Compounds > deleobuvir
Page last updated: 2024-11-13

deleobuvir

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

Description

deleobuvir: a hepatitis C virus polymerase inhibitor [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID56948249
CHEMBL ID2403318
SCHEMBL ID900176
SCHEMBL ID900174
MeSH IDM000599048

Synonyms (30)

Synonym
CHEMBL2403318
bi-207127
BMAIGAHXAJEULY-UKTHLTGXSA-N
(e)-3-(2-(1-(2-(5-bromopyrimidin-2-yl)-3-cyclopentyl-1-methyl-1h-indole-6-carboxamido)cyclobutyl)-1-methyl-1h-benzo[d]imidazol-6-yl)acrylic acid
deleobuvir
863884-77-9
(e)-3-(2-(1-(((2-(5-bromopyrimidin-2-yl)-3-cyclopentyl-1-methyl-1h-indol-6-yl)carbonyl)amino)cyclobutyl)-1-methyl-1h-benzimidazol-6-yl)-2-propenoic acid
58bu988k90 ,
2-propenoic acid, 3-(2-(1-(((2-(5-bromo-2-pyrimidinyl)-3-cyclopentyl-1-methyl-1h-indol-6-yl)carbonyl)amino)cyclobutyl)-1-methyl-1h-benzimidazol-6-yl)-, (2e)-
(2e)-3-(2-(1-(2-(5-bromopyrimidin-2-yl)-3-cyclopentyl-1-methyl-1h-indole-6-carboxamido)cyclobutyl(-1-methyl-1h-benzimidazol-6-yl)prop-2-enoic acid
deleobuvir [usan:inn]
bi207127
bi 207127
unii-58bu988k90
deleobuvir [usan]
deleobuvir [who-dd]
deleobuvir [inn]
1221574-24-8
SCHEMBL900176
SCHEMBL900174
DTXSID40235516
(e)-3-[2-[1-[[[2-(5-bromopyrimidin-2-yl)-3-cyclopentyl-1-methyl-1h-indol-6-yl]carbonyl]amino]cyclobutyl]-1-methyl-1h-benzimidazol-6-yl]-2-propenoic acid
DB14850
Q15708312
(e)-3-[2-[1-[[2-(5-bromopyrimidin-2-yl)-3-cyclopentyl-1-methylindole-6-carbonyl]amino]cyclobutyl]-3-methylbenzimidazol-5-yl]prop-2-enoic acid
CS-0012113
HY-12634
(e)-3-[2-[1-[[[2-(5-bromopyrimidin-2-yl)-3-cyclopentyl-1-methyl-1h-indol-6-yl]carbonyl]amino]cyclobutyl]-1-methyl-1h-benzimidazol-6-yl]-2-propenoicacid
deleobuvir (bi-207127)
AKOS040751520

Research Excerpts

Overview

Deleobuvir is a potent inhibitor of the hepatitis C virus nonstructural protein 5B polymerase.

ExcerptReferenceRelevance
"Deleobuvir is a potent inhibitor of the hepatitis C virus nonstructural protein 5B polymerase. "( Defining the Role of Gut Bacteria in the Metabolism of Deleobuvir: In Vitro and In Vivo Studies.
Johnstone, N; Keith-Luzzi, M; King, I; Li, Y; McCabe, M; Sane, RS; Tweedie, DJ; Whitcher-Johnstone, A; Xu, J, 2015)		2.11

Toxicity

ExcerptReferenceRelevance
" The most frequent adverse events in patients with/without cirrhosis were gastrointestinal and skin events, which were mostly mild or moderate in intensity."( Efficacy and safety of faldaprevir, deleobuvir, and ribavirin in treatment-naive patients with chronic hepatitis C virus infection and advanced liver fibrosis or cirrhosis.
Angus, P; Asselah, T; Böcher, W; Bourlière, M; Bronowicki, JP; Buti, M; Gallivan, JP; Gane, EJ; Lohse, AW; Manns, M; Mensa, FJ; Müllhaupt, B; Roberts, S; Sabo, JP; Schuchmann, M; Soriano, V; Stern, JO; Stickel, F; Voss, F; Zeuzem, S, 2015)		0.69

Pharmacokinetics

ExcerptReferenceRelevance
" Deleobuvir had moderate to high clearance, and the half-life of deleobuvir and radioactivity in plasma were ∼ 3 h, indicating that there were no metabolites with half-lives significantly longer than that of the parent."( Mass balance, metabolite profile, and in vitro-in vivo comparison of clearance pathways of deleobuvir, a hepatitis C virus polymerase inhibitor.
Chen, LZ; Latli, B; Mandarino, DA; Mao, Y; Philip, E; Ramsden, D; Rowland, L; Sabo, JP; Sane, RS, 2015)		1.55

Compound-Compound Interactions

ExcerptReferenceRelevance
"The drug-drug interaction (DDI) potential of deleobuvir, an hepatitis C virus (HCV) polymerase inhibitor, and its two major metabolites, CD 6168 (formed via reduction by gut bacteria) and deleobuvir-acyl glucuronide (AG), was assessed in vitro."( Contribution of Major Metabolites toward Complex Drug-Drug Interactions of Deleobuvir: In Vitro Predictions and In Vivo Outcomes.
Cooper, C; Ramsden, D; Rowland, L; Sabo, JP; Sane, RS; Ting, N; Tweedie, DJ; Whitcher-Johnstone, A, 2016)		0.92
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
RNA-directed RNA polymerase IC50 (µMol)0.01900.01902.52798.8000AID1787869
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
RNA-directed RNA polymerase EC50 (µMol)0.01700.00180.23482.8000AID1787870; AID1787871
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1070917Inhibition of poliovirus RdRp2014Journal of medicinal chemistry, Mar-13, Volume: 57, Issue:5
Conformation-based restrictions and scaffold replacements in the design of hepatitis C virus polymerase inhibitors: discovery of deleobuvir (BI 207127).
AID1070915Antiviral activity against Hepatitis C virus genotype 1b infected in human S22.3 cells assessed as inhibition of viral RNA replication by real-time RT-PCR analysis2014Journal of medicinal chemistry, Mar-13, Volume: 57, Issue:5
Conformation-based restrictions and scaffold replacements in the design of hepatitis C virus polymerase inhibitors: discovery of deleobuvir (BI 207127).
AID758860Antiviral activity against Hepatitis C virus genotype 32013Bioorganic & medicinal chemistry letters, Jul-15, Volume: 23, Issue:14
Structure-based design of novel HCV NS5B thumb pocket 2 allosteric inhibitors with submicromolar gt1 replicon potency: discovery of a quinazolinone chemotype.
AID1070920Inhibition of DNA polymerase-gamma (unknown origin)2014Journal of medicinal chemistry, Mar-13, Volume: 57, Issue:5
Conformation-based restrictions and scaffold replacements in the design of hepatitis C virus polymerase inhibitors: discovery of deleobuvir (BI 207127).
AID1070914Inhibition of DdRp-2 (unknown origin)2014Journal of medicinal chemistry, Mar-13, Volume: 57, Issue:5
Conformation-based restrictions and scaffold replacements in the design of hepatitis C virus polymerase inhibitors: discovery of deleobuvir (BI 207127).
AID758859Antiviral activity against Hepatitis C virus genotype 22013Bioorganic & medicinal chemistry letters, Jul-15, Volume: 23, Issue:14
Structure-based design of novel HCV NS5B thumb pocket 2 allosteric inhibitors with submicromolar gt1 replicon potency: discovery of a quinazolinone chemotype.
AID758856Antiviral activity against Hepatitis C virus genotype 42013Bioorganic & medicinal chemistry letters, Jul-15, Volume: 23, Issue:14
Structure-based design of novel HCV NS5B thumb pocket 2 allosteric inhibitors with submicromolar gt1 replicon potency: discovery of a quinazolinone chemotype.
AID1073854Antiviral activity against Hepatitis C virus genotype 1a by cell-based assay2014Journal of medicinal chemistry, Mar-13, Volume: 57, Issue:5
Discovery and preclinical characterization of the cyclopropylindolobenzazepine BMS-791325, a potent allosteric inhibitor of the hepatitis C virus NS5B polymerase.
AID758862Antiviral activity against Hepatitis C virus genotype 1a2013Bioorganic & medicinal chemistry letters, Jul-15, Volume: 23, Issue:14
Structure-based design of novel HCV NS5B thumb pocket 2 allosteric inhibitors with submicromolar gt1 replicon potency: discovery of a quinazolinone chemotype.
AID1070916Antiviral activity against Hepatitis C virus genotype 1a infected in human 129-S.16 cells assessed as inhibition of viral RNA replication by real-time RT-PCR analysis2014Journal of medicinal chemistry, Mar-13, Volume: 57, Issue:5
Conformation-based restrictions and scaffold replacements in the design of hepatitis C virus polymerase inhibitors: discovery of deleobuvir (BI 207127).
AID1070913Inhibition of DNA polymerase-beta (unknown origin)2014Journal of medicinal chemistry, Mar-13, Volume: 57, Issue:5
Conformation-based restrictions and scaffold replacements in the design of hepatitis C virus polymerase inhibitors: discovery of deleobuvir (BI 207127).
AID1073855Antiviral activity against Hepatitis C virus genotype 1b by cell-based assay2014Journal of medicinal chemistry, Mar-13, Volume: 57, Issue:5
Discovery and preclinical characterization of the cyclopropylindolobenzazepine BMS-791325, a potent allosteric inhibitor of the hepatitis C virus NS5B polymerase.
AID1450606In vivo drug metabolism in human assessed as 3-(2-(1-(2-(5-bromopyrimidin-2-yl)-3-cyclopentyl-1-methyl-1H-indole-6-carboxamido)cyclobutyl)-1-methyl-1H-benzo[d]imidazol-6-yl)propanoic acid metabolite formation in blood at 800 mg,po administered as single d2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Glucuronides as Potential Anionic Substrates of Human Cytochrome P450 2C8 (CYP2C8).
AID1070919Inhibition of HCV genotype 1b NS5Bdelta21 RNA dependent RNA polymerase expressed in Escherichia coli JM109 (DE3)2014Journal of medicinal chemistry, Mar-13, Volume: 57, Issue:5
Conformation-based restrictions and scaffold replacements in the design of hepatitis C virus polymerase inhibitors: discovery of deleobuvir (BI 207127).
AID758858Antiviral activity against Hepatitis C virus genotype 62013Bioorganic & medicinal chemistry letters, Jul-15, Volume: 23, Issue:14
Structure-based design of novel HCV NS5B thumb pocket 2 allosteric inhibitors with submicromolar gt1 replicon potency: discovery of a quinazolinone chemotype.
AID758857Antiviral activity against Hepatitis C virus genotype 52013Bioorganic & medicinal chemistry letters, Jul-15, Volume: 23, Issue:14
Structure-based design of novel HCV NS5B thumb pocket 2 allosteric inhibitors with submicromolar gt1 replicon potency: discovery of a quinazolinone chemotype.
AID1450605In vivo drug metabolism in human assessed as UGT-mediated deleobuvir acyl glucuronide metabolite formation in blood at 800 mg,po administered as single dose measured up to 12 hrs2017Journal of medicinal chemistry, 11-09, Volume: 60, Issue:21
Glucuronides as Potential Anionic Substrates of Human Cytochrome P450 2C8 (CYP2C8).
AID758861Antiviral activity against Hepatitis C virus genotype 1b2013Bioorganic & medicinal chemistry letters, Jul-15, Volume: 23, Issue:14
Structure-based design of novel HCV NS5B thumb pocket 2 allosteric inhibitors with submicromolar gt1 replicon potency: discovery of a quinazolinone chemotype.
AID1070912Inhibition of DNA polymerase-alpha (unknown origin)2014Journal of medicinal chemistry, Mar-13, Volume: 57, Issue:5
Conformation-based restrictions and scaffold replacements in the design of hepatitis C virus polymerase inhibitors: discovery of deleobuvir (BI 207127).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's18 (100.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 16.36

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 Index16.36 (24.57)
Research Supply Index3.33 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (16.36)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials9 (50.00%)5.53%
Reviews1 (5.56%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (44.44%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
diclofenac
Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt.. diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position.		3.2510amino acid;
aromatic amine;
dichlorobenzene;
monocarboxylic acid;
secondary amino compound		antipyretic;
drug allergen;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
environmental contaminant;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
xenobiotic
gemfibrozil
[no description available]		3.2510aromatic etherantilipemic drug
ibuprofen
Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine		3.2510monocarboxylic acidantipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
drug allergen;
environmental contaminant;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
radical scavenger;
xenobiotic
leucine
Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.		9.0798amino acid zwitterion;
L-alpha-amino acid;
leucine;
proteinogenic amino acid;
pyruvate family amino acid		algal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
plant metabolite;
Saccharomyces cerevisiae metabolite
thiazoles
[no description available]		9.07981,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
palladium
Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.		2.110metal allergen;
nickel group element atom;
platinum group metal atom
ribavirin
Rebetron: Rebetron is tradename		8.96881-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide		anticoronaviral agent;
antiinfective agent;
antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
clopidogrel
Clopidogrel: A ticlopidine analog and platelet purinergic P2Y receptor antagonist that inhibits adenosine diphosphate-mediated PLATELET AGGREGATION. It is used to prevent THROMBOEMBOLISM in patients with ARTERIAL OCCLUSIVE DISEASES; MYOCARDIAL INFARCTION; STROKE; or ATRIAL FIBRILLATION.. clopidogrel : A thienopyridine that is 4,5,6,7-tetrahydrothieno[3,2-c]pyridine in which the hydrogen attached to the nitrogen is replaced by an o-chlorobenzyl group, the methylene hydrogen of which is replaced by a methoxycarbonyl group (the S enantiomer). A P2Y12 receptor antagonist, it is used to inhibit blood clots and prevent heart attacks.		3.2510methyl ester;
monochlorobenzenes;
thienopyridine		anticoagulant;
P2Y12 receptor antagonist;
platelet aggregation inhibitor
gemfibrozil 1-o-acylglucuronide
gemfibrozil 1-O-acylglucuronide: urinary metabolite of gemfibrozil; structure in first source		3.2510
ml-3000
[no description available]		3.2510
proline
Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.		9.0798amino acid zwitterion;
glutamine family amino acid;
L-alpha-amino acid;
proline;
proteinogenic amino acid		algal metabolite;
compatible osmolytes;
Escherichia coli metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
estradiol-17 beta-glucuronide
17beta-estradiol 17-glucosiduronic acid : A steroid glucosiduronic acid that consists of 17beta-estradiol having a beta-glucuronyl residue attached at position 17 via a glycosidic linkage.		3.25103-hydroxy steroid;
steroid glucosiduronic acid
lomibuvir
lomibuvir: an antiviral agent with polymerase NS5 inhibitory activity		2.0810thiophenecarboxylic acid
bi 201335
faldaprevir: inhibits hepatitis C virus NS3 protease		14.0798
pf 00868554
filibuvir: inhibits HCV RNA replicase		2.0810triazolopyrimidines
ConditionIndicatedRelationship StrengthStudiesTrials
Chronic Hepatitis C
[description not available]		08.6487
Hepatitis C, Chronic
INFLAMMATION of the LIVER in humans that is caused by HEPATITIS C VIRUS lasting six months or more. Chronic hepatitis C can lead to LIVER CIRRHOSIS.		110.6487
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted
[description not available]		05.3822
Hepatitis C
INFLAMMATION of the LIVER in humans caused by HEPATITIS C VIRUS, a single-stranded RNA virus. Its incubation period is 30-90 days. Hepatitis C is transmitted primarily by contaminated blood parenterally and is often associated with transfusion and intravenous drug abuse. However, in a significant number of cases, the source of hepatitis C infection is unknown.		010.3822
Cirrhosis, Liver
[description not available]		05.8622
Liver Cirrhosis
Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.		05.8622
Anemia
A reduction in the number of circulating ERYTHROCYTES or in the quantity of HEMOGLOBIN.		09.4111