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Statements

Subject Item
n2:DB00300
rdf:type
n3:Drug
n3:description
Tenofovir disoproxil fumarate (a prodrug of tenofovir), marketed by Gilead Sciences under the trade name Viread®, belongs to a class of antiretroviral drugs known as nucleotide analogue reverse transcriptase inhibitors (nRTIs), which block reverse transcriptase, an enzyme crucial to viral production in HIV-infected people. [Wikipedia] In vivo tenofovir disoproxil fumarate is converted to tenofovir, an acyclic nucleoside phosphonate (nucleotide) analog of adenosine 5'-monophosphate.
n3:dosage
n18:271B4E29-363D-11E5-9242-09173F13E4C5 n18:271B4E2A-363D-11E5-9242-09173F13E4C5 n18:271B4E2B-363D-11E5-9242-09173F13E4C5 n18:271B4E2C-363D-11E5-9242-09173F13E4C5 n18:271B4E2D-363D-11E5-9242-09173F13E4C5 n18:271B4E2E-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# FDA label # Gilden D: Tenofovir: Gilead applies for approval; expanded access liberalized. AIDS Treat News. 2001 May 11;(364):2-3, 1. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11569959 # Miller MD, Margot NA, Hertogs K, Larder B, Miller V: Antiviral activity of tenofovir (PMPA) against nucleoside-resistant clinical HIV samples. Nucleosides Nucleotides Nucleic Acids. 2001 Apr-Jul;20(4-7):1025-8. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11562951 # Thompson CA: Prodrug of tenofovir diphosphate approved for combination HIV therapy. Am J Health Syst Pharm. 2002 Jan 1;59(1):18. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11813460 # Gazzard BG: The potential place of tenofovir in antiretroviral treatment regimens. Int J Clin Pract. 2001 Dec;55(10):704-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11777298 # Lu C, Jia Y, Chen L, Ding Y, Yang J, Chen M, Song Y, Sun X, Wen A: Pharmacokinetics and food interaction of a novel prodrug of tenofovir, tenofovir dipivoxil fumarate, in healthy volunteers. J Clin Pharm Ther. 2013 Apr;38(2):136-40. doi: 10.1111/jcpt.12023. Epub 2012 Dec 28. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/23278367 # Maskew M, Westreich D, Firnhaber C, Sanne I: Tenofovir use and pregnancy among women initiating HAART. AIDS. 2012 Nov 28;26(18):2393-7. doi: 10.1097/QAD.0b013e328359a95c. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/22951630 # Uglietti A, Zanaboni D, Gnarini M, Maserati R: Emtricitabine/tenofovir in the treatment of HIV infection: current PK/PD evaluation. Expert Opin Drug Metab Toxicol. 2012 Oct;8(10):1305-14. doi: 10.1517/17425255.2012.714367. Epub 2012 Sep 4. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/22943210 # Ransom CE, Huo Y, Patel K, Scott GB, Watts HD, Williams P, Siberry GK, Livingston EG: Infant growth outcomes after maternal tenofovir disoproxil fumarate use during pregnancy. J Acquir Immune Defic Syndr. 2013 Dec 1;64(4):374-81. doi: 10.1097/QAI.0b013e3182a7adb2. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/24169122
n3:group
approved investigational
n3:halfLife
When a single oral dose is given, the terminal elimination half-life is approximately 17 hours.
n3:indication
Tenofovir is indicated in combination with other antiretroviral agents for the treatment of HIV-1 infection in adults and pediatric patients 2 years of age and older. It is also indicated for the treatment of chronic hepatitis B in adults and pediatric patients 12 years of age and older.
n3:manufacturer
n7:271B4E27-363D-11E5-9242-09173F13E4C5 n7:271B4E26-363D-11E5-9242-09173F13E4C5
owl:sameAs
n6:DB00300 n13:DB00300
dcterms:title
Tenofovir
adms:identifier
n23:408154 n24:DB00300 n25:46508131 n26:PA10204 n27:464205 n28:53808-0810-1 n29:TFO n30:D01982 n31:63625 n32:Tenofovir
n3:mechanismOfAction
Tenofovir inhibits the activity of HIV reverse transcriptase by competing with the natural substrate deoxyadenosine 5’-triphosphate and, after incorporation into DNA, by DNA chain termination. Specifically, the drugs are analogues of the naturally occurring deoxynucleotides needed to synthesize the viral DNA and they compete with the natural deoxynucleotides for incorporation into the growing viral DNA chain. However, unlike the natural deoxynucleotides substrates, NRTIs and NTRTIs (nucleoside/tide reverse transcriptase inhibitors) lack a 3'-hydroxyl group on the deoxyribose moiety. As a result, following incorporation of an NRTI or an NtRTI, the next incoming deoxynucleotide cannot form the next 5'-3' phosphodiester bond needed to extend the DNA chain. Thus, when an NRTI or NtRTI is incorporated, viral DNA synthesis is halted, a process known as chain termination. All NRTIs and NtRTIs are classified as competitive substrate inhibitors.
n3:packager
n7:271B4E25-363D-11E5-9242-09173F13E4C5 n7:271B4E23-363D-11E5-9242-09173F13E4C5 n7:271B4E24-363D-11E5-9242-09173F13E4C5 n7:271B4E1D-363D-11E5-9242-09173F13E4C5 n7:271B4E1E-363D-11E5-9242-09173F13E4C5 n7:271B4E1B-363D-11E5-9242-09173F13E4C5 n7:271B4E1C-363D-11E5-9242-09173F13E4C5 n7:271B4E21-363D-11E5-9242-09173F13E4C5 n7:271B4E22-363D-11E5-9242-09173F13E4C5 n7:271B4E1F-363D-11E5-9242-09173F13E4C5 n7:271B4E20-363D-11E5-9242-09173F13E4C5 n7:271B4E19-363D-11E5-9242-09173F13E4C5 n7:271B4E1A-363D-11E5-9242-09173F13E4C5
n3:patent
n12:5922695 n12:2298059 n12:2261619
n3:routeOfElimination
When tenofovir is given IV, 70-80% of the dose is recovered in the urine as unchanged drug within 72 hours of administration. Tenofovir is eliminated by a combination of glomerular filtration and active tubular secretion. There may be competition for elimination with other compounds that are also renally eliminated.
n3:synonym
Anhydrous tenofovir (R)-PMPA Tenofovir (anh.) Anh. tenofovir Tenofovir
n3:toxicity
Limited clinical experience at doses higher than the therapeutic dose of tenofovir 300 mg is available. In Study 901 tenofovir disoproxil fumarate 600 mg was administered to 8 patients orally for 28 days. No severe adverse reactions were reported. The effects of higher doses are not known.
n3:volumeOfDistribution
* 1.3 ± 0.6 L/kg [tenofovir 1.0 mg/kg IV] * 1.2 ± 0.4 L/kg [tenofovir 3.0 mg/kg IV]
n8:hasAHFSCode
n9:08-18-08-20
n3:foodInteraction
When given with a high-fat meal, the oral bioavailability, AUC, and Cmax increased.
n3:mixture
n20:271B4E17-363D-11E5-9242-09173F13E4C5 n20:271B4E18-363D-11E5-9242-09173F13E4C5 n20:271B4E15-363D-11E5-9242-09173F13E4C5 n20:271B4E16-363D-11E5-9242-09173F13E4C5
n3:proteinBinding
Very low: < 0.7% to human plasma proteins and < 7.2% to serum proteins
n3:salt
n3:synthesisReference
Uma Maheswer Rao Vasireddy, Siva Rama Prasad Vellanki, Raja Babu Balusu, Naga Durga Rao Bandi, Pavan Kumar Jujjavarapu, Sambasiva Rao Ginjupalli, Rama Krishna Pilli, "Process for the preparation of Tenofovir." U.S. Patent US08049009, issued November 01, 2011.
n16:hasConcept
n17:M0254881
foaf:page
n11:viread.htm n15:vir1605.shtml n19:tenofovir.html
n3:IUPAC-Name
n4:271B4E33-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B4E39-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B4E38-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B4E35-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B4E36-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B4E37-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B4E31-363D-11E5-9242-09173F13E4C5 n4:271B4E49-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B4E2F-363D-11E5-9242-09173F13E4C5 n4:271B4E4B-363D-11E5-9242-09173F13E4C5 n4:271B4E32-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B4E30-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Acceptor-Count
n4:271B4E3F-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B4E40-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B4E3A-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B4E3B-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B4E3D-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B4E3C-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B4E3E-363D-11E5-9242-09173F13E4C5
n3:absorption
Tenofovir disoproxil fumarate is the water soluble diester prodrug of the active ingredient tenofoir. The oral bioavailability in fasted patients is approximately 25%. When a single oral dose (300 mg) is given to HIV-1 infected subjects in the fasted state, the maximum serum concentration was achieved in 1.0 ± 0.4 hours (Tmax). Cmax and AUC values are 0.30 ± 0.09 µg/mL and 2.29 ± 0.69 µg∙hr/mL. Administration of food (high fat meal containing 40 to 50% fat) increases the oral bioavailability, with an increase in the AUC of approximately 40%. Cmax is lower in the oral powder, compared to the tablet formulation. However, the mean AUC is similar between the two formulations.
n3:affectedOrganism
Human Immunodeficiency Virus
n3:casRegistryNumber
147127-20-6
n3:category
n3:clearance
The following are renal clearance (CL renal) parameters for subjects with varying degrees of renal function: * 243.5 ± 33.3 mL/min [baseline creatinine clearance >80 mL/min] * 168.6 ± 27.5 mL/min [baseline creatinine clearance 50-80 mL/min] * 100.6 ± 27.5 mL/min [baseline creatinine clearance 30-49 mL/min] * 43.0 ± 31.2 mL/min [baseline creatinine clearance 12-29 mL/min] The following are clearance (CL/F) parameters for subjects with varying degrees of renal function: * 1043.7 ± 115.4 [baseline creatinine clearance >80 mL/min] * 807.7 ± 279.2 [baseline creatinine clearance 50-80 mL/min] * 444.4 ± 209.8 [baseline creatinine clearance 30-49 mL/min] * 177.0 ± 97.1 [baseline creatinine clearance 12-29 mL/min]
n3:containedIn
n14:271B4E28-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B4E45-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B4E47-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B4E48-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B4E4A-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B4E44-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B4E43-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B4E46-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B4E34-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B4E41-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B4E42-363D-11E5-9242-09173F13E4C5