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MedKoo Cat#: 314236 | Name: Rilpivirine free base
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rilpivirine is a pharmaceutical drug, developed by Tibotec, for the treatment of HIV infection. It 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 entered phase III clinical trials in April 2008, and was approved for use in the United States in May 2011. A fixed-dose drug combining rilpivirine with emtricitabine and tenofovir, was approved by the U.S. Food and Drug Administration in August 2011 under the brand name Complera.

Chemical Structure

Rilpivirine free base
Rilpivirine free base
CAS#500287-72-9 (free base)

Theoretical Analysis

MedKoo Cat#: 314236

Name: Rilpivirine free base

CAS#: 500287-72-9 (free base)

Chemical Formula: C22H18N6

Exact Mass: 366.1593

Molecular Weight: 366.42

Elemental Analysis: C, 72.11; H, 4.95; N, 22.94

Price and Availability

Size Price Availability Quantity
10mg USD 150.00 Ready to ship
25mg USD 250.00 Ready to ship
50mg USD 450.00 Ready to ship
100mg USD 650.00 Ready to ship
200mg USD 1,150.00 Ready to ship
500mg USD 1,950.00 Ready to ship
1g USD 3,250.00 Ready to ship
2g USD 5,650.00 Ready to ship
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Related CAS #
700361-47-3 (HCl) 500287-72-9 (free base)
Synonym
TMC278; TMC278; TMC 278; Rilpivirine; Edurant.
IUPAC/Chemical Name
4-{[4-({4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile
InChi Key
YIBOMRUWOWDFLG-ONEGZZNKSA-N
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+
SMILES Code
N#CC1=CC=C(NC2=NC=CC(NC3=C(C)C=C(/C=C/C#N)C=C3C)=N2)C=C1
Appearance
Off-white to grey solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Related CAS# 700361-47-3 (Rilpivirine HCl); 500287-72-9 (Rilpivirine free)
Biological target:
Rilpivirine is a potent and specific diarylpyrimidine (DAPY) non-nucleoside reverse transcriptase inhibitor (NNRTI) that has high antiviral activity against wild-type HIV (EC50=0.4 nM) and mutant viruses (EC50=0.1-2.0 nM).
In vitro activity:
The results from this study show that rilpivirine and estradiol either alone or in combination or pretreated with β-naphthoflavone can evoke marked effects on glycerol and cytokines levels from adipocytes. Reference: Mol Biol Rep. 2019 Jun;46(3):2643-2655. https://pubmed.ncbi.nlm.nih.gov/30927158/
In vivo activity:
This study indicates the importance of maintaining rilpivirine at a sustained threshold after HIV exposure to prevent dissemination of HIV-1 after vaginal infection and low-frequency resistance mutations conferred low-level resistance, suggesting that rilpivirine resistance is difficult to develop after HIV-1 infection during rilpivirine preexposure prophylaxis. Reference: J Virol. 2020 Mar 31;94(8):e01912-19. https://pubmed.ncbi.nlm.nih.gov/31969438/
Solvent mg/mL mM
Solubility
DMSO 50.0 136.50
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 366.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Behl S, Adem A, Hussain A, Singh J. Effects of rilpivirine, 17β-estradiol and β-naphthoflavone on the inflammatory status of release of adipocytokines in 3T3-L1 adipocytes in vitro. Mol Biol Rep. 2019 Jun;46(3):2643-2655. doi: 10.1007/s11033-019-04671-4. Epub 2019 Mar 29. PMID: 30927158. 2. Dezzutti CS, Else LJ, Yandura SE, Shetler C, Russo J, Back DJ, McGowan I. Distinct Pharmacodynamic Activity of Rilpivirine in Ectocervical and Colonic Explant Tissue. Antimicrob Agents Chemother. 2016 Apr 22;60(5):2765-70. doi: 10.1128/AAC.00167-16. PMID: 26902757; PMCID: PMC4862523. 3. Letendre SL, Mills A, Hagins D, Swindells S, Felizarta F, Devente J, Bettacchi C, Lou Y, Ford S, Sutton K, Shaik JS, Crauwels H, D'Amico R, Patel P. Pharmacokinetics and antiviral activity of cabotegravir and rilpivirine in cerebrospinal fluid following long-acting injectable administration in HIV-infected adults. J Antimicrob Chemother. 2020 Mar 1;75(3):648-655. doi: 10.1093/jac/dkz504. PMID: 31873746; PMCID: PMC7021098. 4. Melody K, Roy CN, Kline C, Cottrell ML, Evans D, Shutt K, Pennings PS, Keele BF, Bility M, Kashuba ADM, Ambrose Z. Long-Acting Rilpivirine (RPV) Preexposure Prophylaxis Does Not Inhibit Vaginal Transmission of RPV-Resistant HIV-1 or Select for High-Frequency Drug Resistance in Humanized Mice. J Virol. 2020 Mar 31;94(8):e01912-19. doi: 10.1128/JVI.01912-19. PMID: 31969438; PMCID: PMC7108851.
In vitro protocol:
1. Behl S, Adem A, Hussain A, Singh J. Effects of rilpivirine, 17β-estradiol and β-naphthoflavone on the inflammatory status of release of adipocytokines in 3T3-L1 adipocytes in vitro. Mol Biol Rep. 2019 Jun;46(3):2643-2655. doi: 10.1007/s11033-019-04671-4. Epub 2019 Mar 29. PMID: 30927158. 2. Dezzutti CS, Else LJ, Yandura SE, Shetler C, Russo J, Back DJ, McGowan I. Distinct Pharmacodynamic Activity of Rilpivirine in Ectocervical and Colonic Explant Tissue. Antimicrob Agents Chemother. 2016 Apr 22;60(5):2765-70. doi: 10.1128/AAC.00167-16. PMID: 26902757; PMCID: PMC4862523.
In vivo protocol:
1. Letendre SL, Mills A, Hagins D, Swindells S, Felizarta F, Devente J, Bettacchi C, Lou Y, Ford S, Sutton K, Shaik JS, Crauwels H, D'Amico R, Patel P. Pharmacokinetics and antiviral activity of cabotegravir and rilpivirine in cerebrospinal fluid following long-acting injectable administration in HIV-infected adults. J Antimicrob Chemother. 2020 Mar 1;75(3):648-655. doi: 10.1093/jac/dkz504. PMID: 31873746; PMCID: PMC7021098. 2. Melody K, Roy CN, Kline C, Cottrell ML, Evans D, Shutt K, Pennings PS, Keele BF, Bility M, Kashuba ADM, Ambrose Z. Long-Acting Rilpivirine (RPV) Preexposure Prophylaxis Does Not Inhibit Vaginal Transmission of RPV-Resistant HIV-1 or Select for High-Frequency Drug Resistance in Humanized Mice. J Virol. 2020 Mar 31;94(8):e01912-19. doi: 10.1128/JVI.01912-19. PMID: 31969438; PMCID: PMC7108851.
1: Serris A, Ferre VM, Le Hingrat Q, Bachelard A, Charpentier C, Exarchopoulos M, Damond F, Phung BC, Landman R, Yazdanpanah Y, Descamps D, Joly V, Peytavin G, Ghosn J. Real-world data on long-acting intramuscular maintenance therapy with cabotegravir and rilpivirine mirror Phase 3 results. J Antimicrob Chemother. 2024 Sep 17:dkae308. doi: 10.1093/jac/dkae308. Epub ahead of print. PMID: 39287977. 2: Gerstenberg J, Klinker H, Baier M, von Braun A, Seybold U, Helbig C, Däumer M, Korn K, Stephan C, Schleenvoigt BT. Therapeutic Drug Monitoring of Long- Acting Rilpivirine and Cabotegravir for Treatment of HIV-1 Infection-A Case Series of Five Patients With One Virologic Failure After Development of Two- Class Resistance. Open Forum Infect Dis. 2024 Aug 23;11(9):ofae480. doi: 10.1093/ofid/ofae480. PMID: 39286033; PMCID: PMC11403473. 3: Konishi K, Onozuka D, Okubo M, Kasamatsu Y, Kutsuna S, Shirano M. Long-acting antiretroviral therapy effectiveness and patient satisfaction using patient questionnaires: data from a real-world setting. BMC Infect Dis. 2024 Sep 16;24(1):979. doi: 10.1186/s12879-024-09904-x. PMID: 39278923; PMCID: PMC11404019. 4: McCall KL, Cabral DL, Coghlan JF, Concepcion AM, Denimarck KE, Shalumov SS. Therapeutic failure reported with HIV long-acting injectables: An analysis of the FDA Adverse Event Reporting System from 2021 to 2024. HIV Med. 2024 Sep 5. doi: 10.1111/hiv.13709. Epub ahead of print. PMID: 39234659. 5: Gutner CA, van der Valk M, Portilla J, Jeanmaire E, Belkhir L, Lutz T, DeMoor R, Trehan R, Scherzer J, Pascual-Bernáldez M, Ait-Khaled M, Hernandez B, de Ruiter A, Anand SB, Low EL, Hadi M, Barnes N, Sevdalis N, Mohammed P, Czarnogorski M. Patient Participant Perspectives on Implementation of Long- Acting Cabotegravir and Rilpivirine: Results From the Cabotegravir and Rilpivirine Implementation Study in European Locations (CARISEL) Study. J Int Assoc Provid AIDS Care. 2024 Jan-Dec;23:23259582241269837. doi: 10.1177/23259582241269837. PMID: 39221544; PMCID: PMC11367594. 6: Muccini C, Diotallevi S, Lolatto R, Piromalli G, Spagnuolo V, Castagna A. Improvement in high-density lipoprotein cholesterol in people with HIV who switched from a tenofovir alafenamide-containing regimen to cabotegravir plus rilpivirine. Int J Antimicrob Agents. 2024 Aug 28:107312. doi: 10.1016/j.ijantimicag.2024.107312. Epub ahead of print. PMID: 39214389. 7: Agovi AM, Thompson CT, Craten KJ, Fasanmi E, Pan M, Ojha RP, Thompson EL. Patient and clinic staff perspectives on the implementation of a long-acting injectable antiretroviral therapy program in an urban safety-net health system. Implement Sci Commun. 2024 Aug 29;5(1):93. doi: 10.1186/s43058-024-00631-7. PMID: 39210473; PMCID: PMC11363636. 8: Zakumumpa H, Alinaitwe A, Kyomuhendo M, Nakazibwe B. Long-acting injectable antiretroviral treatment: experiences of people with HIV and their healthcare providers in Uganda. BMC Infect Dis. 2024 Aug 28;24(1):876. doi: 10.1186/s12879-024-09748-5. PMID: 39198739; PMCID: PMC11360315. 9: Fulco PP, Lavoie S. A6 HIV Subtype in a Pharmacist-Directed Cabotegravir/Rilpivirine Screening Protocol. AIDS Patient Care STDS. 2024 Aug 22. doi: 10.1089/apc.2024.0160. Epub ahead of print. PMID: 39172546. 10: Tao K, Zhou J, Nagarajan P, Tzou PL, Shafer RW. Comprehensive database of HIV mutations selected during antiretroviral in vitro passage experiments. Antiviral Res. 2024 Oct;230:105988. doi: 10.1016/j.antiviral.2024.105988. Epub 2024 Aug 16. PMID: 39154752. 11: Cingolani A, Tavelli A, De Benedittis S, Mastrorosa I, Muccini C, Bini T, Carraro A, Compagno M, Mazzitelli M, Guastavigna M, Cernuschi M, Torti C, Antinori A, d'Arminio Monforte A; ICONA Foundation Study group. Long-acting injectable antiretrovirals for HIV treatment in the ICONA cohort: physicians' and nurses' points of view. J Antimicrob Chemother. 2024 Aug 14:dkae273. doi: 10.1093/jac/dkae273. Epub ahead of print. PMID: 39140512. 12: Blanco-Arévalo JL, García-Deltoro M, Torralba M, Vélez-Díaz-Pallarés M, Castro A, Rubio-Rodríguez D, Rubio-Terrés C. HIV-1 resistance and virological failure to treatment with the integrase inhibitors bictegravir, cabotegravir, and dolutegravir: a systematic literature review. AIDS Rev. 2024;26(2):67-79. doi: 10.24875/AIDSRev.24000011. PMID: 39134019. 13: Luc CM, Max B, Pérez S, Herrera K, Huhn G, Dworkin MS. Acceptability of Long-Acting Cabotegravir + Rilpivirine in a Large, Urban, Ambulatory HIV Clinic. J Acquir Immune Defic Syndr. 2024 Aug 5. doi: 10.1097/QAI.0000000000003500. Epub ahead of print. PMID: 39099016. 14: Aparicio LV, García VN, Hernández-Novoa B, Casado G, Jodar F, Pinel M, Velasco DC. Potential healthcare resource use and associated costs of every 2 month injectable cabotegravir plus rilpivirine long-acting regimen implementation in the Spanish National Healthcare System compared to daily oral HIV treatments. BMC Infect Dis. 2024 Aug 2;24(1):775. doi: 10.1186/s12879-024-09595-4. PMID: 39095714; PMCID: PMC11297627. 15: Umumararungu T, Nyandwi JB, Katandula J, Twizeyimana E, Claude Tomani J, Gahamanyi N, Ishimwe N, Olawode EO, Habarurema G, Mpenda M, Uyisenga JP, Saeed SI. Current status of the small molecule anti-HIV drugs in the pipeline or recently approved. Bioorg Med Chem. 2024 Sep 1;111:117860. doi: 10.1016/j.bmc.2024.117860. Epub 2024 Jul 29. PMID: 39094527. 16: Sah S, Verma A, Zahiruddin QS, Rustagi S. Commentary on 'Multicentre service evaluation of injectable cabotegravir and rilpivirine delivery and outcomes across 12 UK clinics (SHARE LAI-net)'. HIV Med. 2024 Aug 1. doi: 10.1111/hiv.13689. Epub ahead of print. PMID: 39091145. 17: Burger D, Wttewaal E, Oosterhof P, Stalenhoef J. Concomitant use of anabolic androgen steroids and cabotegravir/rilpivirine leading to virological failure and development of two-class resistance. AIDS. 2024 Sep 1;38(11):1728-1729. doi: 10.1097/QAD.0000000000003959. Epub 2024 Aug 1. PMID: 39088831; PMCID: PMC11296267. 18: Benedicto AM, Lucantoni F, Fuster-Martínez I, Diaz-Pozo P, Dorcaratto D, Muñoz-Forner E, Victor VM, Esplugues JV, Blas-García A, Apostolova N. Interference with mitochondrial function as part of the antifibrogenic effect of Rilpivirine: A step towards novel targets in hepatic stellate cell activation. Biomed Pharmacother. 2024 Sep;178:117206. doi: 10.1016/j.biopha.2024.117206. Epub 2024 Jul 29. PMID: 39079261. 19: Adegboyega FN, Anifowose LO, Hammad SF, Ghazy MA. Repurposing Antiviral Drugs as Potential Anti-EGFR Agents in NSCLC: A Structure-Based Screening and Molecular Dynamics Analysis. Chem Biodivers. 2024 Jul 30:e202400898. doi: 10.1002/cbdv.202400898. Epub ahead of print. PMID: 39078025. 20: Ripamonti D, Borghetti A, Zazzi M. Appropriateness of virological monitoring with long-acting injectable cabotegravir and rilpivirine. J Antimicrob Chemother. 2024 Jul 27:dkae257. doi: 10.1093/jac/dkae257. Epub ahead of print. PMID: 39066658.