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[CAS NO. 269055-15-4] Etravirine

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Catalog:	HY-90005
Brand:	MCE
CAS:	269055-15-4

Overview

MDL	MFCD09837879
Molecular Weight	435.28
Molecular Formula	C20H15BrN6O
SMILES	N#CC1=CC(C)=C(C(C)=C1)OC2=NC(NC3=CC=C(C=C3)C#N)=NC(N)=C2Br

For research use only. We do not sell to patients.

5 Publications Citing Use of MCE

[1]Antimicrob Agents Chemother. 2015 Dec;59(12):7666-7670.
[2]Int J Antimicrob Agents. 2019 Dec;54(6):814-819.
[3]Sci Rep. 2015 Oct 29;5:15806.
[4]Biol Pharm Bull. 2016;39(3):450-4.
[5]Pharmaceuticals. 2022, 15(10), 1186.

Summary

Etravirine is a non-nucleoside reverse transcriptase inhibitor ( NNRTI ) used for the treatment of HIV .

IC50 & Target

HIV-1

HIV-2

In Vitro

TMC125 is highly active against wild-type HIV-1 (50% effective concentration [EC ₅₀ ]=1.4 to 4.8 nM) and shows some activity against HIV-2 (EC ₅₀ =3.5 μM). TMC125 also inhibits a series of HIV-1 group M subtypes and circulating recombinant forms and a group O virus. TMC125 has activity for 19 viruses with EC ₅₀ of < 5 nM ^[1] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Etravirine has a high genetic barrier to the development of resistance. In phase IIb trials in treatment-experienced patients, including those infected with virus resistant to NNRTIs and protease inhibitors (PIs), TMC125 is active against HIV resistant to currently available NNRTIs, with a similar tolerability profile to that of the control group ^[2] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Clinical Trial

NCT Number	Sponsor	Condition	Start Date	Phase
NCT01641367	AIDS Clinical Trials Group\|National Institute of Allergy and Infectious Diseases (NIAID)\|AbbVie\|Gilead Sciences\|Janssen Pharmaceuticals\|Merck Sharp & Dohme LLC\|Dimagi Inc.	HIV-1 Infection	February 22, 2013	Phase 4
NCT01625169	University of Southern California\|Tibotec Therapeutics, a Division of Ortho Biotech Products, L.P., USA	HIV	April 2010	Not Applicable
NCT00977756	International Maternal Pediatric Adolescent AIDS Clinical Trials Group\|National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections	August 2002
NCT00959894	University of North Carolina, Chapel Hill\|Janssen Pharmaceuticals	HIV Infections	September 2009	Phase 2
NCT00782301	ViiV Healthcare\|Pfizer	Hepatitis B\|Human Immunodeficiency Virus\|Hepatitis C, Chronic	March 2009	Phase 4
NCT01118871	Imperial College London	HIV\|HIV Infections	May 2010	Phase 4
NCT00855088	University of North Carolina, Chapel Hill\|Tibotec Pharmaceutical Limited	HIV+AIDS\|HIV Infections	July 2009	Phase 1
NCT02212379	ANRS, Emerging Infectious Diseases\|Merck Sharp & Dohme LLC\|Janssen-Cilag Ltd.	HIV-1 Infection	January 2015	Phase 2
NCT00531323	St Stephens Aids Trust	HIV Infections	September 2007	Phase 1
NCT04208373	Janssen Research & Development, LLC	Healthy	December 20, 2019	Phase 1
NCT02063360	ViiV Healthcare\|GlaxoSmithKline	Infection, Human Immunodeficiency Virus	February 1, 2014	Phase 1
NCT01199731	ViiV Healthcare\|GlaxoSmithKline	Infection, Human Immunodeficiency Virus	October 5, 2010	Phase 2
NCT00081978	Tibotec Pharmaceuticals, Ireland	HIV Infection	March 2004	Phase 2
NCT00823979	Pfizer	HIV-1	March 25, 2009	Phase 2
NCT00225303	Tibotec Pharmaceuticals, Ireland	HIV Infection	March 2005	Phase 2
NCT01254656	Pfizer\|ViiV Healthcare	HIV-1	February 2011	Phase 2
NCT01199939	Tibotec, Inc\|Tibotec Therapeutics, a Division of Ortho Biotech Products, L.P., USA	Human Immunodeficiency Virus (HIV)	May 2010	Phase 2
NCT00740389	Tibotec Pharmaceuticals, Ireland	HIV\|AIDS\|Fungal Infection	September 2008	Phase 1
NCT01090648	Tibotec Pharmaceuticals, Ireland	HIV-Infections	March 2010	Phase 1
NCT00128830	Tibotec Pharmaceuticals, Ireland	Human Immunodeficiency Virus Type 1	June 2005	Phase 2
NCT01121809	Hospitales Universitarios Virgen del Rocío	HIV-1 Infection\|HIV Infections	April 2010	Phase 4
NCT00412646	Tibotec Pharmaceuticals, Ireland	Anti-Retroviral Agents\|HIV-1	June 2002	Phase 2
NCT00792324	St Stephens Aids Trust	HIV	June 2008	Phase 3
NCT00871234	Indiana University\|Tibotec Therapeutics, a Division of Ortho Biotech Products, L.P., USA	Endothelial Function\|Lipids\|Insulin Resistance\|Inflammation\|HIV Infections	April 2009	Phase 1
NCT00980538	Janssen Sciences Ireland UC	HIV Infections\|HIV-1	December 9, 2009	Phase 3
NCT00254046	Tibotec Pharmaceuticals, Ireland	HIV	November 2005	Phase 3
NCT00867152	ViiV Healthcare\|Shionogi	Healthy Volunteer	April 2009	Phase 1
NCT00896051	Janssen R&D Ireland	HIV Infections\|Acquired Immunodeficiency Syndrome	August 2009	Phase 2
NCT01615601	Janssen Inc.	Human Immunodeficiency Virus (HIV)	October 2011
NCT00665847	Tibotec Pharmaceuticals, Ireland	HIV-1	November 2008	Phase 2
NCT00855413	University of North Carolina, Chapel Hill\|Janssen Pharmaceuticals	Acute HIV Infection\|HIV Infections	March 2009	Phase 4
NCT04273165	IRCCS Eugenio Medea\|University of Rome Tor Vergata	Friedreich Ataxia	September 17, 2020	Phase 2
NCT02818348	Fundación FLS de Lucha Contra el Sida, las Enfermedades Infecciosas y la Promoción de la Salud y la Ciencia	HIV-1 Infection	June 2016	Phase 1
NCT01422330	Janssen R&D Ireland	Human Immunodeficiency Virus (HIV) Infection	September 2011	Phase 4
NCT01876966	Janssen Pharmaceutica N.V., Belgium	HIV	March 2011	Phase 1
NCT01034917	Germans Trias i Pujol Hospital	HIV	December 2009	Phase 3
NCT01427504	University of Colorado, Denver	Hepatitis C\|HIV	August 2011	Not Applicable
NCT00537394	National Institute of Allergy and Infectious Diseases (NIAID)\|AIDS Clinical Trials Group	HIV Infections	January 2008	Phase 3
NCT00359021	Tibotec Pharmaceuticals, Ireland	HIV-1	June 2006	Phase 3
NCT00111280	Tibotec Pharmaceuticals, Ireland	HIV Infection	September 2004	Phase 2
NCT00792584	University Hospital, Geneva\|University of Bern\|University of Lausanne Hospitals\|Hospital Lugano\|University Hospital, Basel, Switzerland\|Hospital of Neuchâtel	Sleep Disorders	November 2008	Not Applicable
NCT00042289	National Institute of Allergy and Infectious Diseases (NIAID)\|Eunice Kennedy Shriver National Institute of Child Health and Human Development (NICHD)	HIV Infections	June 9, 2003
NCT00828815	Tibotec Pharmaceuticals, Ireland	HIV\|Pharmacokinetics	March 2009	Phase 1
NCT00903682	Janssen-Cilag International NV	HIV Infection\|HIV\|Acquired Immunodeficiency Syndrome	June 2009	Phase 2
NCT04630002	ViiV Healthcare	HIV Infections	October 28, 2020	Phase 1
NCT00855335	Janssen Scientific Affairs, LLC	HIV\|HIV Infections\|Pregnancy	April 9, 2009	Phase 3
NCT00460382	French National Agency for Research on AIDS and Viral Hepatitis\|Merck Sharp & Dohme LLC\|Janssen-Cilag Tibotec	HIV Infections	May 2007	Phase 2
NCT00255099	Tibotec Pharmaceuticals, Ireland	HIV	December 2005	Phase 3
NCT01504841	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections	March 14, 2013	Phase 1\|Phase 2
NCT00354627	Tibotec Pharmaceuticals, Ireland	HIV-1	January 2006	Phase 3

Appearance

Solid

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvent & Solubility

In Vitro:

DMSO : 50 mg/mL ( 114.87 mM ; Need ultrasonic)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	2.2974 mL	11.4869 mL	22.9737 mL
5 mM	0.4595 mL	2.2974 mL	4.5947 mL
10 mM	0.2297 mL	1.1487 mL	2.2974 mL

* Please refer to the solubility information to select the appropriate solvent.

In Vivo:

1.

Add each solvent one by one: 10% DMSO >> 40% PEG300 >> 5% Tween-80 >> 45% saline

Solubility: ≥ 2.5 mg/mL (5.74 mM); Clear solution
2.

Add each solvent one by one: 10% DMSO >> 90% corn oil

Solubility: ≥ 2.5 mg/mL (5.74 mM); Clear solution

* All of the co-solvents are available by MCE.

References

[1] Andries, K., et al. TMC125, a novel next-generation nonnucleoside reverse transcriptase inhibitor active against nonnucleoside reverse transcriptase inhibitor-resistant human immunodeficiency virus type 1. Antimicrob Agents Chemother, 2004. 48(12): p. 468
[2] Lazzarin, A., et al. Efficacy and safety of TMC125 (etravirine) in treatment-experienced HIV-1-infected patients in DUET-2: 24-week results from a randomised, double-blind, placebo-controlled trial. Lancet, 2007. 370(9581): p. 39-48.

Synonyms

Benzonitrile, 4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethyl-

4-[[6-Amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethylbenzonitrile

TMC 125

Etravirine

R 165335

Intelence

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