Identification

Name
Tenofovir disoproxil
Accession Number
DB00300  (APRD01248, DB13426)
Type
Small Molecule
Groups
Approved, Investigational
Description

Tenofovir disoproxil fumarate (a prodrug of tenofovir), marketed by Gilead Sciences under the trade name Viread, belongs to a class of antiretroviral drugs known as nucleotide analogue reverse transcriptase inhibitors (nRTIs), which block reverse transcriptase, an enzyme crucial to viral production in HIV-infected people. In vivo tenofovir disoproxil fumarate is converted to tenofovir, an acyclic nucleoside phosphonate (nucleotide) analog of adenosine 5'-monophosphate.

Structure
Thumb
Synonyms
  • Bis(POC)PMPA
  • Tenofovir bis(isopropyloxycarbonyloxymethyl) ester
External IDs
GS-4331
Product Ingredients
IngredientUNIICASInChI Key
Tenofovir disoproxil fumarateOTT9J7900I202138-50-9VCMJCVGFSROFHV-WZGZYPNHSA-N
Active Moieties
NameKindUNIICASInChI Key
TenofovirprodrugW4HFE001U5147127-20-6SGOIRFVFHAKUTI-ZCFIWIBFSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
VireadGranule33 mg/gOralGilead Sciences Ireland Uc2002-02-05Not applicableEu
VireadTablet, coated300 mg/1OralRemedy Repack2017-05-18Not applicableUs
VireadTablet300 mgOralGilead Sciences2004-03-15Not applicableCanada
VireadTablet, coated300 mg/1OralA-S Medication Solutions2001-10-26Not applicableUs54569 533420180907 15195 1iwyatt
VireadTablet, coated300 mg/1OralCardinal Health2001-10-262015-09-30Us
VireadTablet, film coated204 mgOralGilead Sciences Ireland Uc2002-02-05Not applicableEu
VireadPowder40 mg/1gOralGilead Sciences2012-01-18Not applicableUs
VireadTablet, coated200 mg/1OralGilead Sciences2012-01-18Not applicableUs
VireadTablet, film coated123 mgOralGilead Sciences Ireland Uc2002-02-05Not applicableEu
VireadTablet, film coated245 mgOralGilead Sciences Ireland Uc2002-02-05Not applicableEu
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-tenofovirTablet300 mgOralApotex Corporation2017-07-26Not applicableCanada
Auro-tenofovirTablet300 mgOralAuro Pharma Inc2017-07-26Not applicableCanada
Mylan-tenofovir DisoproxilTablet300 mgOralMylan Pharmaceuticals2017-07-31Not applicableCanada
Nat-tenofovirTablet300 mgOralNatco Pharma LimitedNot applicableNot applicableCanada
PMS-tenofovirTablet300 mgOralPharmascience IncNot applicableNot applicableCanada
Tenofovir Disoproxil FumarateTablet, film coated150 mg/1OralAurobindo Pharma Limited2018-01-26Not applicableUs
Tenofovir Disoproxil FumarateTablet, film coated300 mg/1OralAmerincan Health Packaging2018-05-01Not applicableUs
Tenofovir Disoproxil FumarateTablet, film coated300 mg/1OralCamber Pharmaceuticals2018-02-08Not applicableUs
Tenofovir Disoproxil FumarateTablet, film coated300 mg/1OralLaurus Labs Limited2018-02-26Not applicableUs
Tenofovir Disoproxil FumarateTablet, film coated250 mg/1OralAurobindo Pharma Limited2018-01-26Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Apo-efavirenz-emtricitabine-tenofovirTenofovir disoproxil fumarate (300 mg) + Efavirenz (600 mg) + Emtricitabine (200 mg)TabletOralApotex CorporationNot applicableNot applicableCanada
Apo-emtricitabine-tenofovirTenofovir disoproxil fumarate (300 mg) + Emtricitabine (200 mg)TabletOralApotex Corporation2017-07-26Not applicableCanada
AtriplaTenofovir disoproxil fumarate (300 mg/1) + Efavirenz (600 mg/1) + Emtricitabine (200 mg/1)Tablet, film coatedOralRemedy Repack2017-03-29Not applicableUs
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
AtriplaTenofovir disoproxil fumarate (300 mg/1) + Efavirenz (600 mg/1) + Emtricitabine (200 mg/1)Tablet, film coatedOralAvera McKennan Hospital2015-03-062018-06-18Us
AtriplaTenofovir disoproxil fumarate (300 mg/1) + Efavirenz (600 mg/1) + Emtricitabine (200 mg/1)Tablet, film coatedOralGilead Sciences, Llc2006-07-20Not applicableUs
AtriplaTenofovir disoproxil fumarate (300 mg/1) + Efavirenz (600 mg/1) + Emtricitabine (200 mg/1)Tablet, film coatedOralPhysicians Total Care, Inc.2012-10-16Not applicableUs
AtriplaTenofovir disoproxil fumarate (300 mg/1) + Efavirenz (600 mg/1) + Emtricitabine (200 mg/1)Tablet, film coatedOralDoh Central Pharmacy2009-07-01Not applicableUs
AtriplaTenofovir disoproxil fumarate (300 mg) + Efavirenz (600 mg) + Emtricitabine (200 mg)TabletOralGilead Sciences, Llc2007-10-23Not applicableCanada
AtriplaTenofovir disoproxil fumarate (300 mg/1) + Efavirenz (600 mg/1) + Emtricitabine (200 mg/1)Tablet, film coatedOralA-S Medication Solutions2006-07-20Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Tenofovir Disoproxil FumarateTenofovir disoproxil fumarate (300 mg/1)Tablet, film coatedOralAizant Drug Research Solutions Pvt Ltd2018-01-26Not applicableUs
Tenofovir Disoproxil FumarateTenofovir disoproxil fumarate (150 mg/1)Tablet, film coatedOralAizant Drug Research Solutions Pvt Ltd2018-01-26Not applicableUs
Tenofovir Disoproxil FumarateTenofovir disoproxil fumarate (250 mg/1)Tablet, film coatedOralAizant Drug Research Solutions Pvt Ltd2018-01-26Not applicableUs
Tenofovir Disoproxil FumarateTenofovir disoproxil fumarate (200 mg/1)Tablet, film coatedOralAizant Drug Research Solutions Pvt Ltd2018-01-26Not applicableUs
Categories
UNII
F4YU4LON7I
CAS number
201341-05-1
Weight
Average: 519.448
Monoisotopic: 519.173029184
Chemical Formula
C19H30N5O10P
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

Pharmacology

Indication

Tenofovir is indicated in combination with other antiretroviral agents for the treatment of HIV-1 infection in adults and pediatric patients 2 years of age and older. It is also indicated for the treatment of chronic hepatitis B in adults and pediatric patients 12 years of age and older.

Associated Conditions
Pharmacodynamics

Tenofovir belongs to a class of antiretroviral drugs known as nucleotide analogue reverse transcriptase inhibitors (NtRTIs), which block reverse transcriptase, an enzyme crucial to viral production in HIV-infected people. Tenofovir is currently in late-stage clinical trials for the treatment of hepatitis B. Tenofovir disoproxil fumarate is an acyclic nucleoside phosphonate diester analog of adenosine monophosphate. Tenofovir requires initial diester hydrolysis for conversion to tenofovir and subsequent phosphorylations by cellular enzymes to form tenofovir diphosphate. Tenofovir diphosphate is a weak inhibitor of mammalian DNA polymerases α, β, and mitochondrial DNA polymerase γ.

Mechanism of action

Tenofovir inhibits the activity of HIV reverse transcriptase by competing with the natural substrate deoxyadenosine 5'-triphosphate and, after incorporation into DNA, by DNA chain termination. Specifically, the drugs are analogues of the naturally occurring deoxynucleotides needed to synthesize the viral DNA and they compete with the natural deoxynucleotides for incorporation into the growing viral DNA chain. However, unlike the natural deoxynucleotides substrates, NRTIs and NTRTIs (nucleoside/tide reverse transcriptase inhibitors) lack a 3'-hydroxyl group on the deoxyribose moiety. As a result, following incorporation of an NRTI or an NtRTI, the next incoming deoxynucleotide cannot form the next 5'-3' phosphodiester bond needed to extend the DNA chain. Thus, when an NRTI or NtRTI is incorporated, viral DNA synthesis is halted, a process known as chain termination. All NRTIs and NtRTIs are classified as competitive substrate inhibitors.

TargetActionsOrganism
AReverse transcriptase/RNaseH
inhibitor
Human immunodeficiency virus 1
Absorption

Tenofovir disoproxil fumarate is the water soluble diester prodrug of the active ingredient tenofoir. The oral bioavailability in fasted patients is approximately 25%. When a single oral dose (300 mg) is given to HIV-1 infected subjects in the fasted state, the maximum serum concentration was achieved in 1.0 ± 0.4 hours (Tmax). Cmax and AUC values are 0.30 ± 0.09 µg/mL and 2.29 ± 0.69 µg∙hr/mL. Administration of food (high fat meal containing 40 to 50% fat) increases the oral bioavailability, with an increase in the AUC of approximately 40%. Cmax is lower in the oral powder, compared to the tablet formulation. However, the mean AUC is similar between the two formulations.

Volume of distribution
  • 1.3 ± 0.6 L/kg [tenofovir 1.0 mg/kg IV]
  • 1.2 ± 0.4 L/kg [tenofovir 3.0 mg/kg IV]
Protein binding

Very low: < 0.7% to human plasma proteins and < 7.2% to serum proteins

Metabolism

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

Route of elimination

When tenofovir is given IV, 70-80% of the dose is recovered in the urine as unchanged drug within 72 hours of administration. Tenofovir is eliminated by a combination of glomerular filtration and active tubular secretion. There may be competition for elimination with other compounds that are also renally eliminated.

Half life

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

Clearance

The following are renal clearance (CL renal) parameters for subjects with varying degrees of renal function: * 243.5 ± 33.3 mL/min [baseline creatinine clearance >80 mL/min] * 168.6 ± 27.5 mL/min [baseline creatinine clearance 50-80 mL/min] * 100.6 ± 27.5 mL/min [baseline creatinine clearance 30-49 mL/min] * 43.0 ± 31.2 mL/min [baseline creatinine clearance 12-29 mL/min] The following are clearance (CL/F) parameters for subjects with varying degrees of renal function: * 1043.7 ± 115.4 [baseline creatinine clearance >80 mL/min] * 807.7 ± 279.2 [baseline creatinine clearance 50-80 mL/min] * 444.4 ± 209.8 [baseline creatinine clearance 30-49 mL/min] * 177.0 ± 97.1 [baseline creatinine clearance 12-29 mL/min]

Toxicity

Limited clinical experience at doses higher than the therapeutic dose of tenofovir 300 mg is available. In Study 901 tenofovir disoproxil fumarate 600 mg was administered to 8 patients orally for 28 days. No severe adverse reactions were reported. The effects of higher doses are not known.

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

Interactions

Drug Interactions
DrugInteraction
AbacavirTenofovir disoproxil may decrease the excretion rate of Abacavir which could result in a higher serum level.
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.
AcetazolamideThe excretion of Tenofovir disoproxil can be decreased when combined with Acetazolamide.
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.
AcyclovirAcyclovir may increase the nephrotoxic activities of Tenofovir disoproxil.
Food Interactions
  • When given with a high-fat meal, the oral bioavailability, AUC, and Cmax increased.

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]
External Links
Human Metabolome Database
HMDB14445
PubChem Compound
5481350
PubChem Substance
46508131
ChemSpider
4587262
ChEBI
63717
ChEMBL
CHEMBL1538
Therapeutic Targets Database
DAP001430
PharmGKB
PA10204
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Tenofovir_disoproxil
ATC Codes
J05AR12 — Lamivudine and tenofovir disoproxilJ05AR03 — Tenofovir disoproxil and emtricitabineJ05AR06 — Emtricitabine, tenofovir disoproxil and efavirenzJ05AR08 — Emtricitabine, tenofovir disoproxil and rilpivirineJ05AF07 — Tenofovir disoproxilJ05AR09 — Emtricitabine, tenofovir disoproxil, elvitegravir and cobicistatJ05AR11 — Lamivudine, tenofovir disoproxil and efavirenz
AHFS Codes
  • 08:18.08.20 — Nucleoside and Nucleotide Reverse Transcriptase Inhibitors
FDA label
Download (287 KB)
MSDS
Download (57.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceHealthy Volunteers / Human Immunodeficiency Virus (HIV)1
0CompletedOtherContraception / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
0CompletedOtherHealthy Volunteers1
0CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
1Active Not RecruitingScreeningHealthy Volunteers1
1CompletedNot AvailableAcquired Immune Deficiency Syndrome (AIDS)1
1CompletedNot AvailableHIV Prevention1
1CompletedNot AvailableHealthy Volunteers2
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV)2
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
1CompletedNot AvailablePharmacodynamics of 1% Tenofovir Gel Following Coitus / Pharmacokinetics of 1% Tenofovir Gel Following Coitus1
1CompletedNot AvailableRectal Microbicides1
1CompletedBasic ScienceHIV Prevention1
1CompletedBasic ScienceHIV Prevention / Human Immunodeficiency Virus (HIV) Infections1
1CompletedBasic ScienceHIV-1-infection1
1CompletedBasic ScienceHuman Immunodeficiency Virus (HIV) Infections1
1CompletedBasic ScienceTuberculosis Infection1
1CompletedHealth Services ResearchHuman Immunodeficiency Virus (HIV)2
1CompletedOtherHIV-DDI1
1CompletedPrevention18-30 Years of Age / High Risk MSM / HIV Negative1
1CompletedPreventionHealthy Adult Females1
1CompletedPreventionHuman Immunodeficiency Virus (HIV)2
1CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections5
1CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
1CompletedTreatmentHealthy Volunteers6
1CompletedTreatmentHepatitis1
1CompletedTreatmentHepatitis B Chronic Infection4
1CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections5
1CompletedTreatmentInsulin Resistance1
1CompletedTreatmentViral Hepatitis B1
1Not Yet RecruitingOtherHIV Prevention / Medication Adherence1
1RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
1RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
1TerminatedTreatmentHepatitis B Chronic Infection / Viral Hepatitis B1
1Unknown StatusBasic ScienceAtazanavir1
1Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1, 2CompletedOtherPrEP Adherence Monitoring1
1, 2CompletedTreatmentAcute HIV Infection1
1, 2CompletedTreatmentHepatitis B Chronic Infection1
1, 2CompletedTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV)1
1, 2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
1, 2Not Yet RecruitingTreatmentAicardi Goutières Syndrome1
1, 2RecruitingPreventionViral Hepatitis B1
1, 2WithdrawnPreventionMalignant Lymphomas1
2Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
2Active Not RecruitingTreatmentAcute HIV Infection / HIV CNS Involvement1
2Active Not RecruitingTreatmentContraception / Human Immunodeficiency Virus (HIV)1
2Active Not RecruitingTreatmentHepatitis B Chronic Infection3
2Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
2Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2CompletedNot AvailableHuman Immunodeficiency Virus (HIV)1
2CompletedPreventionAmphetamine-Related Disorders / Human Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedPreventionHIV Prevention / HIV Transmission / Human Immunodeficiency Virus (HIV) Infections1
2CompletedPreventionHIV Seroconversion / Stimulant Abuse1
2CompletedPreventionHIV Seropositivity1
2CompletedPreventionHepatitis B Chronic Infection1
2CompletedPreventionHepatitis B Chronic Infection / Human Immunodeficiency Virus (HIV) Infections1
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections9
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Pregnancy1
2CompletedPreventionHuman Immunodeficiency Virus (HIV) / Pregnancy1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections4
2CompletedTreatmentChronic Hepatitis D Infection With Hepatitis B1
2CompletedTreatmentContraception / Human Immunodeficiency Virus (HIV)1
2CompletedTreatmentHepatitis B Chronic Infection7
2CompletedTreatmentHepatitis D1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections15
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies / Metabolic Diseases / Nutrition Disorders1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lymphoma, AIDS Related1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Viral Hepatitis B1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)2
2CompletedTreatmentInfection, Human Immunodeficiency Virus I6
2CompletedTreatmentInfectious Diseases1
2CompletedTreatmentLipodystrophies1
2CompletedTreatmentViral Hepatitis B1
2Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
2RecruitingTreatmentChronic Viral Hepatitis B With Delta-agent1
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2TerminatedPreventionHuman Immunodeficiency Virus (HIV) Infections1
2TerminatedTreatmentHepatitis B Chronic Infection1
2TerminatedTreatmentHepatitis D / Viral Hepatitis B1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV)1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
2TerminatedTreatmentInfection, Human Immunodeficiency Virus I1
2TerminatedTreatmentViral Hepatitis B1
2Unknown StatusPreventionHuman Immunodeficiency Virus (HIV) / Viral Hepatitis B1
2Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
2WithdrawnPreventionHIV-1-infection1
2WithdrawnPreventionHuman Immunodeficiency Virus (HIV) Infections1
2WithdrawnTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
2, 3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
2, 3CompletedPreventionHuman Immunodeficiency Virus (HIV)1
2, 3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
2, 3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
2, 3CompletedTreatmentAcute HIV Infection1
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2, 3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Viral Hepatitis B1
2, 3RecruitingOtherHIV-1-infection1
2, 3RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection / HBV Coinfection / Reactivation of hepatitis B virus infection1
2, 3WithdrawnPreventionHIV Seronegativity / Human Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingPreventionHepatitis B Chronic Infection / Pregnancy1
3Active Not RecruitingPreventionHuman Immunodeficiency Virus (HIV) / STI1
3Active Not RecruitingTreatmentAcute HIV Infection1
3Active Not RecruitingTreatmentChronic HBV Infections / Chronic Infection With HIV / HBV1
3Active Not RecruitingTreatmentChronic HBV Infections / HBV3
3Active Not RecruitingTreatmentChronic Hepatitis B e Antigen Negative / Chronic Hepatitis B e Antigen Positive1
3Active Not RecruitingTreatmentHepatitis B Chronic Infection3
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)3
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections2
3Active Not RecruitingTreatmentHuman Immunodeficiency Virus-type 1 Infection1
3Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I6
3Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I / Kaposi s Sarcoma (KS)1
3Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I / Tuberculosis Infection1
3Active Not RecruitingTreatmentPre-Exposure Prophylaxis of HIV-1 Infection1
3CompletedNot AvailableHuman Immunodeficiency Virus (HIV)1
3CompletedPreventionHIV Prevention1
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections5
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I1
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV)1
3CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections6
3CompletedTreatmentHepatitis B Chronic Infection5
3CompletedTreatmentHepatitis B Virus (HBV)2
3CompletedTreatmentHepatitis D, Chronic1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections22
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections5
3CompletedTreatmentInfection, Human Immunodeficiency Virus I7
3CompletedTreatmentViral Hepatitis B2
3Enrolling by InvitationTreatmentHepatitis B Chronic Infection1
3Not Yet RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections / Stimulant Use / Substance Use Disorder (SUD)1
3RecruitingPreventionHuman Immunodeficiency Virus (HIV) Infections1
3RecruitingPreventionPregnancy / Viral Hepatitis B1
3RecruitingTreatmentHIV-1/HBV Co-Infection1
3RecruitingTreatmentHepatitis B Chronic Infection2
3RecruitingTreatmentHepatitis B, Chronic1
3RecruitingTreatmentInfection, Human Immunodeficiency Virus I1
3RecruitingTreatmentMalignant Lymphomas / Non-Hodgkins / Viral Hepatitis B1
3TerminatedTreatmentHepatitis B Chronic Infection1
3TerminatedTreatmentHepatitis B Chronic Infection / Hepatocellular,Carcinoma1
3TerminatedTreatmentHuman Immunodeficiency Virus (HIV)2
3TerminatedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)1
3Unknown StatusPreventionHuman Immunodeficiency Virus (HIV) / Infection NOS1
3Unknown StatusTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
3Unknown StatusTreatmentChronic HBV With Severe Exacerbation1
3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3WithdrawnPreventionBreastfeeding / Human Immunodeficiency Virus (HIV) Infections / Pregnancy1
4Active Not RecruitingOtherHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
4Active Not RecruitingPreventionInfection, Human Immunodeficiency Virus I1
4Active Not RecruitingTreatmentChronic Infection With HIV1
4Active Not RecruitingTreatmentHepatitis B Chronic Infection4
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
4Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections3
4Active Not RecruitingTreatmentInfection, Human Immunodeficiency Virus I1
4CompletedNot AvailableHealthy Volunteers2
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV)1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
4CompletedNot AvailableHuman Immunodeficiency Virus (HIV) / Proteinuria1
4CompletedNot AvailablePharmacokinetic Study in Healthy Volunteers1
4CompletedBasic ScienceHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
4CompletedDiagnosticCardiovascular Disease (CVD) / HIV-Associated Lipodystrophy Syndrome1
4CompletedHealth Services ResearchHuman Immunodeficiency Virus (HIV)1
4CompletedOtherAdherence, Medication / HIV Prevention / Pre-Exposure Prophylaxis / Risk Behaviors1
4CompletedOtherHuman Immunodeficiency Virus (HIV)1
4CompletedOtherViral Hepatitis B1
4CompletedPreventionAdolescent Behaviors / Gender / Human Immunodeficiency Virus (HIV)1
4CompletedPreventionCentral Nervous System Diseases / Dementias / Human Immunodeficiency Virus (HIV) Infections1
4CompletedPreventionHBV / Pregnancy1
4CompletedPreventionHIV Prevention1
4CompletedPreventionHepatitis B Chronic Infection1
4CompletedPreventionHuman Immunodeficiency Virus (HIV)6
4CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections3
4CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Sleep disorders and disturbances1
4CompletedTreatmentAcute HIV Infection / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentAcute on Chronic Liver Failure / Viral Hepatitis B1
4CompletedTreatmentCardiovascular Disease (CVD) / Human Immunodeficiency Virus (HIV)1
4CompletedTreatmentChronic Viral Hepatitis B Without Delta-agent2
4CompletedTreatmentDyslipidemias / Human Immunodeficiency Virus (HIV)1
4CompletedTreatmentHIV Associated Neurocognitive Disorders (HAND) / Neurocognitive Decline1
4CompletedTreatmentHIV, Combination Therapy1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentHepatitis B Chronic Infection8
4CompletedTreatmentHepatitis B Coinfection / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHepatitis C Infection / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHerpes Simplex Type II1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV)8
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections20
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Viral Hepatitis B2
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHuman Immunodeficiency Virus Type 1 (HIV-1)4
4CompletedTreatmentInfection, Human Immunodeficiency Virus I5
4Enrolling by InvitationPreventionHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
4Enrolling by InvitationTreatmentAntiviral Treatment / Hepatitis B Chronic Infection1
4Enrolling by InvitationTreatmentHepatitis B Chronic Infection1
4Not Yet RecruitingPreventionHepatocellular,Carcinoma1
4Not Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Menopause / Osteoporosis1
4Not Yet RecruitingTreatmentViral Hepatitis B1
4RecruitingOtherPre-Exposure Prophylaxis / Transgender Persons1
4RecruitingPreventionBone Demineralization1
4RecruitingPreventionHIV, Prevention1
4RecruitingPreventionHepatitis B Chronic Infection / Pregnancy1
4RecruitingPreventionHuman Immunodeficiency Virus (HIV)1
4RecruitingPreventionNon-Hodgkin's Lymphoma (NHL) / Non-Hodgkin's Lymphoma, Burkitt's1
4RecruitingPreventionPrEP Adherence Monitoring1
4RecruitingPreventionVertical Transmission of Infectious Disease / Viral Hepatitis B1
4RecruitingSupportive CareHuman Immunodeficiency Virus (HIV)1
4RecruitingTreatmentAntiretroviral Therapy Intolerance / Patients Compliance1
4RecruitingTreatmentHIV-1-infection1
4RecruitingTreatmentHIV-1-infection / Solid Organ Transplant1
4RecruitingTreatmentHepatitis B Chronic Infection7
4RecruitingTreatmentHepatitis, Chronic1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV)1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4TerminatedPreventionHuman Immunodeficiency Virus (HIV)1
4TerminatedTreatmentAcquired Immune Deficiency Syndrome (AIDS)1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV)1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections4
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Osteopenia1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis Infection1
4TerminatedTreatmentHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections1
4TerminatedTreatmentMetabolic Complications / Mitochondrial Toxicity1
4Unknown StatusBasic ScienceHuman Immunodeficiency Virus (HIV)1
4Unknown StatusPreventionHuman Immunodeficiency Virus (HIV)1
4Unknown StatusTreatmentCirrhosis Due to Hepatitis B1
4Unknown StatusTreatmentHepatitis B Chronic Infection3
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV)1
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections2
4WithdrawnTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
4WithdrawnTreatmentHepatitis B Chronic Infection1
4WithdrawnTreatmentViral Hepatitis B1
Not AvailableActive Not RecruitingNot AvailableChronic Renal Diseases1
Not AvailableActive Not RecruitingNot AvailableViral Hepatitis B1
Not AvailableActive Not RecruitingPreventionHuman Immunodeficiency Virus (HIV)2
Not AvailableActive Not RecruitingTreatmentHepatitis B Chronic Infection1
Not AvailableActive Not RecruitingTreatmentViral Hepatitis B1
Not AvailableCompletedNot AvailableContraception / Human Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
Not AvailableCompletedNot AvailableHIV Seropositivity / Pregnancy, High-Risk1
Not AvailableCompletedNot AvailableHIV-infected Thai Children1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV)3
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections5
Not AvailableCompletedNot AvailableInfection, Human Immunodeficiency Virus I1
Not AvailableCompletedNot AvailableThis Study is Designed to Collect Treatment Data of Thai Children on Third Line ARV Therapy1
Not AvailableCompletedBasic ScienceHealthy Volunteers / Pharmacokinetics1
Not AvailableCompletedBasic ScienceHuman Immunodeficiency Virus (HIV)2
Not AvailableCompletedPreventionHuman Immunodeficiency Virus (HIV)3
Not AvailableCompletedPreventionHuman Immunodeficiency Virus (HIV) Infections3
Not AvailableCompletedPreventionHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
Not AvailableCompletedPreventionMicrobicide Applicator1
Not AvailableCompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentAntiretroviral Treatment Outcomes1
Not AvailableCompletedTreatmentChronic Heptitis B1
Not AvailableCompletedTreatmentDyslipidemias / High Cholesterol / Human Immunodeficiency Virus (HIV) Infections / Hyperlipidemias / Hypertriglyceridemias1
Not AvailableCompletedTreatmentHepatitis B Chronic Infection1
Not AvailableCompletedTreatmentHepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV)1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections6
Not AvailableCompletedTreatmentPrimary Biliary Cholangitis1
Not AvailableCompletedTreatmentSpontaneous Reactivation of Hepatitis B1
Not AvailableEnrolling by InvitationNot AvailableThe Safety of Anti-viral Drugs Used in Late Pregnancy1
Not AvailableNot Yet RecruitingNot AvailableAntiviral Drug Adverse Reaction / Viral Hepatitis B1
Not AvailableNot Yet RecruitingPreventionInfection, Human Immunodeficiency Virus I1
Not AvailableRecruitingNot AvailableHIV Chemoprophylaxis / HIV Preexposure Prophylaxis1
Not AvailableRecruitingNot AvailableHIV Prevention1
Not AvailableRecruitingNot AvailableHepatitis B Chronic Infection2
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV)1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV) / Illicit Drug User1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus Infection(HIV)/Acquired Immunodeficiency Syndrome (AIDS)1
Not AvailableRecruitingBasic ScienceHuman Immunodeficiency Virus (HIV)1
Not AvailableRecruitingPreventionHuman Immunodeficiency Virus (HIV)1
Not AvailableRecruitingTreatmentAcute on Chronic Liver Failure1
Not AvailableRecruitingTreatmentHepatitis B Chronic Infection2
Not AvailableRecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableTerminatedNot AvailableHepatitis B Chronic Infection / Viral Hepatitis B1
Not AvailableTerminatedNot AvailableViral Hepatitis B1
Not AvailableTerminatedPreventionHuman Immunodeficiency Virus (HIV)1
Not AvailableTerminatedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Tuberculosis Infection1
Not AvailableUnknown StatusNot AvailableHepatitis B Chronic Infection / Hepatocellular,Carcinoma1
Not AvailableUnknown StatusBasic ScienceHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableUnknown StatusPreventionHuman Immunodeficiency Virus (HIV) / Human Immunodeficiency Virus (HIV) Infections / Immune Reconstitution Inflammatory Syndrome1
Not AvailableUnknown StatusTreatmentHBV Coinfection / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableUnknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableWithdrawnNot AvailableHIV-infected Patients1
Not AvailableWithdrawnNot AvailableHuman Immunodeficiency Virus (HIV)1
Not AvailableWithdrawnBasic ScienceHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableWithdrawnTreatmentHBV1
Not AvailableWithdrawnTreatmentHepatitis B Chronic Infection1
Not AvailableWithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableWithdrawnTreatmentHuman Immunodeficiency Virus (HIV) / Infertilities1

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
TabletOral300 mg/1
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral200 mg/1
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral300 mg/1
TabletOral
Tablet, film coatedOral
GranuleOral33 mg/g
PowderOral40 mg/1g
TabletOral300 mg
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)
CA2298059No2008-12-302018-07-23Canada
CA2261619No2006-05-232017-07-25Canada
US5914331Yes1999-06-222018-01-02Us
US6043230Yes2000-03-282018-01-25Us
US5814639Yes1998-09-292017-03-29Us
US6939964Yes2005-09-062018-07-20Us
US6639071Yes2003-10-282018-08-14Us
US6642245Yes2003-11-042021-05-04Us
US6703396Yes2004-03-092021-09-09Us
US5922695Yes1999-07-132018-01-25Us
US5935946Yes1999-08-102018-01-25Us
US5977089Yes1999-11-022018-01-25Us
US8592397No2013-11-262024-01-13Us
US8716264No2014-05-062024-01-13Us
US9018192No2015-04-282026-06-13Us
US8598185No2013-12-032028-05-01Us
US7125879No2006-10-242022-08-09Us
US6838464No2005-01-042021-02-26Us
US8080551No2011-12-202023-04-11Us
US8101629No2012-01-242022-08-09Us
US7067522No2006-06-272019-12-20Us
US8148374No2012-04-032029-09-03Us
US7635704No2009-12-222026-10-26Us
US7176220No2007-02-132023-11-20Us
US8981103No2015-03-172026-10-26Us
US8633219No2014-01-212030-04-24Us
US8841310No2014-09-232025-12-09Us
US9545414No2017-01-172026-06-13Us
US9457036No2016-10-042024-01-13Us
US9744181No2017-08-292024-01-13Us
US9891239No2018-02-132029-09-03Us
US10039718No2012-10-042032-10-04Us
US8486975No2013-07-162031-10-07Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)276-280 °CNot Available
water solubility13.4 mg/mL in distilled water at 25 °C (disoproxil fumarate salt)FDA label
logP1.25FDA label
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

Taxonomy

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 / Aminopyrimidine / Dialkyl alkylphosphonate / Phosphonic acid diester / Carbonic acid diester / Imidolactam / Pyrimidine / N-substituted imidazole / Phosphonic acid ester / Azole
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic phosphonate (CHEBI:63717)

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]

Enzymes

Kind
Protein
Organism
Human
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. Link [Link]
Kind
Protein
Organism
Human
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. Link [Link]
Kind
Protein
Organism
Human
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...
Gene Name
NME1
Uniprot ID
P15531
Uniprot Name
Nucleoside diphosphate kinase A
Molecular Weight
17148.635 Da
References
  1. Link [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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
References
  1. Link [Link]

Transporters

Kind
Protein
Organism
Human
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
Human
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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]
Kind
Protein
Organism
Human
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]
Kind
Protein
Organism
Human
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]

Drug created on June 13, 2005 07:24 / Updated on November 17, 2018 04:48