Compounds > kynostatin 272
Page last updated: 2024-12-06

kynostatin 272

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

Description

kynostatin 272: structure given in first source; contains allophenylnorstatine as a transition-state mimic [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID60927
CHEMBL ID414640
CHEBI ID80006
SCHEMBL ID1649255
MeSH IDM0208798

Synonyms (31)

Synonym
kynostatin-272
nsc-651714
lecithinized superoxide dismutase & n-(1,1-dimethylethyl)-3-[2-hydroxy-3-[[2-[[(5-isoquinolinyloxy)acetyl]amino]-3-methylthio)-1-oxopropyl]amino]-1-oxo-4-phenylbutyl]-4-thiazolidinecarboxamide, [4r-[3[2s*,3s*(r*)],4r*]]
pc-sod & kni-272
5isoquinoline-o-ch2-co-mta-(2s,3s)-ahpba-thz-nh-tbu
(4r)-n-tert-butyl-3-[(2s,3s)-2-hydroxy-3-[[(2r)-2-[[2-(5-isoquinolyloxy)acetyl]amino]-3-methylsulfanyl-propanoyl]amino]-4-phenyl-butanoyl]thiazolidine-4-carboxamide
kynostatin 272
NSC651714 ,
iqoa-mta-apns-thz-nh-tbu
n-(1,1-dimethylethyl)-3-[2-hydroxy-3-[[2-[[(5-isoquinolinyloxy)acetyl]amino]-3-methylthio)-1-oxopropyl]amino]-1-oxo-4-phenylbutyl]-4-thiazolidinecarboxamide, [4r-[3[2s*,3s*(r*)],4r*]]
147318-81-8
kni-272
KNI ,
(4r)-n-tert-butyl-3-[(2s,3s)-2-hydroxy-3-({n-[(isoquinolin-5-yloxy)acetyl]-s-methyl-l-cysteinyl}amino)-4-phenylbutanoyl]-1,3-thiazolidine-4-carboxamide
1HPX
nsc 651714
ccris 7458
4-thiazolidinecarboxamide, n-(1,1-dimethylethyl)-3-(2-hydroxy-3-((2-(((5-isoquinolinyloxy)acetyl)amino)-3-(methylthio)-1-oxopropyl)amino)-1-oxo-4-phenylbutyl)-, (4r-(3(2s*,3s*(r*)),4r*))-
drg-0219
(4r)-n-tert-butyl-3-[(2s,3s)-2-hydroxy-3-[[(2r)-2-[(2-isoquinolin-5-yloxyacetyl)amino]-3-methylsulfanylpropanoyl]amino]-4-phenylbutanoyl]-1,3-thiazolidine-4-carboxamide
CHEMBL414640
chebi:80006 ,
mul0oe3ybf ,
unii-mul0oe3ybf
SCHEMBL1649255
n-t-butyl-3-((2s,3s)-2-hydroxy-3-(n-((r)-2-(n-(isoquinolin-5-yloxyacetyl)amino))-3-methylthiopropanoylamino)-4-phenylbutanoyl)-1,3-thiazolidine-4-carboxamide,l-
kynostatin
Q27149154
(r)-n-(tert-butyl)-3-((2s,3s)-2-hydroxy-3-((r)-2-(2-(isoquinolin-5-yloxy)acetamido)-3-(methylthio)propanamido)-4-phenylbutanoyl)thiazolidine-4-carboxamide
kni 272; kynostatin; nsc 651714
AKOS040748673

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"The pharmacokinetic (PK) characteristics of KNI-272, a potent and selective HIV-1 protease inhibitor, were evaluated in rats after intravenous (IV) administration."( Plasma pharmacokinetics and urinary and biliary excretion of a new potent tripeptide HIV-1 protease inhibitor, KNI-272, in rats after intravenous administration.
Fujita, K; Kiriyama, A; Kiso, Y; Kuramoto, H; Takada, K; Takemura, S, 1994)		0.29
" In this study, we developed an HPLC assay system for KNI-227 and KNI-272 in rat plasma and examined the pharmacokinetic characteristics in rats after both intravenous (i."( Comparison of a new orally potent tripeptide HIV-1 protease inhibitor (anti-AIDS drug) based on pharmacokinetic characteristics in rats after intravenous and intraduodenal administrations.
Kiriyama, A; Kisanuki, S; Kiso, Y; Mimoto, T; Takada, K, 1993)		0.29
" The pharmacokinetic profile of KNI-272 may limit the drug's efficacy in vivo."( Pharmacokinetics of the protease inhibitor KNI-272 in plasma and cerebrospinal fluid in nonhuman primates after intravenous dosing and in human immunodeficiency virus-infected children after intravenous and oral dosing.
Anderson, BD; Balis, FM; Farley, MQ; Godwin, K; Jarosinski, P; McCully, CL; Mitsuya, H; Mueller, BU; Murphy, R; Pizzo, PA; Zuckerman, J, 1998)		0.3
"The effects of dose on the pharmacokinetic characteristics of KNI-272 were evaluated in rats after intravenous (iv) administration."( Physiologically based pharmacokinetics of KNI-272, a tripeptide HIV-1 protease inhibitor.
Kiriyama, A; Nishiura, T; Takada, K; Yamaji, H, 1999)		0.3

Bioavailability

ExcerptReferenceRelevance
" In this study, KNI-272 was administered to rats as a solution and the effect of four kinds of solvent on the bioavailability (BA) of KNI-272 was determined using rats."( Absorption of new HIV-1 protease inhibitor, KNI-272, after intraduodenal and intragastric administrations to rats: effect of solvent.
Hamada, Y; Kiriyama, A; Kiso, Y; Sugahara, M; Takada, K, 1995)		0.29
" administration, bioavailability of KNI-272 was 42."( Design and synthesis of substrate-based peptidomimetic human immunodeficiency virus protease inhibitors containing the hydroxymethylcarbonyl isostere.
Kiso, Y, 1996)		0.29
"The bioavailability (BA) of a tripeptide protease inhibitor, KNI-272, which has a strong pharmacological potential for treating human immunodeficiency virus type 1 (HIV-1), has been studied in beagle dogs by administering several oral dosage forms."( The bioavailability of oral dosage forms of a new HIV-1 protease inhibitor, KNI-272, in beagle dogs.
Kiriyama, A; Kiso, Y; Sugahara, M; Takada, K; Yoshikawa, Y, 1996)		0.29
" Oral bioavailability ranged from 22 to 55% and was not appreciably different in the fasting and post-prandial state."( A phase I trial of the pharmacokinetics, toxicity, and activity of KNI-272, an inhibitor of HIV-1 protease, in patients with AIDS or symptomatic HIV infection.
Fukasawa, T; Hayashi, H; Humphrey, RW; Kohler, DR; Mitsuya, H; Nguyen, BY; Shay, LE; Shintani, M; Steinberg, SM; Ueno, T; Wyvill, KM; Yarchoan, R, 1999)		0.3
" The present study demonstrated that JE-2147 has potent antiviral activities in vitro and exhibits good oral bioavailability and plasma pharmacokinetic profiles in two species of laboratory animals."( Structure-activity relationship of small-sized HIV protease inhibitors containing allophenylnorstatine.
Fukazawa, T; Hayashi, H; Kato, R; Kiso, Y; Mimoto, T; Misawa, S; Nojima, S; Sato, H; Shintani, M; Takaku, H; Terashima, K; Ueno, T, 1999)		0.3

Dosage Studied

ExcerptRelevanceReference
" These results suggest that, for the development of an oral dosage form of KNI-272, a non-ionic surfactant that dissolves in the duodenum or small intestine and that enhances the absorption of this drug from the gastrointestinal tract into the enterocytes is needed."( Absorption of new HIV-1 protease inhibitor, KNI-272, after intraduodenal and intragastric administrations to rats: effect of solvent.
Hamada, Y; Kiriyama, A; Kiso, Y; Sugahara, M; Takada, K, 1995)		0.29
"The bioavailability (BA) of a tripeptide protease inhibitor, KNI-272, which has a strong pharmacological potential for treating human immunodeficiency virus type 1 (HIV-1), has been studied in beagle dogs by administering several oral dosage forms."( The bioavailability of oral dosage forms of a new HIV-1 protease inhibitor, KNI-272, in beagle dogs.
Kiriyama, A; Kiso, Y; Sugahara, M; Takada, K; Yoshikawa, Y, 1996)		0.29
" The concentrations in plasma were maintained above a concentration that is active in vitro for less than half of the 6-h dosing interval."( Pharmacokinetics of the protease inhibitor KNI-272 in plasma and cerebrospinal fluid in nonhuman primates after intravenous dosing and in human immunodeficiency virus-infected children after intravenous and oral dosing.
Anderson, BD; Balis, FM; Farley, MQ; Godwin, K; Jarosinski, P; McCully, CL; Mitsuya, H; Mueller, BU; Murphy, R; Pizzo, PA; Zuckerman, J, 1998)		0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
peptideAmide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another with formal loss of water. The term is usually applied to structures formed from alpha-amino acids, but it includes those derived from any amino carboxylic acid. X = OH, OR, NH2, NHR, etc.
[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 (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Hiv-1 ProteaseHuman immunodeficiency virus 1Ki0.00000.00000.00000.0000AID977610
Chain B, Hiv-1 ProteaseHuman immunodeficiency virus 1Ki0.00000.00000.00000.0000AID977610
Gag-Pol polyproteinHuman immunodeficiency virus type 1 (BRU ISOLATE)Ki0.00090.00000.08283.3000AID1795271
Gag-Pol polyproteinHuman immunodeficiency virus type 1 (NEW YORK-5 ISOLATE)Ki0.00040.00000.12203.1000AID1795265; AID1795273
Plasmepsin-2Plasmodium falciparum (malaria parasite P. falciparum)Ki1.00000.00050.17301.0000AID290578
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (33)

Assay IDTitleYearJournalArticle
AID290992Inhibition of HIV protease at 1 nM2007Bioorganic & medicinal chemistry letters, Aug-01, Volume: 17, Issue:15
Synthesis and antiviral property of allophenylnorstatine-based HIV protease inhibitors incorporating D-cysteine derivatives as P2/P3 moieties.
AID408207Antiviral activity against HIV1 3B in human MT4 cells assessed as inhibition of viral-induced cytopathic effect by MTT method2008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
Combination of non-natural D-amino acid derivatives and allophenylnorstatine-dimethylthioproline scaffold in HIV protease inhibitors have high efficacy in mutant HIV.
AID408209Selectivity index, ratio of CC50 for human MT4 cells to EC50 for HIV1 3B2008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
Combination of non-natural D-amino acid derivatives and allophenylnorstatine-dimethylthioproline scaffold in HIV protease inhibitors have high efficacy in mutant HIV.
AID1350494Inhibition of recombinant HIV1 protease at 1 nM using H-Lys-Ala-Arg-Val-Tyr-Phe(p-NO2)-Glu-Ala-Nle-NH2 as substrate preincubated for 5 mins followed by substrate addition measured after 3 hrs by fluorescence-based assay2018Journal of medicinal chemistry, 06-28, Volume: 61, Issue:12
Identification of Highly Potent Human Immunodeficiency Virus Type-1 Protease Inhibitors against Lopinavir and Darunavir Resistant Viruses from Allophenylnorstatine-Based Peptidomimetics with P2 Tetrahydrofuranylglycine.
AID408214Antiviral activity against HIV1 3B in presence of 10% fetal calf serum2008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
Combination of non-natural D-amino acid derivatives and allophenylnorstatine-dimethylthioproline scaffold in HIV protease inhibitors have high efficacy in mutant HIV.
AID408211Antiviral activity against nelfinavir-resistant HIV1 NL4322008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
Combination of non-natural D-amino acid derivatives and allophenylnorstatine-dimethylthioproline scaffold in HIV protease inhibitors have high efficacy in mutant HIV.
AID290578Inhibition of Plasmodium falciparum plasmepsin-22007Bioorganic & medicinal chemistry letters, Jun-01, Volume: 17, Issue:11
Additional interaction of allophenylnorstatine-containing tripeptidomimetics with malarial aspartic protease plasmepsin II.
AID408206Inhibition of HIV1 protease at 1 nM2008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
Combination of non-natural D-amino acid derivatives and allophenylnorstatine-dimethylthioproline scaffold in HIV protease inhibitors have high efficacy in mutant HIV.
AID408208Cytotoxicity against human MT4 cells by MTT assay2008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
Combination of non-natural D-amino acid derivatives and allophenylnorstatine-dimethylthioproline scaffold in HIV protease inhibitors have high efficacy in mutant HIV.
AID1350498Antiviral activity against wild-type HIV1 3B infected in human MT4 cells assessed as inhibition of virus-induced cytopathic effect after 5 days in absence of human serum by MTT assay2018Journal of medicinal chemistry, 06-28, Volume: 61, Issue:12
Identification of Highly Potent Human Immunodeficiency Virus Type-1 Protease Inhibitors against Lopinavir and Darunavir Resistant Viruses from Allophenylnorstatine-Based Peptidomimetics with P2 Tetrahydrofuranylglycine.
AID408219Ratio of EC50 for ritonavir and nelfinavir-resistant HIV1 NL432 to EC50 for wild-type HIV1 NL4322008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
Combination of non-natural D-amino acid derivatives and allophenylnorstatine-dimethylthioproline scaffold in HIV protease inhibitors have high efficacy in mutant HIV.
AID46254Inhibitory activity against HIV-1 IIIB in CEM-SS infected cells1999Bioorganic & medicinal chemistry letters, Mar-22, Volume: 9, Issue:6
A new class of anti-HIV agents: synthesis and activity of conjugates of HIV protease inhibitors with a reverse transcriptase inhibitor.
AID1350500Ratio of EC50 for wild-type HIV1 3B infected in human MT4 in presence of 50% of huma serum to EC50 for wild-type HIV-1 3B infected in human MT4 in absence of human serum2018Journal of medicinal chemistry, 06-28, Volume: 61, Issue:12
Identification of Highly Potent Human Immunodeficiency Virus Type-1 Protease Inhibitors against Lopinavir and Darunavir Resistant Viruses from Allophenylnorstatine-Based Peptidomimetics with P2 Tetrahydrofuranylglycine.
AID408213Antiviral activity against ritonavir and nelfinavir-resistant HIV1 NL4322008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
Combination of non-natural D-amino acid derivatives and allophenylnorstatine-dimethylthioproline scaffold in HIV protease inhibitors have high efficacy in mutant HIV.
AID408216Ratio of EC50 for ritonavir-resistant HIV1 NL432 to EC50 for wild-type HIV1 NL4322008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
Combination of non-natural D-amino acid derivatives and allophenylnorstatine-dimethylthioproline scaffold in HIV protease inhibitors have high efficacy in mutant HIV.
AID408210Antiviral activity against wild type HIV1 NL4322008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
Combination of non-natural D-amino acid derivatives and allophenylnorstatine-dimethylthioproline scaffold in HIV protease inhibitors have high efficacy in mutant HIV.
AID397592Therapeutic index, ratio of cytotoxicity against human H9 cells to EC50 for HIV1 RF2001Journal of natural products, Feb, Volume: 64, Issue:2
Natural product-based anti-HIV drug discovery and development facilitated by the NCI developmental therapeutics program.
AID290995Cytotoxicity against MT4 cells by MTT assay2007Bioorganic & medicinal chemistry letters, Aug-01, Volume: 17, Issue:15
Synthesis and antiviral property of allophenylnorstatine-based HIV protease inhibitors incorporating D-cysteine derivatives as P2/P3 moieties.
AID397590Antiviral activity against HIV1 RF in human H9 cells assessed as inhibition of virus-induced cytopathic effect by formazan-based conventional colorimetric technique2001Journal of natural products, Feb, Volume: 64, Issue:2
Natural product-based anti-HIV drug discovery and development facilitated by the NCI developmental therapeutics program.
AID290994Antiviral activity against HIV1 3B in MT4 cells by MTT assay2007Bioorganic & medicinal chemistry letters, Aug-01, Volume: 17, Issue:15
Synthesis and antiviral property of allophenylnorstatine-based HIV protease inhibitors incorporating D-cysteine derivatives as P2/P3 moieties.
AID408212Antiviral activity against ritonavir-resistant HIV1 NL4322008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
Combination of non-natural D-amino acid derivatives and allophenylnorstatine-dimethylthioproline scaffold in HIV protease inhibitors have high efficacy in mutant HIV.
AID408218Ratio of EC50 for nelfinavir-resistant HIV1 NL432 to EC50 for wild-type HIV1 NL4322008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
Combination of non-natural D-amino acid derivatives and allophenylnorstatine-dimethylthioproline scaffold in HIV protease inhibitors have high efficacy in mutant HIV.
AID104286Inhibitory activity against HIV-1 IIIB in MT-4 infected cells1999Bioorganic & medicinal chemistry letters, Mar-22, Volume: 9, Issue:6
A new class of anti-HIV agents: synthesis and activity of conjugates of HIV protease inhibitors with a reverse transcriptase inhibitor.
AID82904Inhibitory activity against HIV protease at a concentration of 5 uM1999Bioorganic & medicinal chemistry letters, Mar-22, Volume: 9, Issue:6
A new class of anti-HIV agents: synthesis and activity of conjugates of HIV protease inhibitors with a reverse transcriptase inhibitor.
AID408217Ratio of EC50 for HIV1 3B in presence of 10% fetal calf serum and alpha1 acid glycoprotein to EC50 for HIV1 3B in presence of 10% fetal calf serum2008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
Combination of non-natural D-amino acid derivatives and allophenylnorstatine-dimethylthioproline scaffold in HIV protease inhibitors have high efficacy in mutant HIV.
AID290996Selectivity index, Ratio of LC50 for MT4 cells to EC50 for HIV1 3B2007Bioorganic & medicinal chemistry letters, Aug-01, Volume: 17, Issue:15
Synthesis and antiviral property of allophenylnorstatine-based HIV protease inhibitors incorporating D-cysteine derivatives as P2/P3 moieties.
AID408215Antiviral activity against HIV1 3B in presence of 10% fetal calf serum and alpha1 acid glycoprotein2008Journal of medicinal chemistry, May-22, Volume: 51, Issue:10
Combination of non-natural D-amino acid derivatives and allophenylnorstatine-dimethylthioproline scaffold in HIV protease inhibitors have high efficacy in mutant HIV.
AID1350499Antiviral activity against wild-type HIV1 3B infected in human MT4 cells assessed as inhibition of virus-induced cytopathic effect after 5 days in presence of 50 % of human serum by MTT assay2018Journal of medicinal chemistry, 06-28, Volume: 61, Issue:12
Identification of Highly Potent Human Immunodeficiency Virus Type-1 Protease Inhibitors against Lopinavir and Darunavir Resistant Viruses from Allophenylnorstatine-Based Peptidomimetics with P2 Tetrahydrofuranylglycine.
AID1795265Protease Inhibition Assay from Article 10.1021/jm980637h: \\Structure-activity relationship of small-sized HIV protease inhibitors containing allophenylnorstatine.\\1999Journal of medicinal chemistry, May-20, Volume: 42, Issue:10
Structure-activity relationship of small-sized HIV protease inhibitors containing allophenylnorstatine.
AID1795271Protease Inhibition Assay from Article 10.1021/bi035701y: \\Secondary mutations M36I and A71V in the human immunodeficiency virus type 1 protease can provide an advantage for the emergence of the primary mutation D30N.\\2003Biochemistry, Dec-30, Volume: 42, Issue:51
Secondary mutations M36I and A71V in the human immunodeficiency virus type 1 protease can provide an advantage for the emergence of the primary mutation D30N.
AID1795273Protease Inhibition Assay from Article 10.1128/aac.37.4.810: \\In vitro anti-human immunodeficiency virus (HIV) activities of transition state mimetic HIV protease inhibitors containing allophenylnorstatine.\\1993Antimicrobial agents and chemotherapy, Apr, Volume: 37, Issue:4
In vitro anti-human immunodeficiency virus (HIV) activities of transition state mimetic HIV protease inhibitors containing allophenylnorstatine.
AID1811Experimentally measured binding affinity data derived from PDB1995Structure (London, England : 1993), Jun-15, Volume: 3, Issue:6
Structure of HIV-1 protease with KNI-272, a tight-binding transition-state analog containing allophenylnorstatine.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB1995Structure (London, England : 1993), Jun-15, Volume: 3, Issue:6
Structure of HIV-1 protease with KNI-272, a tight-binding transition-state analog containing allophenylnorstatine.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (57)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's36 (63.16)18.2507
2000's18 (31.58)29.6817
2010's3 (5.26)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: 10.02

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 Index10.02 (24.57)
Research Supply Index4.13 (2.92)
Research Growth Index4.15 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.02)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (5.17%)5.53%
Reviews3 (5.17%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other52 (89.66%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
acetone
methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).		2.0210ketone body;
methyl ketone;
propanones;
volatile organic compound		EC 3.5.1.4 (amidase) inhibitor;
human metabolite;
polar aprotic solvent
carbamates
[no description available]		2.3920amino-acid anion
dimethyl sulfoxide
Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.		2.0210sulfoxide;
volatile organic compound		alkylating agent;
antidote;
Escherichia coli metabolite;
geroprotector;
MRI contrast agent;
non-narcotic analgesic;
polar aprotic solvent;
radical scavenger
hydrogen
Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.		1.9810elemental hydrogen;
elemental molecule;
gas molecular entity		antioxidant;
electron donor;
food packaging gas;
fuel;
human metabolite
methanol
Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.		2.0210alkyl alcohol;
one-carbon compound;
primary alcohol;
volatile organic compound		amphiprotic solvent;
Escherichia coli metabolite;
fuel;
human metabolite;
mouse metabolite;
Mycoplasma genitalium metabolite
urea
pseudourea: clinical use; structure. isourea : A carboximidic acid that is the imidic acid tautomer of urea, H2NC(=NH)OH, and its hydrocarbyl derivatives.		2.6830isourea;
monocarboxylic acid amide;
one-carbon compound		Daphnia magna metabolite;
Escherichia coli metabolite;
fertilizer;
flour treatment agent;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
diazepam
Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.		1.99101,4-benzodiazepinone;
organochlorine compound		anticonvulsant;
anxiolytic drug;
environmental contaminant;
sedative;
xenobiotic
disopyramide
Disopyramide: A class I anti-arrhythmic agent (one that interferes directly with the depolarization of the cardiac membrane and thus serves as a membrane-stabilizing agent) with a depressant action on the heart similar to that of guanidine. It also possesses some anticholinergic and local anesthetic properties.. disopyramide : A monocarboxylic acid amide that is butanamide substituted by a diisopropylamino group at position 4, a phenyl group at position 2 and a pyridin-2-yl group at position 2. It is used as a anti-arrhythmia drug.		1.9910monocarboxylic acid amide;
pyridines;
tertiary amino compound		anti-arrhythmia drug
alanine
Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.		210alanine zwitterion;
alanine;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid		EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
fundamental metabolite
aspartic acid
Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.		1.9910aspartate family amino acid;
aspartic acid;
L-alpha-amino acid;
proteinogenic amino acid		Escherichia coli metabolite;
mouse metabolite;
neurotransmitter
valine
Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.		1.9810L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid;
valine		algal metabolite;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
Saccharomyces cerevisiae metabolite
acetone cyanohydrin
acetone cyanohydrin: RN given refers to unlabeled cpd; structure		1.9910cyanohydrin
thiazoles
[no description available]		1.98101,3-thiazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
stavudine
Stavudine: A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.. stavudine : A nucleoside analogue obtained by formal dehydration across positions 2 and 3 of thymidine. An inhibitor of HIV-1 reverse transcriptase		3.110dihydrofuran;
nucleoside analogue;
organic molecular entity		antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
dithiothreitol
1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.		2101,4-dimercaptobutane-2,3-diol;
butanediols;
dithiol;
glycol;
thiol		chelator;
human metabolite;
reducing agent
zalcitabine
Zalcitabine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. 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 at low concentrations, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal toxic side effect is axonal degeneration resulting in peripheral neuropathy.. zalcitabine : A pyrimidine 2',3'-dideoxyribonucleoside compound having cytosine as the nucleobase.		3.520pyrimidine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
nitidine chloride
[no description available]		3.110
nigericin
Nigericin: A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus. (From Merck Index, 11th ed). nigericin : A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus.		3.110polycyclic etherantibacterial agent;
antimicrobial agent;
bacterial metabolite;
potassium ionophore
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.		4.4770azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
lamivudine
[no description available]		3.110monothioacetal;
nucleoside analogue;
oxacycle;
primary alcohol		allergen;
anti-HBV agent;
antiviral drug;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor;
HIV-1 reverse transcriptase inhibitor;
prodrug
nelfinavir
Nelfinavir: A potent HIV protease inhibitor. It is used in combination with other antiviral drugs in the treatment of HIV in both adults and children.. nelfinavir : An aryl sulfide that is used (as its mesylate salt) for treatment of HIV and also exhibits some anticancer properties.		2.7230aryl sulfide;
benzamides;
organic heterobicyclic compound;
phenols;
secondary alcohol;
tertiary amino compound		antineoplastic agent;
HIV protease inhibitor
calanolide a
calanolide A: NSC 661122 and costatolide are isomers; a novel HIV-inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerum (Clusiaceae); structure in first source. (+)-calanolide A : An organic heterotetracyclic compound that is 11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one substituted by a hydroxy group at position 12, methyl groups at positions 6, 6, 10 and 11 and a propyl group at position 4 (the 10R,11S,12S stereoisomer). Isolated from Calophyllum lanigerum var austrocoriaceum and Calophyllum brasiliense, it exhibits potent activity against HIV-1 reverse transcriptase.		3.110cyclic ether;
delta-lactone;
organic heterotetracyclic compound;
secondary alcohol		HIV-1 reverse transcriptase inhibitor;
plant metabolite
abbott 77003
Abbott 77003: a symmetry-based inhibitor of HIV-1 protease		1.9810
kni 102
KNI 102: structure given in first source		1.9810peptide
kynostatin 227
kynostatin 227: structure given in first source; contains allophenylnorstatine as a transition-state mimic		4.4870
amprenavir
[no description available]		1.9910carbamate ester;
sulfonamide;
tetrahydrofuryl ester		antiviral drug;
HIV protease inhibitor
lodenosine
lodenosine: anti-HIV nucleoside analog, the flourine atom on lodenosine is located at 2-arabinoside location, while 2'-fluoro-2',3'-dideoxyadenosine has the flourine residue at the 2-ribose sugar location		3.110
dmp 323
(4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-bis[4-(hydroxymethyl)benzyl]-1,3-diazepan-2-one : A 1,3-diazepanone ring with two 4-(hydroxymethyl)benzyl groups as substituents at positions N-1 and N-4, two benzyl groups at C-4 and C-7, and two hydroxy groups at C-5 and C-6 respectively.		1.9910diazepanone;
ureas		anti-HIV agent;
metabolite
lopinavir
[no description available]		2.4820amphetamines;
dicarboxylic acid diamide		anticoronaviral agent;
antiviral drug;
HIV protease inhibitor
3-amino-2-hydroxy-4-phenylbutanoic acid
[no description available]		4.3460
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.		1.9810amino 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
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.		2.1710carbamate ester;
furofuran;
sulfonamide		antiviral drug;
HIV protease inhibitor
sc 52151
SC 52151: HIV protease inhibitor containing the (hydroxylethyl)urea isostere; R-isomer is 1700 times more active than S-isomer		1.9810asparagine derivative
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.		3.39701,3-thiazoles;
carbamate ester;
carboxamide;
L-valine derivative;
ureas		antiviral drug;
environmental contaminant;
HIV protease inhibitor;
xenobiotic
digitoxin
Digitoxin: A cardiac glycoside sometimes used in place of DIGOXIN. It has a longer half-life than digoxin; toxic effects, which are similar to those of digoxin, are longer lasting. (From Martindale, The Extra Pharmacopoeia, 30th ed, p665). digitoxin : A cardenolide glycoside in which the 3beta-hydroxy group of digitoxigenin carries a 2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl trisaccharide chain.		1.9910cardenolide glycosideEC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor
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.		3.3770L-asparagine derivative;
quinolines		antiviral drug;
HIV protease inhibitor
je 2147
[no description available]		2.7230
kni-727
KNI-727: structure in first source		210
12-deoxyphorbol 13-acetate
[no description available]		3.110phorbol estermetabolite
michellamine c
michellamine A: atropisomeric naphthylisoquinoline anti-HIV cytopathic alkaloid dimers; from tropical plant Ancistrocladus abbreviatus; structure given in first source. michellamine A : A dimeric isoquinoline alkaloid isolated from Ancistrocladus abbreviatus and has been shown to exhibit anti-HIV activity.		3.110
costatolide
(-)-calanolide B : An organic heterotetracyclic compound that is 11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2',3'-h]chromen-2-one substituted by a hydroxy group at position 12, methyl groups at positions 6, 6, 10 and 11 and a propyl group at position 4 (the 10S,11R,12S stereoisomer). Isolated from Calophyllum lanigerum var austrocoriaceum and Calophyllum brasiliense, it exhibits potent activity against HIV-1 reverse transcriptase.		3.110cyclic ether;
delta-lactone;
organic heterotetracyclic compound;
secondary alcohol		HIV-1 reverse transcriptase inhibitor;
plant metabolite
fumarprotocetraric acid
fumarprotocetraric acid: RN given refers to (E)-isomer; structure given in first source		3.110carbonyl compound
guttiferone a
guttiferone A: antibacterial from Clusiaceae family; structure in first source		3.110
indinavir sulfate
Indinavir: A potent and specific HIV protease inhibitor that appears to have good oral bioavailability.		2.6930dicarboxylic acid diamide;
N-(2-hydroxyethyl)piperazine;
piperazinecarboxamide		HIV protease inhibitor
cysteine
Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.		210cysteiniumfundamental metabolite
pepstatin
pepstatin: inhibits the aspartic protease endothiapepsin		3.110pentapeptide;
secondary carboxamide		bacterial metabolite;
EC 3.4.23.* (aspartic endopeptidase) inhibitor
indigo carmine
3,5-di-O-(E)-caffeoylquinic acid: from roots of Lychnophora ericoides; structure in first source. 3,5-di-O-caffeoyl quinic acid : A carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities.		3.110
kni 10006
[no description available]		2.0310
warfarin
Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.		2.3920benzenes;
hydroxycoumarin;
methyl ketone
mvt 101
MVT 101: peptide inhibitor		210
didanosine
Didanosine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite.. didanosine : A purine 2',3'-dideoxyribonucleoside that is inosine in which the hydroxy groups at both the 2' and the 3' positions on the sugar moiety have been replaced by hydrogen. An antiviral drug, it is used as a medication to treat HIV/AIDS.		3.7830purine 2',3'-dideoxyribonucleosideantimetabolite;
antiviral drug;
EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor;
geroprotector;
HIV-1 reverse transcriptase inhibitor
conocurvone
conocurvone: a trimeric naphthoquinone derivative; extracted from Conospermum incurvum; structure given in first source		3.110organic heterotricyclic compound;
organooxygen compound
pyrimidinones
Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.		2.0310
ConditionIndicatedRelationship StrengthStudiesTrials
HIV
Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.		03.630
AIDS, Simian
[description not available]		02.0310
Acquired Immune Deficiency Syndrome
[description not available]		04.721
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.		04.721
HIV Coinfection
[description not available]		05.5563
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).		05.5563
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		03.3811