Compounds > l 685434
Page last updated: 2024-11-11

l 685434

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

Description

L 685434: structure given in first source; a pseudopeptide with activity against HIV protease [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5464035
CHEMBL ID296115
CHEMBL ID308780
SCHEMBL ID6362854
MeSH IDM0201491

Synonyms (21)

Synonym
chembl296115 ,
tert-butyl n-[(2s,3s,5r)-5-benzyl-3-hydroxy-5-{[(1s,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]carbamoyl}-1-phenylpentan-2-yl]carbamate
urethane deriv. 1
bdbm1030
126456-36-8
carbamic acid, [(1s,2s,4r)-5-[[(1s,2r)-2,3-dihydro-2-hydroxy-1h-inden-1-yl]amino]-2-hydroxy-5-oxo-1,4-bis(phenylmethyl)pentyl]-, 1,1-dimethylethyl ester
l-685434
tert-butyl n-[(1s,2s,4r)-1,4-dibenzyl-2-hydroxy-5-[[(1s,2r)-2-hydroxyindan-1-yl]amino]-5-oxo-pentyl]carbamate
l-685,434
l 685434
tert-butyl n-[(2s,3s,5r)-5-benzyl-3-hydroxy-6-[[(1s,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]amino]-6-oxo-1-phenylhexan-2-yl]carbamate
[1-benzyl-2-hydroxy-4-(2-hydroxy-indan-1-ylcarbamoyl)-5-phenyl-pentyl]-carbamic acid tert-butyl ester
chembl308780
bdbm50009261
(1s-(1alpha(1r*,2r*,4s*),2alpha))-1,1-dimethylethyl (5-((2,3-dihydro-2-hydroxy-1h-inden-1-yl)amino)-2-hydroxy-5-oxo-1,4-bis(phenylmethyl)pentyl)carbamate
carbamic acid, (5-((2,3-dihydro-2-hydroxy-1h-inden-1-yl)amino)-2-hydroxy-5-oxo-1,4-bis(phenylmethyl)pentyl)-, 1,1-dimethylethyl ester, (1s-(1alpha(1r*,2r*,4s*),2alpha))-
carbamic acid, ((1s,2s,4r)-5-(((1s,2r)-2,3-dihydro-2-hydroxy-1h-inden-1-yl)amino)-2-hydroxy-5-oxo-1,4-bis(phenylmethyl)pentyl)-, 1,1-dimethylethyl ester
SCHEMBL6362854
2-benzyl-5-{[tert-butoxy(hydroxy)methylidene]amino}-4-hydroxy-n-(2-hydroxy-2,3-dihydro-1h-inden-1-yl)-6-phenylhexanimidic acid
DTXSID10925558
AKOS040752318

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" The most potent inhibitor (-)-7 displayed 13% oral bioavailability in dogs."( Design, synthesis, and biological evaluation of monopyrrolinone-based HIV-1 protease inhibitors.
Barbosa, J; Cantin, LD; Charnley, AK; Guise-Zawacki, L; Hirschmann, R; Kuo, LC; Munshi, S; Olsen, DB; Pasternak, A; Schleif, WA; Smith, AB; Sprengeler, PA; Yao, W, 2003)		0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Gag-Pol polyproteinHuman immunodeficiency virus type 1 (NEW YORK-5 ISOLATE)IC50 (µMol)0.00030.00020.10421.7000AID1795249; AID1795278; AID1795281; AID1795289
Protease Human immunodeficiency virus 1IC50 (µMol)0.00030.00010.22487.3200AID160770; AID161379; AID161728; AID162026; AID162180; AID162194; AID162206; AID162513; AID163476
[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 1IC95 (µMol)0.40000.00601.08686.0000AID161883; AID163473
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID161728Inhibition of HIV-1 protease1992Journal of medicinal chemistry, May-15, Volume: 35, Issue:10
HIV-1 protease inhibitors based on hydroxyethylene dipeptide isosteres: an investigation into the role of the P1' side chain on structure-activity.
AID162194In vitro inhibition of HIV-1 protease1995Journal of medicinal chemistry, Jan-20, Volume: 38, Issue:2
A priori prediction of activity for HIV-1 protease inhibitors employing energy minimization in the active site.
AID81070Anti-viral activity was determined2003Journal of medicinal chemistry, May-08, Volume: 46, Issue:10
Design, synthesis, and biological evaluation of monopyrrolinone-based HIV-1 protease inhibitors.
AID160770Inhibitory activity against HIV-1 protease.1998Journal of medicinal chemistry, Mar-12, Volume: 41, Issue:6
Comparative binding energy analysis of HIV-1 protease inhibitors: incorporation of solvent effects and validation as a powerful tool in receptor-based drug design.
AID162513The compound was tested for its affinity against HIV-1 protease1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
HIV protease: a novel chemotherapeutic target for AIDS.
AID162206Inhibitory activity against HIV-1 protease was determined2003Journal of medicinal chemistry, May-08, Volume: 46, Issue:10
Design, synthesis, and biological evaluation of monopyrrolinone-based HIV-1 protease inhibitors.
AID161883Cellular antiviral activity against HIV-1 Protease1997Journal of medicinal chemistry, Aug-01, Volume: 40, Issue:16
An orally bioavailable pyrrolinone inhibitor of HIV-1 protease: computational analysis and X-ray crystal structure of the enzyme complex.
AID226650Ratio of inhibitory activity on HIV-1 protease (IC50) to antiviral activity against HIV-1 in human H9 T-lymphoid cell-ELISA assay(CIC)1992Journal of medicinal chemistry, May-15, Volume: 35, Issue:10
Synthesis and antiviral activity of a series of HIV-1 protease inhibitors with functionality tethered to the P1 or P1' phenyl substituents: X-ray crystal structure assisted design.
AID163476Inhibition of HIV-1 protease1993Journal of medicinal chemistry, Jan-22, Volume: 36, Issue:2
3-Tetrahydrofuran and pyran urethanes as high-affinity P2-ligands for HIV-1 protease inhibitors.
AID161379Inhibition of HIV protease1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Benzocycloalkyl amines as novel C-termini for HIV protease inhibitors.
AID79236Inhibitory activity against HIV-1IIIb in H-9 cells using immunofluorescence1991Journal of medicinal chemistry, Aug, Volume: 34, Issue:8
HIV protease: a novel chemotherapeutic target for AIDS.
AID162026Inhibition of HIV-1 protease1997Journal of medicinal chemistry, Aug-01, Volume: 40, Issue:16
An orally bioavailable pyrrolinone inhibitor of HIV-1 protease: computational analysis and X-ray crystal structure of the enzyme complex.
AID227879Ratio (CIC95/IC50) of cellular antiviral activity over the isolated enzyme potency2003Journal of medicinal chemistry, May-08, Volume: 46, Issue:10
Design, synthesis, and biological evaluation of monopyrrolinone-based HIV-1 protease inhibitors.
AID232360Ratio of CIC95 to IC50 values1997Journal of medicinal chemistry, Aug-01, Volume: 40, Issue:16
An orally bioavailable pyrrolinone inhibitor of HIV-1 protease: computational analysis and X-ray crystal structure of the enzyme complex.
AID221810In vitro anti viral activity against HIV-1 in human H9 T-lymphoid cell culture by fixed cell immunofluorescence assay1992Journal of medicinal chemistry, May-15, Volume: 35, Issue:10
Synthesis and antiviral activity of a series of HIV-1 protease inhibitors with functionality tethered to the P1 or P1' phenyl substituents: X-ray crystal structure assisted design.
AID162180In vitro enzyme inhibitory activity against HIV-1 protease.1992Journal of medicinal chemistry, May-15, Volume: 35, Issue:10
Synthesis and antiviral activity of a series of HIV-1 protease inhibitors with functionality tethered to the P1 or P1' phenyl substituents: X-ray crystal structure assisted design.
AID221809Ex vivo antiviral activity in H9 T-lymphoid cells infected with HIV-1(IIIB).1992Journal of medicinal chemistry, May-15, Volume: 35, Issue:10
HIV-1 protease inhibitors based on hydroxyethylene dipeptide isosteres: an investigation into the role of the P1' side chain on structure-activity.
AID163473Inhibitory concentration was evaluated to inhibit the 95% of HIV-1 protease1993Journal of medicinal chemistry, Jan-22, Volume: 36, Issue:2
3-Tetrahydrofuran and pyran urethanes as high-affinity P2-ligands for HIV-1 protease inhibitors.
AID1795289Protease Inhibition Assay from Article 10.1021/jm00088a004: \\HIV-1 protease inhibitors based on hydroxyethylene dipeptide isosteres: an investigation into the role of the P1' side chain on structure-activity.\\1992Journal of medicinal chemistry, May-15, Volume: 35, Issue:10
HIV-1 protease inhibitors based on hydroxyethylene dipeptide isosteres: an investigation into the role of the P1' side chain on structure-activity.
AID1795249Protease Inhibition Assay from Article 10.1021/jm00054a015: \\3-Tetrahydrofuran and pyran urethanes as high-affinity P2-ligands for HIV-1 protease inhibitors.\\1993Journal of medicinal chemistry, Jan-22, Volume: 36, Issue:2
3-Tetrahydrofuran and pyran urethanes as high-affinity P2-ligands for HIV-1 protease inhibitors.
AID1795281Protease Inhibition Assay from Article 10.1021/jm00088a003: \\Synthesis and antiviral activity of a series of HIV-1 protease inhibitors with functionality tethered to the P1 or P1' phenyl substituents: X-ray crystal structure assisted design.\\1992Journal of medicinal chemistry, May-15, Volume: 35, Issue:10
Synthesis and antiviral activity of a series of HIV-1 protease inhibitors with functionality tethered to the P1 or P1' phenyl substituents: X-ray crystal structure assisted design.
AID1795278Protease Inhibition Assay from Article 10.1021/jm00107a051: \\Benzocycloalkyl amines as novel C-termini for HIV protease inhibitors.\\1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Benzocycloalkyl amines as novel C-termini for HIV protease inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's8 (88.89)18.2507
2000's1 (11.11)29.6817
2010's0 (0.00)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: 11.86

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 Index11.86 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.17 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.86)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (11.11%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (88.89%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
haloperidol
Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.		3.0710aromatic ketone;
hydroxypiperidine;
monochlorobenzenes;
organofluorine compound;
tertiary alcohol		antidyskinesia agent;
antiemetic;
dopaminergic antagonist;
first generation antipsychotic;
serotonergic antagonist
pyrroles
1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.		1.9910pyrrole;
secondary amine
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.		1.9810azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
a 74704
A 74704: structure given in first source		3.0710
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.		2.3920L-asparagine derivative;
quinolines		antiviral drug;
HIV protease inhibitor
cerulenin
Cerulenin: An epoxydodecadienamide isolated from several species, including ACREMONIUM, Acrocylindrum, and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.. cerulenin : An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.		3.0710epoxide;
monocarboxylic acid amide		antifungal agent;
antiinfective agent;
antilipemic drug;
antimetabolite;
antimicrobial agent;
fatty acid synthesis inhibitor
indinavir sulfate
Indinavir: A potent and specific HIV protease inhibitor that appears to have good oral bioavailability.		2.4120dicarboxylic acid diamide;
N-(2-hydroxyethyl)piperazine;
piperazinecarboxamide		HIV protease inhibitor
l 689502
L 689502: HIV-1 protease inhibitor; structure given in first source		1.9810
l 682679
L 682679: structure given in first source		2.6830
pepstatin
pepstatin: inhibits the aspartic protease endothiapepsin		3.0710pentapeptide;
secondary carboxamide		bacterial metabolite;
EC 3.4.23.* (aspartic endopeptidase) inhibitor
u 75875
U 75875: structure given in first source		3.0710
streptomyces pepsin inhibitor
[no description available]		3.0710
ConditionIndicatedRelationship StrengthStudiesTrials
Acquired Immune Deficiency Syndrome
[description not available]		02.8910
Acquired Immunodeficiency Syndrome
An acquired defect of cellular immunity associated with infection by the human immunodeficiency virus (HIV), a CD4-positive T-lymphocyte count under 200 cells/microliter or less than 14% of total lymphocytes, and increased susceptibility to opportunistic infections and malignant neoplasms. Clinical manifestations also include emaciation (wasting) and dementia. These elements reflect criteria for AIDS as defined by the CDC in 1993.		02.8910