Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H19N5 |
Molecular Weight | 329.3984 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC(C)=C(NC2=NC(NC3=CC=C(C=C3)C#N)=NC=C2)C(C)=C1
InChI
InChIKey=ILAYIAGXTHKHNT-UHFFFAOYSA-N
InChI=1S/C20H19N5/c1-13-10-14(2)19(15(3)11-13)24-18-8-9-22-20(25-18)23-17-6-4-16(12-21)5-7-17/h4-11H,1-3H3,(H2,22,23,24,25)
DescriptionCurator's Comment: Description was created using several sources including: http://www.mtnstopshiv.org/news/studies/mtn020 | https://www.ncbi.nlm.nih.gov/pubmed/14693562 | https://clinicaltrials.gov/ct2/show/NCT02010593
Curator's Comment: Description was created using several sources including: http://www.mtnstopshiv.org/news/studies/mtn020 | https://www.ncbi.nlm.nih.gov/pubmed/14693562 | https://clinicaltrials.gov/ct2/show/NCT02010593
Dapivirine, an anti-retroviral (ARV)-based microbicide, is a substituted diaminopyrimidine (DAPY) derivative and a potent non-nucleoside reverse-transcriptase inhibitor (NNRTI) with antiviral activity against HIV-1. Dapivirine showed high activity against wild-type and mutant HIV in in virto HIV models inhibiting a broad panel of HIV-1 isolates from different classes, including a wide range of NNRTI-resistant isolates. Developed by Janssen Sciences (formerly Tibotec Pharmaceuticals), dapivirine was initially tested as an oral treatment for HIV in a number of Phase I/II clinical trials. In 2014 the International Partnership for Microbicides (IPM) began its work on the monthly dapivirine ring. Phase I/II clinical trials in Africa, Europe and the United States proved that dapivirine is safe and well-tolerated. Phase III long-term safety and efficacy studies of the monthly dapivirine ring as part of IPM's Dapivirine Ring Licensure Program confirmed that the monthly dapivirine ring can safely help prevent HIV infection in women. In 2016 the ASPIRE Study reported a 27 percent reduction in HIV-1 acquisition with a trend toward greater protection in women over age 21 and no significant protection for women under age 21.
Originator
Curator's Comment: In 2004, Tibotec granted International Partnership for Microbicides (IPM) a non-exclusive, royalty-free license to develop dapivirine as a microbicide for use in resource-poor countries. This agreement expanded in 2014, when Janssen granted IPM exclusive worldwide rights to dapivirine.
Approval Year
PubMed
Title | Date | PubMed |
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Correlations between factors determining the pharmacokinetics and antiviral activity of HIV-1 non-nucleoside reverse transcriptase inhibitors of the diaryltriazine and diarylpyrimidine classes of compounds. | 2004 |
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Complete inactivation of HIV-1 using photo-labeled non-nucleoside reverse transcriptase inhibitors. | 2011 Jan |
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Optimization of diarylazines as anti-HIV agents with dramatically enhanced solubility. | 2013 Sep 15 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02010593
The dapivirine matrix vaginal ring containing 25 mg of drug substance dispersed in a platinum-catalyzed-cured silicone matrix inserts once every 4 weeks in postmenopausal women over 12 weeks of product use.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14693562
A 24-h treatment with 100 nM TMC120-R147681 (dapivirine) prevented cell-free HIV infection, whereas 10-fold-higher concentrations blocked cell-associated HIV when studied using monocyte-derived dendritic cells (MO-DC) and autologous CD4+ T cells, representing early targets during sexual transmission.
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WHO-ATC |
G01AX17
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NCI_THESAURUS |
C97453
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Dapivirine
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CHEMBL70663
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DB08639
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CD-16
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C73205
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214347
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DTXSID40179244
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8164
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244767-67-7
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100000174408
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ACTIVE MOIETY