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5mg |
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10mg |
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25mg |
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50mg |
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100mg |
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250mg |
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500mg |
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Other Sizes |
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Purity: ≥98%
Rilpivirine (formerly known as R278474; TMC278; DB08864; Edurant; Rekambys; Cabenuva), an approved HIV drug, is a non-nucleoside reverse transcriptase inhibitor (NNRTI) that has been widely used for the treatment of HIV-1 infection. It has to be combined with other drugs against HIV, for example, the combination of cabotegravir and rilpivirine (Cabenuva) was also approved in 2021 for treating HIV infections. Rilpivirine is a second-generation non-nucleoside reverse transcriptase inhibitor (NNRTI) with higher potency, longer half-life and reduced side-effect profile compared with older NNRTIs, such as efavirenz. Rilpivirine showed inhibitory activities to both wild-type HIV (with EC50 value of 0.51 nM) and NNRTI-resistant strains. The conformational flexibility of rilpivirine allowed it to adjust different mutations of the reverse transcriptase. For the singly mutant HIV strains such as L100I, G190S, G190A and V106A, rilpivirine showed higher retained potency than efavirenz and low EC50 values blow 1 nM.
ln Vitro |
All single and double mutants tested (EC50=0.1-2.0 nM) and wild-type HIV-1 (EC50=0.4 nM) are both susceptible to R278474's activity[1]. Within 30 days, R278474 (10-5000 nM; 30 d) does not show any indication of wild-type HIV-1 breakthrough at 1 μM[1]. At a 50% inhibitory concentration (EC50) of less than 1 nM, R278474 inhibits 81% of clinical isolates (about 1200 recombinant clinical isolates), and at an EC50 of less than 10 nM, it inhibits 94%[1]. TMC278 exhibits nanomolar EC50s (2.88-8.45 nM) against group O isolates and subnanomolar EC50s (0.07-1.01 nM) against wild-type HIV-1 group M isolates in MT4 T-cells[2].
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ln Vivo |
Rats treated with R278474 (10-160 mg/kg; po for 1 month) do not exhibit any aberrant effects, with the exception of increased liver weight and species-specific thyroid hypertrophy at higher dose levels[1]. In rats, R278474 (iv) has elimination half-lives ranging from 4.4 hours to 31 hours. In dogs, the exposure (AUCinf) is 8.7 hours per kilogram (1.25 mg/kg), 1.4 hours per kilogram (1.25 mg/kg), and 44 hours per kilogram (1.25 mg/kg) in rabbits[1]. In rats and dogs, R278474 (po) had half-live ranges of 2.8 and 39 hours, respectively, with oral bioavailability of 32% and 31%[1].
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Animal Protocol |
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References |
[1]. Janssen PAJ, et, al. 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). J Med Chem. 2005 Mar 24;48(6):1
[2]. Azijn H, et, al. TMC278, a next-generation nonnucleoside reverse transcriptase inhibitor (NNRTI), active against wild-type and NNRTI-resistant HIV-1. Antimicrob Agents Chemother. 2010 Feb;54(2):718-27. |
Molecular Formula |
C22H18N6
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Molecular Weight |
366.42
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CAS # |
500287-72-9
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SMILES |
N([H])(C1C([H])=C([H])N=C(N([H])C2C([H])=C([H])C(C#N)=C([H])C=2[H])N=1)C1C(C([H])([H])[H])=C([H])C(/C(/[H])=C(\[H])/C#N)=C([H])C=1C([H])([H])[H]
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InChi Key |
YIBOMRUWOWDFLG-ONEGZZNKSA-N
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InChi Code |
InChI=1S/C22H18N6/c1-15-12-18(4-3-10-23)13-16(2)21(15)27-20-9-11-25-22(28-20)26-19-7-5-17(14-24)6-8-19/h3-9,11-13H,1-2H3,(H2,25,26,27,28)/b4-3+
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Chemical Name |
4-{[4-({4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile
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Synonyms |
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Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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Solubility (In Vitro) |
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Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
1 mM | 2.7291 mL | 13.6455 mL | 27.2911 mL | |
5 mM | 0.5458 mL | 2.7291 mL | 5.4582 mL | |
10 mM | 0.2729 mL | 1.3646 mL | 2.7291 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.