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AdipoGen Life Sciences
Rilpivirine
60
CHF
CHF 60.00
In stock
AG-CR1-3750-M0055 mgCHF 60.00
AG-CR1-3750-M02525 mgCHF 240.00
| Product Details | |
|---|---|
| Synonyms | R278474; TMC278; DB08864 |
| Product Type | Chemical |
| Properties | |
| Formula |
C22H18N6 |
| MW | 366.4 |
| CAS | 500287-72-9 |
| Purity Chemicals | ≥98% (HPLC) |
| Appearance | White to off-white solid. |
| Solubility | Soluble in DMSO (25mg/ml). Warming and sonication may be needed. |
| Identity | Determined by 1H-NMR. |
| InChi Key | YIBOMRUWOWDFLG-ONEGZZNKSA-N |
| Smiles | CC1=CC(/C=C/C#N)=CC(C)=C1NC2=NC(NC3=CC=C(C=C3)C#N)=NC=C2 |
| Shipping and Handling | |
| Shipping | AMBIENT |
| Short Term Storage | +4°C |
| Long Term Storage | -20°C |
| Handling Advice | Keep cool and dry. |
| Use/Stability | Stable for at least 2 years after receipt when stored at -20°C. |
| Documents | |
| MSDS |
 Download PDF |
| Product Specification Sheet | |
| Datasheet |
Download PDF |
Description
- Rilpivirine is a non-nucleoside reverse transcriptase inhibitor (NNRTI) that inhibits growth of wild-type HIV with an EC50 value of 0.51nM. It is active against NNRTI-resistant HIV strains with EC50 values less than 1nM for L100I, K103N, V106A, G190A and G190S mutants in vitro. Rilpivirine also reduces growth of greater than 80% of 1,500 NNRTI-resistant clinical isolates (EC50s = <10nM), including strains containing up to eight resistance mutations.
- NNRTIs work by binding to and blocking HIV reverse transcriptase, which prevents HIV from replicating and lowers the amount of HIV in the blood.
- Rilpivirine is an antiviral anti-HIV drug, active against wild-type and NNRTI-resistant HIV-1 with higher potency, longer half-life and reduced side-effect profile compared with Efavirenz (Prod. No. AG-CR1-3751).
- CARD8 inflammasome senses HIV-1 protease activity. In HIV1-infected cells, CARD8 cannot detect the virus because the viral protease remains inactive as a subunit of unprocessed Gag-Pol polyprotein. HIV-1-specific non-nucleoside reverse transcriptase inhibitors (NNRTIs), such us Rilpivirine, can trigger CARD8 sensing because they bind to HIV-1 Pol and enhance intracellular Gag-Pol polyprotein dimerization, which causes premature viral protease activation. Treating HIV-1-infected macrophages and CD4+ T cells with NNRTIs leads to CARD8-mediated caspase-1 activation and pyroptotic cell death. Induction of the CARD8 inflammasome activation has led to rapid clearance of latent HIV-1 in patient CD4+ T cells after virus reactivation.
Product References
- Synthesis of novel diarylpyrimidine analogues and their antiviral activity against human immunodeficiency virus type 1: J. Guillemont, et al.; J. Med. Chem. 48, 2072 (2005)
- 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): P.A. Janssen, et al.; J. Med. Chem. 48, 1901 (2005) (Review)
- Short-term antiviral activity of TMC278 -a novel NNRTI- in treatment-naive HIV-1-infected subjects: F. Goebel, et al.; AIDS 20, 1721 (2006)
- Rilpivirine: A novel non-nucleoside reverse transcriptase inhibitor: L. Garvey & A. Winston; Expert Opin. Drug Discov. 18, 1035 (2009)
- TMC278, a next-generation nonnucleoside reverse transcriptase inhibitor (NNRTI), active against wild-type and NNRTI-resistant HIV-1: H. Azijn, et al.; Antimicrob. Agents Chemother. 54, 718 (2010)
- Rilpivirine, a novel non-nucleoside reverse transcriptase inhibitor for the management of HIV-1 infection: a systematic review: J.J. Schafer & W.R. Short; Antivir. Ther. 17, 1495 (2012) (Review)
- Biochemical Mechanism of HIV-1 Resistance to Rilpivirine: K. Singh, et al.; J. Biol. Chem. 287, 38110 (2012)
- Preexisting mutations in the rilpivirine Phase III trials ECHO and THRIVE: prevalence and impact on virologic response: J. Vingerhoets, et al.; Antivir. Ther. 18, 253 (2013)
- A mature macrophage is a principal HIV-1 cellular reservoir in humanized mice after treatment with long acting antiretroviral therapy: M. Arainga, et al.; Retrovirology 14, 17 (2017)
- CARD8 is an inflammasome sensor for HIV-1 protease activity: Q. Wang, et al.; Science 371, 6535 (2021)
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