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{{short description|Also called Intelence is a drug used for the treatment of HIV}}
{{short description|Also called Intelence is a drug used for the treatment of HIV}}
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| StdInChIKey = PYGWGZALEOIKDF-UHFFFAOYSA-N
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'''Etravirine''' ('''ETR''',<ref>{{cite web |publisher=[[Department of Health and Human Services]] |work=Guidelines for the Use of Antiretroviral Agents in HIV-1-Infected Adults and Adolescents |url=http://aidsinfo.nih.gov/guidelines/html/1/adult-and-adolescent-arv-guidelines/34/appendix-a--key-to-acronyms |archive-url=https://web.archive.org/web/20120831103819/http://www.aidsinfo.nih.gov/guidelines/html/1/adult-and-adolescent-arv-guidelines/34/appendix-a--key-to-acronyms |url-status=dead |archive-date=2012-08-31 |title=Appendix A: Key to Acronyms }}</ref> 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). Unlike the currently available agents in the class, resistance to other NNRTIs does not seem to confer resistance to etravirine.<ref>{{cite journal |author=Stellbrink HJ |title=Antiviral drugs in the treatment of AIDS: what is in the pipeline? |journal=Eur. J. Med. Res. |volume=12 |issue=9 |pages=483–95 |date=October 2007 |pmid=17933730 }}</ref> Etravirine is marketed by [[Janssen Pharmaceuticals|Janssen]], a [[subsidiary]] of [[Johnson & Johnson]]. In January 2008, the [[Food and Drug Administration]] approved its use for patients 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.<ref>{{cite web |url=http://ap.google.com/article/ALeqM5iCFQR1SKu681KqBBwrXJg1B6q5PAD8U8MS3G0 |title=FDA Approves HIV Drug Etravirine |publisher=[[Associated Press]] |date=January 18, 2008 }}{{dead link|date=November 2012|bot=Legobot}}</ref> It was also approved for use in Canada on April 1, 2008.<ref>{{cite press release |title=First New NNRTI in Nearly a Decade to Benefit Canadians with HIV/AIDS |publisher=Janssen-Ortho Inc. |date=2008-04-01 |url=http://www.janssen-ortho.com/JOI/pdf_files/INTELENCE_Press_Release_E.pdf |access-date=2008-07-09 |url-status=dead |archive-url=https://web.archive.org/web/20101102080713/http://janssen-ortho.com/JOI/pdf_files/INTELENCE_Press_Release_E.pdf |archive-date=2010-11-02 }}</ref>
'''Etravirine''' ('''ETR''',<ref>{{cite web |publisher=[[Department of Health and Human Services]] |work=Guidelines for the Use of Antiretroviral Agents in HIV-1-Infected Adults and Adolescents |url=http://aidsinfo.nih.gov/guidelines/html/1/adult-and-adolescent-arv-guidelines/34/appendix-a--key-to-acronyms |archive-url=https://web.archive.org/web/20120831103819/http://www.aidsinfo.nih.gov/guidelines/html/1/adult-and-adolescent-arv-guidelines/34/appendix-a--key-to-acronyms |url-status=dead |archive-date=2012-08-31 |title=Appendix A: Key to Acronyms }}</ref> 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). Unlike the currently available agents in the class, resistance to other NNRTIs does not seem to confer resistance to etravirine.<ref>{{cite journal | vauthors = Stellbrink HJ | title = Antiviral drugs in the treatment of AIDS: what is in the pipeline ? | journal = European Journal of Medical Research | volume = 12 | issue = 9 | pages = 483–495 | date = October 2007 | pmid = 17933730 }}</ref> Etravirine is marketed by [[Janssen Pharmaceuticals|Janssen]], a [[subsidiary]] of [[Johnson & Johnson]]. In January 2008, the [[Food and Drug Administration]] approved its use for patients 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.<ref>{{cite web |url=http://ap.google.com/article/ALeqM5iCFQR1SKu681KqBBwrXJg1B6q5PAD8U8MS3G0 |title=FDA Approves HIV Drug Etravirine |publisher=[[Associated Press]] |date=January 18, 2008 }}{{dead link|date=November 2012|bot=Legobot}}</ref> It was also approved for use in Canada on April 1, 2008.<ref>{{cite press release |title=First New NNRTI in Nearly a Decade to Benefit Canadians with HIV/AIDS |publisher=Janssen-Ortho Inc. |date=2008-04-01 |url=http://www.janssen-ortho.com/JOI/pdf_files/INTELENCE_Press_Release_E.pdf |access-date=2008-07-09 |url-status=dead |archive-url=https://web.archive.org/web/20101102080713/http://janssen-ortho.com/JOI/pdf_files/INTELENCE_Press_Release_E.pdf |archive-date=2010-11-02 }}</ref>


Etravirine is licensed in the [[United States]], [[Canada]], [[Israel]], [[Russia]], Australia and the [[European Union]],<ref>{{cite web |url=http://www.tibotec.com/news/detail.jhtml?itemname=news_48 |publisher=Tibotec |title=Intelence receives marketing authorisation in the European Union for HIV combination therapy |access-date=2008-08-29 |url-status=dead |archive-url=https://web.archive.org/web/20110928020018/http://www.tibotec.com/news/detail.jhtml?itemname=news_48 |archive-date=2011-09-28 }}</ref> and is under regulatory review in [[Switzerland]].<ref>{{cite web |url=http://www.aidsmap.com/en/news/46E8FC38-3BB8-4DDD-9FEC-D6BFD5DD69AA.asp |publisher=[[aidsmap]] |title=Etravirine (TMC125, ''Intelence'') granted accelerated approval in US |access-date=2008-01-24 |archive-url=https://web.archive.org/web/20100102225629/http://aidsmap.com/en/news/46E8FC38-3BB8-4DDD-9FEC-D6BFD5DD69AA.asp |archive-date=2010-01-02 |url-status=dead }}</ref>
Etravirine is licensed in the [[United States]], [[Canada]], [[Israel]], [[Russia]], Australia, New Zealand and the [[European Union]],<ref>{{cite web |url=http://www.tibotec.com/news/detail.jhtml?itemname=news_48 |publisher=Tibotec |title=Intelence receives marketing authorisation in the European Union for HIV combination therapy |access-date=2008-08-29 |url-status=dead |archive-url=https://web.archive.org/web/20110928020018/http://www.tibotec.com/news/detail.jhtml?itemname=news_48 |archive-date=2011-09-28 }}</ref> and is under regulatory review in [[Switzerland]].<ref>{{cite web |url=http://www.aidsmap.com/en/news/46E8FC38-3BB8-4DDD-9FEC-D6BFD5DD69AA.asp |publisher=[[aidsmap]] |title=Etravirine (TMC125, ''Intelence'') granted accelerated approval in US |access-date=2008-01-24 |archive-url=https://web.archive.org/web/20100102225629/http://aidsmap.com/en/news/46E8FC38-3BB8-4DDD-9FEC-D6BFD5DD69AA.asp |archive-date=2010-01-02 |url-status=dead }}</ref>


==Indications and dosage==
==Indications and dosage==
Etravirine, in combination with other anti-retrovirals, is indicated for the treatment of human immunodeficiency virus type 1 (HIV-1) infection in antiretroviral treatment-experienced adult patients, who have evidence of viral replication and HIV-1 strains resistant to a non-nucleoside reverse transcriptase inhibitor (NNRTI) and other antiretroviral agents.
Etravirine, in combination with other anti-retrovirals, is indicated for the treatment of human immunodeficiency virus type 1 (HIV-1) infection in antiretroviral treatment-experienced adult patients, who have evidence of viral replication and HIV-1 strains resistant to a non-nucleoside reverse transcriptase inhibitor (NNRTI) and other antiretroviral agents.


The recommended dose of etravirine is 200&nbsp;mg (2 x 100&nbsp;mg tablets, or 1 x 200&nbsp;mg tablet as of 03/18/2011) taken twice daily following a meal. The type of food does not affect the exposure to etravirine.<ref>{{cite web |url=http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022187s008lbl.pdf |title=Intelence prescribing information |access-date=January 19, 2012 |work=FDA}}</ref>
The recommended dose of etravirine is 200&nbsp;mg (2 x 100&nbsp;mg tablets, or 1 x 200&nbsp;mg tablet as of 03/18/2011) taken twice daily following a meal. The type of food does not affect the exposure to etravirine.<ref>{{cite web |url=http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/022187s008lbl.pdf |title=Intelence prescribing information |access-date=January 19, 2012 |work=FDA}}</ref>


==Contraindication==
==Contraindication==
Each 100&nbsp;mg etravirine tablet contains 160&nbsp;mg of [[lactose]]. Patients with rare hereditary problems of [[galactose]] intolerance, the Lapp [[lactase deficiency]] or [[glucose-galactose malabsorption]] should not take this medicine.<ref>{{cite web |title=Etravine: Summary of product characteristics |url=http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/000900/WC500034180.pdf |page=5 |publisher=[[European Medicines Agency|EMEA]] |access-date=July 13, 2011}}</ref>
Each 100&nbsp;mg etravirine tablet contains 160&nbsp;mg of [[lactose]]. Patients with rare hereditary problems of [[galactose]] intolerance, the Lapp [[lactase deficiency]] or [[glucose-galactose malabsorption]] should not take this medicine.<ref>{{cite web |title=Etravine: Summary of product characteristics |url=http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/000900/WC500034180.pdf |page=5 |publisher=[[European Medicines Agency|EMEA]] |access-date=July 13, 2011 |archive-date=August 20, 2016 |archive-url=https://web.archive.org/web/20160820115226/http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/000900/WC500034180.pdf |url-status=dead }}</ref>


==Mechanism of action==
==Mechanism of action==
Etravirine is a second-generation [[non-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 for [[efavirenz]] and Y181C for [[nevirapine]].<ref name="David Evans">{{cite web |url=http://www.aidsmeds.com/articles/etravirine_tmc125_hiv_2042_13846.shtml |title=Etravirine—Countdown to Launch |access-date=2008-02-02 |author=Evans, David |date=2008-01-15 |publisher=AIDSmeds.com }}</ref> This potency appears to be related to etravirine's flexibility as a molecule. Etravirine is a [[diarylpyrimidine]] (DAPY), a type of [[organic molecule]] with some [[conformational isomerism]] that can bind the enzyme [[reverse transcriptase]] in multiple [[Protein conformation|conformations]], allowing for a more robust interaction between etravirine and the enzyme, even in the presence of mutations.<ref name="pmid15115397">{{cite journal | vauthors = Das K, Clark AD, Lewi PJ, Heeres J, De Jonge MR, Koymans LM, Vinkers HM, Daeyaert F, Ludovici DW, Kukla MJ, De Corte B, Kavash RW, Ho CY, Ye H, Lichtenstein MA, Andries K, Pauwels R, De Béthune MP, Boyer PL, Clark P, Hughes SH, Janssen PA, Arnold E | title = Roles of conformational and positional adaptability in structure-based design of TMC125-R165335 (etravirine) and related non-nucleoside reverse transcriptase inhibitors that are highly potent and effective against wild-type and drug-resistant HIV-1 variants | journal = J. Med. Chem. | volume = 47 | issue = 10 | pages = 2550–60 | date = May 2004 | pmid = 15115397 | doi = 10.1021/jm030558s }}</ref> Other diarylpyrimidine-analogues are currently being used as anti-HIV agents, notably [[rilpivirine]].
Etravirine is a second-generation [[non-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 for [[efavirenz]] and Y181C for [[nevirapine]].<ref name="David Evans">{{cite web |url=http://www.aidsmeds.com/articles/etravirine_tmc125_hiv_2042_13846.shtml |title=Etravirine—Countdown to Launch |access-date=2008-02-02 | vauthors = Evans D |date=2008-01-15 |publisher=AIDSmeds.com |archive-date=2008-01-19 |archive-url=https://web.archive.org/web/20080119222616/http://www.aidsmeds.com/articles/etravirine_tmc125_hiv_2042_13846.shtml |url-status=dead }}</ref> This potency appears to be related to etravirine's flexibility as a molecule. Etravirine is a [[diarylpyrimidine]] (DAPY), a type of [[organic molecule]] with some [[conformational isomerism]] that can bind the enzyme [[reverse transcriptase]] in multiple [[Protein conformation|conformations]], allowing for a more robust interaction between etravirine and the enzyme, even in the presence of mutations.<ref name="pmid15115397">{{cite journal | vauthors = Das K, Clark AD, Lewi PJ, Heeres J, De Jonge MR, Koymans LM, Vinkers HM, Daeyaert F, Ludovici DW, Kukla MJ, De Corte B, Kavash RW, Ho CY, Ye H, Lichtenstein MA, Andries K, Pauwels R, De Béthune MP, Boyer PL, Clark P, Hughes SH, Janssen PA, Arnold E | display-authors = 6 | title = Roles of conformational and positional adaptability in structure-based design of TMC125-R165335 (etravirine) and related non-nucleoside reverse transcriptase inhibitors that are highly potent and effective against wild-type and drug-resistant HIV-1 variants | journal = Journal of Medicinal Chemistry | volume = 47 | issue = 10 | pages = 2550–2560 | date = May 2004 | pmid = 15115397 | doi = 10.1021/jm030558s }}</ref> Other diarylpyrimidine-analogues are currently being used as anti-HIV agents, notably [[rilpivirine]].


==Warnings and risks==
==Warnings and risks==
In 2009, the prescribing information for etravirine was modified to include "postmarketing reports of cases of [[Stevens–Johnson syndrome]], [[toxic epidermal necrolysis]] and [[erythema multiforme]], as well as [[hypersensitivity]] reactions characterized by rash, constitutional findings, and sometimes organ dysfunction, including [[liver failure]]. Intelence therapy should be immediately discontinued when signs and symptoms of severe skin or hypersensitivity reactions develop."<ref>{{cite web |url=https://www.fda.gov/Safety/MedWatch/SafetyInformation/SafetyAlertsforHumanMedicalProducts/ucm180579.htm |title=FDA Medwatch Safety Information |access-date=2009-08-27 }}</ref>
In 2009, the prescribing information for etravirine was modified to include "postmarketing reports of cases of [[Stevens–Johnson syndrome]], [[toxic epidermal necrolysis]] and [[erythema multiforme]], as well as [[hypersensitivity]] reactions characterized by rash, constitutional findings, and sometimes organ dysfunction, including [[liver failure]]. Intelence therapy should be immediately discontinued when signs and symptoms of severe skin or hypersensitivity reactions develop."<ref>{{cite web |url=https://www.fda.gov/Safety/MedWatch/SafetyInformation/SafetyAlertsforHumanMedicalProducts/ucm180579.htm |title=FDA Medwatch Safety Information |website=[[Food and Drug Administration]] |access-date=2009-08-27 }}</ref>


==Repositioning==
==Repositioning==


Etravine has been studied for use in a [[drug repositioning]] application. In a paper<ref>{{cite journal| title=Drug repositioning screening identifies etravirine as a potential therapeutic for friedreich's ataxia |journal=Movement Disorders| volume=34 | issue=3 | pages=323–334 | doi=10.1002/mds.27604 | pmid=30624801 | year=2019 | last1=Alfedi | first1=Giulia | last2=Luffarelli | first2=Riccardo | last3=Condò | first3=Ivano | last4=Pedini | first4=Giorgia | last5=Mannucci | first5=Liliana | last6=Massaro | first6=Damiano S. | last7=Benini | first7=Monica | last8=Toschi | first8=Nicola | last9=Alaimo | first9=Giorgia | last10=Panarello | first10=Luca | last11=Pacini | first11=Laura | last12=Fortuni | first12=Silvia | last13=Serio | first13=Dario | last14=Malisan | first14=Florence | last15=Testi | first15=Roberto | last16=Rufini | first16=Alessandra |s2cid=58567610}}</ref> published in the medical journal [[Movement Disorders (journal)|''Movement Disorders'']], etravirine was shown to cause an increase in [[frataxin]] production. Frataxin deficiency is a key component to [[Friedreich's ataxia]], a genetically inherited disease that causes the progressive loss of coordination and muscle strength leading to motor incapacitation and the full-time use of a wheelchair.
Etravine has been studied for use in a [[drug repositioning]] application. In a paper<ref>{{cite journal | vauthors = Alfedi G, Luffarelli R, Condò I, Pedini G, Mannucci L, Massaro DS, Benini M, Toschi N, Alaimo G, Panarello L, Pacini L, Fortuni S, Serio D, Malisan F, Testi R, Rufini A | display-authors = 6 | title = Drug repositioning screening identifies etravirine as a potential therapeutic for friedreich's ataxia | journal = Movement Disorders | volume = 34 | issue = 3 | pages = 323–334 | date = March 2019 | pmid = 30624801 | doi = 10.1002/mds.27604 | s2cid = 58567610 }}</ref> published in the medical journal [[Movement Disorders (journal)|''Movement Disorders'']], etravirine was shown to cause an increase in [[frataxin]] production. Frataxin deficiency is a key component to [[Friedreich's ataxia]], a genetically inherited disease that causes the progressive loss of coordination and muscle strength leading to motor incapacitation and the full-time use of a wheelchair.


==References==
==Chemistry==
⚫
{{Reflist}}


Etravine forms as colourless [[Orthorhombic crystal system|orthorhombic]] crystals in space group Pna2<sub>1</sub>.<ref name=":0">{{Cite journal | vauthors = Rajput L, Sanphui P, Desiraju GR |date=2013-08-07 |title=New Solid Forms of the Anti-HIV Drug Etravirine: Salts, Cocrystals, and Solubility |journal=Crystal Growth & Design |language=en |volume=13 |issue=8 |pages=3681–3690 |doi=10.1021/cg4007058 |issn=1528-7483}}</ref> The structures of these and of a number of solvate and salt forms have been reported.<ref name=":0" /><ref>{{cite journal | vauthors = Muresan-Pop M, Macavei S, Turza A, Borodi G | title = New solvates and a salt of the anti-HIV compound etravirine | journal = Acta Crystallographica Section C: Structural Chemistry | volume = 77 | issue = Pt 11 | pages = 698–706 | date = November 2021 | pmid = 34738540 | doi = 10.1107/S2053229621010482 | s2cid = 243761396 }}</ref>


== References ==
⚫
{{Reflist}}


== External links ==
== External links ==
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{{Portal bar | Medicine | Viruses }}
{{Portal bar | Medicine | Viruses }}


[[Category:CYP3A4 inducers]]
[[Category:Hepatotoxins]]
[[Category:Hepatotoxins]]
[[Category:Non-nucleoside reverse transcriptase inhibitors]]
[[Category:Non-nucleoside reverse transcriptase inhibitors]]
[[Category:Aminopyrimidines]]
[[Category:Aminopyrimidines]]
[[Category:Johnson & Johnson brands]]
[[Category:Drugs developed by Johnson & Johnson]]
[[Category:Nitriles]]
[[Category:Nitriles]]
[[Category:Organobromides]]
[[Category:Organobromides]]
[[Category:Belgian inventions]]
[[Category:Belgian inventions]]
[[Category:Diaryl ethers]]

Revision as of 16:03, 17 March 2024

Etravirine
Clinical data
Trade namesIntelence
AHFS/Drugs.comMonograph
MedlinePlusa608016
License data
Pregnancy
category
  • AU: B1
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding99.9%
MetabolismHepatic (CYP3A4, CYP2C9 & CYP2C19-mediated)
Elimination half-life41±20 hours
ExcretionFaeces (93.7%), urine (1.2%)
Identifiers
  • 4-[6-Amino-5-bromo-2-[(4-cyanophenyl)amino] pyrimidin-4-yl]oxy-3,5-dimethylbenzonitrile
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
NIAID ChemDB
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.207.546 Edit this at Wikidata
Chemical and physical data
FormulaC20H15BrN6O
Molar mass435.285 g·mol−1
3D model (JSmol)
  • N#Cc3cc(c(Oc1nc(nc(c1Br)N)Nc2ccc(C#N)cc2)c(c3)C)C
  • 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) checkY
  • Key:PYGWGZALEOIKDF-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Etravirine (ETR,[1] 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). Unlike the currently available agents in the class, resistance to other NNRTIs does not seem to confer resistance to etravirine.[2] Etravirine is marketed by Janssen, a subsidiary of Johnson & Johnson. In January 2008, the Food and Drug Administration approved its use for patients 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.[3] It was also approved for use in Canada on April 1, 2008.[4]

Etravirine is licensed in the United States, Canada, Israel, Russia, Australia, New Zealand and the European Union,[5] and is under regulatory review in Switzerland.[6]

Indications and dosage

Etravirine, in combination with other anti-retrovirals, is indicated for the treatment of human immunodeficiency virus type 1 (HIV-1) infection in antiretroviral treatment-experienced adult patients, who have evidence of viral replication and HIV-1 strains resistant to a non-nucleoside reverse transcriptase inhibitor (NNRTI) and other antiretroviral agents.

The recommended dose of etravirine is 200 mg (2 x 100 mg tablets, or 1 x 200 mg tablet as of 03/18/2011) taken twice daily following a meal. The type of food does not affect the exposure to etravirine.[7]

Contraindication

Each 100 mg etravirine tablet contains 160 mg of lactose. Patients with rare hereditary problems of galactose intolerance, the Lapp lactase deficiency or glucose-galactose malabsorption should not take this medicine.[8]

Mechanism of action

Etravirine is a second-generation non-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 for efavirenz and Y181C for nevirapine.[9] This potency appears to be related to etravirine's flexibility as a molecule. Etravirine is a diarylpyrimidine (DAPY), a type of organic molecule with some conformational isomerism that can bind the enzyme reverse transcriptase in multiple conformations, allowing for a more robust interaction between etravirine and the enzyme, even in the presence of mutations.[10] Other diarylpyrimidine-analogues are currently being used as anti-HIV agents, notably rilpivirine.

Warnings and risks

In 2009, the prescribing information for etravirine was modified to include "postmarketing reports of cases of Stevens–Johnson syndrome, toxic epidermal necrolysis and erythema multiforme, as well as hypersensitivity reactions characterized by rash, constitutional findings, and sometimes organ dysfunction, including liver failure. Intelence therapy should be immediately discontinued when signs and symptoms of severe skin or hypersensitivity reactions develop."[11]

Repositioning

Etravine has been studied for use in a drug repositioning application. In a paper[12] published in the medical journal Movement Disorders, etravirine was shown to cause an increase in frataxin production. Frataxin deficiency is a key component to Friedreich's ataxia, a genetically inherited disease that causes the progressive loss of coordination and muscle strength leading to motor incapacitation and the full-time use of a wheelchair.

Chemistry

Etravine forms as colourless orthorhombic crystals in space group Pna21.[13] The structures of these and of a number of solvate and salt forms have been reported.[13][14]

References

  1. ^ "Appendix A: Key to Acronyms". Guidelines for the Use of Antiretroviral Agents in HIV-1-Infected Adults and Adolescents. Department of Health and Human Services. Archived from the original on 2012-08-31.
  2. ^ Stellbrink HJ (October 2007). "Antiviral drugs in the treatment of AIDS: what is in the pipeline ?". European Journal of Medical Research. 12 (9): 483–495. PMID 17933730.
  3. ^ "FDA Approves HIV Drug Etravirine". Associated Press. January 18, 2008.[dead link]
  4. ^ "First New NNRTI in Nearly a Decade to Benefit Canadians with HIV/AIDS" (PDF) (Press release). Janssen-Ortho Inc. 2008-04-01. Archived from the original (PDF) on 2010-11-02. Retrieved 2008-07-09.
  5. ^ "Intelence receives marketing authorisation in the European Union for HIV combination therapy". Tibotec. Archived from the original on 2011-09-28. Retrieved 2008-08-29.
  6. ^ "Etravirine (TMC125, Intelence) granted accelerated approval in US". aidsmap. Archived from the original on 2010-01-02. Retrieved 2008-01-24.
  7. ^ "Intelence prescribing information" (PDF). FDA. Retrieved January 19, 2012.
  8. ^ "Etravine: Summary of product characteristics" (PDF). EMEA. p. 5. Archived from the original (PDF) on August 20, 2016. Retrieved July 13, 2011.
  9. ^ Evans D (2008-01-15). "Etravirine—Countdown to Launch". AIDSmeds.com. Archived from the original on 2008-01-19. Retrieved 2008-02-02.
  10. ^ Das K, Clark AD, Lewi PJ, Heeres J, De Jonge MR, Koymans LM, et al. (May 2004). "Roles of conformational and positional adaptability in structure-based design of TMC125-R165335 (etravirine) and related non-nucleoside reverse transcriptase inhibitors that are highly potent and effective against wild-type and drug-resistant HIV-1 variants". Journal of Medicinal Chemistry. 47 (10): 2550–2560. doi:10.1021/jm030558s. PMID 15115397.
  11. ^ "FDA Medwatch Safety Information". Food and Drug Administration. Retrieved 2009-08-27.
  12. ^ Alfedi G, Luffarelli R, Condò I, Pedini G, Mannucci L, Massaro DS, et al. (March 2019). "Drug repositioning screening identifies etravirine as a potential therapeutic for friedreich's ataxia". Movement Disorders. 34 (3): 323–334. doi:10.1002/mds.27604. PMID 30624801. S2CID 58567610.
  13. ^ a b Rajput L, Sanphui P, Desiraju GR (2013-08-07). "New Solid Forms of the Anti-HIV Drug Etravirine: Salts, Cocrystals, and Solubility". Crystal Growth & Design. 13 (8): 3681–3690. doi:10.1021/cg4007058. ISSN 1528-7483.
  14. ^ Muresan-Pop M, Macavei S, Turza A, Borodi G (November 2021). "New solvates and a salt of the anti-HIV compound etravirine". Acta Crystallographica Section C: Structural Chemistry. 77 (Pt 11): 698–706. doi:10.1107/S2053229621010482. PMID 34738540. S2CID 243761396.
  • "Etravirine". Drug Information Portal. U.S. National Library of Medicine.
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