Compounds > g 52
Page last updated: 2024-12-08

g 52

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Description

GRL-0519: an HIV-1 protease inhibitor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID46891890
CHEMBL ID1232930
SCHEMBL ID15047627
MeSH IDM0059801

Synonyms (18)

Synonym
CHEMBL1232930 ,
grl-0519
G52 ,
(3r,3as,3br,6as,7as)-octahydrodifuro[2,3-b:3',2'-d]furan-3-yl [(1s,2r)-1-benzyl-2-hydroxy-3-{[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino}propyl]carbamate
grl-0519 & aag
[(3ar,3bs,4r,6as,7as)-2,3,3a,3b,4,5,6a,7a-octahydrodifuro[[?],[?]]furan-4-yl] n-[(1s,2r)-1-benzyl-2-hydroxy-3-[isobutyl-(4-methoxyphenyl)sulfonyl-amino]propyl]carbamate
grl-0519 & hsa
grl-0519 & alpha1-acid glycoprotein
4HDP
4HDF
4HE9
4HDB
4HEG
3OK9
SCHEMBL15047627
bdbm50489369
(3r,3as,3br,6as,7as)-octahydrodifuro[2,3-b:3',2'-d]furan-3-yl [(2s,3r)-3-hydroxy-4-{[(4-methoxyphenyl)sulfonyl](2-methylpropyl)amino}-1-phenylbutan-2-yl]carbamate
Q27460554
[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)
Chain A, ProteaseHuman immunodeficiency virus 1Ki0.00000.00000.00000.0000AID977610
Chain B, ProteaseHuman immunodeficiency virus 1Ki0.00000.00000.00000.0000AID977610
Protease Human immunodeficiency virus 1Ki0.00950.00000.04433.1000AID725236; AID725237; AID725238; AID725239; AID725245
Protease Human immunodeficiency virus 1Ki0.00030.00000.02841.1000AID725240; AID770192
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Protease Human immunodeficiency virus 1K0.03950.03950.30460.9600AID738152
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (20)

Assay IDTitleYearJournalArticle
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2013Journal of medicinal chemistry, Feb-14, Volume: 56, Issue:3
Novel P2 tris-tetrahydrofuran group in antiviral compound 1 (GRL-0519) fills the S2 binding pocket of selected mutants of HIV-1 protease.
AID725239Inhibition of HIV-1 protease R8Q mutant using Abz-Thr-Ile-Nle-p-nitro-Phe-Gln-Arg-NH2 as substrate incubated for 5 mins prior to substrate addition measured for 5 mins by fluorescence assay2013Journal of medicinal chemistry, Feb-14, Volume: 56, Issue:3
Novel P2 tris-tetrahydrofuran group in antiviral compound 1 (GRL-0519) fills the S2 binding pocket of selected mutants of HIV-1 protease.
AID725238Inhibition of HIV-1 protease D30N mutant using Abz-Thr-Ile-Nle-p-nitro-Phe-Gln-Arg-NH2 as substrate incubated for 5 mins prior to substrate addition measured for 5 mins by fluorescence assay2013Journal of medicinal chemistry, Feb-14, Volume: 56, Issue:3
Novel P2 tris-tetrahydrofuran group in antiviral compound 1 (GRL-0519) fills the S2 binding pocket of selected mutants of HIV-1 protease.
AID725244Ratio of Ki for HIV-1 protease I50V mutant to Ki for HIV-1 wildtype protease2013Journal of medicinal chemistry, Feb-14, Volume: 56, Issue:3
Novel P2 tris-tetrahydrofuran group in antiviral compound 1 (GRL-0519) fills the S2 binding pocket of selected mutants of HIV-1 protease.
AID770192Inhibition of HIV1 protease2013Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17
Highly potent HIV-1 protease inhibitors with novel tricyclic P2 ligands: design, synthesis, and protein-ligand X-ray studies.
AID770193Antiviral activity against HIV1 LAV2013Journal of medicinal chemistry, Sep-12, Volume: 56, Issue:17
Highly potent HIV-1 protease inhibitors with novel tricyclic P2 ligands: design, synthesis, and protein-ligand X-ray studies.
AID725236Inhibition of HIV-1 protease I54M mutant using Abz-Thr-Ile-Nle-p-nitro-Phe-Gln-Arg-NH2 as substrate incubated for 5 mins prior to substrate addition measured for 5 mins by fluorescence assay2013Journal of medicinal chemistry, Feb-14, Volume: 56, Issue:3
Novel P2 tris-tetrahydrofuran group in antiviral compound 1 (GRL-0519) fills the S2 binding pocket of selected mutants of HIV-1 protease.
AID738145Ratio of amprenavir dissociation constant K to compound dissociation constant K for HIV1 protease Q7K, L10F, I13V, I15V, D30V, V32I, L33F, E35D, M36I, S37N, I47V, I54L, Q58E, I62V, L63P, A71V, I84V, N88D, L89T, L90M mutant2013Journal of medicinal chemistry, May-23, Volume: 56, Issue:10
Extreme multidrug resistant HIV-1 protease with 20 mutations is resistant to novel protease inhibitors with P1'-pyrrolidinone or P2-tris-tetrahydrofuran.
AID725245Inhibition of HIV-1 protease V82A mutant using Abz-Thr-Ile-Nle-p-nitro-Phe-Gln-Arg-NH2 as substrate incubated for 5 mins prior to substrate addition measured for 5 mins by fluorescence assay2013Journal of medicinal chemistry, Feb-14, Volume: 56, Issue:3
Novel P2 tris-tetrahydrofuran group in antiviral compound 1 (GRL-0519) fills the S2 binding pocket of selected mutants of HIV-1 protease.
AID738150Inhibition of transferrin receptor-fused HIV1 protease Q7K, L10F, I13V, I15V, D30V, V32I, L33F, E35D, M36I, S37N, I47V, I54L, Q58E, I62V, L63P, A71V, I84V, N88D, L89T, L90M mutant autoprocessing expressed in Escherichia coli up to 100 uM by SDS-PAGE analy2013Journal of medicinal chemistry, May-23, Volume: 56, Issue:10
Extreme multidrug resistant HIV-1 protease with 20 mutations is resistant to novel protease inhibitors with P1'-pyrrolidinone or P2-tris-tetrahydrofuran.
AID738144Inhibition of HIV1 protease dimerization transfected in COS7 cells relative to darunavir2013Journal of medicinal chemistry, May-23, Volume: 56, Issue:10
Extreme multidrug resistant HIV-1 protease with 20 mutations is resistant to novel protease inhibitors with P1'-pyrrolidinone or P2-tris-tetrahydrofuran.
AID725242Ratio of Ki for HIV-1protease I54M mutant to Ki for HIV-1 wildtype protease2013Journal of medicinal chemistry, Feb-14, Volume: 56, Issue:3
Novel P2 tris-tetrahydrofuran group in antiviral compound 1 (GRL-0519) fills the S2 binding pocket of selected mutants of HIV-1 protease.
AID725246Ratio of Ki for HIV-1 protease R8Q mutant to Ki for HIV-1 wildtype protease2013Journal of medicinal chemistry, Feb-14, Volume: 56, Issue:3
Novel P2 tris-tetrahydrofuran group in antiviral compound 1 (GRL-0519) fills the S2 binding pocket of selected mutants of HIV-1 protease.
AID725243Ratio of Ki for HIV-1 protease D30N mutant to Ki for HIV-1 wildtype protease2013Journal of medicinal chemistry, Feb-14, Volume: 56, Issue:3
Novel P2 tris-tetrahydrofuran group in antiviral compound 1 (GRL-0519) fills the S2 binding pocket of selected mutants of HIV-1 protease.
AID725241Ratio of Ki for HIV-1 protease V82A mutant to Ki for HIV-1 wildtype protease2013Journal of medicinal chemistry, Feb-14, Volume: 56, Issue:3
Novel P2 tris-tetrahydrofuran group in antiviral compound 1 (GRL-0519) fills the S2 binding pocket of selected mutants of HIV-1 protease.
AID738152Binding affinity to HIV1 protease Q7K, L10F, I13V, I15V, D30V, V32I, L33F, E35D, M36I, S37N, I47V, I54L, Q58E, I62V, L63P, A71V, I84V, N88D, L89T, L90M mutant expressed in Escherichia coli BL21 (DE3) assessed as dissociation constant by isothermal titrati2013Journal of medicinal chemistry, May-23, Volume: 56, Issue:10
Extreme multidrug resistant HIV-1 protease with 20 mutations is resistant to novel protease inhibitors with P1'-pyrrolidinone or P2-tris-tetrahydrofuran.
AID725237Inhibition of HIV-1 protease I50V mutant using Abz-Thr-Ile-Nle-p-nitro-Phe-Gln-Arg-NH2 as substrate incubated for 5 mins prior to substrate addition measured for 5 mins by fluorescence assay2013Journal of medicinal chemistry, Feb-14, Volume: 56, Issue:3
Novel P2 tris-tetrahydrofuran group in antiviral compound 1 (GRL-0519) fills the S2 binding pocket of selected mutants of HIV-1 protease.
AID738153Binding affinity to HIV1 protease Q7K, L10F, I13V, I15V, D30V, V32I, L33F, E35D, M36I, S37N, I47V, I54L, Q58E, I62V, L63P, A71V, I84V, N88D, L89T, L90M mutant expressed in Escherichia coli BL21 (DE3) assessed as association constant by isothermal titratio2013Journal of medicinal chemistry, May-23, Volume: 56, Issue:10
Extreme multidrug resistant HIV-1 protease with 20 mutations is resistant to novel protease inhibitors with P1'-pyrrolidinone or P2-tris-tetrahydrofuran.
AID725240Inhibition of HIV-1 wildtype protease using Abz-Thr-Ile-Nle-p-nitro-Phe-Gln-Arg-NH2 as substrate incubated for 5 mins prior to substrate addition measured for 5 mins by fluorescence assay2013Journal of medicinal chemistry, Feb-14, Volume: 56, Issue:3
Novel P2 tris-tetrahydrofuran group in antiviral compound 1 (GRL-0519) fills the S2 binding pocket of selected mutants of HIV-1 protease.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2010ChemMedChem, Nov-08, Volume: 5, Issue:11
Probing multidrug-resistance and protein-ligand interactions with oxatricyclic designed ligands in HIV-1 protease inhibitors.
[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's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's6 (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]

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
carbamates
[no description available]		2.4920amino-acid anion
tetrahydrofuran
oxolane : A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.		2.0810cyclic ether;
oxolanes;
saturated organic heteromonocyclic parent;
volatile organic compound		polar aprotic solvent
amprenavir
[no description available]		2.7830carbamate ester;
sulfonamide;
tetrahydrofuryl ester		antiviral drug;
HIV protease inhibitor
lopinavir
[no description available]		2.0810amphetamines;
dicarboxylic acid diamide		anticoronaviral agent;
antiviral drug;
HIV protease inhibitor
atazanavir
atazanavir : A heavily substituted carbohydrazide that is an antiretroviral drug of the protease inhibitor (PI) class used to treat infection of human immunodeficiency virus (HIV).		2.0810carbohydrazideantiviral drug;
HIV protease inhibitor
atazanavir sulfate
Atazanavir Sulfate: An azapeptide and HIV-PROTEASE INHIBITOR that is used in the treatment of HIV INFECTIONS and AIDS in combination with other ANTI-HIV AGENTS.		2.0810organic sulfate salt
darunavir
Darunavir: An HIV PROTEASE INHIBITOR that is used in the treatment of AIDS and HIV INFECTIONS. Due to the emergence of ANTIVIRAL DRUG RESISTANCE when used alone, it is administered in combination with other ANTI-HIV AGENTS.. darunavir : An N,N-disubstituted benzenesulfonamide bearing an unsubstituted amino group at the 4-position, used for the treatment of HIV infection. A second-generation HIV protease inhibitor, darunavir was designed to form robust interactions with the protease enzyme from many strains of HIV, including those from treatment-experienced patients with multiple resistance mutations to other protease inhibitors.		2.7830carbamate ester;
furofuran;
sulfonamide		antiviral drug;
HIV protease inhibitor
ritonavir
Ritonavir: An HIV protease inhibitor that works by interfering with the reproductive cycle of HIV. It also inhibits CYTOCHROME P-450 CYP3A.. ritonavir : An L-valine derivative that is L-valinamide in which alpha-amino group has been acylated by a [(2-isopropyl-1,3-thiazol-4-yl)methyl]methylcarbamoyl group and in which a hydrogen of the carboxamide amino group has been replaced by a (2R,4S,5S)-4-hydroxy-1,6-diphenyl-5-{[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}hexan-2-yl group. A CYP3A inhibitor and antiretroviral drug from the protease inhibitor class used to treat HIV infection and AIDS, it is often used as a fixed-dose combination with another protease inhibitor, lopinavir. Also used in combination with dasabuvir sodium hydrate, ombitasvir and paritaprevir (under the trade name Viekira Pak) for treatment of chronic hepatitis C virus genotype 1 infection as well as cirrhosis of the liver.		2.08101,3-thiazoles;
carbamate ester;
carboxamide;
L-valine derivative;
ureas		antiviral drug;
environmental contaminant;
HIV protease inhibitor;
xenobiotic
saquinavir
Saquinavir: An HIV protease inhibitor which acts as an analog of an HIV protease cleavage site. It is a highly specific inhibitor of HIV-1 and HIV-2 proteases, and also inhibits CYTOCHROME P-450 CYP3A.. saquinavir : An aspartic acid derivative obtained by formal condensation of the primary amino group of (2S,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)octahydroisoquinolin-2(1H)-yl]-3-hydroxy-1-phenylbutan-2-ylamine with the carboxy group of N(2)(-quinolin-2-ylcarbonyl)-L-asparagine. An inhibitor of HIV-1 protease.		2.4920L-asparagine derivative;
quinolines		antiviral drug;
HIV protease inhibitor
grl 02031
GRL 02031: a protease inhibitor with anti-HIV1 activity; structure in first source		2.0810
indinavir sulfate
Indinavir: A potent and specific HIV protease inhibitor that appears to have good oral bioavailability.		2.0810dicarboxylic acid diamide;
N-(2-hydroxyethyl)piperazine;
piperazinecarboxamide		HIV protease inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
HIV Coinfection
[description not available]		02.0510
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).		02.0510