucleoside reverse transcriptase inhibitors.
AID1165078Selectivity index, ratio of CC50 for mock-infected human MT4 cells to EC50 for HIV1 3B infected in human MT4 cells2014European journal of medicinal chemistry, Nov-24, Volume: 87Design, synthesis and anti-HIV evaluation of novel diarylnicotinamide derivatives (DANAs) targeting the entrance channel of the NNRTI binding pocket through structure-guided molecular hybridization.
AID648421Cytotoxicity against human MT4 cells after 5 days by MTT assay2012European journal of medicinal chemistry, May, Volume: 51Synthesis and biological evaluation of piperidine-substituted triazine derivatives as HIV-1 non-nucleoside reverse transcriptase inhibitors.
AID1165076Antiviral activity against HIV1 RES056 expressing reverse transcriptase K103N + Y181C mutant infected in human MT4 cells assessed as inhibition of virus-induced syncytium formation after 5 days by MTT assay2014European journal of medicinal chemistry, Nov-24, Volume: 87Design, synthesis and anti-HIV evaluation of novel diarylnicotinamide derivatives (DANAs) targeting the entrance channel of the NNRTI binding pocket through structure-guided molecular hybridization.
AID619637Antiviral activity against HIV-1 3B harboring RT Y181C mutant infected in human MT4 cells assessed as inhibition of virus-induced syncytium formation after 5 days by MTT assay2011European journal of medicinal chemistry, Oct, Volume: 46, Issue:10
Arylazolylthioacetanilide. Part 8: Design, synthesis and biological evaluation of novel 2-(2-(2,4-dichlorophenyl)-2H-1,2,4-triazol-3-ylthio)-N-arylacetamides as potent HIV-1 inhibitors.
AID1197832Antiviral activity against HIV1 RES056 expressing reverse transcriptase K103N + Y181C double mutant infected in human MT4 cells assessed as reduction in virus-induced cytopathic effect after 5 days by MTT assay2015European journal of medicinal chemistry, Mar-06, Volume: 92Fused heterocycles bearing bridgehead nitrogen as potent HIV-1 NNRTIs. Part 3: optimization of [1,2,4]triazolo[1,5-a]pyrimidine core via structure-based and physicochemical property-driven approaches.
AID1446817Antiviral activity against HIV1 harboring Y181C mutant infected in human MT4 cells assessed as protection against virus-induced cytopathic effect measured at 5 days post infection by MTT assay2017European journal of medicinal chemistry, Apr-21, Volume: 130Discovery of uracil-bearing DAPYs derivatives as novel HIV-1 NNRTIs via crystallographic overlay-based molecular hybridization.
AID1200843Antiviral activity against HIV1 3B infected in human MT4 cells assessed as reduction in virus-induced cytopathic effect after 5 days by MTT assay2015European journal of medicinal chemistry, Mar-26, Volume: 93Fused heterocycles bearing bridgehead nitrogen as potent HIV-1 NNRTIs. Part 4: design, synthesis and biological evaluation of novel imidazo[1,2-a]pyrazines.
AID484290Binding affinity to beta-lactamase AmpC at 700 uM after 30 mins by SDS-PAGE2010Journal of medicinal chemistry, May-27, Volume: 53, Issue:10
Colloid formation by drugs in simulated intestinal fluid.
AID648420Antiviral activity against HIV1 3B infected in human MT4 cells assessed as protection against virus-induced cytotoxicity after 5 days by MTT assay2012European journal of medicinal chemistry, May, Volume: 51Synthesis and biological evaluation of piperidine-substituted triazine derivatives as HIV-1 non-nucleoside reverse transcriptase inhibitors.
AID105861Compound was tested for potency to achieve protection of MT-4 cells from 106A strain of HIV-1 virus2001Bioorganic & medicinal chemistry letters, Sep-03, Volume: 11, Issue:17
Evolution of anti-HIV drug candidates. Part 1: From alpha-anilinophenylacetamide (alpha-APA) to imidoyl thiourea (ITU).
AID197787In vitro ability to inhibit mutant P236L reverse transcriptase2000Journal of medicinal chemistry, Mar-09, Volume: 43, Issue:5
Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: lead identification and SAR of 3- and 4-substituted derivatives.
AID143390Inhibitory activity against non-nucleoside reverse transcriptase inhibitors (NNRTI) -resistant HIV-1 strain A17 variant with Y181C plus K103N mutations in RT (reverse transcriptase)2001Bioorganic & medicinal chemistry letters, Feb-26, Volume: 11, Issue:4
Anti-HIV activity of aromatic and heterocyclic thiazolyl thiourea compounds.
AID1292010Antiviral activity against HIV1 RES056 harboring reverse transcriptase K103N/YI81C double mutant infected in human MT4 cells assessed as cell viability after 4 days by MTT assay2016European journal of medicinal chemistry, Jun-10, Volume: 115Design, synthesis and evaluation of novel HIV-1 NNRTIs with dual structural conformations targeting the entrance channel of the NNRTI binding pocket.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (5.88)18.2507
2000's6 (35.29)29.6817
2010's10 (58.82)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: 19.52

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 Index19.52 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index4.78 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.52)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other17 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]