Identification

Name
Etravirine
Accession Number
DB06414  (DB07191)
Type
Small Molecule
Groups
Approved
Description

Etravirine is an antiretroviral agent more specifically classified as a Non-Nucleoside Reverse Transcriptase Inhibitor(NNRTI). Etraverine is used clinically for the treatment of human immunodeficiency virus type 1 (HIV-1) infection. On January 18, 2007, the FDA granted accelerated approved for the use of etravirine 100mg tablets in the treatment of adult HIV-1 infection documented to be resistant to therapy with other NNRTIs and antiretroviral agents. On March 26, 2012, approval was extended for use in treatment-experienced pediatric patients 6 to 18 years of age, weighing at least 16 kg. Etravarine must always be used in combination with other antiretroviral drugs.

Etravirine exerts its effects via direct inhibition of the reverse transcriptase enzyme of human immunodeficiency virus type 1 (HIV-1), and consequently blocks DNA-dependent and RNA-dependent polymerase activity. Etravirine does not inhibit human DNA polymerase alpha, beta or gamma.

Common side effects of use include mild to moderate rash within the first 6 weeks of therapy, nausea, diarrhea and peripheral neuropathy. Patients are advised to immediately contact their healthcare provider if a rash develops.

In 2009, postmarketing case reports of Stevens-Johnson Syndrome, toxic epidermal necrolysis, erythema multiforme, and other hypersensitivity reactions lead to a revision of etravirine's "Warnings and Precautions," as well as notification of health care providers.

In 2013, reports of Autoimmune disorders (such as Graves’ disease, polymyositis, and Guillain-Barré syndrome) in the setting of immune reconstitution, as well as more in depth information about the development of rashes in patients taking etravirine, lead to a modification of etravirine's monograph.

Structure
Thumb
Synonyms
  • Etravirina
External IDs
R-165335 / R165335 / TMC 125 / TMC-125 / TMC125
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
IntelenceTablet200 mgOralJanssen Cilag International Nv2008-08-28Not applicableEu
IntelenceTablet100 mgOralJanssen Pharmaceuticals2008-03-27Not applicableCanada
IntelenceTablet200 mg/1OralJanssen, Lp2010-12-22Not applicableUs
IntelenceTablet100 mg/1OralRemedy Repack2013-03-182013-03-19Us
IntelenceTablet200 mg/1OralPhysicians Total Care, Inc.2012-10-10Not applicableUs
IntelenceTablet25 mgOralJanssen Pharmaceuticals2013-06-14Not applicableCanada
IntelenceTablet100 mgOralJanssen Cilag International Nv2008-08-28Not applicableEu
IntelenceTablet200 mg/1OralA-S Medication Solutions2010-12-22Not applicableUs
IntelenceTablet100 mg/1OralPhysicians Total Care, Inc.2008-02-21Not applicableUs
IntelenceTablet25 mgOralJanssen Cilag International Nv2008-08-28Not applicableEu
Categories
UNII
0C50HW4FO1
CAS number
269055-15-4
Weight
Average: 435.277
Monoisotopic: 434.049071779
Chemical Formula
C20H15BrN6O
InChI Key
PYGWGZALEOIKDF-UHFFFAOYSA-N
InChI
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)
IUPAC Name
4-({6-amino-5-bromo-2-[(4-cyanophenyl)amino]pyrimidin-4-yl}oxy)-3,5-dimethylbenzonitrile
SMILES
CC1=CC(=CC(C)=C1OC1=C(Br)C(N)=NC(NC2=CC=C(C=C2)C#N)=N1)C#N

Pharmacology

Indication

Indicated as an adjunct therapy in the treatment of adult HIV-1 infections resistant to therapy with other NNRTIs and antiretroviral agents.

Associated Conditions
Pharmacodynamics

Clinical trials have shown no prolongation of QT intervals on electrocardiograms after 8 days of dosing.

Mechanism of action

Etravirine exerts its effects via direct inhibition of the reverse transcriptase enzyme of human immunodeficiency virus type 1 (HIV-1). It directly binds reverse transcriptase and consequently blocks DNA-dependent and RNA-dependent polymerase activity. Etravirine does not inhibit human DNA polymerase alpha, beta or gamma.

TargetActionsOrganism
UGag-Pol polyproteinNot AvailableHIV-1
UGag-Pol polyproteinNot AvailableHIV-1
Absorption

Maximum oral absorption is achieved in 2.5-4 hours.

Absorption is unaffected by the concomitant use of oral ranitidine or omeprazole, which decrease gastric acidity.

Administration under fasting conditions resulted in a near 50% decrease in systemic exposure (AUC) when compared to administration after a meal.

Volume of distribution

Distribution of etravirine into compartments other than plasma has not been evaluated in humans.

Protein binding

Plasma protein binding is about 99.9% in vitro. In vitro, 99.6% is bound to albumin, and 97.66% - 99.02% is bound to 1-alpha glycoprotein.

Metabolism

Metabolized (in vitro) by the liver CYP450 enzymes: CYP3A4, CYP2C9, CYP2C19. The major metabolites formed by a methyl hydroxylation of the dimethylbenzonitrile moiety retained less than 90% of etravirine's activity.

Route of elimination

After a 800mg dose of radio-labelled etraverine, 93.7% was found to undergo fecal elimination, with 81.2% - 86.4% eliminated unchanged. 1.2% of the dose was renally eliminated, changed.

Etravirine is dialyzable (hemodialysis).

Half life

Half life of 9.05-41 hours.

Clearance

Renal clearance of etravirine is negligible (<1.2%), thus no dose adjustments are required in patients with renal impairment.

Clearance is shown to be reduced in patients with Hepatitis B and/or co-infection, however, the safety profile of etravirine does not call for dosage adjustments.

Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Etravirine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Etravirine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Etravirine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Etravirine.
5-androstenedioneThe metabolism of 5-androstenedione can be increased when combined with Etravirine.
6-Deoxyerythronolide BThe metabolism of Etravirine can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be increased when combined with Etravirine.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Etravirine.
AbirateroneThe metabolism of Etravirine can be decreased when combined with Abiraterone.
AcalabrutinibThe metabolism of Etravirine can be decreased when combined with Acalabrutinib.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D04112
PubChem Compound
193962
PubChem Substance
175427070
ChemSpider
168313
BindingDB
50103642
ChEBI
63589
ChEMBL
CHEMBL308954
PharmGKB
PA166014703
HET
65B
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Etravirine
ATC Codes
J05AG04 — Etravirine
AHFS Codes
  • 08:18.08.16 — Nonnucleoside Reverse Transcriptase Inhibitors
PDB Entries
1sv5 / 3m8p / 3mec / 3med
FDA label
Download (642 KB)
MSDS
Download (122 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableEndothelial Function / Human Immunodeficiency Virus (HIV) Infections / Inflammatory Reaction / Insulin Resistance / Lipids1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceHealthy Volunteers / Human Immunodeficiency Virus (HIV) Infections1
1CompletedBasic ScienceHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
1CompletedBasic ScienceInfection, Human Immunodeficiency Virus I1
1CompletedHealth Services ResearchHuman Immunodeficiency Virus (HIV)1
1CompletedOtherHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
1CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Infections, Fungal1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Pharmacokinetics1
1, 2Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAnti-Retroviral Agents / Human Immunodeficiency Virus Type 1 (HIV-1)1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections5
2CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)2
2CompletedTreatmentInfection, Human Immunodeficiency Virus I2
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2TerminatedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)2
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Type 1 (HIV-1)1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV)3
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections / Pregnancy1
3CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)2
3CompletedTreatmentInfection, Human Immunodeficiency Virus I1
4Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I1
4CompletedNot AvailableAcquired Immune Deficiency Syndrome (AIDS)1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV)1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4TerminatedTreatmentAcute HIV Infection / Human Immunodeficiency Virus (HIV) Infections1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
4WithdrawnTreatmentChronic Hepatitis C Virus (HCV) Infection / Human Immunodeficiency Virus (HIV) / Viral Hepatitis B1
Not AvailableCompletedNot AvailableHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV)1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentSleep disorders and disturbances1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral100 mg
TabletOral100 mg/1
TabletOral200 mg
TabletOral200 mg/1
TabletOral25 mg/1
TabletOral25 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2651665No2010-04-272027-06-06Canada
CA2350801No2008-05-202019-09-24Canada
US6878717Yes2005-04-122020-05-05Us
US7037917Yes2006-05-022021-06-13Us
US8003789Yes2011-08-232020-05-01Us
US7887845Yes2011-02-152019-09-25Us

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0169 mg/mLALOGPS
logP3.67ALOGPS
logP5.54ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)12.49ChemAxon
pKa (Strongest Basic)4.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area120.64 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity111.87 m3·mol-1ChemAxon
Polarizability41.09 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0101900000-33e354fd9e3dbad9ddb6
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4r-0100900000-da01bbb7f5f5d708476e

Taxonomy

Description
This compound belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Ethers
Direct Parent
Diarylethers
Alternative Parents
Aniline and substituted anilines / Benzonitriles / Phenol ethers / Phenoxy compounds / m-Xylenes / Halopyrimidines / Aminopyrimidines and derivatives / Imidolactams / Aryl bromides / Heteroaromatic compounds
show 7 more
Substituents
Diaryl ether / Phenoxy compound / M-xylene / Xylene / Aniline or substituted anilines / Benzonitrile / Phenol ether / Aminopyrimidine / Halopyrimidine / Aryl bromide
show 20 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organobromine compound, aromatic ether, aminopyrimidine, dinitrile (CHEBI:63589)

Targets

Kind
Protein
Organism
HIV-1
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Gag-Pol polyprotein: Mediates, with Gag polyrotein, the essential events in virion assembly, including binding the plasma membrane, making the protein-protein interactions necessary to create spher...
Gene Name
gag-pol
Uniprot ID
P03366
Uniprot Name
Gag-Pol polyprotein
Molecular Weight
163287.51 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
HIV-1
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Gag-Pol polyprotein: Mediates, with Gag polyrotein, the essential events in virion assembly, including binding the plasma membrane, making the protein-protein interactions necessary to create spher...
Gene Name
gag-pol
Uniprot ID
P04585
Uniprot Name
Gag-Pol polyprotein
Molecular Weight
162041.05 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Perez VE, Sanchez-Parra C, Serrano Villar S: [Etravirine drug interactions]. Enferm Infecc Microbiol Clin. 2009 Dec;27 Suppl 2:27-31. doi: 10.1016/S0213-005X(09)73216-1. [PubMed:20116625]
  2. Kakuda TN, Scholler-Gyure M, Hoetelmans RM: Pharmacokinetic interactions between etravirine and non-antiretroviral drugs. Clin Pharmacokinet. 2011 Jan;50(1):25-39. doi: 10.2165/11534740-000000000-00000. [PubMed:21142266]
  3. Scholler-Gyure M, Kakuda TN, Raoof A, De Smedt G, Hoetelmans RM: Clinical pharmacokinetics and pharmacodynamics of etravirine. Clin Pharmacokinet. 2009;48(9):561-74. doi: 10.2165/10895940-000000000-00000. [PubMed:19725591]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Perez VE, Sanchez-Parra C, Serrano Villar S: [Etravirine drug interactions]. Enferm Infecc Microbiol Clin. 2009 Dec;27 Suppl 2:27-31. doi: 10.1016/S0213-005X(09)73216-1. [PubMed:20116625]
  2. Kakuda TN, Scholler-Gyure M, Hoetelmans RM: Pharmacokinetic interactions between etravirine and non-antiretroviral drugs. Clin Pharmacokinet. 2011 Jan;50(1):25-39. doi: 10.2165/11534740-000000000-00000. [PubMed:21142266]
  3. Scholler-Gyure M, Kakuda TN, Raoof A, De Smedt G, Hoetelmans RM: Clinical pharmacokinetics and pharmacodynamics of etravirine. Clin Pharmacokinet. 2009;48(9):561-74. doi: 10.2165/10895940-000000000-00000. [PubMed:19725591]
  4. Scholler-Gyure M, Kakuda TN, De Smedt G, Vanaken H, Bouche MP, Peeters M, Woodfall B, Hoetelmans RM: A pharmacokinetic study of etravirine (TMC125) co-administered with ranitidine and omeprazole in HIV-negative volunteers. Br J Clin Pharmacol. 2008 Oct;66(4):508-16. doi: 10.1111/j.1365-2125.2008.03214.x. Epub 2008 Apr 25. [PubMed:18492125]
  5. Etravirine FDA label [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Curator comments
There is conflicting information in the literature regarding the severity of inhibition of CYP2C19, with some sources suggesting weak inhibition [A15663], some suggesting moderate inhibition [F1510], and some general comments regarding CYP2C19 inhibition [A15662, A15664, A38838].
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Perez VE, Sanchez-Parra C, Serrano Villar S: [Etravirine drug interactions]. Enferm Infecc Microbiol Clin. 2009 Dec;27 Suppl 2:27-31. doi: 10.1016/S0213-005X(09)73216-1. [PubMed:20116625]
  2. Kakuda TN, Scholler-Gyure M, Hoetelmans RM: Pharmacokinetic interactions between etravirine and non-antiretroviral drugs. Clin Pharmacokinet. 2011 Jan;50(1):25-39. doi: 10.2165/11534740-000000000-00000. [PubMed:21142266]
  3. Scholler-Gyure M, Kakuda TN, Raoof A, De Smedt G, Hoetelmans RM: Clinical pharmacokinetics and pharmacodynamics of etravirine. Clin Pharmacokinet. 2009;48(9):561-74. doi: 10.2165/10895940-000000000-00000. [PubMed:19725591]
  4. Yanakakis LJ, Bumpus NN: Biotransformation of the antiretroviral drug etravirine: metabolite identification, reaction phenotyping, and characterization of autoinduction of cytochrome P450-dependent metabolism. Drug Metab Dispos. 2012 Apr;40(4):803-14. doi: 10.1124/dmd.111.044404. Epub 2012 Jan 23. [PubMed:22269145]
  5. Viani RM: Role of etravirine in the management of treatment-experienced patients with human immunodeficiency virus type 1. HIV AIDS (Auckl). 2010;2:141-9. Epub 2010 Jun 28. [PubMed:22096392]
  6. Selected Properties of Etravirine, HIVCLINIC.ca [File]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Kakuda TN, Scholler-Gyure M, Hoetelmans RM: Pharmacokinetic interactions between etravirine and non-antiretroviral drugs. Clin Pharmacokinet. 2011 Jan;50(1):25-39. doi: 10.2165/11534740-000000000-00000. [PubMed:21142266]
  2. Scholler-Gyure M, Kakuda TN, Raoof A, De Smedt G, Hoetelmans RM: Clinical pharmacokinetics and pharmacodynamics of etravirine. Clin Pharmacokinet. 2009;48(9):561-74. doi: 10.2165/10895940-000000000-00000. [PubMed:19725591]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent phospholipid efflux translocator that acts as a positive regulator of biliary lipid secretion. Functions as a floppase that translocates specifically phosphatidylcholine (PC) from ...
Gene Name
ABCB4
Uniprot ID
P21439
Uniprot Name
Phosphatidylcholine translocator ABCB4
Molecular Weight
141521.845 Da
References
  1. Kakuda TN, Scholler-Gyure M, Hoetelmans RM: Pharmacokinetic interactions between etravirine and non-antiretroviral drugs. Clin Pharmacokinet. 2011 Jan;50(1):25-39. doi: 10.2165/11534740-000000000-00000. [PubMed:21142266]
  2. Scholler-Gyure M, Kakuda TN, Raoof A, De Smedt G, Hoetelmans RM: Clinical pharmacokinetics and pharmacodynamics of etravirine. Clin Pharmacokinet. 2009;48(9):561-74. doi: 10.2165/10895940-000000000-00000. [PubMed:19725591]

Drug created on March 19, 2008 10:32 / Updated on November 18, 2018 04:52