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Identification
NameTenofovir
Accession NumberDB00300  (APRD01248)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionTenofovir disoproxil fumarate (a prodrug of tenofovir), marketed by Gilead Sciences under the trade name Viread®, belongs to a class of antiretroviral drugs known as nucleotide analogue reverse transcriptase inhibitors (nRTIs), which block reverse transcriptase, an enzyme crucial to viral production in HIV-infected people. [Wikipedia] In vivo tenofovir disoproxil fumarate is converted to tenofovir, an acyclic nucleoside phosphonate (nucleotide) analog of adenosine 5'-monophosphate.
Structure
Thumb
Synonyms
(R)-9-(2-phosphonomethoxypropyl)adenine
(R)-PMPA
Anh. tenofovir
Anhydrous tenofovir
Tenofovir
Tenofovir (anh.)
External Identifiers
  • GS-1275
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
VireadTablet300 mgOralGilead Sciences Canada Inc2004-03-15Not applicableCanada
VireadTablet, coated300 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
VireadTablet, coated200 mg/1OralGilead Sciences, Inc.2012-01-18Not applicableUs
VireadTablet, coated300 mg/1OralREMEDYREPACK INC.2008-07-29Not applicableUs
VireadTablet, coated300 mg/1OralGilead Sciences, Inc.2001-10-26Not applicableUs
VireadTablet, coated250 mg/1OralGilead Sciences, Inc.2012-01-18Not applicableUs
VireadTablet, coated300 mg/1OralA S Medication Solutions2001-10-26Not applicableUs
VireadPowder40 mg/gOralGilead Sciences, Inc.2012-01-18Not applicableUs
VireadTablet, coated300 mg/1OralAvera Mc Kennan Hospital2015-05-18Not applicableUs
VireadTablet, coated300 mg/1OralA S Medication Solutions2001-10-26Not applicableUs
VireadTablet, coated150 mg/1OralGilead Sciences, Inc.2012-01-18Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
AtriplaLake Erie Medical DBA Quality Care Products LLC
CompleraPhysicians Total Care, Inc.
StribildState of Florida DOH Central Pharmacy
TruvadaH.J. Harkins Company, Inc.
Salts
Name/CASStructureProperties
Tenofovir disoproxil fumarate
202138-50-9
Thumb
  • InChI Key: VCMJCVGFSROFHV-WZGZYPNHSA-N
  • Monoisotopic Mass: 635.183987333
  • Average Mass: 635.5149
DBSALT000172
Tenofovir monohydrate
206184-49-8
Thumb
  • InChI Key: PINIEAOMWQJGBW-FYZOBXCZSA-N
  • Monoisotopic Mass: 305.088905633
  • Average Mass: 305.231
DBSALT001819
Categories
UNIIW4HFE001U5
CAS number147127-20-6
WeightAverage: 287.2123
Monoisotopic: 287.078340473
Chemical FormulaC9H14N5O4P
InChI KeySGOIRFVFHAKUTI-ZCFIWIBFSA-N
InChI
InChI=1S/C9H14N5O4P/c1-6(18-5-19(15,16)17)2-14-4-13-7-8(10)11-3-12-9(7)14/h3-4,6H,2,5H2,1H3,(H2,10,11,12)(H2,15,16,17)/t6-/m1/s1
IUPAC Name
({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid
SMILES
C[[email protected]](CN1C=NC2=C1N=CN=C2N)OCP(O)(O)=O
Pharmacology
IndicationTenofovir 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.
Structured Indications
PharmacodynamicsTenofovir 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 actionTenofovir 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Reverse transcriptase/RNaseHProteinyes
inhibitor
Human immunodeficiency virus 1Q72547 details
Related Articles
AbsorptionTenofovir 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 bindingVery 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.

SubstrateEnzymesProduct
Tenofovir
Tenofovir MonophosphateDetails
Tenofovir Monophosphate
Tenofovir DiphosphateDetails
Route of eliminationWhen 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 lifeWhen 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]
ToxicityLimited 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
PathwayCategorySMPDB ID
Tenofovir Metabolism PathwayDrug metabolismSMP00630
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Tenofovir.Approved
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Tenofovir.Approved
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Tenofovir.Approved
AcetovanilloneThe risk or severity of adverse effects can be increased when Acetovanillone is combined with Tenofovir.Investigational
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Tenofovir.Approved, Vet Approved
AclarubicinThe serum concentration of Aclarubicin can be increased when it is combined with Tenofovir.Investigational
AdapaleneThe risk or severity of adverse effects can be increased when Adapalene is combined with Tenofovir.Approved
Adefovir DipivoxilThe therapeutic efficacy of Tenofovir can be decreased when used in combination with Adefovir Dipivoxil.Approved, Investigational
AgomelatineThe serum concentration of Agomelatine can be increased when it is combined with Tenofovir.Approved, Investigational
AlbendazoleThe metabolism of Albendazole can be decreased when combined with Tenofovir.Approved, Vet Approved
AlmotriptanThe metabolism of Almotriptan can be decreased when combined with Tenofovir.Approved, Investigational
AlosetronThe metabolism of Alosetron can be decreased when combined with Tenofovir.Approved, Withdrawn
AmikacinThe serum concentration of Amikacin can be increased when it is combined with Tenofovir.Approved, Vet Approved
AminophenazoneThe metabolism of Aminophenazone can be decreased when combined with Tenofovir.Approved, Withdrawn
AminophyllineThe metabolism of Aminophylline can be decreased when combined with Tenofovir.Approved
AmiodaroneThe metabolism of Amiodarone can be decreased when combined with Tenofovir.Approved, Investigational
AmitriptylineThe metabolism of Amitriptyline can be decreased when combined with Tenofovir.Approved
AmrubicinThe serum concentration of Amrubicin can be increased when it is combined with Tenofovir.Approved, Investigational
AnagrelideThe metabolism of Anagrelide can be decreased when combined with Tenofovir.Approved
AnisodamineThe risk or severity of adverse effects can be increased when Anisodamine is combined with Tenofovir.Investigational
annamycinThe serum concentration of annamycin can be increased when it is combined with Tenofovir.Investigational
AntipyrineThe risk or severity of adverse effects can be increased when Antipyrine is combined with Tenofovir.Approved
ApixabanThe metabolism of Apixaban can be decreased when combined with Tenofovir.Approved
ApramycinThe serum concentration of Apramycin can be increased when it is combined with Tenofovir.Experimental, Vet Approved
ApremilastThe risk or severity of adverse effects can be increased when Apremilast is combined with Tenofovir.Approved, Investigational
AprepitantThe metabolism of Aprepitant can be decreased when combined with Tenofovir.Approved, Investigational
ArbekacinThe serum concentration of Arbekacin can be increased when it is combined with Tenofovir.Approved
ASA404The metabolism of ASA404 can be decreased when combined with Tenofovir.Investigational
AsenapineThe metabolism of Asenapine can be decreased when combined with Tenofovir.Approved
AtazanavirThe serum concentration of Atazanavir can be decreased when it is combined with Tenofovir.Approved, Investigational
AV650The metabolism of AV650 can be decreased when combined with Tenofovir.Approved, Investigational
AxitinibThe metabolism of Axitinib can be decreased when combined with Tenofovir.Approved, Investigational
AzapropazoneThe risk or severity of adverse effects can be increased when Azapropazone is combined with Tenofovir.Withdrawn
AzelastineThe risk or severity of adverse effects can be increased when Azelastine is combined with Tenofovir.Approved
BalsalazideThe risk or severity of adverse effects can be increased when Balsalazide is combined with Tenofovir.Approved, Investigational
BendamustineThe metabolism of Bendamustine can be decreased when combined with Tenofovir.Approved, Investigational
BenoxaprofenThe risk or severity of adverse effects can be increased when Benoxaprofen is combined with Tenofovir.Withdrawn
Benzyl alcoholThe metabolism of Benzyl alcohol can be decreased when combined with Tenofovir.Approved
BetaxololThe metabolism of Betaxolol can be decreased when combined with Tenofovir.Approved
Betulinic AcidThe risk or severity of adverse effects can be increased when Betulinic Acid is combined with Tenofovir.Investigational
BortezomibThe metabolism of Bortezomib can be decreased when combined with Tenofovir.Approved, Investigational
BromazepamThe metabolism of Bromazepam can be decreased when combined with Tenofovir.Approved, Illicit
BromfenacThe risk or severity of adverse effects can be increased when Bromfenac is combined with Tenofovir.Approved
BucillamineThe risk or severity of adverse effects can be increased when Bucillamine is combined with Tenofovir.Investigational
BupivacaineThe metabolism of Bupivacaine can be decreased when combined with Tenofovir.Approved, Investigational
BupropionThe metabolism of Bupropion can be decreased when combined with Tenofovir.Approved
CaffeineThe metabolism of Caffeine can be decreased when combined with Tenofovir.Approved
CarbamazepineThe metabolism of Carbamazepine can be decreased when combined with Tenofovir.Approved, Investigational
CarmustineThe metabolism of Carmustine can be decreased when combined with Tenofovir.Approved
CarprofenThe risk or severity of adverse effects can be increased when Carprofen is combined with Tenofovir.Approved, Vet Approved, Withdrawn
CarvedilolThe metabolism of Carvedilol can be decreased when combined with Tenofovir.Approved, Investigational
CastanospermineThe risk or severity of adverse effects can be increased when Castanospermine is combined with Tenofovir.Experimental
CelecoxibThe risk or severity of adverse effects can be increased when Celecoxib is combined with Tenofovir.Approved, Investigational
ChloroquineThe risk or severity of adverse effects can be increased when Chloroquine is combined with Tenofovir.Approved, Vet Approved
ChlorpromazineThe metabolism of Chlorpromazine can be decreased when combined with Tenofovir.Approved, Vet Approved
ChlorzoxazoneThe metabolism of Chlorzoxazone can be decreased when combined with Tenofovir.Approved
CidofovirCidofovir may decrease the excretion rate of Tenofovir which could result in a higher serum level.Approved
CilostazolThe metabolism of Cilostazol can be decreased when combined with Tenofovir.Approved
CinacalcetThe metabolism of Cinacalcet can be decreased when combined with Tenofovir.Approved
CinnarizineThe metabolism of Cinnarizine can be decreased when combined with Tenofovir.Approved
CisaprideThe metabolism of Cisapride can be decreased when combined with Tenofovir.Approved, Investigational, Withdrawn
ClenbuterolThe metabolism of Clenbuterol can be decreased when combined with Tenofovir.Approved, Vet Approved
ClevidipineThe metabolism of Clevidipine can be decreased when combined with Tenofovir.Approved
ClomipramineThe metabolism of Clomipramine can be decreased when combined with Tenofovir.Approved, Vet Approved
ClonidineThe metabolism of Clonidine can be decreased when combined with Tenofovir.Approved
ClonixinThe risk or severity of adverse effects can be increased when Clonixin is combined with Tenofovir.Approved
ClopidogrelThe metabolism of Clopidogrel can be decreased when combined with Tenofovir.Approved, Nutraceutical
ClozapineThe metabolism of Clozapine can be decreased when combined with Tenofovir.Approved
CobicistatThe risk or severity of adverse effects can be increased when Cobicistat is combined with Tenofovir.Approved
Conjugated Equine EstrogensThe metabolism of Conjugated Equine Estrogens can be decreased when combined with Tenofovir.Approved
CurcuminThe risk or severity of adverse effects can be increased when Curcumin is combined with Tenofovir.Investigational
CyclobenzaprineThe metabolism of Cyclobenzaprine can be decreased when combined with Tenofovir.Approved
D-LimoneneThe risk or severity of adverse effects can be increased when D-Limonene is combined with Tenofovir.Investigational
DacarbazineThe metabolism of Dacarbazine can be decreased when combined with Tenofovir.Approved, Investigational
DapagliflozinThe metabolism of Dapagliflozin can be decreased when combined with Tenofovir.Approved
DarunavirThe serum concentration of Darunavir can be increased when it is combined with Tenofovir.Approved
DasatinibThe metabolism of Dasatinib can be decreased when combined with Tenofovir.Approved, Investigational
DaunorubicinThe serum concentration of Daunorubicin can be increased when it is combined with Tenofovir.Approved
DesipramineThe metabolism of Desipramine can be decreased when combined with Tenofovir.Approved
DexfenfluramineThe metabolism of Dexfenfluramine can be decreased when combined with Tenofovir.Approved, Illicit, Withdrawn
DiazepamThe metabolism of Diazepam can be decreased when combined with Tenofovir.Approved, Illicit, Vet Approved
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with Tenofovir.Approved, Vet Approved
DidanosineThe therapeutic efficacy of Didanosine can be decreased when used in combination with Tenofovir.Approved
DiflunisalThe risk or severity of adverse effects can be increased when Diflunisal is combined with Tenofovir.Approved
DihydrostreptomycinThe serum concentration of Dihydrostreptomycin can be increased when it is combined with Tenofovir.Vet Approved
DinoprostoneThe metabolism of Dinoprostone can be decreased when combined with Tenofovir.Approved
DiphenhydramineThe metabolism of Diphenhydramine can be decreased when combined with Tenofovir.Approved
DomperidoneThe metabolism of Domperidone can be decreased when combined with Tenofovir.Approved, Investigational, Vet Approved
DoxepinThe metabolism of Doxepin can be decreased when combined with Tenofovir.Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Tenofovir.Approved, Investigational
DroxicamThe risk or severity of adverse effects can be increased when Droxicam is combined with Tenofovir.Approved
DuloxetineThe metabolism of Duloxetine can be decreased when combined with Tenofovir.Approved
DuvelisibThe risk or severity of adverse effects can be increased when Duvelisib is combined with Tenofovir.Investigational
E6201The risk or severity of adverse effects can be increased when E6201 is combined with Tenofovir.Investigational
EbselenThe risk or severity of adverse effects can be increased when Ebselen is combined with Tenofovir.Investigational
EltrombopagThe metabolism of Eltrombopag can be decreased when combined with Tenofovir.Approved
EpirizoleThe risk or severity of adverse effects can be increased when Epirizole is combined with Tenofovir.Approved
EpirubicinThe serum concentration of Epirubicin can be increased when it is combined with Tenofovir.Approved
ErgotamineThe metabolism of Ergotamine can be decreased when combined with Tenofovir.Approved
ErlotinibThe metabolism of Erlotinib can be decreased when combined with Tenofovir.Approved, Investigational
EstradiolThe metabolism of Estradiol can be decreased when combined with Tenofovir.Approved, Investigational, Vet Approved
EstroneThe metabolism of Estrone can be decreased when combined with Tenofovir.Approved
Estrone sulfateThe metabolism of Estrone sulfate can be decreased when combined with Tenofovir.Approved
EtanerceptThe risk or severity of adverse effects can be increased when Etanercept is combined with Tenofovir.Approved, Investigational
EthanolThe metabolism of Ethanol can be decreased when combined with Tenofovir.Approved
EtodolacThe risk or severity of adverse effects can be increased when Etodolac is combined with Tenofovir.Approved, Investigational, Vet Approved
EtofenamateThe risk or severity of adverse effects can be increased when Etofenamate is combined with Tenofovir.Approved
EtoposideThe metabolism of Etoposide can be decreased when combined with Tenofovir.Approved
EtoricoxibThe risk or severity of adverse effects can be increased when Etoricoxib is combined with Tenofovir.Approved, Investigational
Evening primrose oilThe risk or severity of adverse effects can be increased when Evening primrose oil is combined with Tenofovir.Approved
exisulindThe risk or severity of adverse effects can be increased when exisulind is combined with Tenofovir.Investigational
FenbufenThe risk or severity of adverse effects can be increased when Fenbufen is combined with Tenofovir.Approved
FenoprofenThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Tenofovir.Approved
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Tenofovir.Approved, Withdrawn
FlunarizineThe metabolism of Flunarizine can be decreased when combined with Tenofovir.Approved
FlunitrazepamThe metabolism of Flunitrazepam can be decreased when combined with Tenofovir.Approved, Illicit
FlunixinThe risk or severity of adverse effects can be increased when Flunixin is combined with Tenofovir.Vet Approved
FluorouracilThe metabolism of Fluorouracil can be decreased when combined with Tenofovir.Approved
FluoxetineThe metabolism of Fluoxetine can be decreased when combined with Tenofovir.Approved, Vet Approved
FlurbiprofenThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Tenofovir.Approved, Investigational
FlutamideThe metabolism of Flutamide can be decreased when combined with Tenofovir.Approved
FluvoxamineThe metabolism of Fluvoxamine can be decreased when combined with Tenofovir.Approved, Investigational
FramycetinThe serum concentration of Framycetin can be increased when it is combined with Tenofovir.Approved
FrovatriptanThe metabolism of Frovatriptan can be decreased when combined with Tenofovir.Approved, Investigational
GanciclovirThe serum concentration of Tenofovir can be increased when it is combined with Ganciclovir.Approved, Investigational
GeneticinThe serum concentration of Geneticin can be increased when it is combined with Tenofovir.Experimental
GenisteinThe metabolism of Genistein can be decreased when combined with Tenofovir.Investigational
GentamicinThe serum concentration of Gentamicin can be increased when it is combined with Tenofovir.Approved, Vet Approved
GENTAMICIN C1AThe serum concentration of GENTAMICIN C1A can be increased when it is combined with Tenofovir.Experimental
GrepafloxacinThe metabolism of Grepafloxacin can be decreased when combined with Tenofovir.Withdrawn
GuanabenzThe metabolism of Guanabenz can be decreased when combined with Tenofovir.Approved
HaloperidolThe metabolism of Haloperidol can be decreased when combined with Tenofovir.Approved
HesperetinThe metabolism of Hesperetin can be decreased when combined with Tenofovir.Approved
HexobarbitalThe metabolism of Hexobarbital can be decreased when combined with Tenofovir.Approved
HigenamineThe risk or severity of adverse effects can be increased when Higenamine is combined with Tenofovir.Investigational
HMPL-004The risk or severity of adverse effects can be increased when HMPL-004 is combined with Tenofovir.Investigational
Hygromycin BThe serum concentration of Hygromycin B can be increased when it is combined with Tenofovir.Vet Approved
IbuprofenThe risk or severity of adverse effects can be increased when Ibuprofen is combined with Tenofovir.Approved
IbuproxamThe risk or severity of adverse effects can be increased when Ibuproxam is combined with Tenofovir.Withdrawn
IcatibantThe risk or severity of adverse effects can be increased when Icatibant is combined with Tenofovir.Approved
IdarubicinThe serum concentration of Idarubicin can be increased when it is combined with Tenofovir.Approved
IloperidoneThe metabolism of Iloperidone can be decreased when combined with Tenofovir.Approved
ImatinibThe metabolism of Imatinib can be decreased when combined with Tenofovir.Approved
ImipramineThe metabolism of Imipramine can be decreased when combined with Tenofovir.Approved
ImiquimodThe metabolism of Imiquimod can be decreased when combined with Tenofovir.Approved, Investigational
IndomethacinThe risk or severity of adverse effects can be increased when Indomethacin is combined with Tenofovir.Approved, Investigational
IndoprofenThe risk or severity of adverse effects can be increased when Indoprofen is combined with Tenofovir.Withdrawn
INNO-206The serum concentration of INNO-206 can be increased when it is combined with Tenofovir.Investigational
IsoxicamThe risk or severity of adverse effects can be increased when Isoxicam is combined with Tenofovir.Withdrawn
IxazomibThe metabolism of Ixazomib can be decreased when combined with Tenofovir.Approved
KanamycinThe serum concentration of Kanamycin can be increased when it is combined with Tenofovir.Approved, Vet Approved
KebuzoneThe risk or severity of adverse effects can be increased when Kebuzone is combined with Tenofovir.Experimental
KetoprofenThe risk or severity of adverse effects can be increased when Ketoprofen is combined with Tenofovir.Approved, Vet Approved
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Tenofovir.Approved
LedipasvirThe serum concentration of Tenofovir can be increased when it is combined with Ledipasvir.Approved
LeflunomideThe risk or severity of adverse effects can be increased when Leflunomide is combined with Tenofovir.Approved, Investigational
LevobupivacaineThe metabolism of Levobupivacaine can be decreased when combined with Tenofovir.Approved
LidocaineThe metabolism of Lidocaine can be decreased when combined with Tenofovir.Approved, Vet Approved
LisofyllineThe risk or severity of adverse effects can be increased when Lisofylline is combined with Tenofovir.Investigational
LomefloxacinThe metabolism of Lomefloxacin can be decreased when combined with Tenofovir.Approved
LopinavirLopinavir may increase the nephrotoxic activities of Tenofovir.Approved
LorcaserinThe metabolism of Lorcaserin can be decreased when combined with Tenofovir.Approved
LornoxicamThe risk or severity of adverse effects can be increased when Lornoxicam is combined with Tenofovir.Approved
LoxoprofenThe risk or severity of adverse effects can be increased when Loxoprofen is combined with Tenofovir.Approved
LumiracoxibThe risk or severity of adverse effects can be increased when Lumiracoxib is combined with Tenofovir.Approved, Investigational
Magnesium salicylateThe risk or severity of adverse effects can be increased when Magnesium salicylate is combined with Tenofovir.Approved
MalathionThe metabolism of Malathion can be decreased when combined with Tenofovir.Approved, Investigational
MaprotilineThe metabolism of Maprotiline can be decreased when combined with Tenofovir.Approved
MasoprocolThe risk or severity of adverse effects can be increased when Masoprocol is combined with Tenofovir.Approved
Meclofenamic acidThe risk or severity of adverse effects can be increased when Meclofenamic acid is combined with Tenofovir.Approved, Vet Approved
Mefenamic acidThe risk or severity of adverse effects can be increased when Mefenamic acid is combined with Tenofovir.Approved
MelatoninThe metabolism of Melatonin can be decreased when combined with Tenofovir.Approved, Nutraceutical, Vet Approved
MeloxicamThe risk or severity of adverse effects can be increased when Meloxicam is combined with Tenofovir.Approved, Vet Approved
MenadioneThe metabolism of Menadione can be decreased when combined with Tenofovir.Approved, Nutraceutical
MephenytoinThe metabolism of Mephenytoin can be decreased when combined with Tenofovir.Investigational, Withdrawn
MesalazineThe risk or severity of adverse effects can be increased when Mesalazine is combined with Tenofovir.Approved
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Tenofovir.Withdrawn
MethadoneThe metabolism of Methadone can be decreased when combined with Tenofovir.Approved
MethoxyfluraneThe metabolism of Methoxyflurane can be decreased when combined with Tenofovir.Approved, Vet Approved
MetrizamideThe serum concentration of Metrizamide can be increased when it is combined with Tenofovir.Approved
MexiletineThe metabolism of Mexiletine can be decreased when combined with Tenofovir.Approved
MianserinThe metabolism of Mianserin can be decreased when combined with Tenofovir.Approved
MirtazapineThe metabolism of Mirtazapine can be decreased when combined with Tenofovir.Approved
MizoribineThe risk or severity of adverse effects can be increased when Mizoribine is combined with Tenofovir.Investigational
muraglitazarThe metabolism of muraglitazar can be decreased when combined with Tenofovir.Investigational
Mycophenolate mofetilThe risk or severity of adverse effects can be increased when Mycophenolate mofetil is combined with Tenofovir.Approved, Investigational
Mycophenolic acidThe risk or severity of adverse effects can be increased when Mycophenolic acid is combined with Tenofovir.Approved
NabumetoneThe risk or severity of adverse effects can be increased when Nabumetone is combined with Tenofovir.Approved
NafamostatThe risk or severity of adverse effects can be increased when Nafamostat is combined with Tenofovir.Investigational
NaftifineThe risk or severity of adverse effects can be increased when Naftifine is combined with Tenofovir.Approved
NaproxenThe risk or severity of adverse effects can be increased when Naproxen is combined with Tenofovir.Approved, Vet Approved
NCX 4016The risk or severity of adverse effects can be increased when NCX 4016 is combined with Tenofovir.Investigational
NeamineThe serum concentration of Neamine can be increased when it is combined with Tenofovir.Experimental
NeomycinThe serum concentration of Neomycin can be increased when it is combined with Tenofovir.Approved, Vet Approved
NepafenacThe risk or severity of adverse effects can be increased when Nepafenac is combined with Tenofovir.Approved
NetilmicinThe serum concentration of Netilmicin can be increased when it is combined with Tenofovir.Approved
NicotineThe metabolism of Nicotine can be decreased when combined with Tenofovir.Approved
NifedipineThe metabolism of Nifedipine can be decreased when combined with Tenofovir.Approved
Niflumic AcidThe risk or severity of adverse effects can be increased when Niflumic Acid is combined with Tenofovir.Approved
NimesulideThe risk or severity of adverse effects can be increased when Nimesulide is combined with Tenofovir.Approved, Withdrawn
Nitric OxideThe metabolism of Nitric Oxide can be decreased when combined with Tenofovir.Approved
NitroaspirinThe risk or severity of adverse effects can be increased when Nitroaspirin is combined with Tenofovir.Investigational
NortriptylineThe metabolism of Nortriptyline can be decreased when combined with Tenofovir.Approved
OlanzapineThe metabolism of Olanzapine can be decreased when combined with Tenofovir.Approved, Investigational
OlopatadineThe risk or severity of adverse effects can be increased when Olopatadine is combined with Tenofovir.Approved
OlsalazineThe risk or severity of adverse effects can be increased when Olsalazine is combined with Tenofovir.Approved
OmeprazoleThe metabolism of Omeprazole can be decreased when combined with Tenofovir.Approved, Investigational, Vet Approved
OndansetronThe metabolism of Ondansetron can be decreased when combined with Tenofovir.Approved
OrgoteinThe risk or severity of adverse effects can be increased when Orgotein is combined with Tenofovir.Vet Approved
OxaliplatinThe metabolism of Oxaliplatin can be decreased when combined with Tenofovir.Approved, Investigational
OxaprozinThe risk or severity of adverse effects can be increased when Oxaprozin is combined with Tenofovir.Approved
OxtriphyllineThe metabolism of Oxtriphylline can be decreased when combined with Tenofovir.Approved
OxyphenbutazoneThe risk or severity of adverse effects can be increased when Oxyphenbutazone is combined with Tenofovir.Withdrawn
PalonosetronThe metabolism of Palonosetron can be decreased when combined with Tenofovir.Approved, Investigational
PantoprazoleThe metabolism of Pantoprazole can be decreased when combined with Tenofovir.Approved
ParecoxibThe risk or severity of adverse effects can be increased when Parecoxib is combined with Tenofovir.Approved
ParomomycinThe serum concentration of Paromomycin can be increased when it is combined with Tenofovir.Approved, Investigational
PazopanibThe metabolism of Pazopanib can be decreased when combined with Tenofovir.Approved
PentamidineThe metabolism of Pentamidine can be decreased when combined with Tenofovir.Approved
PentoxifyllineThe metabolism of Pentoxifylline can be decreased when combined with Tenofovir.Approved, Investigational
PerphenazineThe metabolism of Perphenazine can be decreased when combined with Tenofovir.Approved
PhenacetinThe metabolism of Phenacetin can be decreased when combined with Tenofovir.Withdrawn
PhenylbutazoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Tenofovir.Approved, Vet Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Tenofovir.Approved, Investigational
PimozideThe metabolism of Pimozide can be decreased when combined with Tenofovir.Approved
PipotiazineThe metabolism of Pipotiazine can be decreased when combined with Tenofovir.Approved
PirarubicinThe serum concentration of Pirarubicin can be increased when it is combined with Tenofovir.Investigational
PirfenidoneThe risk or severity of adverse effects can be increased when Pirfenidone is combined with Tenofovir.Investigational
PiroxicamThe risk or severity of adverse effects can be increased when Piroxicam is combined with Tenofovir.Approved, Investigational
PlicamycinThe serum concentration of Plicamycin can be increased when it is combined with Tenofovir.Approved, Withdrawn
PomalidomideThe metabolism of Pomalidomide can be decreased when combined with Tenofovir.Approved
PraziquantelThe metabolism of Praziquantel can be decreased when combined with Tenofovir.Approved, Vet Approved
PrimaquineThe metabolism of Primaquine can be decreased when combined with Tenofovir.Approved
ProgesteroneThe metabolism of Progesterone can be decreased when combined with Tenofovir.Approved, Vet Approved
ProguanilThe metabolism of Proguanil can be decreased when combined with Tenofovir.Approved
PromazineThe metabolism of Promazine can be decreased when combined with Tenofovir.Approved, Vet Approved
PropacetamolThe risk or severity of adverse effects can be increased when Propacetamol is combined with Tenofovir.Approved
PropafenoneThe metabolism of Propafenone can be decreased when combined with Tenofovir.Approved
PropofolThe metabolism of Propofol can be decreased when combined with Tenofovir.Approved, Investigational, Vet Approved
PropranololThe metabolism of Propranolol can be decreased when combined with Tenofovir.Approved, Investigational
PTC299The risk or severity of adverse effects can be increased when PTC299 is combined with Tenofovir.Investigational
PuromycinThe serum concentration of Puromycin can be increased when it is combined with Tenofovir.Experimental
PyrazinamideThe metabolism of Pyrazinamide can be decreased when combined with Tenofovir.Approved
QuinineThe metabolism of Quinine can be decreased when combined with Tenofovir.Approved
RamelteonThe metabolism of Ramelteon can be decreased when combined with Tenofovir.Approved, Investigational
RanitidineThe metabolism of Ranitidine can be decreased when combined with Tenofovir.Approved
RasagilineThe metabolism of Rasagiline can be decreased when combined with Tenofovir.Approved
ResveratrolThe risk or severity of adverse effects can be increased when Resveratrol is combined with Tenofovir.Experimental, Investigational
RibostamycinThe serum concentration of Ribostamycin can be increased when it is combined with Tenofovir.Approved
RifabutinThe metabolism of Rifabutin can be decreased when combined with Tenofovir.Approved
RiluzoleThe metabolism of Riluzole can be decreased when combined with Tenofovir.Approved, Investigational
RitonavirThe metabolism of Ritonavir can be decreased when combined with Tenofovir.Approved, Investigational
RizatriptanThe metabolism of Rizatriptan can be decreased when combined with Tenofovir.Approved
RofecoxibThe risk or severity of adverse effects can be increased when Rofecoxib is combined with Tenofovir.Investigational, Withdrawn
RopiniroleThe metabolism of Ropinirole can be decreased when combined with Tenofovir.Approved, Investigational
RopivacaineThe metabolism of Ropivacaine can be decreased when combined with Tenofovir.Approved
RotigotineThe metabolism of Rotigotine can be decreased when combined with Tenofovir.Approved
SalicylamideThe risk or severity of adverse effects can be increased when Salicylamide is combined with Tenofovir.Approved
Salicylic acidThe risk or severity of adverse effects can be increased when Salicylic acid is combined with Tenofovir.Approved, Vet Approved
SalsalateThe risk or severity of adverse effects can be increased when Salsalate is combined with Tenofovir.Approved
SelegilineThe metabolism of Selegiline can be decreased when combined with Tenofovir.Approved, Investigational, Vet Approved
SeratrodastThe risk or severity of adverse effects can be increased when Seratrodast is combined with Tenofovir.Approved, Investigational
SertralineThe metabolism of Sertraline can be decreased when combined with Tenofovir.Approved
SimeprevirThe serum concentration of Simeprevir can be decreased when it is combined with Tenofovir.Approved
SisomicinThe serum concentration of Sisomicin can be increased when it is combined with Tenofovir.Investigational
SP1049CThe serum concentration of SP1049C can be increased when it is combined with Tenofovir.Investigational
SpectinomycinThe serum concentration of Spectinomycin can be increased when it is combined with Tenofovir.Approved, Vet Approved
SRT501The risk or severity of adverse effects can be increased when SRT501 is combined with Tenofovir.Investigational
StreptomycinThe serum concentration of Streptomycin can be increased when it is combined with Tenofovir.Approved, Vet Approved
StreptozocinThe serum concentration of Streptozocin can be increased when it is combined with Tenofovir.Approved
SulfasalazineThe risk or severity of adverse effects can be increased when Sulfasalazine is combined with Tenofovir.Approved
SulindacThe risk or severity of adverse effects can be increased when Sulindac is combined with Tenofovir.Approved
SuprofenThe risk or severity of adverse effects can be increased when Suprofen is combined with Tenofovir.Approved, Withdrawn
TacrineThe metabolism of Tacrine can be decreased when combined with Tenofovir.Withdrawn
TamoxifenThe metabolism of Tamoxifen can be decreased when combined with Tenofovir.Approved
TelaprevirThe serum concentration of Tenofovir can be increased when it is combined with Telaprevir.Approved
TelithromycinThe metabolism of Telithromycin can be decreased when combined with Tenofovir.Approved
TemafloxacinThe metabolism of Temafloxacin can be decreased when combined with Tenofovir.Withdrawn
TenoxicamThe risk or severity of adverse effects can be increased when Tenoxicam is combined with Tenofovir.Approved
TepoxalinThe risk or severity of adverse effects can be increased when Tepoxalin is combined with Tenofovir.Vet Approved
TerbinafineThe metabolism of Terbinafine can be decreased when combined with Tenofovir.Approved, Investigational, Vet Approved
TeriflunomideThe risk or severity of adverse effects can be increased when Teriflunomide is combined with Tenofovir.Approved
ThalidomideThe metabolism of Thalidomide can be decreased when combined with Tenofovir.Approved, Investigational, Withdrawn
TheobromineThe metabolism of Theobromine can be decreased when combined with Tenofovir.Approved
TheophyllineThe metabolism of Theophylline can be decreased when combined with Tenofovir.Approved
ThiabendazoleThe metabolism of Thiabendazole can be decreased when combined with Tenofovir.Approved, Vet Approved
ThioridazineThe metabolism of Thioridazine can be decreased when combined with Tenofovir.Approved
ThiothixeneThe metabolism of Thiothixene can be decreased when combined with Tenofovir.Approved
Tiaprofenic acidThe risk or severity of adverse effects can be increased when Tiaprofenic acid is combined with Tenofovir.Approved
TinoridineThe risk or severity of adverse effects can be increased when Tinoridine is combined with Tenofovir.Investigational
TipranavirThe serum concentration of Tipranavir can be decreased when it is combined with Tenofovir.Approved, Investigational
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Tenofovir.Approved
TobramycinThe serum concentration of Tobramycin can be increased when it is combined with Tenofovir.Approved, Investigational
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Tolfenamic Acid is combined with Tenofovir.Approved
TolmetinThe risk or severity of adverse effects can be increased when Tolmetin is combined with Tenofovir.Approved
ToremifeneThe metabolism of Toremifene can be decreased when combined with Tenofovir.Approved, Investigational
TranilastThe risk or severity of adverse effects can be increased when Tranilast is combined with Tenofovir.Approved, Investigational
TriamtereneThe metabolism of Triamterene can be decreased when combined with Tenofovir.Approved
TrifluoperazineThe metabolism of Trifluoperazine can be decreased when combined with Tenofovir.Approved
Trisalicylate-cholineThe risk or severity of adverse effects can be increased when Trisalicylate-choline is combined with Tenofovir.Approved
UlipristalThe metabolism of Ulipristal can be decreased when combined with Tenofovir.Approved
ValaciclovirValaciclovir may decrease the excretion rate of Tenofovir which could result in a higher serum level.Approved, Investigational
ValdecoxibThe risk or severity of adverse effects can be increased when Valdecoxib is combined with Tenofovir.Investigational, Withdrawn
ValganciclovirThe serum concentration of Tenofovir can be increased when it is combined with Valganciclovir.Approved, Investigational
ValrubicinThe serum concentration of Valrubicin can be increased when it is combined with Tenofovir.Approved
VerapamilThe metabolism of Verapamil can be decreased when combined with Tenofovir.Approved
WarfarinThe metabolism of Warfarin can be decreased when combined with Tenofovir.Approved
ZaltoprofenThe risk or severity of adverse effects can be increased when Zaltoprofen is combined with Tenofovir.Approved
ZileutonThe risk or severity of adverse effects can be increased when Zileuton is combined with Tenofovir.Approved, Investigational, Withdrawn
ZiprasidoneThe metabolism of Ziprasidone can be decreased when combined with Tenofovir.Approved
ZolmitriptanThe metabolism of Zolmitriptan can be decreased when combined with Tenofovir.Approved, Investigational
ZolpidemThe metabolism of Zolpidem can be decreased when combined with Tenofovir.Approved
ZomepiracThe risk or severity of adverse effects can be increased when Zomepirac is combined with Tenofovir.Withdrawn
ZorubicinThe serum concentration of Zorubicin can be increased when it is combined with Tenofovir.Experimental
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
ATC CodesNot Available
AHFS Codes
  • 08:18.08.20
PDB EntriesNot Available
FDA labelDownload (287 KB)
MSDSDownload (57.7 KB)
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Gilead sciences inc
  • Gilead Sciences, Inc.
Packagers
Dosage forms
FormRouteStrength
Tablet, film coatedOral
TabletOral
PowderOral40 mg/g
TabletOral300 mg
Tablet, coatedOral150 mg/1
Tablet, coatedOral200 mg/1
Tablet, coatedOral250 mg/1
Tablet, coatedOral300 mg/1
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)
CA2261619 No2006-05-232017-07-25Canada
CA2298059 No2008-12-302018-07-23Canada
US5814639 Yes1996-03-292016-03-29Us
US5914331 Yes1998-01-022018-01-02Us
US5922695 Yes1998-01-252018-01-25Us
US5935946 Yes1998-01-252018-01-25Us
US5977089 Yes1998-01-252018-01-25Us
US6043230 Yes1998-01-252018-01-25Us
US6639071 Yes1998-08-142018-08-14Us
US6642245 Yes2001-05-042021-05-04Us
US6703396 Yes2001-09-092021-09-09Us
US6838464 No2001-02-262021-02-26Us
US6939964 Yes1998-07-202018-07-20Us
US7067522 No1999-12-202019-12-20Us
US7125879 No2002-08-092022-08-09Us
US7176220 No2003-11-202023-11-20Us
US7635704 No2006-10-262026-10-26Us
US8080551 No2003-04-112023-04-11Us
US8101629 No2002-08-092022-08-09Us
US8148374 No2009-09-032029-09-03Us
US8592397 No2004-01-132024-01-13Us
US8598185 No2008-05-012028-05-01Us
US8633219 No2010-04-242030-04-24Us
US8716264 No2004-01-132024-01-13Us
US8841310 No2005-12-092025-12-09Us
US8981103 No2006-10-262026-10-26Us
US9018192 No2006-06-132026-06-13Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point276-280 °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 Solubility1.87 mg/mLALOGPS
logP-1.5ALOGPS
logP-3.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.35ChemAxon
pKa (Strongest Basic)5.12ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area136.38 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity67.53 m3·mol-1ChemAxon
Polarizability25.54 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct Parent6-aminopurines
Alternative Parents
Substituents
  • 6-aminopurine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Primary aromatic amine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Organophosphonic acid derivative
  • Organophosphonic acid
  • Imidazole
  • Azole
  • Azacycle
  • Hydrocarbon derivative
  • Primary amine
  • Organophosphorus compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

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
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
inhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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 activity is critical for regulation of the phosphate utilization and the AMP de novo biosynthesis pathways. Plays a key role in hematopoiesis.
Gene Name:
AK2
Uniprot ID:
P54819
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 phosphorylates only AMP when using GTP as phosphate donor. Also displays broad nucleoside diphosphate kinase activity.
Gene Name:
AK4
Uniprot ID:
P27144
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-site intermediate. Possesses nucleoside-diphosphate kinase, serine/threonine-specific protein kinase, geranyl and farnesyl pyrophosphate kinase, histidine protein kinase and 3'-5' exonuclease activities....
Gene Name:
NME1
Uniprot ID:
P15531
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 DNA non-specifically (PubMed:8392752). Exhibits histidine protein kinase activity.
Gene Name:
NME2
Uniprot ID:
P22392
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 molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
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, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
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
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
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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on December 03, 2016 04:02