Indinavir: Difference between revisions

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{{subpages}}
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[[Image:Indinavir structure.jpg|right|thumb|250px|{{#ifexist:Template:Indinavir structure.jpg/credit|{{Indinavir structure.jpg/credit}}<br/>|}}Indinavir]]
 
{{Chem infobox
|align=right
|image=[[Image:Indinavir structure.jpg|center|thumb|250px]]
|width=250px
|molname=indinavir
|synonyms=  compound J
|molformula= C<sub>36</sub>H<sub>47</sub>N<sub>5</sub>O<sub>4</sub>
|molmass= 613.7895
|uses=HIV
|properties=protease inhibitor
|hazards=see drug interactions
|iupac= see chemistry section
|casnumber=150378-17-9
}}
 


'''Indinavir''', also called '''indinavir sulfate''' or '''Compound J''' and sold under the trade name '''Crixivan®''',  is a [[protease inhibitor]] used to treat [[HIV]]/[[AIDS]].  The HIV-1 protease in required to cleave the viral gag-pol polyprotein into individual functional proteins to make an infectious mature viral particle.  Indinavir binds to the HIV-1 protease, inhibiting its function and stopping the production of infectious viral particles.  Protease inhibitors are usually used with two or more other anti-HIV medications.  Symptoms of overdose include [[myocardial infarction|heart attack]] and [[angina pectoris|chest pain]].
'''Indinavir''', also called '''indinavir sulfate''' or '''Compound J''' and sold under the trade name '''Crixivan®''',  is a [[protease inhibitor]] used to treat [[HIV]]/[[AIDS]].  The HIV-1 protease in required to cleave the viral gag-pol polyprotein into individual functional proteins to make an infectious mature viral particle.  Indinavir binds to the HIV-1 protease, inhibiting its function and stopping the production of infectious viral particles.  Protease inhibitors are usually used with two or more other anti-HIV medications.  Symptoms of overdose include [[myocardial infarction|heart attack]] and [[angina pectoris|chest pain]].
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== Drug interactions ==
== Drug interactions ==


The absorption of indinavir is decreased by St. John's Wort, antacids, such as [[aluminum]], [[bismuth]], [[calcium]], [[magnesium]] and [[magnesium oxide]], by [[omeprazole]] and related compounds ([[esomeprazole]], [[lansoprazole]], [[pantoprazole]] and [[rabeprazole]]) and by [[Rifampin]] and its derivitive [[Rifabutin]].  
The absorption of indinavir is decreased by [[St. John's Wort]], [[Vitamin C]], antacids, such as [[aluminium]], [[bismuth]], [[calcium]], [[magnesium]] and [[magnesium oxide]], by [[efavirenz]], [[omeprazole]] and related compounds ([[esomeprazole]], [[lansoprazole]], [[pantoprazole]] and [[rabeprazole]]) and by [[Rifampin]] and its derivitive [[Rifabutin]]. The effects of indinavir are increased when taken with [[clarithromycine]], [[delavirdine]] or [[ketoconazole]].  [[Saquinavir]], also a protease inhibitor, may be an agonist of indinavir.


Indinavir increases the anticoagulant effect of [[anisindione]], [[acenocoumarol]], [[dicumarol]], and [[warfarin]] and also increases the effect of [[benzodiazepine]]. Benzodiazepine related drugs include [[Alprazolam]], [[Chlordiazepoxide]], [[Clonazepam]], [[Clorazepate]], [[Diazepam]], [[Estazolam]], [[Flurazepam]], [[Halazepam]], [[Midazolam]], [[Prazepam]], [[Quazepam]] and [[Triazolam]].
Indinavir increases the anticoagulant effect of [[anisindione]], [[acenocoumarol]], [[dicumarol]], and [[warfarin]] and also increases the effect of [[benzodiazepine]]. Benzodiazepine related drugs include [[Alprazolam]], [[Chlordiazepoxide]], [[Clonazepam]], [[Clorazepate]], [[Diazepam]], [[Estazolam]], [[Flurazepam]], [[Halazepam]], [[Midazolam]], [[Prazepam]], [[Quazepam]] and [[Triazolam]].


 
An increased risk of cardiotoxicity and [[arrhythmia]]s occurs when taken with [[astemizole]], [[cisapride]] or [[terfenadine]].  The effects and toxicity of [[amiodarone]], [[atorvastatin]], [[carbamazepine]], [[cyclosporine]], [[fentanyl]], [[fusidic acid]], [[pimozide]], [[sildenafil]],  [[tacrolimus]] and [[Vardenafil]] are increased when taken with indinavir.  The effect and toxicity of ergot derivatives, such as [[ergotamine]] and [[dihydroergotamine]], and [[erlotinib]], [[quinupristin]], [[ranolazine]] and [[trazodone]] are also increased. An increase in extrapyramidal symptoms may occur with [[risperidone]] and increased risks of [[hyperbilirubinemia]] are associated with [[atazanavir]] use.
 
Vardenafil The protease inhibitor increases the effect and toxicity of vardenafil
Cyclosporine The protease inhibitor increases the effect of cyclosporine  
Fentanyl The protease inhibitor increases the effect and toxicity of fentanyl  
Pimozide The protease inhibitor increases the effect and toxicity of pimozide  
Sildenafil The protease inhibitor increases the effect and toxicity of sildenafil  
Vitamin C Vitamin C decreases indinavir levels
Trazodone This strong CYP3A4 inhibitor increases the effect and toxicity of trazodone
Terfenadine Increased risk of cardiotoxicity and arrhythmias
Astemizole Increased risk of cardiotoxicity and arrhythmias
Cisapride Increased risk of cardiotoxicity and arrhythmias
Delavirdine Delavirdine increases the effect of indinavir  
Clarithromycin Clarithromycin increases the effect and toxicity of indinavir
Carbamazepine Indinavir increases the effect and toxicity of carbamazepine
Atorvastatin Increases the effect and toxicity of atorvastatin
Amiodarone Indinavir increases the effect and toxicity of amiodarone
Efavirenz Efavirenz decreases the effect of indinavir
Erlotinib This CYP3A4 inhibitor increases levels/toxicity of erlotinib  
 
Fusidic Acid Increases the effect and toxicity of fusidic acid
Ketoconazole Ketoconazole increases the efefct of indinavir
Ranolazine Increased levels of ranolazine - risk of toxicity 
Sunitinib Possible increase in sunitinib levels
Tacrolimus Increases the effect and toxicity of tacrolimus
Saquinavir Possible antagonism of action
Risperidone Increased risk of extrapyramidal symptoms  
Quinupristin This combination presents an increased risk of toxicity
 
Atazanavir Increased risk of hyperbilirubinemia with this association
Ergotamine Increases the effect and toxicity of the ergot derivative
Dihydroergotamine Increases the effect and toxicity of the ergot derivative
 


== External Links ==
== External Links ==
{{DailyMed}}
{{CZMed}}[[Category:Suggestion Bot Tag]]
Drug Bank at http://www.drugbank.ca/cgi-bin/getCard.cgi?CARD=DB00224.txt

Latest revision as of 17:00, 31 August 2024

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Indinavir structure.jpg
indinavir
IUPAC name: see chemistry section
Synonyms: compound J
Formula: C36H47N5O4

 Uses: HIV

 Properties: protease inhibitor

 Hazards: see drug interactions

Mass (g/mol): CAS #:
613.7895 150378-17-9



Indinavir, also called indinavir sulfate or Compound J and sold under the trade name Crixivan®, is a protease inhibitor used to treat HIV/AIDS. The HIV-1 protease in required to cleave the viral gag-pol polyprotein into individual functional proteins to make an infectious mature viral particle. Indinavir binds to the HIV-1 protease, inhibiting its function and stopping the production of infectious viral particles. Protease inhibitors are usually used with two or more other anti-HIV medications. Symptoms of overdose include heart attack and chest pain.

Its IUPAC chemical name is (2S)-N-tert-butyl-1-[(2S,4R)-2-hydroxy-5-[[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino]-5-oxo-4-(phenylmethyl)pentyl]-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide and it has chemical formula C36H47N5O4.

Drug interactions

The absorption of indinavir is decreased by St. John's Wort, Vitamin C, antacids, such as aluminium, bismuth, calcium, magnesium and magnesium oxide, by efavirenz, omeprazole and related compounds (esomeprazole, lansoprazole, pantoprazole and rabeprazole) and by Rifampin and its derivitive Rifabutin. The effects of indinavir are increased when taken with clarithromycine, delavirdine or ketoconazole. Saquinavir, also a protease inhibitor, may be an agonist of indinavir.

Indinavir increases the anticoagulant effect of anisindione, acenocoumarol, dicumarol, and warfarin and also increases the effect of benzodiazepine. Benzodiazepine related drugs include Alprazolam, Chlordiazepoxide, Clonazepam, Clorazepate, Diazepam, Estazolam, Flurazepam, Halazepam, Midazolam, Prazepam, Quazepam and Triazolam.

An increased risk of cardiotoxicity and arrhythmias occurs when taken with astemizole, cisapride or terfenadine. The effects and toxicity of amiodarone, atorvastatin, carbamazepine, cyclosporine, fentanyl, fusidic acid, pimozide, sildenafil, tacrolimus and Vardenafil are increased when taken with indinavir. The effect and toxicity of ergot derivatives, such as ergotamine and dihydroergotamine, and erlotinib, quinupristin, ranolazine and trazodone are also increased. An increase in extrapyramidal symptoms may occur with risperidone and increased risks of hyperbilirubinemia are associated with atazanavir use.

External Links

The most up-to-date information about Indinavir and other drugs can be found at the following sites.