Synonym
R165335; R-165335; R 165335; TMC 125; TMC-125; TMC125; Etravirine; Intelence;
IUPAC/Chemical Name
4-(6-Amino-5-bromo-2-(4-cyanoanilino)pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile
InChi Key
PYGWGZALEOIKDF-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H15BrN6O/c1-11-7-14(10-23)8-12(2)17(11)28-19-16(21)18(24)26-20(27-19)25-15-5-3-13(9-22)4-6-15/h3-8H,1-2H3,(H3,24,25,26,27)
SMILES Code
N#CC1=CC(C)=C(OC2=NC(NC3=CC=C(C#N)C=C3)=NC(N)=C2Br)C(C)=C1
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
435.29
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.
| 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 |
1: Nelson M, Hill A, van Delft Y, Moecklinghoff C. Etravirine as a Switching Option for Patients with HIV RNA Suppression: A Review of Recent Trials. AIDS Res Treat. 2014;2014:636584. doi: 10.1155/2014/636584. Epub 2014 Feb 25. Review. PubMed PMID: 24715982; PubMed Central PMCID: PMC3955667.
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4: McNicholl IR. Does once-daily etravirine have a role in the management of HIV-1 infection? Drugs. 2013 Mar;73(3):207-12. doi: 10.1007/s40265-013-0022-6. Review. PubMed PMID: 23420097.
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7: Dickinson L, Khoo S, Back D. Pharmacokinetic evaluation of etravirine. Expert Opin Drug Metab Toxicol. 2010 Dec;6(12):1575-85. doi: 10.1517/17425255.2010.535811. Review. PubMed PMID: 21077784.
8: Fullerton DS, Watson MJ, Anderson D, Witek J, Martin SC, Mrus JM. Pharmacoeconomics of etravirine. Expert Rev Pharmacoecon Outcomes Res. 2010 Oct;10(5):485-95. doi: 10.1586/erp.10.55. Review. PubMed PMID: 20950062.
9: Yeni P, Mills A, Peeters M, Vingerhoets J, Kakuda TN, De Smedt G, Woodfall B. Etravirine in the treatment of HIV-1: a clinical overview for healthcare professionals. Curr HIV Res. 2010 Oct;8(7):564-76. Review. PubMed PMID: 20946097.
10: Kakuda TN, Schöller-Gyüre M, Hoetelmans RM. Clinical perspective on antiretroviral drug-drug interactions with the non-nucleoside reverse transcriptase inhibitor etravirine. Antivir Ther. 2010;15(6):817-29. doi: 10.3851/IMP1652. Review. PubMed PMID: 20834094.
11: Towner WJ, Cassetti I, Domingo P, Nijs S, Kakuda TN, Vingerhoets J, Woodfall B. Etravirine: clinical review of a treatment option for HIV type-1-infected patients with non-nucleoside reverse transcriptase inhibitor resistance. Antivir Ther. 2010;15(6):803-16. doi: 10.3851/IMP1651. Review. PubMed PMID: 20834093.
12: Grinsztejn B, Di Perri G, Towner W, Woodfall B, De Smedt G, Peeters M. A review of the safety and tolerability profile of the next-generation NNRTI etravirine. AIDS Res Hum Retroviruses. 2010 Jul;26(7):725-33. doi: 10.1089/aid.2009.0293. Review. PubMed PMID: 20624073.
13: Martínez E, Nelson M. Simplification of antiretroviral therapy with etravirine. AIDS Rev. 2010 Jan-Mar;12(1):52-9. Review. PubMed PMID: 20216910.
14: Domingo P. [Role of etravirine in combination antiretroviral therapy]. Enferm Infecc Microbiol Clin. 2009 Dec;27 Suppl 2:46-51. doi: 10.1016/S0213-005X(09)73219-7. Review. Spanish. PubMed PMID: 20116628.
15: Santos Gil Ide L. [Etravirine in special populations]. Enferm Infecc Microbiol Clin. 2009 Dec;27 Suppl 2:40-5. doi: 10.1016/S0213-005X(09)73218-5. Review. Spanish. PubMed PMID: 20116627.
16: Llibre JM, Santos JR, Clotet B. [Etravirine: genetic barrier and resistance development]. Enferm Infecc Microbiol Clin. 2009 Dec;27 Suppl 2:32-9. doi: 10.1016/S0213-005X(09)73217-3. Review. Spanish. PubMed PMID: 20116626.
17: Pérez VE, Sánchez-Parra C, Serrano Villar S. [Etravirine drug interactions]. Enferm Infecc Microbiol Clin. 2009 Dec;27 Suppl 2:27-31. doi: 10.1016/S0213-005X(09)73216-1. Review. Spanish. PubMed PMID: 20116625.
18: Portilla J. [Safety and tolerability of etravirine]. Enferm Infecc Microbiol Clin. 2009 Dec;27 Suppl 2:21-6. doi: 10.1016/S0213-005X(09)73215-X. Review. Spanish. PubMed PMID: 20116624.
19: Garcés PA, Tena EV. [Etravirine in first-line therapy]. Enferm Infecc Microbiol Clin. 2009 Dec;27 Suppl 2:12-20. doi: 10.1016/S0213-005X(09)73214-8. Review. Spanish. PubMed PMID: 20116623.
20: Palter DP, Corbera EF, Tiraboschi JM. [Etravirine in highly treatment-experienced patients]. Enferm Infecc Microbiol Clin. 2009 Dec;27 Suppl 2:6-11. doi: 10.1016/S0213-005X(09)73213-6. Review. Spanish. PubMed PMID: 20116622.
