Compounds > 12-hydroxynevirapine
Page last updated: 2024-12-08

12-hydroxynevirapine

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

Description

## 12-Hydroxynevirapine: A Metabolite with Potential

12-Hydroxynevirapine is a **metabolite** of the antiretroviral drug **nevirapine**. It is formed in the body when nevirapine is metabolized by the liver.

**Why is it important for research?**

12-Hydroxynevirapine is gaining attention for its potential **therapeutic benefits**:

* **Antiviral activity:** Studies suggest that 12-hydroxynevirapine might possess **antiviral activity** against HIV, similar to nevirapine itself. However, its exact mechanism of action and efficacy are still being investigated.
* **Improved pharmacokinetic properties:** 12-Hydroxynevirapine could offer **improved pharmacokinetic properties** compared to nevirapine, potentially leading to better drug absorption, distribution, metabolism, and elimination. This might translate into improved efficacy and reduced side effects.
* **Overcoming drug resistance:** 12-Hydroxynevirapine could potentially **overcome drug resistance** to nevirapine. This is a significant challenge in HIV treatment, as viruses can mutate and become resistant to current medications.
* **New drug development:** 12-Hydroxynevirapine could serve as a **lead compound for the development of novel antiretroviral drugs**. By understanding its structure and mechanism of action, researchers can design new, more effective drugs with fewer side effects.

**However, research on 12-hydroxynevirapine is still in its early stages.** More studies are needed to fully understand its potential benefits and risks.

**It's important to note that:**

* 12-Hydroxynevirapine is not currently available as a separate drug.
* It is a metabolite of nevirapine, and its levels in the body depend on the dose and metabolism of the parent drug.
* Further research is necessary to establish its safety and efficacy for clinical use.

**In summary, 12-hydroxynevirapine is a promising metabolite with potential for new therapeutic applications in the fight against HIV. However, further research is crucial to confirm its benefits and ensure its safe and effective use.**

12-hydroxynevirapine : A dipyridodiazepine that is nevirapine in which one of the hydrogens of the methyl group has been substituted by a hydroxy group. It is a metabolite of the anti-HIV drug, nevirapine. [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]

Cross-References

ID SourceID
PubMed CID453338
CHEMBL ID39343
CHEBI ID145206
SCHEMBL ID8888369

Synonyms (34)

Synonym
bdbm1577
nevirapin 4-substituted deriv. 2
2-cyclopropyl-7-(hydroxymethyl)-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one
chembl39343 ,
133627-24-4
11-cyclopropyl-4-(hydroxymethyl)-5h-dipyrido[[?],[?]][1,4]diazepin-6-one
n11-cyclopropyl-4-hydroxymethyl-5,11-dihydro-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one
12-hydroxy-nvp
12-hydroxy-nevirapine
11-cyclopropyl-4-(hydroxymethyl)-5,11-dihydro-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one
12-hydroxynevirapine
CHEBI:145206
11-cyclopropyl-4-(hydroxymethyl)-5h-dipyrido[2,3-e:2',3'-f][1,4]diazepin-6-one
n(11)-cyclopropyl-4-hydroxymethyl-5,11-dihydro-6h-dipyrido(3,2-b:2,3-e)(1,4)diazepin-6-one
12-oh-nvp
n11-cyclopropyl-4-hydroxymethyl-5,11-dihydro-6h-dipyrido(3,2-b:2,3-e)(1,4)diazepin-6-one
12-hydroxy nevirapine
n11-cyclopropyl-4-hydroxymethyl-5,11-dihydro-6h-dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-one
unii-y6l0287cm4
y6l0287cm4 ,
SCHEMBL8888369
11-cyclopropyl-5,11-dihydro-4-hydroxymethyl-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one
SEBABOMFNCVZGF-UHFFFAOYSA-N
11-cyclopropyl-5,11-dihydro-4-(hydroxymethyl)-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one
DTXSID90158261
2-cyclopropyl-7-(hydroxymethyl)-2,4,9,15-tetraazatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-10-one
AKOS030241452
2-cyclopropyl-7-(hydroxymethyl)-2,4,9,15-tetrazatricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-10-one
6h-dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-one, 11-cyclopropyl-5,11-dihydro-4-(hydroxymethyl)-
11-cyclopropyl-5,11-dihydro-4-(hydroxymethyl)-6h-dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-one
nevirapine metabolite m5
CS-0646374
STARBLD0035142
HY-148642
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
drug metabolitenull
[role 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]

Drug Classes (3)

ClassDescription
cyclopropanesCyclopropane and its derivatives formed by substitution.
dipyridodiazepineAn organic heterotricyclic compound whose skeleton consists of a diazepine ring which is fused to two pyridine rings.
aromatic primary alcoholAny primary alcohol in which the alcoholic hydroxy group is attached to a carbon which is itself bonded to an aromatic ring.
[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]

Pathways (1)

PathwayProteinsCompounds
Nevirapine Metabolism Pathway821

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Gag-Pol polyproteinHuman immunodeficiency virus type 1 BH10IC50 (µMol)3.00000.08001.71283.9300AID1795327
Reverse transcriptase/RNaseH Human immunodeficiency virus 1IC50 (µMol)3.00000.00011.076810.0000AID197775; AID197946; AID198067
[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)
Reverse transcriptase/RNaseH Human immunodeficiency virus 1Activity3.00000.00091.30738.0000AID199980
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID198067Inhibition of HIV-1 reverse transcriptase at 37 degree Centigrade2001Journal of medicinal chemistry, Jan-18, Volume: 44, Issue:2
Estimation of binding affinities for HEPT and nevirapine analogues with HIV-1 reverse transcriptase via Monte Carlo simulations.
AID199980Inhibitory activity against human immunodeficiency virus type 1 reverse transcriptase (HIV-1 RT)2002Journal of medicinal chemistry, Jul-04, Volume: 45, Issue:14
Prediction of activity for nonnucleoside inhibitors with HIV-1 reverse transcriptase based on Monte Carlo simulations.
AID1654202Drug level in C57BL/6J mouse primary hepatocytes treated with 10 uM NVP assessed as Cytochrome P450-mediated compound formation incubated for 24 hrs by uHPLC-MS analysis2020Journal of medicinal chemistry, 06-25, Volume: 63, Issue:12
Twelfth-Position Deuteration of Nevirapine Reduces 12-Hydroxy-Nevirapine Formation and Nevirapine-Induced Hepatocyte Death.
AID198746In vitro inhibitory activity against human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) at a concentration of 10 ug/mL.1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Novel non-nucleoside inhibitors of HIV-1 reverse transcriptase. 1. Tricyclic pyridobenzo- and dipyridodiazepinones.
AID198758Percent inhibitory activity against wild type (WT) HIV type I reverse transcriptase at a concentration of 1 uM1995Journal of medicinal chemistry, Nov-24, Volume: 38, Issue:24
Novel non-nucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. 5. 4-Substituted and 2,4-disubstituted analogs of nevirapine.
AID198756Percent inhibitory activity against Y181C HIV type I reverse transcriptase at a concentration of 1 uM1995Journal of medicinal chemistry, Nov-24, Volume: 38, Issue:24
Novel non-nucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. 5. 4-Substituted and 2,4-disubstituted analogs of nevirapine.
AID197946In vitro inhibitory activity against human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT)1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Novel non-nucleoside inhibitors of HIV-1 reverse transcriptase. 1. Tricyclic pyridobenzo- and dipyridodiazepinones.
AID197775Compound was evaluated for inhibition of WT HIV type I reverse transcriptase.1995Journal of medicinal chemistry, Nov-24, Volume: 38, Issue:24
Novel non-nucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. 5. 4-Substituted and 2,4-disubstituted analogs of nevirapine.
AID1795327HIV-1 RT Assay from Article 10.1021/jm00024a011: \\Novel non-nucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. 5. 4-Substituted and 2,4-disubstituted analogs of nevirapine.\\1995Journal of medicinal chemistry, Nov-24, Volume: 38, Issue:24
Novel non-nucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. 5. 4-Substituted and 2,4-disubstituted analogs of nevirapine.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (40.00)18.2507
2000's2 (40.00)29.6817
2010's0 (0.00)24.3611
2020's1 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.58

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 Index12.58 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.58)

All Compounds (24.57)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
nevirapine
Nevirapine: A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV INFECTIONS and AIDS.. nevirapine : A dipyridodiazepine that is 5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine which is substituted by methyl, oxo, and cyclopropyl groups at positions 4, 6, and 11, respectively. A non-nucleoside reverse transcriptase inhibitor with activity against HIV-1, it is used in combination with other antiretrovirals for the treatment of HIV infection.		8.1150cyclopropanes;
dipyridodiazepine		antiviral drug;
HIV-1 reverse transcriptase inhibitor
1-(ethoxymethyl)-5-isopropyl-6-(phenylsulfanyl)uracil
1-(ethoxymethyl)-5-isopropyl-6-(phenylsulfanyl)uracil : A pyrimidone that is uracil in which positions 1, 5, and 6 are substituted by ethoxymethyl, isopropyl, and phenylsulfanyl groups, respectively.		2.4120aryl sulfide;
pyrimidone
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.		1.9710azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
efavirenz
efavirenz: HIV-1 reverse transcriptase inhibitor. efavirenz : 1,4-Dihydro-2H-3,1-benzoxazin-2-one substituted at the 4 position by cyclopropylethynyl and trifluoromethyl groups (S configuration) and at the 6 position by chlorine. A non-nucleoside reverse transcriptase inhibitor with activity against HIV, it is used with other antiretrovirals for combination therapy of HIV infection.		2.0110acetylenic compound;
benzoxazine;
cyclopropanes;
organochlorine compound;
organofluorine compound		antiviral drug;
HIV-1 reverse transcriptase inhibitor
1-((2-hydroxyethoxy)methyl)-6-(phenylthio)thymine
1-[(2-hydroxyethoxy)methyl]-6-(phenylsulfanyl)thymine : A pyrimidone that is thymine which is substituted at positions 1 and 6 by a (2-hydroxyethoxy)methyl group and a phenylsulfanyl group, respectively.		2.4120aryl sulfide;
primary alcohol;
pyrimidone		antiviral drug;
HIV-1 reverse transcriptase inhibitor
5-ethyl-1-ethoxymethyl-6-(phenylthio)uracil
5-ethyl-1-ethoxymethyl-6-(phenylthio)uracil: inhibits human HIV-1; structure given in first source		2.4120
emivirine
emivirine: a non-nucleoside inhibitor of HIV-1 reverse transcriptase. emivirine : A pyrimidone that is uracil which is substituted at positions 1, 5 and 6 by ethoxymethyl, isopropyl, and benzyl groups, respectively. A non-nucleoside inhibitor of HIV-1 reverse transcriptase, emivirine was an unsuccessful experimental agent for the treatment of HIV.		2.4120pyrimidoneantiviral drug;
HIV-1 reverse transcriptase inhibitor
5-ethyl-1-benzyloxymethyl-6-(phenylthio)uracil
[no description available]		2.4120
gw420867x
GW420867X: structure in first source		2.0110
r 82150
R 82150: structure given in first source; inhibits HIV-1 replication		2.0110
r-82913
R-82913: antiviral target on reverse transcriptase of HIV-1		2.0110
r 86183
[no description available]		2.0110
nsc 629243
NSC 629243: structure given in first source; an anti-HIV drug		2.0110
hby 097
HBY 097: a quinoxaline derivative		2.0110
trovirdine
trovirdine: HIV-1 reverse transcriptase inhibitor		2.0110
uc-781
[no description available]		2.0110
ly 73497
LY 73497: HIV-1 reverse transcriptase inhibitor; structure in first source		2.0110
ConditionIndicatedRelationship StrengthStudiesTrials