Tenofovir disoproxil

Identification

Summary

Tenofovir disoproxil is a nucleotide analog reverse transcriptase inhibitor used in the treatment of Hepatitis B infection and used in the management of HIV-1 infection.

Brand Names

Atripla, Cimduo, Complera, Delstrigo, Stribild, Symfi, Truvada, Viread

Generic Name

Tenofovir disoproxil

DrugBank Accession Number

DB00300

Background

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

Similar Structures

Weight: Average: 519.448
Monoisotopic: 519.173029184
Chemical Formula: C₁₉H₃₀N₅O₁₀P

Synonyms

Bis(POC)PMPA
Tenofovir bis(isopropyloxycarbonyloxymethyl) ester

External IDs

GS-4331

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Pharmacology

Indication

Tenofovir disoproxil is indicated in combination with other antiretroviral agents for the treatment of HIV-1 infection in patients ≥2 years old and weighing ≥10 kg.¹⁹ It is also indicated for the treatment of chronic hepatitis B in patients ≥2 years old and weighing ≥10 kg.¹⁹

Tenofovir disoproxil is also an ingredient in several combination products, all of which are indicated either alone or in combination with other antiretrovirals for the treatment of HIV-1 infection.^{12,13,14,15,16,17,18}

In addition, tenofovir disoproxil is available in combination with emtricitabine (under the brand name Truvada) for use as pre-exposure prophylaxis (PrEP) in at-risk adults and adolescents weighing ≥ 35kg to reduce the risk of sexually-acquired HIV-1 infection.¹⁸

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Adjunct therapy in treatment of	Hepatitis b chronic infection		••••••••••••	•••••• •••••••••	•••• •••••• •• •• •• •• ••••	••••••• ••••••
Adjunct therapy in treatment of	Human immunodeficiency virus type 1 (hiv-1) infection		••••••••••••	•••••• •••••••••	•••• •••••• •• •• •• •• ••••	••••••• ••••••
Used in combination for prophylaxis of	Human immunodeficiency virus type 1 (hiv-1) infection	Combination Product in combination with: Emtricitabine (DB00879)	••••••••••••	••••••••••• •••••	•• •••• ••• •••• •••••• •• ••••• •• ••	••••••
Used as adjunct in combination to treat	Human immunodeficiency virus type 1 (hiv-1) infection	Combination Product in combination with: Emtricitabine (DB00879)	••••••••••••	•••••• •••••••••	•••••• • •• ••	••••••
Used in combination to treat	Human immunodeficiency virus type 1 (hiv-1) infection	Combination Product in combination with: Lamivudine (DB00709), Efavirenz (DB00625)	••••••••••••	•••••• •••••••••	••••• ••• ••	••••••

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 ²⁴, ^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.

Target	Actions	Organism
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 ²⁴.

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) ²⁴.

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.

Hover over products below to view reaction partners

Tenofovir disoproxil
- Tenofovir Monophosphate
  - Tenofovir Diphosphate

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) ²⁴.

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 ²⁴.

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.

Pathways

Pathway	Category
Tenofovir Metabolism Pathway	Drug metabolism

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Interactions

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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
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Abacavir	Tenofovir disoproxil may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Tenofovir disoproxil.
Abrocitinib	The serum concentration of Tenofovir disoproxil can be increased when it is combined with Abrocitinib.
Aceclofenac	Aceclofenac may increase the nephrotoxic activities of Tenofovir disoproxil.
Acemetacin	Acemetacin may increase the nephrotoxic activities of Tenofovir disoproxil.

Food Interactions

Take with or without food.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Tenofovir disoproxil fumarate	OTT9J7900I	202138-50-9	VCMJCVGFSROFHV-WZGZYPNHSA-N
Tenofovir disoproxil maleate	7BI6HE4F8S	1276030-80-8	VCMJCVGFSROFHV-VIEYUMQNSA-N
Tenofovir disoproxil phosphate	05F4G8DO5I	1453166-76-1	DJCLNKKHALBVLK-PFEQFJNWSA-N
Tenofovir disoproxil succinate	94882WB39E	1637632-97-3	CCGIINMVANPRGB-PFEQFJNWSA-N

Active Moieties

Name	Kind	UNII	CAS	InChI Key
Tenofovir	prodrug	W4HFE001U5	147127-20-6	SGOIRFVFHAKUTI-ZCFIWIBFSA-N

Product Images

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Tenofovir	Tablet	300 mg	Oral	Sivem Pharmaceuticals Ulc	2022-05-12	Not applicable
Tenofovir	Tablet	300 mg	Oral	Sanis Health Inc	2021-08-20	Not applicable
Tenofovir Disoproxil Fumarate	Tablet, film coated	250 mg/1	Oral	Aizant Drug Research Solutions Pvt Ltd	2018-01-26	Not applicable
Tenofovir Disoproxil Fumarate	Tablet, film coated	200 mg/1	Oral	Aizant Drug Research Solutions Pvt Ltd	2018-01-26	Not applicable
Tenofovir Disoproxil Fumarate	Tablet, film coated	300 mg/1	Oral	Aizant Drug Research Solutions Pvt Ltd	2018-01-26	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Ag-tenofovir	Tablet	300 mg	Oral	Angita Pharma Inc.	2022-06-09	Not applicable
Apo-tenofovir	Tablet	300 mg	Oral	Apotex Corporation	2017-07-26	Not applicable
Auro-tenofovir	Tablet	300 mg	Oral	Auro Pharma Inc	2017-07-26	Not applicable
Jamp-tenofovir	Tablet	300 mg	Oral	Jamp Pharma Corporation	2018-10-24	Not applicable
Mint-tenofovir	Tablet	300 mg	Oral	Mint Pharmaceuticals Inc	2021-09-07	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
ACRIPTEGA	Tenofovir disoproxil fumarate (300 MG) + Dolutegravir (50 MG) + Lamivudine (300 MG)	Tablet, coated	Oral	บริษัท ซาย ฟาร์มา จำกัด จำกัด	2019-12-27	Not applicable
Ag-emtricitabine / Tenofovir Disoproxil Fumarate	Tenofovir disoproxil fumarate (300 mg) + Emtricitabine (200 mg)	Tablet	Oral	Angita Pharma Inc.	2020-11-09	Not applicable
Apo-efavirenz-emtricitabine-tenofovir	Tenofovir disoproxil fumarate (300 mg) + Efavirenz (600 mg) + Emtricitabine (200 mg)	Tablet	Oral	Apotex Corporation	2018-09-04	Not applicable
Apo-emtricitabine-tenofovir	Tenofovir disoproxil fumarate (300 mg) + Emtricitabine (200 mg)	Tablet	Oral	Apotex Corporation	2017-07-26	Not applicable
Atripla	Tenofovir disoproxil fumarate (300 mg/1) + Efavirenz (600 mg/1) + Emtricitabine (200 mg/1)	Tablet, film coated	Oral	Lake Erie Medical Dba Quality Care Produts Llc	2006-07-20	2014-12-31

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Tenofovir Disoproxil Fumarate	Tenofovir disoproxil fumarate (200 mg/1)	Tablet, film coated	Oral	Aizant Drug Research Solutions Pvt Ltd	2018-01-26	Not applicable
Tenofovir Disoproxil Fumarate	Tenofovir disoproxil fumarate (300 mg/1)	Tablet, film coated	Oral	Aizant Drug Research Solutions Pvt Ltd	2018-01-26	Not applicable
Tenofovir Disoproxil Fumarate	Tenofovir disoproxil fumarate (150 mg/1)	Tablet, film coated	Oral	Aizant Drug Research Solutions Pvt Ltd	2018-01-26	Not applicable
Tenofovir Disoproxil Fumarate	Tenofovir disoproxil fumarate (250 mg/1)	Tablet, film coated	Oral	Aizant Drug Research Solutions Pvt Ltd	2018-01-26	Not applicable
TERNAVIR 245 MG FILM KAPLI TABLET, 30 ADET	Tenofovir disoproxil (245 mg)	Tablet, film coated	Oral	ATABAY KİMYA SAN. VE TİC. A.Ş.	2013-11-19	Not applicable

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][C@@](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

Gilden D: Tenofovir: Gilead applies for approval; expanded access liberalized. AIDS Treat News. 2001 May 11;(364):2-3, 1. [Article]
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. [Article]
Thompson CA: Prodrug of tenofovir diphosphate approved for combination HIV therapy. Am J Health Syst Pharm. 2002 Jan 1;59(1):18. [Article]
Gazzard BG: The potential place of tenofovir in antiretroviral treatment regimens. Int J Clin Pract. 2001 Dec;55(10):704-9. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
FDA Approved Drug Products: Atripla (efavirenz, emtricitabine, and tenofovir disoproxil fumarate) tablets for oral use [Link]
FDA Approved Drug Products: Cimduo (lamivudine and tenofovir disoproxil fumarate) tablets for oral use [Link]
FDA Approved Drug Products: Complera (emtricitabine, rilpivirine, tenofovir disoproxil fumarate) tablets for oral use [Link]
FDA Approved Drug Products: Delstrigo (doravirine, lamivudine, and tenofovir disoproxil fumarate) tablets for oral use [Link]
FDA Approved Drug Products: Stribild (elvitegravir, cobicistat, emtricitabine, tenofovir disoproxil fumarate) tablets for oral use [Link]
FDA Approved Drug Products: Symfi (efavirenz, lamivudine, and tenofovir disoproxil fumarate) tablets for oral use [Link]
FDA Approved Drug Products: Truvada (emtricitabine and tenofovir disoproxil fumarate) tablets for oral use [Link]
FDA Approved Drug Products: Viread (tenofovir disoproxil fumarate) powder/tablets for oral use [Link]
Tenofovir Disoproxil FDA label [File]
Auspar: Tenofovir disoproxil fumarate [File]
Stribild FDA label [File]
Truvada FDA label [File]
Viread EPAR [File]

External Links

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

MSDS

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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	Prevention	Hormone Therapy / Human Immunodeficiency Virus (HIV) Infections	1
4	Active Not Recruiting	Prevention	PrEP Adherence Monitoring	1
4	Active Not Recruiting	Treatment	Fatty Liver Disease / Human Immunodeficiency Virus (HIV) Infections	1
4	Active Not Recruiting	Treatment	HBV Coinfection / HCC	1
4	Active Not Recruiting	Treatment	Human Immunodeficiency Virus (HIV) Infections	2

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

Form	Route	Strength
Tablet	Oral
Tablet, film coated	Oral	245 MG
Tablet	Oral	200.000 mg
Tablet	Oral	300.00 mg
Tablet, film coated	Oral
Tablet	Oral	400.000 mg
Tablet, coated	Oral
Tablet, film coated	Oral	150 mg
Tablet, film coated	Oral	123 MG
Tablet, film coated	Oral	163 MG
Tablet, film coated	Oral	204 MG
Powder	Not applicable	1 kg/1kg
Tablet	Oral	300 mg/1
Tablet, film coated	Oral	150 mg/1
Tablet, film coated	Oral	200 mg/1
Tablet, film coated	Oral	250 mg/1
Tablet, film coated	Oral	300 mg/1
Tablet, film coated	Oral	245 MG
Tablet, coated	Oral	245 mg
Tablet	Oral	300.000 mg
Tablet, film coated	Oral
Tablet, film coated	Oral	200 mg
Granule	Oral	33 MG/G
Powder	Oral	40 mg/1g
Tablet	Oral	300 mg
Tablet, coated	Oral	150 mg/1
Tablet, coated	Oral	200 mg/1
Tablet, coated	Oral	250 mg/1
Tablet, coated	Oral	300 mg/1
Tablet, coated	Oral	300 MG
Tablet, film coated	Oral	300 MG

Prices

Unit description	Cost	Unit
Viread 300 mg tablet	33.95USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
CA2298059	No	2008-12-30	2018-07-23
CA2261619	No	2006-05-23	2017-07-25
US5914331	Yes	1999-06-22	2018-01-02
US6043230	Yes	2000-03-28	2018-01-25
US5814639	Yes	1998-09-29	2017-03-29
US6939964	Yes	2005-09-06	2018-07-20
US6639071	Yes	2003-10-28	2018-08-14
US6642245	Yes	2003-11-04	2021-05-04
US6703396	Yes	2004-03-09	2021-09-09
US5922695	Yes	1999-07-13	2018-01-25
US5935946	Yes	1999-08-10	2018-01-25
US5977089	Yes	1999-11-02	2018-01-25
US8592397	No	2013-11-26	2024-01-13
US8716264	No	2014-05-06	2024-01-13
US9018192	No	2015-04-28	2026-06-13
US8598185	No	2013-12-03	2028-05-01
US7125879	No	2006-10-24	2022-08-09
US6838464	No	2005-01-04	2021-02-26
US8080551	No	2011-12-20	2023-04-11
US8101629	No	2012-01-24	2022-08-09
US7067522	No	2006-06-27	2019-12-20
US8148374	Yes	2012-04-03	2030-03-03
US7635704	Yes	2009-12-22	2027-04-26
US7176220	Yes	2007-02-13	2027-02-27
US8981103	Yes	2015-03-17	2027-04-26
US8633219	Yes	2014-01-21	2030-10-24
US8841310	No	2014-09-23	2025-12-09
US9545414	No	2017-01-17	2026-06-13
US9457036	No	2016-10-04	2024-01-13
US9744181	No	2017-08-29	2024-01-13
US9891239	Yes	2018-02-13	2030-03-03
US10039718	Yes	2018-08-07	2033-04-06
US8486975	No	2013-07-16	2031-10-07
US10603282	No	2020-03-31	2036-11-29
US10842751	No	2020-11-24	2036-11-29
US10857102	No	2020-12-08	2033-01-14

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	113-115	https://www.chemicalbook.com/ChemicalProductProperty_US_CB7946998.aspx
boiling point (°C)	642.7	https://www.lookchem.com/Tenofovir-disoproxil-fumarate/
water solubility	13.4 mg/mL in distilled water at 25 °C (disoproxil fumarate salt)	https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021752s005lbl.pdf
logP	1.25	https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021752s005lbl.pdf
pKa	3.75	https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021752s005lbl.pdf

Predicted Properties

Property	Value	Source
Water Solubility	0.712 mg/mL	ALOGPS
logP	-0.02	ALOGPS
logP	2.65	Chemaxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	18.59	Chemaxon
pKa (Strongest Basic)	4.13	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	10	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	185.44 Å²	Chemaxon
Rotatable Bond Count	17	Chemaxon
Refractivity	118.59 m³·mol^-1	Chemaxon
Polarizability	49.18 Å³	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.5998
Blood Brain Barrier	+	0.9194
Caco-2 permeable	-	0.617
P-glycoprotein substrate	Substrate	0.7203
P-glycoprotein inhibitor I	Non-inhibitor	0.8706
P-glycoprotein inhibitor II	Non-inhibitor	0.948
Renal organic cation transporter	Non-inhibitor	0.8985
CYP450 2C9 substrate	Non-substrate	0.8609
CYP450 2D6 substrate	Non-substrate	0.9117
CYP450 3A4 substrate	Non-substrate	0.6458
CYP450 1A2 substrate	Non-inhibitor	0.7177
CYP450 2C9 inhibitor	Non-inhibitor	0.7873
CYP450 2D6 inhibitor	Non-inhibitor	0.8271
CYP450 2C19 inhibitor	Non-inhibitor	0.7634
CYP450 3A4 inhibitor	Non-inhibitor	0.8353
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.85
Ames test	Non AMES toxic	0.511
Carcinogenicity	Non-carcinogens	0.7811
Biodegradation	Not ready biodegradable	0.9914
Rat acute toxicity	2.4903 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8936
hERG inhibition (predictor II)	Non-inhibitor	0.7957

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0udr-2096000000-e25060b3fa10d4c755ec
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0fr2-1396050000-d468ba1f00504776ee6b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0f79-1095300000-7a0b9f5de1d4235a3c8c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00li-0093100000-b9ed0c28d7b3f76be18b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4l-9000000000-93ba9e0fba8ce60f8a0d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000i-3920000000-ba4904ec38fac42ba2c9

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	198.72456	predicted	DeepCCS 1.0 (2019)
[M+H]+	201.12013	predicted	DeepCCS 1.0 (2019)
[M+Na]+	207.03264	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Reverse transcriptase/RNaseH

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

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. [Article]
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. [Article]
Link [Link]
FDA label, Viread [File]

Details2. DNA polymerase/reverse transcriptase

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

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. [Article]
Link [Link]
FDA label, Viread [File]

Enzymes

Details1. Adenylate kinase 2, mitochondrial

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

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. [Article]
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. [Article]
Link [Link]

Details2. Adenylate kinase 4, mitochondrial

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

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. [Article]
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. [Article]
Link [Link]

Details3. Nucleoside diphosphokinase (Protein Group)

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:

Name	UniProt ID
Nucleoside diphosphate kinase A	P15531
Nucleoside diphosphate kinase B	P22392

References

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. [Article]
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. [Article]
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. [Article]
Suboptimal CD4 gains in HIV-infected patients receiving didanosine plus tenofovir [File]

Details4. Creatine Kinases (Protein Group)

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:

Name	UniProt ID
Creatine kinase B-type	P12277
Creatine kinase M-type	P06732
Creatine kinase S-type, mitochondrial	P17540
Creatine kinase U-type, mitochondrial	P12532

References

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. [Article]
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. [Article]
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. [Article]

Transporters

Details1. Solute carrier family 22 member 6

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

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. [Article]
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. [Article]

Details2. Solute carrier family 22 member 8

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

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. [Article]
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. [Article]

Details3. Multidrug resistance-associated protein 7

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

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. [Article]
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. [Article]

Details4. Multidrug resistance-associated protein 4

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

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. [Article]
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. [Article]

Details5. Canalicular multispecific organic anion transporter 1

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

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. [Article]
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. [Article]

Details6. P-glycoprotein 1

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

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. [Article]
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]
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. [Article]
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. [Article]
HIV insite, UCSF: Tenofovir Alafenamide [Link]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54

Tenofovir disoproxil

Identification

Structure for Tenofovir disoproxil (DB00300)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

Enzymes

References

References

Components:

References

Components:

References

Transporters

References

References

References

References

References

References