Page last updated: 2024-12-08

l 734005

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

Description

5-chloro-3-phenylthioindole-2-carboxamide: structure given in first source; an inhibitor of HIV-1 reverse transcriptase [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID189896
CHEMBL ID286759
SCHEMBL ID2343449
MeSH IDM0221415

Synonyms (19)

Synonym
148473-16-9
5-chloro-3-(phenylsulfanyl)-1h-indole-2-carboxamide
bdbm2284
5cl3phs-2indolconh2 inhibitor 10
5cl3phs-2indolconh2
5-chloro-3-(phenylthio)-2-indolecarboxamide
5-chloro-3-phenylsulfanyl-1h-indole-2-carboxamide
CHEMBL286759
1h-indole-2-carboxamide, 5-chloro-3-(phenylthio)-
5-chloro-3-phenylthioindole-2-carboxamide
l 734005
l-734,005
l 734,005
l-734005
SCHEMBL2343449
DTXSID10163993
FT-0758550
5-chloro-3-(phenylthio)-1h-indole-2-carboxamide; 1h-indole-2-carboxamide, 5-chloro-3-(phenylthio)-; 5-chloro-3-phenylthioindole-2-carboxamide
BCP29746

Research Excerpts

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

Dosage Studied

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
"Rhesus monkeys were dosed orally with 10 mg/kg 5-chloro-3-phenylthioindole-2-carboxamide (L-734,005), a nonnucleoside human immunodeficiency virus type 1 (HIV-1) reverse transcriptase inhibitor, in polyethylene glycol 300."( Biotransformation of 5-chloro-3-phenylthioindole-2-carboxamide (L-734,005) in rhesus monkeys and rat liver microsomes to a potent HIV-1 reverse transcriptase inhibitor.
Balani, SK; Goldman, ME; Kauffman, LR; O'Brien, JA; Olah, TV; Pitzenberger, SM; Ramjit, HG; Schorn, TW; Smith, SJ; Varga, SL,
)
0.13
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Gag-Pol polyproteinHIV-1 M:B_HXB2RIC50 (µMol)0.83800.00060.91418.3200AID1795381
Adenosine receptor A2aHomo sapiens (human)IC50 (µMol)1.04000.00071.559410.0000AID3047
Adenosine receptor A2bHomo sapiens (human)IC50 (µMol)1.04000.00050.30231.5000AID3047
Protease Human immunodeficiency virus 1IC50 (µMol)0.83800.00010.22487.3200AID200169; AID3047; AID94311
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (63)

Processvia Protein(s)Taxonomy
viral life cycleGag-Pol polyproteinHIV-1 M:B_HXB2R
establishment of integrated proviral latencyGag-Pol polyproteinHIV-1 M:B_HXB2R
synaptic transmission, dopaminergicAdenosine receptor A2aHomo sapiens (human)
response to amphetamineAdenosine receptor A2aHomo sapiens (human)
regulation of DNA-templated transcriptionAdenosine receptor A2aHomo sapiens (human)
phagocytosisAdenosine receptor A2aHomo sapiens (human)
apoptotic processAdenosine receptor A2aHomo sapiens (human)
inflammatory responseAdenosine receptor A2aHomo sapiens (human)
cellular defense responseAdenosine receptor A2aHomo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
protein kinase C-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
cell-cell signalingAdenosine receptor A2aHomo sapiens (human)
synaptic transmission, cholinergicAdenosine receptor A2aHomo sapiens (human)
central nervous system developmentAdenosine receptor A2aHomo sapiens (human)
blood coagulationAdenosine receptor A2aHomo sapiens (human)
sensory perceptionAdenosine receptor A2aHomo sapiens (human)
locomotory behaviorAdenosine receptor A2aHomo sapiens (human)
blood circulationAdenosine receptor A2aHomo sapiens (human)
negative regulation of cell population proliferationAdenosine receptor A2aHomo sapiens (human)
response to xenobiotic stimulusAdenosine receptor A2aHomo sapiens (human)
response to inorganic substanceAdenosine receptor A2aHomo sapiens (human)
positive regulation of glutamate secretionAdenosine receptor A2aHomo sapiens (human)
positive regulation of acetylcholine secretion, neurotransmissionAdenosine receptor A2aHomo sapiens (human)
regulation of norepinephrine secretionAdenosine receptor A2aHomo sapiens (human)
response to purine-containing compoundAdenosine receptor A2aHomo sapiens (human)
response to caffeineAdenosine receptor A2aHomo sapiens (human)
positive regulation of synaptic transmission, GABAergicAdenosine receptor A2aHomo sapiens (human)
synaptic transmission, glutamatergicAdenosine receptor A2aHomo sapiens (human)
positive regulation of urine volumeAdenosine receptor A2aHomo sapiens (human)
vasodilationAdenosine receptor A2aHomo sapiens (human)
eating behaviorAdenosine receptor A2aHomo sapiens (human)
negative regulation of vascular permeabilityAdenosine receptor A2aHomo sapiens (human)
negative regulation of neuron apoptotic processAdenosine receptor A2aHomo sapiens (human)
positive regulation of circadian sleep/wake cycle, sleepAdenosine receptor A2aHomo sapiens (human)
negative regulation of alpha-beta T cell activationAdenosine receptor A2aHomo sapiens (human)
astrocyte activationAdenosine receptor A2aHomo sapiens (human)
neuron projection morphogenesisAdenosine receptor A2aHomo sapiens (human)
positive regulation of protein secretionAdenosine receptor A2aHomo sapiens (human)
negative regulation of inflammatory responseAdenosine receptor A2aHomo sapiens (human)
regulation of mitochondrial membrane potentialAdenosine receptor A2aHomo sapiens (human)
membrane depolarizationAdenosine receptor A2aHomo sapiens (human)
regulation of calcium ion transportAdenosine receptor A2aHomo sapiens (human)
positive regulation of synaptic transmission, glutamatergicAdenosine receptor A2aHomo sapiens (human)
excitatory postsynaptic potentialAdenosine receptor A2aHomo sapiens (human)
inhibitory postsynaptic potentialAdenosine receptor A2aHomo sapiens (human)
prepulse inhibitionAdenosine receptor A2aHomo sapiens (human)
apoptotic signaling pathwayAdenosine receptor A2aHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A2aHomo sapiens (human)
positive regulation of long-term synaptic potentiationAdenosine receptor A2aHomo sapiens (human)
positive regulation of apoptotic signaling pathwayAdenosine receptor A2aHomo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A2bHomo sapiens (human)
positive regulation of chronic inflammatory response to non-antigenic stimulusAdenosine receptor A2bHomo sapiens (human)
G protein-coupled receptor signaling pathwayAdenosine receptor A2bHomo sapiens (human)
activation of adenylate cyclase activityAdenosine receptor A2bHomo sapiens (human)
positive regulation of vascular endothelial growth factor productionAdenosine receptor A2bHomo sapiens (human)
positive regulation of cGMP-mediated signalingAdenosine receptor A2bHomo sapiens (human)
cGMP-mediated signalingAdenosine receptor A2bHomo sapiens (human)
positive regulation of chemokine productionAdenosine receptor A2bHomo sapiens (human)
positive regulation of interleukin-6 productionAdenosine receptor A2bHomo sapiens (human)
mast cell degranulationAdenosine receptor A2bHomo sapiens (human)
positive regulation of mast cell degranulationAdenosine receptor A2bHomo sapiens (human)
relaxation of vascular associated smooth muscleAdenosine receptor A2bHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A2bHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2bHomo sapiens (human)
vasodilationAdenosine receptor A2bHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
peptidase activityGag-Pol polyproteinHIV-1 M:B_HXB2R
integrase activityGag-Pol polyproteinHIV-1 M:B_HXB2R
G protein-coupled adenosine receptor activityAdenosine receptor A2aHomo sapiens (human)
protein bindingAdenosine receptor A2aHomo sapiens (human)
calmodulin bindingAdenosine receptor A2aHomo sapiens (human)
lipid bindingAdenosine receptor A2aHomo sapiens (human)
enzyme bindingAdenosine receptor A2aHomo sapiens (human)
type 5 metabotropic glutamate receptor bindingAdenosine receptor A2aHomo sapiens (human)
identical protein bindingAdenosine receptor A2aHomo sapiens (human)
protein-containing complex bindingAdenosine receptor A2aHomo sapiens (human)
alpha-actinin bindingAdenosine receptor A2aHomo sapiens (human)
G protein-coupled adenosine receptor activityAdenosine receptor A2bHomo sapiens (human)
protein bindingAdenosine receptor A2bHomo sapiens (human)
G protein-coupled receptor activityAdenosine receptor A2bHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
plasma membraneAdenosine receptor A2aHomo sapiens (human)
intermediate filamentAdenosine receptor A2aHomo sapiens (human)
plasma membraneAdenosine receptor A2aHomo sapiens (human)
membraneAdenosine receptor A2aHomo sapiens (human)
dendriteAdenosine receptor A2aHomo sapiens (human)
axolemmaAdenosine receptor A2aHomo sapiens (human)
asymmetric synapseAdenosine receptor A2aHomo sapiens (human)
presynaptic membraneAdenosine receptor A2aHomo sapiens (human)
neuronal cell bodyAdenosine receptor A2aHomo sapiens (human)
postsynaptic membraneAdenosine receptor A2aHomo sapiens (human)
presynaptic active zoneAdenosine receptor A2aHomo sapiens (human)
glutamatergic synapseAdenosine receptor A2aHomo sapiens (human)
plasma membraneAdenosine receptor A2bHomo sapiens (human)
Schaffer collateral - CA1 synapseAdenosine receptor A2bHomo sapiens (human)
presynapseAdenosine receptor A2bHomo sapiens (human)
glutamatergic synapseAdenosine receptor A2bHomo sapiens (human)
plasma membraneAdenosine receptor A2bHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (10)

Assay IDTitleYearJournalArticle
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.
AID94311Compound is evaluated in vitro for the inhibition 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.
AID3047Compound is evaluated in vitro for the inhibition 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.
AID106942Anti-HIV activity protecting MT-4 cells from HIV-1 induced cytopathogenicity2003Journal of medicinal chemistry, Jun-05, Volume: 46, Issue:12
Novel indolyl aryl sulfones active against HIV-1 carrying NNRTI resistance mutations: synthesis and SAR studies.
AID246359Protection of infected MT-4 cells from wtIIIB-HIV-1-induced cytopathogenicity2005Journal of medicinal chemistry, Jan-13, Volume: 48, Issue:1
Docking and 3-D QSAR studies on indolyl aryl sulfones. Binding mode exploration at the HIV-1 reverse transcriptase non-nucleoside binding site and design of highly active N-(2-hydroxyethyl)carboxamide and N-(2-hydroxyethyl)carbohydrazide derivatives.
AID232923Selectivity ratio of CC50/EC502003Journal of medicinal chemistry, Jun-05, Volume: 46, Issue:12
Novel indolyl aryl sulfones active against HIV-1 carrying NNRTI resistance mutations: synthesis and SAR studies.
AID265460Antiviral activity against HIV12006Journal of medicinal chemistry, Jun-01, Volume: 49, Issue:11
Design, molecular modeling, synthesis, and anti-HIV-1 activity of new indolyl aryl sulfones. Novel derivatives of the indole-2-carboxamide.
AID106747Cytotoxicity, reducing the vaiability of mock-infected cells2003Journal of medicinal chemistry, Jun-05, Volume: 46, Issue:12
Novel indolyl aryl sulfones active against HIV-1 carrying NNRTI resistance mutations: synthesis and SAR studies.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (16.67)18.2507
2000's3 (50.00)29.6817
2010's2 (33.33)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: 12.66

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.66 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.73 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.66)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]