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| Clinical data | |
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| Trade names | Intelence |
| Other names | TMC125 |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a608016 |
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| Routes of administration | By mouth |
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| Pharmacokinetic data | |
| Protein binding | 99.9% |
| Metabolism | Liver (CYP3A4,CYP2C9 &CYP2C19-mediated) |
| Eliminationhalf-life | 41±20 hours |
| Excretion | Faeces (93.7%), urine (1.2%) |
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| PDB ligand | |
| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.207.546 |
| Chemical and physical data | |
| Formula | C20H15BrN6O |
| Molar mass | 435.285 g·mol−1 |
| 3D model (JSmol) | |
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Etravirine (ETR,[3]), sold under the brand nameIntelence is anantiretroviral medication used for the treatment ofHIV.[1] Etravirine is a human immunodeficiency virus type 1 (HIV-1)non-nucleoside reverse transcriptase inhibitor (NNRTI).[1] Unlike agents in the class, resistance to other NNRTIs does not seem to confer resistance to etravirine.[4] Etravirine is marketed byJanssen, asubsidiary ofJohnson & Johnson. In January 2008, the USFood and Drug Administration (FDA) approved its use for people with established resistance to other drugs, making it the 30th anti-HIV drug approved in the United States and the first to be approved in 2008.[5] It was also approved for use in Canada in April 2008.[6]
Etravirine is licensed in the United States, Canada, Israel, Russia, Australia, New Zealand, and the European Union,[7] and is under regulatory review in Switzerland.[8]
In the US, etravirine isindicated for the treatment of HIV-1 infection in treatment-experienced patients aged two years of age and older.[1]
In the EU, etravirine, in combination with a boosted protease inhibitor and other antiretrovirals, is indicated for the treatment of human-immunodeficiency-virus-type-1 (HIV-1) infection in antiretroviral-treatment-experienced people aged six years of age and older.[2]
People with rare hereditary problems ofgalactose intolerance, the Lapplactase deficiency orglucose-galactose malabsorption should not take this etravine.[9]
In 2009, the FDA prescribing information for etravirine was modified to include "postmarketing reports of cases ofStevens–Johnson syndrome,toxic epidermal necrolysis, anderythema multiforme, as well ashypersensitivity reactions characterized by rash, constitutional findings, and sometimes organ dysfunction, includingliver failure."[10]
Etravirine is a second-generationnon-nucleoside reverse transcriptase inhibitor (NNRTI), designed to be active against HIV with mutations that confer resistance to the two most commonly prescribed first-generation NNRTIs, mutation K103N forefavirenz and Y181C fornevirapine.[11] This potency appears to be related to etravirine's flexibility as a molecule. Etravirine is adiarylpyrimidine (DAPY), a type oforganic molecule with someconformational isomerism that can bind the enzymereverse transcriptase in multipleconformations, allowing for a more robust interaction between etravirine and the enzyme, even in the presence of mutations.[12]
Etravine forms as colourlessorthorhombic crystals in space group Pna21.[13] The structures of these and of a number of solvate and salt forms have been reported.[13][14]
Etravine has been studied for use in adrug repositioning application. Etravirine was shown to cause an increase infrataxin production.[15]
