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

MedKoo CAT#: 314236

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

Description: 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.


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10mg
USD 150
100mg
USD 650
1g
USD 1950
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25mg
USD 250
200mg
USD 850
2g
USD 2950
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50mg
USD 450
500mg
USD 1250
5g
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Rilpivirine free base, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 314236
Name: Rilpivirine free base
CAS#: 500287-72-9 (free base)
Chemical Formula: C22H18N6
Exact Mass: 366.15929
Molecular Weight: 366.42
Elemental Analysis: C, 72.11; H, 4.95; N, 22.94


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


Technical Data

Appearance:
Off-white to grey solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

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).

Harmonized System Code:
293490


Additional Information

Related CAS#
700361-47-3 (Rilpivirine HCl);
500287-72-9 (Rilpivirine free)


References

1: Institute for Quality and Efficiency in Health Care. Rilpivirine / Emtricitabine / Tenofovir (New Therapeutic Indication) -- Benefit Assessment According to §35a Social Code Book V [Internet]. Cologne, Germany: Institute for Quality and Efficiency in Health Care (IQWiG); 2014 Mar 28. Available from http://www.ncbi.nlm.nih.gov/books/NBK385725/ PubMed PMID: 27905770.

2: Institute for Quality and Efficiency in Health Care. Rilpivirine -- Benefit Assessment According to §35a Social Code Book V [Internet]. Cologne, Germany: Institute for Quality and Efficiency in Health Care (IQWiG); 2012 Apr 12. Available from http://www.ncbi.nlm.nih.gov/books/NBK385641/ PubMed PMID: 27905736.

3: Saravanan S, Kausalya B, Gomathi S, Sivamalar S, Pachamuthu B, Poongulali S, Pradeep A, Sunil SS, Mothi SN, Smith DM, Kantor R. Etravirine and Rilpivirine drug resistance among HIV-1 subtype C infected Children failing non -nucleoside reverse transcriptase inhibitor-based regimens in South India. AIDS Res Hum Retroviruses. 2016 Nov 21. [Epub ahead of print] PubMed PMID: 27869478.

4: Di Biagio A, Riccardi N, Taramasso L, Capetti A, Cenderello G, Signori A, Vitiello P, Guerra M, de Socio GV, Cassola G, Quirino T, Viscoli C. Switch from unboosted protease inhibitor to a single-tablet regimen containing rilpivirine improves cholesterol and triglycerides. Int J Antimicrob Agents. 2016 Nov;48(5):551-554. doi: 10.1016/j.ijantimicag.2016.07.009. PubMed PMID: 27566908.

5: Aouri M, Barcelo C, Guidi M, Rotger M, Cavassini M, Hizrel C, Buclin T, Decosterd LA, Csajka C; Swiss HIV Cohort Study.. Population pharmacokinetics and pharmacogenetics analysis of Rilpivirine in HIV-1 infected individuals. Antimicrob Agents Chemother. 2016 Oct 31. pii: AAC.00899-16. [Epub ahead of print] PubMed PMID: 27799217.

6: Ogbuagu O. Rilpivirine, emtricitabine and tenofovir alafenamide: single-tablet combination for the treatment of HIV-1 infection in selected patients. Expert Rev Anti Infect Ther. 2016 Dec;14(12):1113-1126. PubMed PMID: 27797606.

7: Lombaard J, Bunupuradah T, Flynn PM, Ramapuram J, Ssali F, Crauwels H, Hoogstoel A, Van Eygen V, Stevens M. Rilpivirine as a Treatment for HIV-infected Antiretroviral-naïve Adolescents: Week 48 Safety, Efficacy, Virology and Pharmacokinetics. Pediatr Infect Dis J. 2016 Nov;35(11):1215-1221. PubMed PMID: 27294305.

8: Capetti AF, Sterrantino G, Cossu MV, Orofino G, Barbarini G, De Socio GV, Di Giambenedetto S, Di Biagio A, Celesia BM, Argenteri B, Rizzardini G. Switch to Dolutegravir plus Rilpivirine Dual Therapy in cART-Experienced Subjects: An Observational Cohort. PLoS One. 2016 Oct 14;11(10):e0164753. doi: 10.1371/journal.pone.0164753. PubMed PMID: 27741309; PubMed Central PMCID: PMC5065232.

9: Troya J, Ryan P, Ribera E, Podzamczer D, Hontañón V, Terrón JA, Boix V, Moreno S, Barrufet P, Castaño M, Carrero A, Galindo MJ, Suárez-Lozano I, Knobel H, Raffo M, Solís J, Yllescas M, Esteban H, González-García J, Berenguer J, Imaz A; GESIDA-8314 Study Group.. Abacavir/Lamivudine plus Rilpivirine Is an Effective and Safe Strategy for HIV-1 Suppressed Patients: 48 Week Results of the SIMRIKI Retrospective Study. PLoS One. 2016 Oct 11;11(10):e0164455. doi: 10.1371/journal.pone.0164455. PubMed PMID: 27727331; PubMed Central PMCID: PMC5058546.

10: Collins SE, Grant PM, Uwinkindi F, Talbot A, Seruyange E, Slamowitz D, Mugeni A, Remera E, Niyonsenga SP, Nyirimigabo J, Uwizihiwe JP, Dongier P, Muhayimpundu R, Mazarati JB, Zolopa A, Nsanzimana S. A Randomized Switch From Nevirapine-Based Antiretroviral Therapy to Single Tablet Rilpivirine/Emtricitabine/Tenofovir Disoproxil Fumarate in Virologically Suppressed Human Immunodeficiency Virus-1-Infected Rwandans. Open Forum Infect Dis. 2016 Jul 1;3(3):ofw141. PubMed PMID: 27704000; PubMed Central PMCID: PMC5047400.

11: McGowan I, Dezzutti CS, Siegel A, Engstrom J, Nikiforov A, Duffill K, Shetler C, Richardson-Harman N, Abebe K, Back D, Else L, Egan D, Khoo S, Egan JE, Stall R, Williams PE, Rehman KK, Adler A, Brand RM, Chen B, Achilles S, Cranston RD. Long-acting rilpivirine as potential pre-exposure prophylaxis for HIV-1 prevention (the MWRI-01 study): an open-label, phase 1, compartmental, pharmacokinetic and pharmacodynamic assessment. Lancet HIV. 2016 Dec;3(12):e569-e578. doi: 10.1016/S2352-3018(16)30113-8. PubMed PMID: 27658864.

12: Parsons TL, Marzinke MA. Development and validation of a liquid chromatographic-tandem mass spectrometric method for the multiplexed quantification of etravirine, maraviroc, raltegravir, and rilpivirine in human plasma and tissue. J Pharm Biomed Anal. 2016 Nov 30;131:333-344. doi: 10.1016/j.jpba.2016.08.016. PubMed PMID: 27632783.

13: Curran A, Rojas J, Cabello A, Troya J, Imaz A, Domingo P, Martinez E, Ryan P, Górgolas M, Podzamczer D, Knobel H, Gutiérrez F, Ribera E. Effectiveness and safety of an abacavir/lamivudine + rilpivirine regimen for the treatment of HIV-1 infection in naive patients. J Antimicrob Chemother. 2016 Dec;71(12):3510-3514. PubMed PMID: 27591292.

14: Prathipati PK, Mandal S, Destache CJ. Simultaneous quantification of tenofovir, emtricitabine, rilpivirine, elvitegravir and dolutegravir in mouse biological matrices by LC-MS/MS and its application to a pharmacokinetic study. J Pharm Biomed Anal. 2016 Sep 10;129:473-81. doi: 10.1016/j.jpba.2016.07.040. PubMed PMID: 27497648; PubMed Central PMCID: PMC5003708.

15: Bernaud C, Khatchatourian L, Rodallec A, Hall N, Perre P, Morrier M, Pineau S, Jovelin T, André-Garnier E, Raffi F, Allavena C. Optimizing the virological success of tenofovir DF/FTC/rilpivirine in HIV-infected naive and virologically suppressed patients through strict clinical and virological selection. Infect Dis (Lond). 2016 Oct;48(10):754-9. doi: 10.1080/23744235.2016.1194528. PubMed PMID: 27389932.

16: Hayashida T, Hachiya A, Ode H, Nishijima T, Tsuchiya K, Sugiura W, Takiguchi M, Oka S, Gatanaga H. Rilpivirine resistance mutation E138K in HIV-1 reverse transcriptase predisposed by prevalent polymorphic mutations. J Antimicrob Chemother. 2016 Oct;71(10):2760-6. doi: 10.1093/jac/dkw224. PubMed PMID: 27330069.

17: Falcon-Neyra L, Palladino C, Navarro Gómez ML, Soler-Palacín P, González-Tomé MI, De Ory SJ, Frick MA, Fortuny C, Noguera-Julian A, Moreno EB, Santos JL, Olbrich P, López-Cortés LF, Briz V, Neth O; CoRISpe working group.. Off-label use of rilpivirine in combination with emtricitabine and tenofovir in HIV-1-infected pediatric patients: A multicenter study. Medicine (Baltimore). 2016 Jun;95(24):e3842. doi: 10.1097/MD.0000000000003842. PubMed PMID: 27310962; PubMed Central PMCID: PMC4998448.

18: Lambert-Niclot S, Allavena C, Grude M, Flandre P, Sayon S, Andre E, Wirden M, Rodallec A, Jovelin T, Katlama C, Calvez V, Raffi F, Marcelin AG. Usefulness of an HIV DNA resistance genotypic test in patients who are candidates for a switch to the rilpivirine/emtricitabine/tenofovir disoproxil fumarate combination. J Antimicrob Chemother. 2016 Aug;71(8):2248-51. doi: 10.1093/jac/dkw146. PubMed PMID: 27231280.

19: Neukam K, Espinosa N, Collado A, Delgado-Fernández M, Jiménez-Aguilar P, Rivero-Juárez A, Hontañón-Antoñana V, Gómez-Berrocal A, Ruiz-Morales J, Merino D, Carrero A, Téllez F, Ríos MJ, Hernández-Quero J, de Lagarde-Sebastián M, Pérez-Camacho I, Vera-Méndez F, Macías J, Pineda JA; hEPAtic Study Group.. Hepatic Safety of Rilpivirine/Emtricitabine/Tenofovir Disoproxil Fumarate Fixed-Dose Single-Tablet Regimen in HIV-Infected Patients with Active Hepatitis C Virus Infection: The hEPAtic Study. PLoS One. 2016 May 19;11(5):e0155842. doi: 10.1371/journal.pone.0155842. PubMed PMID: 27195797; PubMed Central PMCID: PMC4873169.

20: Foca M, Yogev R, Wiznia A, Hazra R, Jean-Philippe P, Graham B, Britto P, Carey VJ, King J, Acosta EP, Cressey TR; IMPAACT P1058A Team.. Rilpivirine Pharmacokinetics Without and With Darunavir/Ritonavir Once Daily in Adolescents and Young Adults. Pediatr Infect Dis J. 2016 Sep;35(9):e271-4. doi: 10.1097/INF.0000000000001214. PubMed PMID: 27187753.