Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H19N5.ClH |
Molecular Weight | 365.859 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC1=CC(C)=C(NC2=NC(NC3=CC=C(C=C3)C#N)=NC=C2)C(C)=C1
InChI
InChIKey=RHIYZDNOTUMYCA-UHFFFAOYSA-N
InChI=1S/C20H19N5.ClH/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);1H
Molecular Formula | C20H19N5 |
Molecular Weight | 329.3984 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|
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 |
|
TMC125, a novel next-generation nonnucleoside reverse transcriptase inhibitor active against nonnucleoside reverse transcriptase inhibitor-resistant human immunodeficiency virus type 1. | 2004 Dec |
|
In vitro evaluation of nonnucleoside reverse transcriptase inhibitors UC-781 and TMC120-R147681 as human immunodeficiency virus microbicides. | 2004 Jan |
|
A series of diaryltriazines and diarylpyrimidines are highly potent nonnucleoside reverse transcriptase inhibitors with possible applications as microbicides. | 2004 Oct |
|
In search of a novel anti-HIV drug: multidisciplinary coordination in the discovery of 4-[[4-[[4-[(1E)-2-cyanoethenyl]-2,6-dimethylphenyl]amino]-2- pyrimidinyl]amino]benzonitrile (R278474, rilpivirine). | 2005 Mar 24 |
|
Potent nonnucleoside reverse transcriptase inhibitors target HIV-1 Gag-Pol. | 2006 Nov |
|
Inhibition of HIV-1 by non-nucleoside reverse transcriptase inhibitors via an induced fit mechanism-Importance of slow dissociation and relaxation rates for antiviral efficacy. | 2010 Oct 15 |
|
Synthesis, evaluation and structure-activity relationships of triazine dimers as novel antiviral agents. | 2012 Dec 1 |
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.
Substance Class |
Chemical
Created
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Record UNII |
55D48BY90H
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Record Status |
Validated (UNII)
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Record Version |
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