Identification

Name
Tenofovir disoproxil
Accession Number
DB00300
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). This drug is prescribed in combination with other drugs for the management of HIV infection as well as for Hepatitis B therapy. Tenofovir disoproxil was initially approved in 2001 Label.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 519.448
Monoisotopic: 519.173029184
Chemical Formula
C19H30N5O10P
Synonyms
  • Bis(POC)PMPA
  • Tenofovir bis(isopropyloxycarbonyloxymethyl) ester
External IDs
  • GS-4331

Pharmacology

Indication

Tenofovir is indicated in combination with other antiretroviral agents for the management 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 Label. This drug is also a component of multiple products used for the management of HIV-1 infection 14, 15.

Safety and effectiveness of tenofovir disoproxil in pediatric patients younger than 2 years of age has not been established to this date Label.

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

This drug prevents viral DNA chain elongation through inhibition of enzymes necessary for host cell infection viral replication in HIV-1 and Hepatitis B infections 9, 10.

In vitro effects

The antiviral activity of tenofovir against in laboratory and clinical isolates of HIV-1 was studied in lymphoblastoid cell lines, primary monocyte/macrophage cells, in addition to peripheral blood lymphocytes. The EC50 (50% effective concentration) values of tenofovir against HIV-1 virus ranged between 0.04 μM to 8.5 μM.

Combination of tenofovir disoproxil with other drugs

In drug combination studies of tenofovir with nucleoside reverse transcriptase inhibitors (abacavir, didanosine, lamivudine, stavudine, zalcitabine, zidovudine), non-nucleoside reverse transcriptase inhibitors (delavirdine, efavirenz, nevirapine), and protease inhibitors (amprenavir, indinavir, nelfinavir, ritonavir, saquinavir), additive and synergistic effects were seen. Tenofovir demonstrated antiviral activities in cell cultures against HIV-1 Label.

Mechanism of action

Tenofovir belongs to a class of antiretroviral drugs known as nucleotide analog reverse transcriptase inhibitors (NtRTIs), which block reverse transcriptase, an enzyme necessary for viral production in HIV-infected individuals. This enables the management of HIV viral load through decreased viral replication Label.

Tenofovir disoproxil fumarate is the fumarate salt of the prodrug tenofovir disoproxil. Tenofovir disoproxil is absorbed and converted to its active form, tenofovir, a nucleoside monophosphate (nucleotide) analog. Tenofovir is then converted to the active metabolite, tenofovir diphosphate, a chain terminator, by constitutively expressed enzymes in the cell. Tenofovir diphosphate inhibits HIV-1 reverse transcriptase and the Hepatitis B polymerase by direct binding competition with the natural deoxyribonucleotide substrate (deoxyadenosine 5’-triphosphate) and, after integration into DNA, causes viral DNA chain termination 16, Label.

A note on resistance

HIV-1 isolates with decreased susceptibility to tenofovir have been identified in cell culture studies. These viruses expressed a K65R substitution in reverse transcriptase and showed a 2– 4 fold decrease in susceptibility to treatment with tenofovir Label.

TargetActionsOrganism
AReverse transcriptase/RNaseH
inhibitor
Human immunodeficiency virus 1
UDNA polymerase/reverse transcriptase
inhibitor
HBV-D
Absorption

After oral administration of tenofovir disoproxil to patients with HIV infection, tenofovir disoproxil is quickly absorbed and metabolized to tenofovir 16.

Administration of tenofovir disoproxil 300 mg tablets after a high-fat meal increases the oral bioavailability of this drug, as demonstrated by an increase in tenofovir AUC0-∞ of about 40% as well as an increase in Cmax of about 14%. On the contrary, the administration of tenofovir disoproxil with a light meal did not exert a relevant effect on the pharmacokinetics of tenofovir when compared to administration under fasting conditions. The presence of ingested food slows the time to tenofovir Cmax by approximately 1 hour. Cmax and AUC of tenofovir are 0.33 ± 0.12 μg/mL and 3.32 ± 1.37 μg•hr/mL after several doses of tenofovir disoproxil 300 mg once daily in the fed state when meal content is not controlled Label.

Volume of distribution

The volume of distribution at steady-state is 1.3 ± 0.6 L/kg and 1.2 ± 0.4 L/kg, following intravenous administration of tenofovir 1.0 mg/kg and 3.0 mg/kg Label.

After oral administration of tenofovir disoproxil, tenofovir is distributed to the majority tissues with the highest concentrations measured in the kidney, liver and the intestinal contents (based on data from preclinical studies) 16.

Protein binding

In vitro binding of tenofovir to human plasma or serum proteins is <0.7 and <7.2%, respectively, over the tenofovir concentration range 0.01 to 25 μg/mL Label.

Metabolism

Tenofovir disoproxil fumarate is the fumarate salt of the prodrug tenofovir disoproxil. Tenofovir disoproxil is absorbed and converted to its active form, tenofovir, a nucleoside monophosphate (nucleotide) analog. Tenofovir is then converted to the active metabolite, tenofovir diphosphate, a chain terminator, by constitutively expressed enzymes in the cell Label. Two phosphorylation steps are required to convert tenofovir disoproxil to the active drug form 11.

The cytochrome P450 enzyme system is not involved with the metabolism of tenofovir disoproxil or tenofovir Label.

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Route of elimination

Following IV administration of tenofovir, approximately 70–80% of the dose is recovered in the urine as unchanged tenofovir within 72 hours of dosing. Tenofovir is eliminated by a combination of glomerular filtration and active tubular secretion Label. There may be competition for elimination with other compounds that are also eliminated by the kidneys.

Half-life

When a single oral dose is given, the terminal elimination half-life is approximately 17 hours Label.

Clearance

The clearance of tenofovir is highly dependent on renal function and may vary greatly. Total clearance has been estimated to be approximately 230 ml/h/kg (approximately 300 ml/min) 16.

On average, renal clearance has been estimated to be approximately 160 ml/h/kg (approximately 210 ml/min), which is in excess of the glomerular filtration rate. This shows that active tubular secretion is an essential part of the elimination of tenofovir 16.

The FDA label provides specific guidelines for dosing according to renal function. It is important to consult product labeling before administering tenofovir to individuals with renal dysfunction, as the clearance of this drug may vary greatly among these patients Label.

Adverse Effects
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Toxicity

A note on breastfeeding

The Centers for Disease Control and Prevention recommend that HIV-1-infected mothers not breast-feed their infants to prevent postnatal transmission of HIV-1. Mothers should be advised not to breast-feed if they are receiving tenofovir disoproxil Label.

Carcinogenesis

Long-term oral carcinogenicity studies of tenofovir disoproxil fumarate in mice and rats were performed at exposures up to approximately 16 times (mice) and 5 times (rats) those observed in humans at the therapeutic dose for HIV-1 infection. At the higher dose in female mice, liver adenomas were increased at exposures 16 times that in humans. In rats, the study was negative for carcinogenic findings at exposures up to 5 times that observed in humans at the therapeutic dose Label.

Pregnancy

This drug is considered a pregnancy Category B drug. Reproduction studies have been performed in rats and rabbits at doses up to 14 and 19 times the recommended human dose based on body surface area comparisons and revealed no evidence of impaired fertility or harm to the fetus due to tenofovir. There are, however, no adequate and well-controlled studies in pregnant women.

Because animal reproduction studies are not consistently reflective of human effects, tenofovir disoproxil should be used during pregnancy only if clearly required. To monitor fetal outcomes of pregnant women taking tenofovir disoproxil, an Antiretroviral Pregnancy Registry has been formed. Healthcare providers are encouraged and advised to register patients by calling the number listed on the FDA label for tenofovir disoproxil Label.

Mutagenesis

Tenofovir disoproxil fumarate was mutagenic in the in vitro mouse lymphoma assay and negative for mutagenesis in an in vitro bacterial mutagenicity test (Ames test). In an in vivo mouse micronucleus assay, tenofovir disoproxil fumarate was negative when administered to male mice.

Impairment of Fertility

There were no observed effects on fertility, mating performance or early embryonic development when tenofovir disoproxil fumarate was given to male rats at a dose comparable to 10 times the human dose based on body surface area comparisons for 28 days before mating and to female rats for 15 days before mating through day seven of gestation. There was, however, changes in the estrous cycle in female rats Label.

Affected organisms
  • Human Immunodeficiency Virus
Pathways
PathwayCategory
Tenofovir Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AbacavirTenofovir disoproxil may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Tenofovir disoproxil.
AcarboseTenofovir disoproxil may decrease the excretion rate of Acarbose which could result in a higher serum level.
AceclofenacAceclofenac may increase the nephrotoxic activities of Tenofovir disoproxil.
AcemetacinAcemetacin may increase the nephrotoxic activities of Tenofovir disoproxil.
AcetaminophenTenofovir disoproxil may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Tenofovir disoproxil which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may increase the nephrotoxic activities of Tenofovir disoproxil.
AclidiniumTenofovir disoproxil may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineTenofovir disoproxil may decrease the excretion rate of Acrivastine which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description
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  • Severity
    Severity
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    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level
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  • Action
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Food Interactions
  • Take with or without food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Tenofovir disoproxil fumarateOTT9J7900I202138-50-9VCMJCVGFSROFHV-WZGZYPNHSA-N
Tenofovir disoproxil maleate7BI6HE4F8S1276030-80-8VCMJCVGFSROFHV-VIEYUMQNSA-N
Tenofovir disoproxil phosphate05F4G8DO5I1453166-76-1DJCLNKKHALBVLK-PFEQFJNWSA-N
Tenofovir disoproxil succinate94882WB39E1637632-97-3CCGIINMVANPRGB-PFEQFJNWSA-N
Active Moieties
NameKindUNIICASInChI Key
TenofovirprodrugW4HFE001U5147127-20-6SGOIRFVFHAKUTI-ZCFIWIBFSA-N
Product Images
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Tenofovir Disoproxil FumarateTablet, film coated300 mg/1OralAizant Drug Research Solutions Pvt Ltd2018-01-26Not applicableUS flag
Tenofovir Disoproxil FumarateTablet, film coated150 mg/1OralAizant Drug Research Solutions Pvt Ltd2018-01-26Not applicableUS flag
Tenofovir Disoproxil FumarateTablet, film coated250 mg/1OralAizant Drug Research Solutions Pvt Ltd2018-01-26Not applicableUS flag
Tenofovir Disoproxil FumarateTablet, film coated200 mg/1OralAizant Drug Research Solutions Pvt Ltd2018-01-26Not applicableUS flag
VireadTablet, coated300 mg/1OralA-S Medication Solutions2001-10-26Not applicableUS flag54569 533420180907 15195 1iwyatt
VireadTablet, coated300 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUS flag53808 081020180907 15195 vd1a0b
VireadTablet, coated250 mg/1OralGilead Sciences, Inc.2012-01-18Not applicableUS flag
VireadTablet, film coated163 mgOralGilead Sciences Ireland Uc2002-02-05Not applicableEU flag
VireadTablet, film coated123 mgOralGilead Sciences Ireland Uc2002-02-05Not applicableEU flag
VireadTablet, film coated245 mgOralGilead Sciences Ireland Uc2002-02-05Not applicableEU flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-tenofovirTabletOralApotex Corporation2017-07-26Not applicableCanada flag
Auro-tenofovirTabletOralAuro Pharma Inc2017-07-26Not applicableCanada flag
Jamp-tenofovirTabletOralJamp Pharma Corporation2018-10-24Not applicableCanada flag
Mylan-tenofovir DisoproxilTabletOralMylan Pharmaceuticals2017-07-31Not applicableCanada flag
Nat-tenofovirTabletOralNatco Pharma Limited2018-03-15Not applicableCanada flag
PMS-tenofovirTabletOralPharmascience Inc2018-04-25Not applicableCanada flag
Tenofovir Disoproxil FumarateTablet, film coated300 mg/1OralREMEDYREPACK INC.2017-12-122020-05-07US flag
Tenofovir disoproxil fumarateTablet300 mg/1OralCipla USA Inc.2018-01-26Not applicableUS flag
Tenofovir Disoproxil FumarateTablet, film coated200 mg/1OralAurobindo Pharma Limited2018-01-26Not applicableUS flag
Tenofovir Disoproxil FumarateTablet, film coated300 mg/1OralAvKARE2019-01-10Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Ag-emtricitabine / Tenofovir Disoproxil FumarateTenofovir disoproxil fumarate (300 mg) + Emtricitabine (200 mg)TabletOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Apo-efavirenz-emtricitabine-tenofovirTenofovir disoproxil fumarate (300 mg) + Efavirenz (600 mg) + Emtricitabine (200 mg)TabletOralApotex Corporation2018-09-04Not applicableCanada flag
Apo-emtricitabine-tenofovirTenofovir disoproxil fumarate (300 mg) + Emtricitabine (200 mg)TabletOralApotex Corporation2017-07-26Not applicableCanada flag
AtriplaTenofovir disoproxil fumarate (300 mg/1) + Efavirenz (600 mg/1) + Emtricitabine (200 mg/1)Tablet, film coatedOralGilead Sciences, Llc2006-07-20Not applicableUS flag
AtriplaTenofovir disoproxil fumarate (300 mg/1) + Efavirenz (600 mg/1) + Emtricitabine (200 mg/1)Tablet, film coatedOralA-S Medication Solutions2006-07-202019-11-30US flag
AtriplaTenofovir disoproxil fumarate (300 mg/1) + Efavirenz (600 mg/1) + Emtricitabine (200 mg/1)Tablet, film coatedOralDoh Central Pharmacy2009-07-01Not applicableUS flag
AtriplaTenofovir disoproxil fumarate (300 mg/1) + Efavirenz (600 mg/1) + Emtricitabine (200 mg/1)Tablet, film coatedOralPhysicians Total Care, Inc.2012-10-16Not applicableUS flag
AtriplaTenofovir disoproxil fumarate (300 mg/1) + Efavirenz (600 mg/1) + Emtricitabine (200 mg/1)Tablet, film coatedOralLake Erie Medical Dba Quality Care Produts Llc2006-07-202014-12-31US flag
AtriplaTenofovir disoproxil fumarate (300 mg/1) + Efavirenz (600 mg/1) + Emtricitabine (200 mg/1)Tablet, film coatedOralAvera McKennan Hospital2015-03-062017-05-24US flag
AtriplaTenofovir disoproxil fumarate (300 mg/1) + Efavirenz (600 mg/1) + Emtricitabine (200 mg/1)Tablet, film coatedOralA-S Medication Solutions2006-07-20Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Tenofovir Disoproxil FumarateTenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralAizant Drug Research Solutions Pvt Ltd2018-01-26Not applicableUS flag
Tenofovir Disoproxil FumarateTenofovir disoproxil fumarate (150 mg/1)Tablet, film coatedOralAizant Drug Research Solutions Pvt Ltd2018-01-26Not applicableUS flag
Tenofovir Disoproxil FumarateTenofovir disoproxil fumarate (250 mg/1)Tablet, film coatedOralAizant Drug Research Solutions Pvt Ltd2018-01-26Not applicableUS flag
Tenofovir Disoproxil FumarateTenofovir disoproxil fumarate (200 mg/1)Tablet, film coatedOralAizant Drug Research Solutions Pvt Ltd2018-01-26Not applicableUS flag

Categories

ATC Codes
J05AR27 — Lamivudine, tenofovir disoproxil and dolutegravirJ05AF07 — Tenofovir disoproxilJ05AR08 — Emtricitabine, tenofovir disoproxil and rilpivirineJ05AR11 — Lamivudine, tenofovir disoproxil and efavirenzJ05AR09 — Emtricitabine, tenofovir disoproxil, elvitegravir and cobicistatJ05AR06 — Emtricitabine, tenofovir disoproxil and efavirenzJ05AR24 — Lamivudine, tenofovir disoproxil and doravirineJ05AR12 — Lamivudine and tenofovir disoproxilJ05AR03 — Tenofovir disoproxil and emtricitabine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Imidazopyrimidines
Sub Class
Purines and purine derivatives
Direct Parent
6-aminopurines
Alternative Parents
Dialkyl alkylphosphonates / Aminopyrimidines and derivatives / Phosphonic acid esters / N-substituted imidazoles / Imidolactams / Carbonic acid diesters / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds
show 4 more
Substituents
6-aminopurine / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Carbonic acid derivative / Carbonic acid diester / Carbonyl group / Dialkyl alkylphosphonate
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic phosphonate (CHEBI:63717)

Chemical Identifiers

UNII
F4YU4LON7I
CAS number
201341-05-1
InChI Key
JFVZFKDSXNQEJW-CQSZACIVSA-N
InChI
InChI=1S/C19H30N5O10P/c1-12(2)33-18(25)28-9-31-35(27,32-10-29-19(26)34-13(3)4)11-30-14(5)6-24-8-23-15-16(20)21-7-22-17(15)24/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22)/t14-/m1/s1
IUPAC Name
bis({[(propan-2-yloxy)carbonyl]oxy}methyl) {[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methanephosphonate
SMILES
[H][[email protected]@](C)(CN1C=NC2=C(N)N=CN=C12)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C

References

Synthesis Reference

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.

US08049009
General References
  1. Gilden D: Tenofovir: Gilead applies for approval; expanded access liberalized. AIDS Treat News. 2001 May 11;(364):2-3, 1. [PubMed:11569959]
  2. 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:11562951]
  3. Thompson CA: Prodrug of tenofovir diphosphate approved for combination HIV therapy. Am J Health Syst Pharm. 2002 Jan 1;59(1):18. [PubMed:11813460]
  4. Gazzard BG: The potential place of tenofovir in antiretroviral treatment regimens. Int J Clin Pract. 2001 Dec;55(10):704-9. [PubMed:11777298]
  5. 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:23278367]
  6. 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:22951630]
  7. 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:22943210]
  8. 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:24169122]
  9. Duwal S, Schutte C, von Kleist M: Pharmacokinetics and pharmacodynamics of the reverse transcriptase inhibitor tenofovir and prophylactic efficacy against HIV-1 infection. PLoS One. 2012;7(7):e40382. doi: 10.1371/journal.pone.0040382. Epub 2012 Jul 11. [PubMed:22808148]
  10. Delaney WE 4th, Ray AS, Yang H, Qi X, Xiong S, Zhu Y, Miller MD: Intracellular metabolism and in vitro activity of tenofovir against hepatitis B virus. Antimicrob Agents Chemother. 2006 Jul;50(7):2471-7. doi: 10.1128/AAC.00138-06. [PubMed:16801428]
  11. Figueroa DB, Tillotson J, Li M, Piwowar-Manning E, Hendrix CW, Holtz TH, Bokoch K, Bekker LG, van Griensven F, Mannheimer S, Hughes JP, Grant RM, Bumpus NN: Discovery of genetic variants of the kinases that activate tenofovir among individuals in the United States, Thailand, and South Africa: HPTN067. PLoS One. 2018 Apr 11;13(4):e0195764. doi: 10.1371/journal.pone.0195764. eCollection 2018. [PubMed:29641561]
  12. Tenofovir Disoproxil FDA label [File]
  13. Auspar: Tenofovir disoproxil fumarate [File]
  14. Stribild FDA label [File]
  15. Truvada FDA label [File]
  16. Viread EPAR [File]
Human Metabolome Database
HMDB14445
PubChem Compound
5481350
PubChem Substance
46508131
ChemSpider
4587262
BindingDB
77145
RxNav
300195
ChEBI
63717
ChEMBL
CHEMBL1538
ZINC
ZINC000003929022
Therapeutic Targets Database
DAP001430
PharmGKB
PA10204
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Tenofovir_disoproxil
AHFS Codes
  • 08:18.08.20 — Nucleoside and Nucleotide Reverse Transcriptase Inhibitors
MSDS
Download (57.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingOtherAdherence, Medication / HIV Prevention / Pre-Exposure Prophylaxis / Risk Behaviors1
4Active Not RecruitingOtherHuman Immunodeficiency Virus (HIV) Infections1
4Active Not RecruitingOtherPre-Exposure Prophylaxis / Transgender Persons1
4Active Not RecruitingPreventionAdherence1
4Active Not RecruitingPreventionHepatitis B Chronic Infection / Pregnancy1
4Active Not RecruitingTreatmentHepatitis B Chronic Infection3
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Menopause / Osteoporosis1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1) Infection / Solid Organ Transplant1
4CompletedNot AvailableHealthy Volunteers1
4CompletedBasic ScienceHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1

Pharmacoeconomics

Manufacturers
  • Gilead sciences inc
  • Gilead Sciences, Inc.
Packagers
  • A-S Medication Solutions LLC
  • Bristol-Myers Squibb Co.
  • Cardinal Health
  • Dept Health Central Pharmacy
  • Gilead Sciences Inc.
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Nycomed Inc.
  • Patheon Inc.
  • PCA LLC
  • Physicians Total Care Inc.
  • Quality Care
  • Remedy Repack
Dosage Forms
FormRouteStrength
Tablet, coatedOral50 mg
Tablet, film coatedOral600 mg
Tablet, coatedOral400 mg
Tablet, film coatedOral100 MG
TabletOral
Tablet, film coatedOral200 mg
Tablet, coatedOral200 mg
Tablet, coatedOral600 mg
Tablet, film coatedOral150 MG
Tablet, coatedOral150 mg
Tablet, coatedOral123 MG
Tablet, coatedOral163 MG
Tablet, coatedOral204 MG
Tablet, coatedOral245 MG
PowderNot applicable1 kg/1kg
TabletOral300 mg/1
Tablet, film coatedOral
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral200 mg/1
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral300 mg/1
Tablet, coatedOral300 mg
TabletOral
Tablet, film coatedOral300 mg
Tablet, film coatedOral
TabletOral300 mg
TabletOral600 mg
GranuleOral33 mg/g
PowderOral40 mg/1g
Tablet, coatedOral150 mg/1
Tablet, coatedOral200 mg/1
Tablet, coatedOral250 mg/1
Tablet, coatedOral300 mg/1
Tablet, film coatedOral123 mg
Tablet, film coatedOral163 mg
Tablet, film coatedOral204 mg
Tablet, film coatedOral245 mg
Prices
Unit descriptionCostUnit
Viread 300 mg tablet33.95USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2298059No2008-12-302018-07-23Canada flag
CA2261619No2006-05-232017-07-25Canada flag
US5914331Yes1999-06-222018-01-02US flag
US6043230Yes2000-03-282018-01-25US flag
US5814639Yes1998-09-292017-03-29US flag
US6939964Yes2005-09-062018-07-20US flag
US6639071Yes2003-10-282018-08-14US flag
US6642245Yes2003-11-042021-05-04US flag
US6703396Yes2004-03-092021-09-09US flag
US5922695Yes1999-07-132018-01-25US flag
US5935946Yes1999-08-102018-01-25US flag
US5977089Yes1999-11-022018-01-25US flag
US8592397No2013-11-262024-01-13US flag
US8716264No2014-05-062024-01-13US flag
US9018192No2015-04-282026-06-13US flag
US8598185No2013-12-032028-05-01US flag
US7125879No2006-10-242022-08-09US flag
US6838464No2005-01-042021-02-26US flag
US8080551No2011-12-202023-04-11US flag
US8101629No2012-01-242022-08-09US flag
US7067522No2006-06-272019-12-20US flag
US8148374No2012-04-032029-09-03US flag
US7635704No2009-12-222026-10-26US flag
US7176220No2007-02-132023-11-20US flag
US8981103No2015-03-172026-10-26US flag
US8633219No2014-01-212030-04-24US flag
US8841310No2014-09-232025-12-09US flag
US9545414No2017-01-172026-06-13US flag
US9457036No2016-10-042024-01-13US flag
US9744181No2017-08-292024-01-13US flag
US9891239No2018-02-132029-09-03US flag
US10039718No2018-08-072032-10-04US flag
US8486975No2013-07-162031-10-07US flag
US10603282No2016-11-292036-11-29US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)113-115https://www.chemicalbook.com/ChemicalProductProperty_US_CB7946998.aspx
boiling point (°C)642.7https://www.lookchem.com/Tenofovir-disoproxil-fumarate/
water solubility13.4 mg/mL in distilled water at 25 °C (disoproxil fumarate salt)https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021752s005lbl.pdf
logP1.25https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021752s005lbl.pdf
pKa3.75https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021752s005lbl.pdf
Predicted Properties
PropertyValueSource
Water Solubility0.712 mg/mLALOGPS
logP-0.02ALOGPS
logP2.65ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)18.59ChemAxon
pKa (Strongest Basic)4.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area185.44 Å2ChemAxon
Rotatable Bond Count17ChemAxon
Refractivity118.59 m3·mol-1ChemAxon
Polarizability49.18 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5998
Blood Brain Barrier+0.9194
Caco-2 permeable-0.617
P-glycoprotein substrateSubstrate0.7203
P-glycoprotein inhibitor INon-inhibitor0.8706
P-glycoprotein inhibitor IINon-inhibitor0.948
Renal organic cation transporterNon-inhibitor0.8985
CYP450 2C9 substrateNon-substrate0.8609
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateNon-substrate0.6458
CYP450 1A2 substrateNon-inhibitor0.7177
CYP450 2C9 inhibitorNon-inhibitor0.7873
CYP450 2D6 inhibitorNon-inhibitor0.8271
CYP450 2C19 inhibitorNon-inhibitor0.7634
CYP450 3A4 inhibitorNon-inhibitor0.8353
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.85
Ames testNon AMES toxic0.511
CarcinogenicityNon-carcinogens0.7811
BiodegradationNot ready biodegradable0.9914
Rat acute toxicity2.4903 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8936
hERG inhibition (predictor II)Non-inhibitor0.7957
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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

Targets

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
  1. Fung HB, Stone EA, Piacenti FJ: Tenofovir disoproxil fumarate: a nucleotide reverse transcriptase inhibitor for the treatment of HIV infection. Clin Ther. 2002 Oct;24(10):1515-48. [PubMed:12462284]
  2. DeChristoforo R, Penzak SR: Tenofovir: a nucleotide analogue reverse-transcriptase inhibitor for treatment of HIV infection. Am J Health Syst Pharm. 2004 Jan 1;61(1):86-98; quiz 99-100. [PubMed:14725126]
  3. Link [Link]
  4. FDA label, Viread [File]
Kind
Protein
Organism
HBV-D
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Rna-dna hybrid ribonuclease activity
Specific Function
Multifunctional enzyme that converts the viral RNA genome into dsDNA in viral cytoplasmic capsids. This enzyme displays a DNA polymerase activity that can copy either DNA or RNA templates, and a ri...
Gene Name
P
Uniprot ID
P24024
Uniprot Name
Protein P
Molecular Weight
93588.765 Da
References
  1. De Clercq E, Ferir G, Kaptein S, Neyts J: Antiviral treatment of chronic hepatitis B virus (HBV) infections. Viruses. 2010 Jun;2(6):1279-305. doi: 10.3390/v2061279. Epub 2010 May 31. [PubMed:21994680]
  2. Link [Link]
  3. FDA label, Viread [File]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
References
  1. Antoniou T, Park-Wyllie LY, Tseng AL: Tenofovir: a nucleotide analog for the management of human immunodeficiency virus infection. Pharmacotherapy. 2003 Jan;23(1):29-43. [PubMed:12523458]
  2. Topalis D, Snoeck R, Andrei G: Tenofovir Activating Kinases May Impact the Outcome of HIV Treatment and Prevention. EBioMedicine. 2015 Aug 3;2(9):1018-9. doi: 10.1016/j.ebiom.2015.07.042. eCollection 2015 Sep. [PubMed:26501093]
  3. Link [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Nucleoside triphosphate adenylate kinase activity
Specific Function
Involved in maintaining the homeostasis of cellular nucleotides by catalyzing the interconversion of nucleoside phosphates. Efficiently phosphorylates AMP and dAMP using ATP as phosphate donor, but...
Gene Name
AK4
Uniprot ID
P27144
Uniprot Name
Adenylate kinase 4, mitochondrial
Molecular Weight
25267.83 Da
References
  1. Antoniou T, Park-Wyllie LY, Tseng AL: Tenofovir: a nucleotide analog for the management of human immunodeficiency virus infection. Pharmacotherapy. 2003 Jan;23(1):29-43. [PubMed:12523458]
  2. Dahlin A, Wittwer M, de la Cruz M, Woo JM, Bam R, Scharen-Guivel V, Flaherty J, Ray AS, Cihlar T, Gupta SK, Giacomini KM: A pharmacogenetic candidate gene study of tenofovir-associated Fanconi syndrome. Pharmacogenet Genomics. 2015 Feb;25(2):82-92. doi: 10.1097/FPC.0000000000000110. [PubMed:25485598]
  3. Link [Link]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
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...

Components:
References
  1. Koch K, Chen Y, Feng JY, Borroto-Esoda K, Deville-Bonne D, Gallois-Montbrun S, Janin J, Morera S: Nucleoside diphosphate kinase and the activation of antiviral phosphonate analogs of nucleotides: binding mode and phosphorylation of tenofovir derivatives. Nucleosides Nucleotides Nucleic Acids. 2009 Aug;28(8):776-92. doi: 10.1080/15257770903155899. [PubMed:20183617]
  2. Watanabe D, Yoshino M, Yagura H, Hirota K, Yonemoto H, Bando H, Yajima K, Koizumi Y, Otera H, Tominari S, Nishida Y, Kuwahara T, Uehira T, Shirasaka T: Increase in serum mitochondrial creatine kinase levels induced by tenofovir administration. J Infect Chemother. 2012 Oct;18(5):675-82. doi: 10.1007/s10156-012-0393-8. Epub 2012 Feb 22. [PubMed:22350406]
  3. Figueroa DB, Tillotson J, Li M, Piwowar-Manning E, Hendrix CW, Holtz TH, Bokoch K, Bekker LG, van Griensven F, Mannheimer S, Hughes JP, Grant RM, Bumpus NN: Discovery of genetic variants of the kinases that activate tenofovir among individuals in the United States, Thailand, and South Africa: HPTN067. PLoS One. 2018 Apr 11;13(4):e0195764. doi: 10.1371/journal.pone.0195764. eCollection 2018. [PubMed:29641561]
  4. Suboptimal CD4 gains in HIV-infected patients receiving didanosine plus tenofovir [File]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Ubiquitin protein ligase binding
Specific Function
Reversibly catalyzes the transfer of phosphate between ATP and various phosphogens (e.g. creatine phosphate). Creatine kinase isoenzymes play a central role in energy transduction in tissues with l...

Components:
References
  1. Koch K, Chen Y, Feng JY, Borroto-Esoda K, Deville-Bonne D, Gallois-Montbrun S, Janin J, Morera S: Nucleoside diphosphate kinase and the activation of antiviral phosphonate analogs of nucleotides: binding mode and phosphorylation of tenofovir derivatives. Nucleosides Nucleotides Nucleic Acids. 2009 Aug;28(8):776-92. doi: 10.1080/15257770903155899. [PubMed:20183617]
  2. Varga A, Graczer E, Chaloin L, Liliom K, Zavodszky P, Lionne C, Vas M: Selectivity of kinases on the activation of tenofovir, an anti-HIV agent. Eur J Pharm Sci. 2013 Jan 23;48(1-2):307-15. doi: 10.1016/j.ejps.2012.11.007. Epub 2012 Nov 28. [PubMed:23201309]
  3. Figueroa DB, Tillotson J, Li M, Piwowar-Manning E, Hendrix CW, Holtz TH, Bokoch K, Bekker LG, van Griensven F, Mannheimer S, Hughes JP, Grant RM, Bumpus NN: Discovery of genetic variants of the kinases that activate tenofovir among individuals in the United States, Thailand, and South Africa: HPTN067. PLoS One. 2018 Apr 11;13(4):e0195764. doi: 10.1371/journal.pone.0195764. eCollection 2018. [PubMed:29641561]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
  1. Cihlar T, Ho ES, Lin DC, Mulato AS: Human renal organic anion transporter 1 (hOAT1) and its role in the nephrotoxicity of antiviral nucleotide analogs. Nucleosides Nucleotides Nucleic Acids. 2001 Apr-Jul;20(4-7):641-8. [PubMed:11563082]
  2. Uwai Y, Ida H, Tsuji Y, Katsura T, Inui K: Renal transport of adefovir, cidofovir, and tenofovir by SLC22A family members (hOAT1, hOAT3, and hOCT2). Pharm Res. 2007 Apr;24(4):811-5. Epub 2007 Feb 15. [PubMed:17372702]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
  1. Uwai Y, Ida H, Tsuji Y, Katsura T, Inui K: Renal transport of adefovir, cidofovir, and tenofovir by SLC22A family members (hOAT1, hOAT3, and hOCT2). Pharm Res. 2007 Apr;24(4):811-5. Epub 2007 Feb 15. [PubMed:17372702]
  2. Moss DM, Neary M, Owen A: The role of drug transporters in the kidney: lessons from tenofovir. Front Pharmacol. 2014 Nov 11;5:248. doi: 10.3389/fphar.2014.00248. eCollection 2014. [PubMed:25426075]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
Evidence in the literature is minimal, and this transporter action is currently under study.
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
ATP-dependent transporter probably involved in cellular detoxification through lipophilic anion extrusion.
Gene Name
ABCC10
Uniprot ID
Q5T3U5
Uniprot Name
Multidrug resistance-associated protein 7
Molecular Weight
161627.375 Da
References
  1. Pushpakom SP, Liptrott NJ, Rodriguez-Novoa S, Labarga P, Soriano V, Albalater M, Hopper-Borge E, Bonora S, Di Perri G, Back DJ, Khoo S, Pirmohamed M, Owen A: Genetic variants of ABCC10, a novel tenofovir transporter, are associated with kidney tubular dysfunction. J Infect Dis. 2011 Jul 1;204(1):145-53. doi: 10.1093/infdis/jir215. [PubMed:21628669]
  2. Moss DM, Neary M, Owen A: The role of drug transporters in the kidney: lessons from tenofovir. Front Pharmacol. 2014 Nov 11;5:248. doi: 10.3389/fphar.2014.00248. eCollection 2014. [PubMed:25426075]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
  1. Imaoka T, Kusuhara H, Adachi M, Schuetz JD, Takeuchi K, Sugiyama Y: Functional involvement of multidrug resistance-associated protein 4 (MRP4/ABCC4) in the renal elimination of the antiviral drugs adefovir and tenofovir. Mol Pharmacol. 2007 Feb;71(2):619-27. Epub 2006 Nov 16. [PubMed:17110501]
  2. Tun-Yhong W, Chinpaisal C, Pamonsinlapatham P, Kaewkitichai S: Tenofovir Disoproxil Fumarate Is a New Substrate of ATP-Binding Cassette Subfamily C Member 11. Antimicrob Agents Chemother. 2017 Mar 24;61(4). pii: AAC.01725-16. doi: 10.1128/AAC.01725-16. Print 2017 Apr. [PubMed:28167562]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Izzedine H, Hulot JS, Villard E, Goyenvalle C, Dominguez S, Ghosn J, Valantin MA, Lechat P, Deray AG: Association between ABCC2 gene haplotypes and tenofovir-induced proximal tubulopathy. J Infect Dis. 2006 Dec 1;194(11):1481-91. Epub 2006 Oct 26. [PubMed:17083032]
  2. Perazella MA: Tenofovir-induced kidney disease: an acquired renal tubular mitochondriopathy. Kidney Int. 2010 Dec;78(11):1060-3. doi: 10.1038/ki.2010.344. [PubMed:21076445]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. Storch CH, Theile D, Lindenmaier H, Haefeli WE, Weiss J: Comparison of the inhibitory activity of anti-HIV drugs on P-glycoprotein. Biochem Pharmacol. 2007 May 15;73(10):1573-81. Epub 2007 Jan 24. [PubMed:17328866]
  2. 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. [PubMed:28689442]
  3. van Gelder J, Deferme S, Naesens L, De Clercq E, van den Mooter G, Kinget R, Augustijns P: Intestinal absorption enhancement of the ester prodrug tenofovir disoproxil fumarate through modulation of the biochemical barrier by defined ester mixtures. Drug Metab Dispos. 2002 Aug;30(8):924-30. [PubMed:12124311]
  4. Moss DM, Domanico P, Watkins M, Park S, Randolph R, Wring S, Rajoli RKR, Hobson J, Rannard S, Siccardi M, Owen A: Simulating Intestinal Transporter and Enzyme Activity in a Physiologically Based Pharmacokinetic Model for Tenofovir Disoproxil Fumarate. Antimicrob Agents Chemother. 2017 Jun 27;61(7). pii: AAC.00105-17. doi: 10.1128/AAC.00105-17. Print 2017 Jul. [PubMed:28416547]
  5. HIV insite, UCSF: Tenofovir Alafenamide [Link]

Drug created on June 13, 2005 07:24 / Updated on November 30, 2020 13:38

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