Page last updated: 2024-12-08

8-hydroxyefavirenz

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

Cross-References

ID SourceID
PubMed CID487643
CHEMBL ID1309
MeSH IDM0571211

Synonyms (27)

Synonym
(4s)-6-chloro-4-(2-cyclopropylethynyl)-8-hydroxy-4-(trifluoromethyl)-1h-3,1-benzoxazin-2-one
2h-3,1-benzoxazin-2-one, 6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-8-hydroxy-4-(trifluoromethyl)-, (4s)-
bdbm50097571
(s)-6-chloro-4-cyclopropylethynyl-8-hydroxy-4-trifluoromethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one
8-hydroxyefavirenz
CHEMBL1309 ,
205754-33-2
P8S49CKH6L ,
8-hydroxy efavirenz
8-oh efavirenz
8-oh efv
8-hydroxy efv
6-chloro-4-(cyclopropylethynyl)-8-hydroxy-4-(trifluoromethyl)-1,4-dihydro-2h-3,1-benzoxazin-2-one
unii-p8s49ckh6l
8-hydroxy-efavirenz-glucuronide
8-hydroxy-efavirenz
AKOS030255837
DTXSID50942769
6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-4h-3,1-benzoxazine-2,8-diol
2h-3,1-benzoxazin-2-one,6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-8-hydroxy-4-(trifluoromethyl)-, (4s)-
Q27286382
A935414
(4s)-6-chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-8-hydroxy-4-(trifluoromethyl)-2h-3,1-benzoxazin-2-one
HY-137397
CS-0138367
oovompcqlmfedt-zdusscgksa-n
PD117321

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"Efavirenz is an anti-HIV drug that presents relevant short- and long-term central nervous system adverse reactions."( Unmasking efavirenz neurotoxicity: Time matters to the underlying mechanisms.
Antunes, AMM; Cipriano, M; Diogo, LN; Grilo, NM; João Correia, M; Matilde Marques, M; Miranda, JP; Monteiro, EC; Pereira, SA; Serpa, J, 2017
)
0.46

Pharmacokinetics

ExcerptReferenceRelevance
" A population pharmacokinetic (PK) model was developed from a randomized, cross-over, drug-interaction study in healthy male Korean subjects (n = 17)."( Population pharmacogenetic-based pharmacokinetic modeling of efavirenz, 7-hydroxy- and 8-hydroxyefavirenz.
Abdelhady, AM; Desta, Z; Jiang, F; Overholser, BR; Shin, JG; Yeo, CW, 2014
)
0.63

Dosage Studied

ExcerptRelevanceReference
" The developed model may serve as the foundation for further exploration of pharmacogenetic-based dosing of EFV."( Population pharmacogenetic-based pharmacokinetic modeling of efavirenz, 7-hydroxy- and 8-hydroxyefavirenz.
Abdelhady, AM; Desta, Z; Jiang, F; Overholser, BR; Shin, JG; Yeo, CW, 2014
)
0.63
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pathways (1)

PathwayProteinsCompounds
Efavirenz Pathway, Pharmacokinetics83

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1IC50 (µMol)2.34100.00011.076810.0000AID198237
[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)
Cholesterol 24-hydroxylaseHomo sapiens (human)Kd7.30000.05002.00005.0000AID1653622; AID1653623
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
protein localization to membrane raftCholesterol 24-hydroxylaseHomo sapiens (human)
bile acid biosynthetic processCholesterol 24-hydroxylaseHomo sapiens (human)
cholesterol catabolic processCholesterol 24-hydroxylaseHomo sapiens (human)
xenobiotic metabolic processCholesterol 24-hydroxylaseHomo sapiens (human)
nervous system developmentCholesterol 24-hydroxylaseHomo sapiens (human)
sterol metabolic processCholesterol 24-hydroxylaseHomo sapiens (human)
progesterone metabolic processCholesterol 24-hydroxylaseHomo sapiens (human)
regulation of long-term synaptic potentiationCholesterol 24-hydroxylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
iron ion bindingCholesterol 24-hydroxylaseHomo sapiens (human)
steroid hydroxylase activityCholesterol 24-hydroxylaseHomo sapiens (human)
heme bindingCholesterol 24-hydroxylaseHomo sapiens (human)
cholesterol 24-hydroxylase activityCholesterol 24-hydroxylaseHomo sapiens (human)
testosterone 16-beta-hydroxylase activityCholesterol 24-hydroxylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
endoplasmic reticulumCholesterol 24-hydroxylaseHomo sapiens (human)
endoplasmic reticulum membraneCholesterol 24-hydroxylaseHomo sapiens (human)
dendriteCholesterol 24-hydroxylaseHomo sapiens (human)
presynapseCholesterol 24-hydroxylaseHomo sapiens (human)
postsynapseCholesterol 24-hydroxylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (32)

Assay IDTitleYearJournalArticle
AID1653619Activation of recombinant human C-terminal 4His-tagged CYP46A1 delta(2 to 50) mutant expressed in Escherichia coli at 20 uM using cholesterol as substrate measured after 30 mins in presence of cytochrome P450 oxidoreductase by gas chromatography-mass spec2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
In Vitro Activation of Cytochrome P450 46A1 (CYP46A1) by Efavirenz-Related Compounds.
AID1220388Drug metabolism of the compound assessed as CYP1A1 (unknown origin)-mediated formation of dihydroxylated metabolites with retention time of 1.56 mins at 5 uM by UPLC-MS/MS analysis2013Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2
Compartmentalization and antiviral effect of efavirenz metabolites in blood plasma, seminal plasma, and cerebrospinal fluid.
AID1220365Seminal plasma concentration in human treated with 100 mg of efavirenz administered every 4 hrs by UPLC-MS/MS analysis2013Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2
Compartmentalization and antiviral effect of efavirenz metabolites in blood plasma, seminal plasma, and cerebrospinal fluid.
AID1653625Activation of recombinant human C-terminal 4His-tagged CYP46A1 delta(2 to 50) R415A mutant expressed in Escherichia coli at 20 uM using cholesterol as substrate measured after 30 mins in presence of cytochrome P450 oxidoreductase by gas chromatography-mas2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
In Vitro Activation of Cytochrome P450 46A1 (CYP46A1) by Efavirenz-Related Compounds.
AID1653624Activation of recombinant human C-terminal 4His-tagged CYP46A1 delta(2 to 50) mutant expressed in Escherichia coli at 20 uM using cholesterol as substrate measured after 30 mins in presence of cytochrome P450 oxidoreductase and L-Glu by gas chromatography2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
In Vitro Activation of Cytochrome P450 46A1 (CYP46A1) by Efavirenz-Related Compounds.
AID1220369Fraction unbound in human seminal plasma treated with 100 mg of efavirenz administered every 4 hrs by ultrafiltration method2013Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2
Compartmentalization and antiviral effect of efavirenz metabolites in blood plasma, seminal plasma, and cerebrospinal fluid.
AID1653623Binding affinity to recombinant human C-terminal 4His-tagged CYP46A1 delta(2 to 50) mutant expressed in Escherichia coli in presence of substrate by UV-spectrophotometric method2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
In Vitro Activation of Cytochrome P450 46A1 (CYP46A1) by Efavirenz-Related Compounds.
AID1220371Blood plasma protein binding in human treated with 100 mg of efavirenz administered every 4 hrs by ultrafiltration method2013Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2
Compartmentalization and antiviral effect of efavirenz metabolites in blood plasma, seminal plasma, and cerebrospinal fluid.
AID1220387Drug metabolism of the compound assessed as CYP2B6 (unknown origin)-mediated formation of dihydroxylated metabolites with retention time of 1.56 mins at 5 uM by UPLC-MS/MS analysis2013Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2
Compartmentalization and antiviral effect of efavirenz metabolites in blood plasma, seminal plasma, and cerebrospinal fluid.
AID1653628Activation of recombinant human C-terminal 4His-tagged CYP46A1 delta(2 to 50) F416A mutant expressed in Escherichia coli at 20 uM using cholesterol as substrate measured after 30 mins in presence of cytochrome P450 oxidoreductase by gas chromatography-mas2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
In Vitro Activation of Cytochrome P450 46A1 (CYP46A1) by Efavirenz-Related Compounds.
AID1220364Blood plasma concentration in human treated with 100 mg of efavirenz administered every 4 hrs by UPLC-MS/MS analysis2013Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2
Compartmentalization and antiviral effect of efavirenz metabolites in blood plasma, seminal plasma, and cerebrospinal fluid.
AID1653632Activation of recombinant human C-terminal 4His-tagged CYP46A1 delta(2 to 50) Y427F mutant expressed in Escherichia coli at 20 uM using cholesterol as substrate measured after 30 mins in presence of cytochrome P450 oxidoreductase by gas chromatography-mas2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
In Vitro Activation of Cytochrome P450 46A1 (CYP46A1) by Efavirenz-Related Compounds.
AID1653627Activation of recombinant human C-terminal 4His-tagged CYP46A1 delta(2 to 50) K358A mutant expressed in Escherichia coli at 20 uM using cholesterol as substrate measured after 30 mins in presence of cytochrome P450 oxidoreductase by gas chromatography-mas2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
In Vitro Activation of Cytochrome P450 46A1 (CYP46A1) by Efavirenz-Related Compounds.
AID1653620Inhibition of recombinant human C-terminal 4His-tagged CYP46A1 delta(2 to 50) mutant expressed in Escherichia coli at 60 to 100 uM using cholesterol as substrate measured after 30 mins in presence of cytochrome P450 oxidoreductase by gas chromatography-ma2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
In Vitro Activation of Cytochrome P450 46A1 (CYP46A1) by Efavirenz-Related Compounds.
AID1653631Activation of recombinant human C-terminal 4His-tagged CYP46A1 delta(2 to 50) K358L mutant expressed in Escherichia coli at 20 uM using cholesterol as substrate measured after 30 mins in presence of cytochrome P450 oxidoreductase by gas chromatography-mas2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
In Vitro Activation of Cytochrome P450 46A1 (CYP46A1) by Efavirenz-Related Compounds.
AID1653630Activation of recombinant human C-terminal 4His-tagged CYP46A1 delta(2 to 50) K358R mutant expressed in Escherichia coli at 20 uM using cholesterol as substrate measured after 30 mins in presence of cytochrome P450 oxidoreductase by gas chromatography-mas2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
In Vitro Activation of Cytochrome P450 46A1 (CYP46A1) by Efavirenz-Related Compounds.
AID1653618Activation of recombinant human C-terminal 4His-tagged CYP46A1 delta(2 to 50) mutant expressed in Escherichia coli using cholesterol as substrate measured after 30 mins in presence of cytochrome P450 oxidoreductase by gas chromatography-mass spectrometry2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
In Vitro Activation of Cytochrome P450 46A1 (CYP46A1) by Efavirenz-Related Compounds.
AID1653626Activation of recombinant human C-terminal 4His-tagged CYP46A1 delta(2 to 50) F405A mutant expressed in Escherichia coli at 20 uM using cholesterol as substrate measured after 30 mins in presence of cytochrome P450 oxidoreductase by gas chromatography-mas2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
In Vitro Activation of Cytochrome P450 46A1 (CYP46A1) by Efavirenz-Related Compounds.
AID1220376Drug metabolism in human liver microsomes assessed as formation of metabolites with retention time of 1.92 mins at 20 uM by UPLC-MS/MS analysis2013Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2
Compartmentalization and antiviral effect of efavirenz metabolites in blood plasma, seminal plasma, and cerebrospinal fluid.
AID166708Inhibitory activity against RNA2001Bioorganic & medicinal chemistry letters, Mar-12, Volume: 11, Issue:5
Synthesis and biological activities of potential metabolites of the non-nucleoside reverse transcriptase inhibitor efavirenz.
AID1220386Drug metabolism in human liver microsomes assessed as formation of metabolites with retention time of 1.73 mins at 20 uM by UPLC-MS/MS analysis2013Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2
Compartmentalization and antiviral effect of efavirenz metabolites in blood plasma, seminal plasma, and cerebrospinal fluid.
AID1220382Antiviral activity against HIV1 expressing Env-green fluorescent fusion protein infected in PBMC assessed as inhibition of viral activity after 72 hrs by flow cytometry analysis2013Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2
Compartmentalization and antiviral effect of efavirenz metabolites in blood plasma, seminal plasma, and cerebrospinal fluid.
AID1220378Drug metabolism of the compound assessed as CYP1A1 (unknown origin)-mediated formation of dihydroxylated metabolites with retention time of 1.73 mins at 5 uM by UPLC-MS/MS analysis2013Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2
Compartmentalization and antiviral effect of efavirenz metabolites in blood plasma, seminal plasma, and cerebrospinal fluid.
AID1220377Drug metabolism of the compound assessed as CYP2B6 (unknown origin)-mediated formation of dihydroxylated metabolites with retention time of 1.73 mins at 5 uM by UPLC-MS/MS analysis2013Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2
Compartmentalization and antiviral effect of efavirenz metabolites in blood plasma, seminal plasma, and cerebrospinal fluid.
AID1653622Binding affinity to recombinant human C-terminal 4His-tagged CYP46A1 delta(2 to 50) mutant expressed in Escherichia coli in absence of substrate by UV-spectrophotometric method2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
In Vitro Activation of Cytochrome P450 46A1 (CYP46A1) by Efavirenz-Related Compounds.
AID198237Inhibitory activity against HIV-1 reverse transcriptase2001Bioorganic & medicinal chemistry letters, Mar-12, Volume: 11, Issue:5
Synthesis and biological activities of potential metabolites of the non-nucleoside reverse transcriptase inhibitor efavirenz.
AID1220380Drug metabolism of the compound assessed as CYP2B6 (unknown origin)-mediated formation of metabolites with retention time of 1.92 mins at 5 uM by UPLC-MS/MS analysis2013Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2
Compartmentalization and antiviral effect of efavirenz metabolites in blood plasma, seminal plasma, and cerebrospinal fluid.
AID1220366Drug level in human cerebrospinal fluid treated with 100 mg of efavirenz administered every 4 hrs by UPLC-MS/MS analysis2013Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2
Compartmentalization and antiviral effect of efavirenz metabolites in blood plasma, seminal plasma, and cerebrospinal fluid.
AID1653629Activation of recombinant human C-terminal 4His-tagged CYP46A1 delta(2 to 50) Y427A mutant expressed in Escherichia coli at 20 uM using cholesterol as substrate measured after 30 mins in presence of cytochrome P450 oxidoreductase by gas chromatography-mas2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
In Vitro Activation of Cytochrome P450 46A1 (CYP46A1) by Efavirenz-Related Compounds.
AID1220379Ratio of drug level in seminal plasma to blood plasma in human at 100 mg administered every 4 hrs by UPLC-MS/MS analysis2013Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2
Compartmentalization and antiviral effect of efavirenz metabolites in blood plasma, seminal plasma, and cerebrospinal fluid.
AID1220373Seminal plasma protein binding in human treated with 100 mg of efavirenz administered every 4 hrs by ultrafiltration method2013Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2
Compartmentalization and antiviral effect of efavirenz metabolites in blood plasma, seminal plasma, and cerebrospinal fluid.
AID1220375Drug metabolism in human liver microsomes assessed as formation of dihydroxylated metabolites with retention time of 1.56 mins at 20 uM by UPLC-MS/MS analysis2013Drug metabolism and disposition: the biological fate of chemicals, Feb, Volume: 41, Issue:2
Compartmentalization and antiviral effect of efavirenz metabolites in blood plasma, seminal plasma, and cerebrospinal fluid.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (15)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (6.67)29.6817
2010's13 (86.67)24.3611
2020's1 (6.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 13.08

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 Index13.08 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index5.97 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.08)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (13.33%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other13 (86.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]