Identification
- Summary
Tenofovir alafenamide is a nucleoside analog reverse transcriptase inhibitor used for the treatment of chronic hepatitis B virus infection in adults with compensated liver disease.
- Brand Names
- Biktarvy, Descovy, Genvoya, Odefsey, Vemlidy
- Generic Name
- Tenofovir alafenamide
- DrugBank Accession Number
- DB09299
- Background
Tenofovir alafenamide is a novel tenofovir prodrug developed in order to improve renal safety when compared to the counterpart tenofovir disoproxil.1 Both of these prodrugs were first created to cover the polar phosphonic acid group on tenofovir by using a novel oxycarbonyloxymethyl linkers to improve the oral bioavailability and intestinal diffusion.8 Tenofovir alafenamide is an alanine ester form characterized for presenting low systemic levels but high intracellular concentration.2 It has been reported to produce a large antiviral efficacy at doses ten times lower than tenofovir disoproxil.6 Tenofovir alafenamide is indicated to treat chronic hepatitis B,9 treat HIV-1,11,12,13,14 and prevent HIV-1 infections.11,17
Tenofovir alafenamide was developed by Gilead Sciences Inc and granted FDA approval on 5 November 2015.10
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Tenofovir alafenamide (DB09299)
- Weight
- Average: 476.474
Monoisotopic: 476.193705056 - Chemical Formula
- C21H29N6O5P
- Synonyms
- Tenofovir alafenamide
- External IDs
- GS 7340
- GS 7340 03
- GS 734003
- GS-7340
- GS-7340-03
- GS-734003
- GS7340
- GS734003
Pharmacology
- Indication
Tenofovir alafenamide is indicated for the treatment of hepatitis B virus infection in adults and pediatric patients 12 years of age and older with compensated liver disease.18
In combination with emtricitabine and other antiretrovirals, it is indicated for the treatment of HIV-1 infection in adolescent and adult patients with a weight higher than 35 kg.11 This combination is also indicated to prevent HIV-1 infections in high risk adolescent and adult patients, excluding patients at risk from receptive vaginal sex.11,17 When combined with antiretrovirals other than protease inhibitors that require a CYP3A inhibitor, it can be used to treat pediatric patients weighing 25-35 kg.11
In the combination product with emtricitabine and bictegravir, tenofovir alafenamide is considered a complete treatment regimen for HIV-1 infections for treatment-naive patients or patients virologically suppressed for at least three months with no history of treatment failure.12,20,19
Additionally, the combination product including elvitegravir, cobicistat, emtricitabine and tenofovir alafenamide and the combination product including emtricitabine, rilpivirine and tenofovir alafenamide can be used in the treatment of HIV-1 infection in patients older than 12 years with no previous antiretroviral therapy history or who are virologically suppressed for at least 6 months with no history of treatment failure.13
The combination product including darunavir, cobicistat, emtricitabine, and tenofovir alafenamide is indicated for the treatment of HIV-1 infection in adults without prior antiretroviral therapy or in patients virologically suppressed for 6 months and no reported resistance to darunavir or tenofovir.14
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Chronic hepatitis b infection •••••••••••• ••••••••••• •••••• ••••••••• ••••••••••• ••••• ••••••• •••••• Used in combination to treat Hiv-1-infection Combination Product in combination with: Emtricitabine (DB00879), Cobicistat (DB09065), Darunavir (DB01264) •••••••••••• ••••• •• •••••••••• •• •••••••••• •• •••••••••• •• •••••••••• ••••••••••••• •••••••••• ••• • ••••••• ••••••••••••••• Used in combination to treat Hiv-1-infection Combination Product in combination with: Rilpivirine (DB08864), Emtricitabine (DB00879), Elvitegravir (DB09101), Cobicistat (DB09065) •••••••••••• ••••••••••••• •••••••••• ••• • ••••••• •• ••••••• •• ••••••••• ••••••• Used in combination to treat Hiv-1-infection Combination Product in combination with: Bictegravir (DB11799), Emtricitabine (DB00879) •••••••••••• ••••••••••••• ••••••••• ••• • ••••••• •• ••••••• •• ••••••••• •••••••• ••••••••• ••••• Used in combination to treat Human immunodeficiency virus type 1 (hiv-1) infection Combination Product in combination with: Bictegravir (DB11799), Emtricitabine (DB00879) •••••••••••• •••••• •• ••••• •• •• •••••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Tenofovir alafenamide has been shown to be a potent inhibitor of hepatitis B viral replication.4
Tenofovir alafenamide presents a better renal tolerance when compared with the counterpart tenofovir disoproxil. This improved safety profile seems to be related to a lower plasma concentration of tenofovir.1
In clinical trials, tenofovir alafenamide was shown to present 5-fold more potent antiviral activity against HIV-1 when compared to tenofovir disoproxil.1
- Mechanism of action
Tenofovir alafenamide presents 91% lower plasma concentration with an intracellular presence of about 20-fold higher when compared to tenofovir disoproxil.2 This is due to its prolonged systemic exposure and its higher intracellular accumulation of the active metabolite tenofovir diphosphate.5
Tenofovir alafenamide accumulates more in peripheral blood mononuclear cells compared to red blood cells.5
Once activated, tenofovir acts with different mechanisms including the inhibition of viral polymerase, causing chain termination and the inhibition of viral synthesis.9 To know more about the specific mechanism of action of the active form, please visit the drug entry of tenofovir.
Target Actions Organism AReverse transcriptase/RNaseH inhibitorHuman immunodeficiency virus 1 NReverse transcriptase inhibitorHBV NDNA polymerase inhibitorHuman herpesvirus 2 (strain 186) - Absorption
As compared to the parent molecule, tenofovir, tenofovir alafenamide presents a lipophilic group that masks the negative charge of the parent moiety which improves its oral bioavailability.1
Tenofovir alafenamide is highly stable in plasma and, after administration of this prodrug, there is a low concentration of tenofovir in plasma. After oral administration, tenofovir alafenamide is rapidly absorbed by the gut. When a single dose is administered, a peak concentration of 16 ng/ml of the parent compound, corresponding to about 73% of the dose, is observed after 2 hours with an AUC of 270 ng*h/mL.1,5 Once inside the body, tenofovir alafenamide enters hepatocytes by passive diffusion regulated by the organic anion transporters 1B1 and 1B3 for its activation.4
Administration of tenofovir alafenamide concomitantly with a high-fat meal results in an increase of about 65% in its internal exposure.15
- Volume of distribution
In clinical trials, the reported volume of distribution of tenofovir alafenamide was higher than 100 L.7
- Protein binding
Tenofovir alafenamide is reported to bind to plasma proteins and ex vivo studies have registered that approximately 80% of the administered dose of this drug is presented in a bound state.3
- Metabolism
To be activated, tenofovir alafenamide is required to be hydrolyzed to the parent compound tenofovir by the activity of cathepsin A or carboxylesterase 1. Tenofovir alafenamide presents significant plasma stability and hence, its activation is performed inside the target cells.1
After activation, tenofovir is further processed and after 1-2 days, it is detected in plasma almost completely transformed to uric acid.1
Hover over products below to view reaction partners
- Route of elimination
Tenofovir alafenamide has been registered to present a bile elimination that corresponds to 47% of the administered dose and a renal elimination the represents about 36%. From the recovered dose in urine, about 75% is represented as unchanged tenofovir followed by uric acid and a small dose of tenofovir alafenamide. On the other hand, in feces, 99% of the recovered dose corresponds to tenofovir.1
- Half-life
The reported half-life for tenofovir alafenamide is of 0.51 hours.3
- Clearance
The reported clearance rate of tenofovir alafenamide is 117 L/h. In patients with severe renal impairment, this value can be decreased by 50%, reporting a rate of 61.7 L/h.16
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
The LD50 of tenofovir alafenamide has not been reported. In cases of overdose, continuous monitoring of vital signs is required as the adverse effects in high doses has not been evaluated. However, in case of overdose, tenofovir is efficiently removed by hemodialysis with an extraction coefficient of 54%.15
Carcinogenic reports have only been performed with tenofovir disoproxil and it is important to consider that tenofovir alafenamide does not present a high systemic exposure. However, long-term exposure with 10-fold dosages of tenofovir disoproxil was reported to produce liver adenomas in females. Tenofovir alafenamide was not reported to present mutagenic potential and it did not present effects on fertility.15
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir The serum concentration of Tenofovir alafenamide can be increased when it is combined with Abacavir. Abametapir The serum concentration of Tenofovir alafenamide can be increased when it is combined with Abametapir. Abatacept The metabolism of Tenofovir alafenamide can be increased when combined with Abatacept. Abemaciclib The serum concentration of Tenofovir alafenamide can be increased when it is combined with Abemaciclib. Abrocitinib The serum concentration of Tenofovir alafenamide can be increased when it is combined with Abrocitinib. - Food Interactions
- Avoid St. John's Wort. St. John's Wort can cause drug interaction and decrease the serum concentration of tenofovir alafenamide.
- Take at the same time every day.
- Take with or without food. Recommendations vary from product to product - consult individual product monographs for additional information.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Tenofovir alafenamide fumarate FWF6Q91TZO 1392275-56-7 SVUJNSGGPUCLQZ-LVWWUONPSA-N - Active Moieties
Name Kind UNII CAS InChI Key Tenofovir prodrug W4HFE001U5 147127-20-6 SGOIRFVFHAKUTI-ZCFIWIBFSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Vemlidy Tablet 25 mg Oral Gilead Sciences 2017-06-20 Not applicable Canada 
Vemlidy Tablet, film coated 25 mg Oral Gilead Sciences Ireland Uc 2020-12-16 Not applicable EU 
Vemlidy Tablet 25 mg/1 Oral Gilead Sciences, Inc. 2016-11-10 Not applicable US 
Vemlidy Tablet, film coated 25 mg Oral Gilead Sciences Ireland Uc 2020-12-16 Not applicable EU - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Biktarvy Tenofovir alafenamide fumarate (25 mg) + Bictegravir sodium (50 mg) + Emtricitabine (200 mg) Tablet Oral Gilead Sciences 2018-08-08 Not applicable Canada Biktarvy Tenofovir alafenamide fumarate (25 mg) + Bictegravir sodium (50 mg) + Emtricitabine (200 mg) Tablet, film coated Oral Gilead Sciences Ireland Uc 2021-06-01 Not applicable EU Biktarvy Tenofovir alafenamide fumarate (15 mg/1) + Bictegravir sodium (30 mg/1) + Emtricitabine (120 mg/1) Tablet Oral Gilead Sciences, Inc. 2021-10-07 Not applicable US Biktarvy Tenofovir alafenamide fumarate (25 mg/1) + Bictegravir sodium (50 mg/1) + Emtricitabine (200 mg/1) Tablet Oral A-S Medication Solutions 2018-02-07 Not applicable US Biktarvy Tenofovir alafenamide fumarate (25 mg) + Bictegravir sodium (50 mg) + Emtricitabine (200 mg) Tablet, film coated Oral Gilead Sciences Ireland Uc 2020-12-15 Not applicable EU
Categories
- ATC Codes
- J05AR19 — Emtricitabine, tenofovir alafenamide and rilpivirine
- J05AR — Antivirals for treatment of HIV infections, combinations
- J05A — DIRECT ACTING ANTIVIRALS
- J05 — ANTIVIRALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J05AR — Antivirals for treatment of HIV infections, combinations
- J05A — DIRECT ACTING ANTIVIRALS
- J05 — ANTIVIRALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J05AR — Antivirals for treatment of HIV infections, combinations
- J05A — DIRECT ACTING ANTIVIRALS
- J05 — ANTIVIRALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J05AF — Nucleoside and nucleotide reverse transcriptase inhibitors
- J05A — DIRECT ACTING ANTIVIRALS
- J05 — ANTIVIRALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J05AR — Antivirals for treatment of HIV infections, combinations
- J05A — DIRECT ACTING ANTIVIRALS
- J05 — ANTIVIRALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Amino Acids
- Amino Acids, Peptides, and Proteins
- Antiinfectives for Systemic Use
- Antiviral Agents
- Antivirals for Systemic Use
- Antivirals used in combination for the treatment of HIV infections
- BCRP/ABCG2 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A4 Substrates (strength unknown)
- Cytochrome P-450 Substrates
- Direct Acting Antivirals
- Hepatitis B Virus Nucleoside Analog Reverse Transcriptase Inhibitor
- Heterocyclic Compounds, Fused-Ring
- Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor
- Nephrotoxic agents
- Nucleoside and Nucleotide Reverse Transcriptase Inhibitors
- OAT1/SLC22A6 Substrates
- OAT3/SLC22A8 Substrates
- OATP1B1/SLCO1B1 Substrates
- OATP1B3 substrates
- Organophosphonates
- Organophosphorus Compounds
- P-glycoprotein substrates
- Purines
- Tenofovir and prodrugs
- Vitamin B Complex
- Vitamins
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Alpha amino acid esters
- Alternative Parents
- Alanine and derivatives / 6-aminopurines / Phenoxy compounds / Aminopyrimidines and derivatives / Phosphonic amide esters / Phosphonic acid esters / N-substituted imidazoles / Imidolactams / Heteroaromatic compounds / Carboxylic acid esters show 8 more
- Substituents
- 6-aminopurine / Alanine or derivatives / Alpha-amino acid ester / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Carbonyl group show 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Herpes simplex virus
- Hepatitis B virus
- HIV-1
Chemical Identifiers
- UNII
- EL9943AG5J
- CAS number
- 379270-37-8
- InChI Key
- LDEKQSIMHVQZJK-CAQYMETFSA-N
- InChI
- InChI=1S/C21H29N6O5P/c1-14(2)31-21(28)16(4)26-33(29,32-17-8-6-5-7-9-17)13-30-15(3)10-27-12-25-18-19(22)23-11-24-20(18)27/h5-9,11-12,14-16H,10,13H2,1-4H3,(H,26,29)(H2,22,23,24)/t15-,16+,33+/m1/s1
- IUPAC Name
- propan-2-yl (2S)-2-{[(S)-({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)(phenoxy)phosphoryl]amino}propanoate
- SMILES
- CC(C)OC(=O)[C@H](C)N[P@](=O)(CO[C@H](C)CN1C=NC2=C(N)N=CN=C12)OC1=CC=CC=C1
References
- General References
- Aloy B, Tazi I, Bagnis CI, Gauthier M, Janus N, Launay-Vacher V, Deray G, Tourret J: Is Tenofovir Alafenamide Safer than Tenofovir Disoproxil Fumarate for the Kidneys? AIDS Rev. 2016 Oct-Dec;18(4):184-192. [Article]
- Grant PM, Cotter AG: Tenofovir and bone health. Curr Opin HIV AIDS. 2016 May;11(3):326-32. doi: 10.1097/COH.0000000000000248. [Article]
- Deeks ED: Bictegravir/Emtricitabine/Tenofovir Alafenamide: A Review in HIV-1 Infection. Drugs. 2018 Nov;78(17):1817-1828. doi: 10.1007/s40265-018-1010-7. [Article]
- Ogawa E, Furusyo N, Nguyen MH: Tenofovir alafenamide in the treatment of chronic hepatitis B: design, development, and place in therapy. Drug Des Devel Ther. 2017 Nov 6;11:3197-3204. doi: 10.2147/DDDT.S126742. eCollection 2017. [Article]
- Ray AS, Fordyce MW, Hitchcock MJ: Tenofovir alafenamide: A novel prodrug of tenofovir for the treatment of Human Immunodeficiency Virus. Antiviral Res. 2016 Jan;125:63-70. doi: 10.1016/j.antiviral.2015.11.009. Epub 2015 Nov 27. [Article]
- Antela A, Aguiar C, Compston J, Hendry BM, Boffito M, Mallon P, Pourcher-Martinez V, Di Perri G: The role of tenofovir alafenamide in future HIV management. HIV Med. 2016 May;17 Suppl 2:4-16. doi: 10.1111/hiv.12401. [Article]
- Markowitz M, Zolopa A, Squires K, Ruane P, Coakley D, Kearney B, Zhong L, Wulfsohn M, Miller MD, Lee WA: Phase I/II study of the pharmacokinetics, safety and antiretroviral activity of tenofovir alafenamide, a new prodrug of the HIV reverse transcriptase inhibitor tenofovir, in HIV-infected adults. J Antimicrob Chemother. 2014 May;69(5):1362-9. doi: 10.1093/jac/dkt532. Epub 2014 Feb 6. [Article]
- Taylor JB, Triggle DJ. (2007). Comprehensive Medicinal Chemistry II. Elsevier.
- Pubmed books [Link]
- FDA approvals [Link]
- FDA Approved Drug Products: Descovy (Emtricitabine and Tenofovir Alafenamide) Oral Tablets [Link]
- FDA Approved Drug Products: Bictegravir, Emtricitabine, and Tenofovir Alafenamide Oral Tablets [Link]
- FDA Approved Drug Products: Elvitegravir, Cobicistat, Emtricitabine, and Tenofovir Alafenamide Oral Tablets [Link]
- FDA Approved Drug Products: Darunavir, Cobicistat, Emtricitabine, and Tenofovir Alafenamide Oral Tablets [Link]
- Health Canada Approved Drug Products: Tenofovir Alafenamide Oral Tablets [Link]
- European Medicines Agency Assessment Report: Tenofovir Alafenamide [Link]
- FDA Press Announcements: FDA approves second drug to prevent HIV infection as part of ongoing efforts to end the HIV epidemic [Link]
- FDA Approved Drug Products: VEMLIDY (tenofovir alafenamide) tablets, for oral use (October 2022) [Link]
- EMA Approved Drug Products: Biktarvy (bictegravir, emtricitabine, tenofovir alafenamide) Oral Tablets [Link]
- FDA Approved Drug Products: BIKTARVY (bictegravir, emtricitabine, and tenofovir alafenamide) tablets, for oral use [Link]
- External Links
- KEGG Drug
- D10428
- PubChem Compound
- 9574768
- PubChem Substance
- 310265191
- ChemSpider
- 7849225
- 1721603
- ChEBI
- 90926
- ChEMBL
- CHEMBL2107825
- ZINC
- ZINC000100055899
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Tenofovir_alafenamide
- FDA label
- Download (1.08 MB)
- MSDS
- Download (254 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Active Not Recruiting Health Services Research Human Immunodeficiency Virus (HIV) Infections 1 4 Active Not Recruiting Prevention Hormone Therapy / Human Immunodeficiency Virus (HIV) Infections 1 4 Active Not Recruiting Treatment Acute HIV Infection 1 4 Active Not Recruiting Treatment Chronic Hepatitis B Infection 1 4 Active Not Recruiting Treatment Drug Use / Human Immunodeficiency Virus (HIV) Infections / Reduction, Harm 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, coated Oral Tablet, film coated Oral 150 mg Tablet, coated Oral 25 mg Tablet Oral Tablet Oral 800.000 mg Tablet, film coated Oral Tablet, film coated Oral 28043 MG Tablet Oral 25 mg/1 Tablet Oral 25 mg Tablet, film coated Oral Tablet, film coated Oral 25.0 mg Tablet, film coated Oral 25 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7800788 No 2010-09-21 2022-02-02 US US5914331 Yes 1999-06-22 2018-01-02 US US5814639 Yes 1998-09-29 2017-03-29 US US6642245 Yes 2003-11-04 2021-05-04 US US6703396 Yes 2004-03-09 2021-09-09 US US7470506 Yes 2008-12-30 2019-12-23 US US8597876 Yes 2013-12-03 2019-12-23 US US7700645 Yes 2010-04-20 2027-06-26 US US8518987 Yes 2013-08-27 2024-08-16 US US7125879 No 2006-10-24 2022-08-09 US US6838464 No 2005-01-04 2021-02-26 US US8080551 No 2011-12-20 2023-04-11 US US8101629 No 2012-01-24 2022-08-09 US US7067522 No 2006-06-27 2019-12-20 US US8148374 Yes 2012-04-03 2030-03-03 US US7635704 Yes 2009-12-22 2027-04-26 US US7176220 Yes 2007-02-13 2027-02-27 US US8981103 Yes 2015-03-17 2027-04-26 US US8633219 Yes 2014-01-21 2030-10-24 US US9296769 Yes 2016-03-29 2033-02-15 US US7803788 No 2010-09-28 2022-02-02 US US8754065 Yes 2014-06-17 2033-02-15 US US7390791 Yes 2008-06-24 2025-10-17 US US9891239 Yes 2018-02-13 2030-03-03 US US9889115 Yes 2018-02-13 2019-12-23 US US9216996 No 2015-12-22 2033-12-19 US US9708342 No 2017-07-18 2035-06-19 US US9732092 No 2017-08-15 2033-12-19 US US10039718 Yes 2018-08-07 2033-04-06 US US10385067 No 2019-08-20 2035-06-19 US US10548846 No 2020-02-04 2036-11-08 US US10786515 No 2020-09-29 2038-07-19 US US10786518 No 2020-09-29 2038-07-19 US US11744802 No 2016-11-08 2036-11-08 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 104-107 ºC 'MSDS' boiling point (°C) 640 ºC at 760 mmHg 'MSDS' water solubility 4.86 mg/ml at 20 ºC Product monograph. Gilead Sciences Canada logP 1.6 Product monograph. Gilead Sciences Canada pKa 3.96 Product monograph. Gilead Sciences Canada - Predicted Properties
Property Value Source Water Solubility 0.236 mg/mL ALOGPS logP 1.49 ALOGPS logP 1.88 Chemaxon logS -3.3 ALOGPS pKa (Strongest Acidic) 11.36 Chemaxon pKa (Strongest Basic) 5.12 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 143.48 Å2 Chemaxon Rotatable Bond Count 12 Chemaxon Refractivity 122.74 m3·mol-1 Chemaxon Polarizability 47.88 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0007-9103000000-737254a45b827a74dbc3 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-2114900000-106ce5efc9eca6bf7694 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-006y-9003100000-eb4bc3fad2c599361183 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0079-9522300000-493d24f75bb0677d7c5b Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000l-9812100000-3facd0a35b7cdf8f91a0 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-000x-8972100000-8a40cff04deb28c73ec1 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 200.68626 predictedDeepCCS 1.0 (2019) [M+H]+ 203.08183 predictedDeepCCS 1.0 (2019) [M+Na]+ 208.99437 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Human immunodeficiency virus 1
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Rna-dna hybrid ribonuclease activity
- Specific Function
- Not Available
- Gene Name
- pol
- Uniprot ID
- Q72547
- Uniprot Name
- Reverse transcriptase/RNaseH
- Molecular Weight
- 65223.615 Da
References
- McConville C, Boyd P, Major I: Efficacy of Tenofovir 1% Vaginal Gel in Reducing the Risk of HIV-1 and HSV-2 Infection. Clin Med Insights Womens Health. 2014 Feb 13;7:1-8. doi: 10.4137/CMWH.S10353. eCollection 2014. [Article]
- Ray AS, Fordyce MW, Hitchcock MJ: Tenofovir alafenamide: A novel prodrug of tenofovir for the treatment of Human Immunodeficiency Virus. Antiviral Res. 2016 Jan;125:63-70. doi: 10.1016/j.antiviral.2015.11.009. Epub 2015 Nov 27. [Article]
- Kind
- Protein
- Organism
- HBV
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- Rna-directed dna polymerase activity
- Gene Name
- rt
- Uniprot ID
- Q3MS49
- Uniprot Name
- Reverse transcriptase
- Molecular Weight
- 4735.565 Da
References
- McConville C, Boyd P, Major I: Efficacy of Tenofovir 1% Vaginal Gel in Reducing the Risk of HIV-1 and HSV-2 Infection. Clin Med Insights Womens Health. 2014 Feb 13;7:1-8. doi: 10.4137/CMWH.S10353. eCollection 2014. [Article]
- Ray AS, Fordyce MW, Hitchcock MJ: Tenofovir alafenamide: A novel prodrug of tenofovir for the treatment of Human Immunodeficiency Virus. Antiviral Res. 2016 Jan;125:63-70. doi: 10.1016/j.antiviral.2015.11.009. Epub 2015 Nov 27. [Article]
- Kind
- Protein
- Organism
- Human herpesvirus 2 (strain 186)
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- Dna binding
- Gene Name
- Not Available
- Uniprot ID
- I6TLU5
- Uniprot Name
- DNA polymerase
- Molecular Weight
- 137296.405 Da
References
- McConville C, Boyd P, Major I: Efficacy of Tenofovir 1% Vaginal Gel in Reducing the Risk of HIV-1 and HSV-2 Infection. Clin Med Insights Womens Health. 2014 Feb 13;7:1-8. doi: 10.4137/CMWH.S10353. eCollection 2014. [Article]
- Ray AS, Fordyce MW, Hitchcock MJ: Tenofovir alafenamide: A novel prodrug of tenofovir for the treatment of Human Immunodeficiency Virus. Antiviral Res. 2016 Jan;125:63-70. doi: 10.1016/j.antiviral.2015.11.009. Epub 2015 Nov 27. [Article]
Enzymes
- Kind
- Protein
- Organism
- Not Available
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Protective protein appears to be essential for both the activity of beta-galactosidase and neuraminidase, it associates with these enzymes and exerts a protective function necessary for their stability and activity. This protein is also a carboxypeptidase and can deamidate tachykinins.
- Specific Function
- Carboxypeptidase activity
- Gene Name
- CTSA
- Uniprot ID
- P10619
- Uniprot Name
- Lysosomal protective protein
- Molecular Weight
- 54465.655 Da
References
- Aloy B, Tazi I, Bagnis CI, Gauthier M, Janus N, Launay-Vacher V, Deray G, Tourret J: Is Tenofovir Alafenamide Safer than Tenofovir Disoproxil Fumarate for the Kidneys? AIDS Rev. 2016 Oct-Dec;18(4):184-192. [Article]
- Deeks ED: Bictegravir/Emtricitabine/Tenofovir Alafenamide: A Review in HIV-1 Infection. Drugs. 2018 Nov;78(17):1817-1828. doi: 10.1007/s40265-018-1010-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Triglyceride lipase activity
- Specific Function
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
- Gene Name
- CES1
- Uniprot ID
- P23141
- Uniprot Name
- Liver carboxylesterase 1
- Molecular Weight
- 62520.62 Da
References
- Aloy B, Tazi I, Bagnis CI, Gauthier M, Janus N, Launay-Vacher V, Deray G, Tourret J: Is Tenofovir Alafenamide Safer than Tenofovir Disoproxil Fumarate for the Kidneys? AIDS Rev. 2016 Oct-Dec;18(4):184-192. [Article]
- Deeks ED: Bictegravir/Emtricitabine/Tenofovir Alafenamide: A Review in HIV-1 Infection. Drugs. 2018 Nov;78(17):1817-1828. doi: 10.1007/s40265-018-1010-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- 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
- FDA Approved Drug Products: Bictegravir, Emtricitabine, and Tenofovir Alafenamide Oral Tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Nucleoside diphosphate kinase activity
- Specific Function
- Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Also displays broad nucleoside diphosphate kinase activity. Plays an important role in cellular energy homeost...
- Gene Name
- AK1
- Uniprot ID
- P00568
- Uniprot Name
- Adenylate kinase isoenzyme 1
- Molecular Weight
- 21634.725 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Atp binding
- Specific Function
- Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Plays an important role in cellular energy homeostasis and in adenine nucleotide metabolism. Adenylate kinase ...
- Gene Name
- AK2
- Uniprot ID
- P54819
- Uniprot Name
- Adenylate kinase 2, mitochondrial
- Molecular Weight
- 26477.44 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Ribosomal small subunit binding
- Specific Function
- Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-sit...
- Gene Name
- NME1
- Uniprot ID
- P15531
- Uniprot Name
- Nucleoside diphosphate kinase A
- Molecular Weight
- 17148.635 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Transcription factor activity, sequence-specific dna binding
- Specific Function
- Major role in the synthesis of nucleoside triphosphates other than ATP. Negatively regulates Rho activity by interacting with AKAP13/LBC. Acts as a transcriptional activator of the MYC gene; binds ...
- Gene Name
- NME2
- Uniprot ID
- P22392
- Uniprot Name
- Nucleoside diphosphate kinase B
- Molecular Weight
- 17297.935 Da
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Binder
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Deeks ED: Bictegravir/Emtricitabine/Tenofovir Alafenamide: A Review in HIV-1 Infection. Drugs. 2018 Nov;78(17):1817-1828. doi: 10.1007/s40265-018-1010-7. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- Soriano V, Labarga P, Fernandez-Montero JV, Mendoza C, Benitez-Gutierrez L, Pena JM, Barreiro P: Drug interactions in HIV-infected patients treated for hepatitis C. Expert Opin Drug Metab Toxicol. 2017 Aug;13(8):807-816. doi: 10.1080/17425255.2017.1351942. Epub 2017 Jul 13. [Article]
- Begley R, Das M, Zhong L, Ling J, Kearney BP, Custodio JM: Pharmacokinetics of Tenofovir Alafenamide When Coadministered With Other HIV Antiretrovirals. J Acquir Immune Defic Syndr. 2018 Aug 1;78(4):465-472. doi: 10.1097/QAI.0000000000001699. [Article]
- Custodio JM, Fordyce M, Garner W, Vimal M, Ling KH, Kearney BP, Ramanathan S: Pharmacokinetics and Safety of Tenofovir Alafenamide in HIV-Uninfected Subjects with Severe Renal Impairment. Antimicrob Agents Chemother. 2016 Aug 22;60(9):5135-40. doi: 10.1128/AAC.00005-16. Print 2016 Sep. [Article]
- Murakami E, Wang T, Park Y, Hao J, Lepist EI, Babusis D, Ray AS: Implications of efficient hepatic delivery by tenofovir alafenamide (GS-7340) for hepatitis B virus therapy. Antimicrob Agents Chemother. 2015;59(6):3563-9. doi: 10.1128/AAC.00128-15. Epub 2015 Apr 13. [Article]
- Aloy B, Tazi I, Bagnis CI, Gauthier M, Janus N, Launay-Vacher V, Deray G, Tourret J: Is Tenofovir Alafenamide Safer than Tenofovir Disoproxil Fumarate for the Kidneys? AIDS Rev. 2016 Oct-Dec;18(4):184-192. [Article]
- HIV insite, UCSF: Tenofovir Alafenamide [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Atpase activity, coupled to transmembrane movement of substances
- Specific Function
- May be an organic anion pump relevant to cellular detoxification.
- Gene Name
- ABCC4
- Uniprot ID
- O15439
- Uniprot Name
- Multidrug resistance-associated protein 4
- Molecular Weight
- 149525.33 Da
References
- Aloy B, Tazi I, Bagnis CI, Gauthier M, Janus N, Launay-Vacher V, Deray G, Tourret J: Is Tenofovir Alafenamide Safer than Tenofovir Disoproxil Fumarate for the Kidneys? AIDS Rev. 2016 Oct-Dec;18(4):184-192. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Aloy B, Tazi I, Bagnis CI, Gauthier M, Janus N, Launay-Vacher V, Deray G, Tourret J: Is Tenofovir Alafenamide Safer than Tenofovir Disoproxil Fumarate for the Kidneys? AIDS Rev. 2016 Oct-Dec;18(4):184-192. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- Aloy B, Tazi I, Bagnis CI, Gauthier M, Janus N, Launay-Vacher V, Deray G, Tourret J: Is Tenofovir Alafenamide Safer than Tenofovir Disoproxil Fumarate for the Kidneys? AIDS Rev. 2016 Oct-Dec;18(4):184-192. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- Molecular Weight
- 72313.47 Da
References
- Deeks ED: Bictegravir/Emtricitabine/Tenofovir Alafenamide: A Review in HIV-1 Infection. Drugs. 2018 Nov;78(17):1817-1828. doi: 10.1007/s40265-018-1010-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Ogawa E, Furusyo N, Nguyen MH: Tenofovir alafenamide in the treatment of chronic hepatitis B: design, development, and place in therapy. Drug Des Devel Ther. 2017 Nov 6;11:3197-3204. doi: 10.2147/DDDT.S126742. eCollection 2017. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
References
- Ogawa E, Furusyo N, Nguyen MH: Tenofovir alafenamide in the treatment of chronic hepatitis B: design, development, and place in therapy. Drug Des Devel Ther. 2017 Nov 6;11:3197-3204. doi: 10.2147/DDDT.S126742. eCollection 2017. [Article]
Drug created at November 08, 2015 21:16 / Updated at February 20, 2024 23:54