Etravirine - CAS 269055-15-4
Catalog number:
B0084-064674
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C20H15BrN6O
Molecular Weight:
435.28
COA:
Inquire
Targets:
HIV
Description:
Etravirine (ETR, brand name Intelence, formerly known as TMC125) is a drug used for the treatment of HIV. Etravirine is a non-nucleoside reverse transcriptase inhibitor (NNRTI). Etravirine works by reducing the amount of HIV and increasing the number of CD4 or T cells in the blood. Unlike the currently available agents in the class, resistance to other NNRTIs does not seem to confer resistance to etravirine.
Ordering Information
Catalog Number Size Price Stock Quantity
B0084-064674 50 mg $288 In stock
Bulk Inquiry
Publictions citing BOC Sciences Products
  • >> More
Purity:
>98%
Synonyms:
R-165335,TMC125
MSDS:
Inquire
1. Aromatic chloride to nitrile transformation: medicinal and synthetic chemistry
Lyn H. Jones,* Nicholas W. Summerhill,* Nigel A. Swain and James E. Mills. Med. Chem. Commun., 2010, 1, 309–318
The non-nucleoside reverse transcriptase inhibitor (NNRTI) and anti-HIV drug etravirine contains two aromatic nitrile moieties and structure–activity relationships suggest that at least one can be effectively replaced by a chlorine atom. A key structural component for resilience to drug resistant mutations in this class is an effective edge-to-face p-interaction with an immutable tryptophan residue in the allosteric reverse transcriptase (RT) binding pocket. Crystal structures of etravirine and capavirine with RT show that the hydrogen atom ortho-to the chlorine atoms in capravirine and nitrile moiety in etravirine is indeed interacting with the immutable Trp229 and both molecules possess excellent mutant viral profiles. We also have a matching pair of imidazole NNRTIs with excellent mutant profiles from our own work that supports these observations (compounds 5 and 6, Fig. 2). Additionally, the nitrile moiety in these ligands points through a hole in the enzyme towards solvent, an arrangement that is ideally suited to the shape and electrostatics of this residue (see below).
2. In silico de novo design of novel NNRTIs: a bio-molecular modelling approach
Nilanjana Jain (Pancholi), Swagata Gupta, Neelima Saprec and Nitin S. Sapre*. RSC Adv.,2015, 5,14814–14827
Another NNRTI, delaviridine, which is bulkier in size than nevirapine, exhibit better interactions with RT, viz. hydrogen bond interactions with K103 and hydrophobic interactions with P236. Efavirenz (Sustiva, Stocrin, EFV, DMP-266) is a potent NNRTI that binds to HIV-1 RT at a site distinct from the polymerase catalytic site, which has also been found to be effective when combined with either nevirapine, nelfinavir or indinavir. Etravirine (ETR/TMC125), a second-generation NNRTI, exhibited an enhanced barrier to resistance and is found to be extremely effective in achieving the viral suppression as well as improving the immunity in treatment-experienced HIV-infected patients. Among the newly discovered NNRTIs, rilpivirine is an antiretroviral exhibiting better bioavailability, easier formulation and administration compared to etravirine, and the FDA approved NNRTIs are given in Table 1.
3. Influence of microporosity in SBA-15 on the release properties of anticancer drug dasatinib
T. Kjellman, X. Xia, V. Alfredsson* and A. E. Garcia-Bennett*. J. Mater. Chem. B,2014, 2, 5265–5271
The presence of the intrawall pores in mesoporous materials can have significant effect on the release behaviour of loaded drug molecules which the work by Mellaerts et al. suggests. They recently studied the dissolution of the poorly soluble compound etravirine within a standard SBA-15 material. It was concluded that etravirine molecules were adsorbed either individually (the suggested location to be in the small intrawall pores) or as clusters (suggested location in the mesopores). On the basis of an infrared spectroscopy investigation it was found that individually adsorbed drug molecules have a different dissolution path to molecules adsorbed as clusters.
4. Advances in the development of pyridinone derivatives as non-nucleoside reverse transcriptase inhibitors
Hugo Vite-Caritino, Oscar Mendez-Lucio, Hector Reyes, Alberto Cabrera, Daniel Chavezc and Jose L. Medina-Franco*. RSC Adv.,2016, 6,2119–2130
There are five NNRTIs approved for clinical use which can be grouped in three generations based on their activity profile and approval (Fig. 2A). The first generation: nevirapine (approved by the USA Food and Drug Administration, FDA in 1996), delavirdine (approved in 1997) and efavirenz (approved in 1998). Nevirapine and efavirenz continue to be an important part of HAART, in particular efavirenz which is the most extensively used NNRTI. Overall, delavirdine is much less used because of its poor pharmacokinetics. The first generation of NNRTIs is characterized by a low genetic barrier to resistance (i.e. only one mutation is enough to reduce the efficacy of these compounds), hence they are usually co-administered with at least two other non-NNRTI antiretroviral drugs. Etravirine, also administered in combination with other antiretroviral drugs, was the first next generation NNRTI to be approved by the FDA in 2008. This drug was characterized by retaining activity against mutant strains. Rilpivirine was the next drug approved in 2011 by the FDA for clinical use. This drug belong to the same chemical class of etravirine (Fig. 2A) but has a better activity profile against mutant strains (vide infra). Efavirenz and rilpivirine are part of the combination therapies Atripla and Completra which are amongst the most effective therapies. However, the rapid mutation of the virus, side effects, and not optimal pharmacological properties of current NNRTIs prompts the need to develop novel NNRTIs. For instance, hepatotoxicity and severe rash are associated with the use of nevirapine.
Molecular Weight Calculator Molarity Calculator Solution Dilution Calculator

Related HIV Products


CAS 147127-20-6 Tenofovir

Tenofovir
(CAS: 147127-20-6)

Tenofovir blocks reverse transcriptase and hepatitis B virus infections.

CAS 136470-78-5 Abacavir

Abacavir
(CAS: 136470-78-5)

Abacavir sulfate is a Nucleoside analog reverse transcriptase inhibitor (NRTI); guanosine analog used to treat HIV and AIDS.

CAS 174022-42-5 Bevirimat

Bevirimat
(CAS: 174022-42-5)

Bevirimat, also known as MPC-4326 and PA-457, is an anti-HIV drug derived from a betulinic acid-like compound, first isolated from Syzygium claviflorum, a Chine...

CAS 313682-08-5 Brecanavir

Brecanavir
(CAS: 313682-08-5)

Brecanavir is a tyrosyl-based arylsulfonamide, high-affinity, protease inhibitor (PI) for the treatment of human immunodeficiency virus type-1. This compound po...

CAS 127779-20-8 Saquinavir

Saquinavir
(CAS: 127779-20-8)

A selective HIV protease inhibitor. Antiviral.

CAS 473921-12-9 Lersivirine

Lersivirine
(CAS: 473921-12-9)

Lersivirine is a next-generation non-nucleoside reverse transcriptase inhibitor (NNRTI) under development for the treatment of HIV-1 infection. It prevents HIV ...

BMS-663749
(CAS: 864953-33-3)

BMS-663749 is HIV-1 attachment inhibitor.

CAS 206361-99-1 Darunavir

Darunavir
(CAS: 206361-99-1)

Darunavir is a second generation protease inhibitor that targets the HIV-1 protease. It demonstrates extremely potent activity against the infectivity and repli...

CAS 1155419-89-8 BI 224436

BI 224436
(CAS: 1155419-89-8)

BI 224436 is a novel HIV-1 non-catalytic-site integrase inhibitor; has antiviral EC50s of <15 nM against different HIV-1 laboratory strains and cellular cytotox...

CAS 150378-17-9 Indinavir

Indinavir
(CAS: 150378-17-9)

Indinavir is a member of the novel hydroxyaminopentane amide class of HIV-1 protease inhibitors. Indinavir is used as an antiviral.

CGP 57813
(CAS: 150608-41-6)

CGP 57813 has been found to be a HIV-1 protease inhibitor that has been once developed by Novartis.

PD 134922
(CAS: 150351-30-7)

PD 134922 has been found to be a HIV-1 protease inhibitor that could probably be effective against HIV infections.

CAS 864953-39-9 BMS-663068 Tris

BMS-663068 Tris
(CAS: 864953-39-9)

BMS-663068 tris is an HIV-1 attachment inhibitor in development for the treatment of HIV-1 infection.

CAS 1180-71-8 Limonin

Limonin
(CAS: 1180-71-8)

Limonin is a triterpenoid enriched in citrus fruits, which has antivirus and antitumor ability.

CAS 134624-73-0 Stavudine sodium

Stavudine sodium
(CAS: 134624-73-0)

Stavudine sodium is a dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV. Stavudine sodium is an analog of thymi...

CAS 864953-29-7 BMS-663068

BMS-663068
(CAS: 864953-29-7)

BMS-663068 is an HIV-1 attachment inhibitor in development for the treatment of HIV-1 infection. It is a prodrug for BMS-626529, which binds to the viral envelo...

CAS 333353-44-9 NBD-556

NBD-556
(CAS: 333353-44-9)

NBD-556 is small molecule mimetic of CD4. NBD-556 recognizes the HIV-1 envelope protein gp120 and induces restructuring of gp120 analogous to CD4 binding. The C...

CAS 134678-17-4 Lamivudine

Lamivudine
(CAS: 134678-17-4)

Lamivudine is a potent nucleoside analog reverse transcriptase inhibitor, used for treatment of chronic HBV and HIV/AIDS.

CAS 185991-07-5 AMD3465 hexahydrobromide

AMD3465 hexahydrobromide
(CAS: 185991-07-5)

AMD3465 is a potent and highly selective monomacrocyclic CXCR4 antagonist (IC50= 0.75 nM). It potently inhibits HIV cell entry in vitro and causes leukocytosis ...

CAS 159989-64-7 Nelfinavir

Nelfinavir
(CAS: 159989-64-7)

Nelfinavir is a HIV protease inhibitor; antiretroviral; and anti-tumor agent.

Chemical Structure

CAS 269055-15-4 Etravirine

Quick Inquiry

Verification code

Featured Items