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    Also known as: Tenofovir disoproxil fumarate, 202138-50-9, Tenofovir df, Virea, Tenofovir disoproxil fumarate [usan], Pmpa-prodrug
    Molecular Formula
    C23H34N5O14P
    Molecular Weight
    635.5  g/mol
    InChI Key
    VCMJCVGFSROFHV-WZGZYPNHSA-N
    FDA UNII
    OTT9J7900I
    Tenofovir Disoproxil Fumarate
    An adenine analog REVERSE TRANSCRIPTASE INHIBITOR with antiviral activity against HIV-1 and HEPATITIS B. It is used to treat HIV INFECTIONS and CHRONIC HEPATITIS B, in combination with other ANTIVIRAL AGENTS, due to the emergence of ANTIVIRAL DRUG RESISTANCE when it is used alone.
    1 2D Structure

    Tenofovir Disoproxil Fumarate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-(propan-2-yloxycarbonyloxymethoxy)phosphoryl]oxymethyl propan-2-yl carbonate;(E)-but-2-enedioic acid
    2.1.2 InChI
    InChI=1S/C19H30N5O10P.C4H4O4/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;5-3(6)1-2-4(7)8/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22);1-2H,(H,5,6)(H,7,8)/b;2-1+/t14-;/m1./s1
    2.1.3 InChI Key
    VCMJCVGFSROFHV-WZGZYPNHSA-N
    2.1.4 Canonical SMILES
    CC(C)OC(=O)OCOP(=O)(COC(C)CN1C=NC2=C(N=CN=C21)N)OCOC(=O)OC(C)C.C(=CC(=O)O)C(=O)O
    2.1.5 Isomeric SMILES
    C[C@H](CN1C=NC2=C(N=CN=C21)N)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C.C(=C/C(=O)O)\C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    OTT9J7900I
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (r)-9-(2-phosphonylmethoxypropyl)adenine

    2. 9-(2-phosphonomethoxypropyl)adenine

    3. 9-(2-phosphonylmethoxypropyl)adenine

    4. 9-(2-phosphonylmethoxypropyl)adenine, (+-)-isomer

    5. 9-(2-phosphonylmethoxypropyl)adenine, (r)-isomer - T357098

    6. 9-(2-phosphonylmethoxypropyl)adenine, (s)-isomer

    7. 9-pmpa (tenofovir)

    8. Disoproxil Fumarate, Tenofovir

    9. Disoproxil, Tenofovir

    10. Fumarate, Tenofovir Disoproxil

    11. Tenofovir

    12. Tenofovir Disoproxil

    13. Tenofovir Disoproxil Fumarate

    2.3.2 Depositor-Supplied Synonyms

    1. Tenofovir Disoproxil Fumarate

    2. 202138-50-9

    3. Tenofovir Df

    4. Virea

    5. Tenofovir Disoproxil Fumarate [usan]

    6. Pmpa-prodrug

    7. Gs-4331-05

    8. Gsk548470

    9. Gsk-548470

    10. Ott9j7900i

    11. Tenofovir Disoproxil (fumarate)

    12. Tenofovir (disoproxil Fumarate)

    13. Chebi:63718

    14. Gs-4331-05-

    15. 9-((r)-2-((bis(((isopropoxycarbonyl)oxy)methoxy)phosphinyl)methoxy)propyl)adenine Fumarate

    16. (r)-(((((1-(6-amino-9h-purin-9-yl)propan-2-yl)oxy)methyl)phosphoryl)bis(oxy))bis(methylene) Diisopropyl Dicarbonate Fumarate

    17. (r)-5-((2-(6-amino-9h-purin-9-yl)-1-methylethoxy)methyl)-2,4,6,8-tetraoxa-5-phosphanonanedioic Acid, Bis(1-methylethyl) Ester, 5-oxide, (e)-2-butenedioate (1:1)

    18. 2,4,6,8-tetraoxa-5-phosphanonanedioic Acid, 5-[[(1r)-2-(6-amino-9h-purin-9-yl)-1-methylethoxy]methyl]-, 1,9-bis(1-methylethyl) Ester, 5-oxide, (2e)-2-butenedioate (1:1)

    19. 9-((r)-2-((bis(((isopropoxycarbonyl)oxy)methoxy)phosphinyl)methoxy)propyl)adenine Fumarate (1:1)

    20. Bis(hydroxymethyl) (((r)-2-(6-amino-9h-purin-9-yl)-1-methylethoxy)methyl)phosphonate, Bis(isopropyl Carbonate) (ester), Fumarate (1:1)

    21. Tenofovir Disoproxil Fumarate

    22. (2e)-but-2-enedioic Acid Bis({[(propan-2-yloxy)carbonyl]oxy}methyl) {[(2r)-1-(6-amino-9h-purin-9-yl)propan-2-yl]oxy}methanephosphonate

    23. [[(2r)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-(propan-2-yloxycarbonyloxymethoxy)phosphoryl]oxymethyl Propan-2-yl Carbonate;(e)-but-2-enedioic Acid

    24. Hsdb 7165

    25. Tenofovirdisoproxilfumarate

    26. Unii-ott9j7900i

    27. Mfcd08141829

    28. Gs 4331-05

    29. Viread (tn)

    30. Tenofovir-disoproxil-fumarate

    31. Chembl1486

    32. Schembl40021

    33. Tenofoviri Disoproxili Fumaras

    34. Mls004774141

    35. Gs-1278 Disoproxil Fumarate

    36. Schembl2670560

    37. Dtxsid5050426

    38. Ex-a590

    39. S1400

    40. Tenofovir Disoproxil Fumarate- Bio-x

    41. Akos016340707

    42. Akos025149493

    43. Ccg-270300

    44. Cs-1346

    45. Gs-us-104-0321

    46. Ks-1246

    47. 9-((r)-2-((bis(((isopropoxycarbonyl)oxy)methoxy)phosphinyl)methoxy)propyl)adenine, Fumarate

    48. Bt164457

    49. Hy-13782

    50. Smr003500786

    51. Tenofovir (as Disoproxil Fumarate)

    52. Tenofovir Disoproxil Fumarate (jan/usan)

    53. Tenofovir Disoproxil Fumarate [mi]

    54. Bcp0726000258

    55. Tenofovir Disoproxil Fumarate [jan]

    56. Tenofovir Disoproxil Fumarate [hsdb]

    57. Am20090676

    58. Tenofovir Disoproxil Fumarate [mart.]

    59. Tenofovir Disoproxil Fumarate [vandf]

    60. Tenofovir Disoproxil Fumarate [usp-rs]

    61. Tenofovir Disoproxil Fumarate [who-dd]

    62. Tenofovir Disoproxil Fumarate [who-ip]

    63. D01982

    64. Tenofovir Disoproxil Fumarate, >=98% (hplc)

    65. Tenofovir Disoproxil Fumarate [ema Epar]

    66. Tenofovir Disoproxil Fumarate [orange Book]

    67. Q-201788

    68. Atripla Component Tenofovir Disoproxil Fumarate

    69. Eviplera Component Tenofovir Disoproxil Fumarate

    70. Odefsey Component Tenofovir Disoproxil Fumarate

    71. Q27132754

    72. Stribild Component Tenofovir Disoproxil Fumarate

    73. Temixys Component Tenofovir Disoproxil Fumarate

    74. Tenofoviri Disoproxili Fumaras [who-ip Latin]

    75. Truvada Component Tenofovir Disoproxil Fumarate

    76. Delstrigo Component Tenofovir Disoproxil Fumarate

    77. Tenofovir Disoproxil Fumarate Component Delstrigo

    78. Tenofovir Disoproxil Fumarate Component Of Atripla

    79. Tenofovir Disoproxil Fumarate Component Of Odefsey

    80. Tenofovir Disoproxil Fumarate Component Of Temixys

    81. Tenofovir Disoproxil Fumarate Component Of Truvada

    82. Tenofovir Disoproxil Fumarate Component Of Eviplera

    83. Tenofovir Disoproxil Fumarate Component Of Stribild

    84. (r)-(((((1-(6-amino-9h-purin-9-yl)propan-2-yl)oxy)methyl)phosphoryl)bis(oxy))bis(methylene)diisopropyldicarbonatefumarate

    85. [[(1r)-2-(6-aminopurin-9-yl)-1-methyl-ethoxy]methyl-(isopropoxycarbonyloxymethoxy)phosphoryl]oxymethyl Isopropyl Carbonate; Fumaric Acid

    86. 9-((r)-2-((bis(((isopropoxycarbonyl)oxy)-methoxy)phosphinyl)methoxy)propyl)adenine Fumarate (1:1)

    87. 9-[(r)-2[[bis[[(isopropoxycarbonyl)oxy]methoxy]phosphinyl]methoxy]propyl]adenine Fumarate (1:1)

    88. Bis({[(propan-2-yloxy)carbonyl]oxy}methyl) ({[(2r)-1-(6-amino-9h-purin-9-yl)propan-2-yl]oxy}methyl)phosphonate (2e)-but-2-enedioate

    89. Tenofovir Disoproxil Fumarate, Pharmaceutical Secondary Standard; Certified Reference Material

    2.4 Create Date
    2006-03-21
    3 Chemical and Physical Properties
    Molecular Weight 635.5 g/mol
    Molecular Formula C23H34N5O14P
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count18
    Rotatable Bond Count19
    Exact Mass635.18398777 g/mol
    Monoisotopic Mass635.18398777 g/mol
    Topological Polar Surface Area260 Ų
    Heavy Atom Count43
    Formal Charge0
    Complexity817
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameTenofovir disoproxil fumarate
    PubMed HealthTenofovir (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelVIREAD is the brand name for tenofovir disoproxil fumarate (a prodrug of tenofovir) which is a fumaric acid salt of bis-isopropoxycarbonyloxymethyl ester derivative of tenofovir. In vivo tenofovir disoproxil fumarate is converted to tenofovir, an acy...
    Active IngredientTenofovir disoproxil fumarate
    Dosage FormTablet
    Routeoral; Oral
    Strength300mg
    Market StatusTentative Approval
    CompanyMacleods Pharma; Aurobindo Pharma; Invagen Pharms; Cipla; Matrix Labs; Teva Pharms; Strides Arcolab

    2 of 4  
    Drug NameViread
    Drug LabelVIREAD is the brand name for tenofovir disoproxil fumarate (a prodrug of tenofovir) which is a fumaric acid salt of bis-isopropoxycarbonyloxymethyl ester derivative of tenofovir. In vivo tenofovir disoproxil fumarate is converted to tenofovir, an acy...
    Active IngredientTenofovir disoproxil fumarate
    Dosage FormTablet; Powder
    RouteOral
    Strength40mg/scoopful; 200mg; 250mg; 150mg; 300mg
    Market StatusPrescription
    CompanyGilead Sciences

    3 of 4  
    Drug NameTenofovir disoproxil fumarate
    PubMed HealthTenofovir (By mouth)
    Drug ClassesAntiretroviral Agent
    Drug LabelVIREAD is the brand name for tenofovir disoproxil fumarate (a prodrug of tenofovir) which is a fumaric acid salt of bis-isopropoxycarbonyloxymethyl ester derivative of tenofovir. In vivo tenofovir disoproxil fumarate is converted to tenofovir, an acy...
    Active IngredientTenofovir disoproxil fumarate
    Dosage FormTablet
    Routeoral; Oral
    Strength300mg
    Market StatusTentative Approval
    CompanyMacleods Pharma; Aurobindo Pharma; Invagen Pharms; Cipla; Matrix Labs; Teva Pharms; Strides Arcolab

    4 of 4  
    Drug NameViread
    Drug LabelVIREAD is the brand name for tenofovir disoproxil fumarate (a prodrug of tenofovir) which is a fumaric acid salt of bis-isopropoxycarbonyloxymethyl ester derivative of tenofovir. In vivo tenofovir disoproxil fumarate is converted to tenofovir, an acy...
    Active IngredientTenofovir disoproxil fumarate
    Dosage FormTablet; Powder
    RouteOral
    Strength40mg/scoopful; 200mg; 250mg; 150mg; 300mg
    Market StatusPrescription
    CompanyGilead Sciences

    4.2 Therapeutic Uses

    Anti-HIV Agents, Reverse Transcriptase Inhibitors

    National Library of Medicine's Medical Subject Headings online file (MeSH, 2012)

    Tenofovir disoproxil fumarate is used in conjunction with other antiretroviral agents for the treatment of human immunodeficiency virus type 1 (HIV-1) infections in adults. /Included in US product labeling/

    American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 747

    Tenofovir is used for the management of chronic hepatitis B virus (HBV) infection in adults. This indication is based on histologic, virologic, biochemical, and serologic responses in adults with hepatitis B e antigen (HBeAg)-positive or -negative chronic HBV with compensated liver function.

    American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 748

    Tenofovir disoproxil fumarate (TDF), emtricitabine (FTC), and efavirenz (EFV) are the three components of the once-daily, single tablet regimen (Atripla) for treatment of HIV-1 infection. Previous cell culture studies have demonstrated that the double combination of tenofovir (TFV), the parent drug of TDF, and FTC were additive to synergistic in their anti-HIV activity, which correlated with increased levels of intracellular phosphorylation of both compounds. In this study, /researchers/ demonstrated the combinations of TFV+FTC, TFV+EFV, FTC+EFV, and TFV+FTC+EFV synergistically inhibit HIV replication in cell culture and synergistically inhibit HIV-1 reverse transcriptase (RT) catalyzed DNA synthesis in biochemical assays. Several different methods were applied to define synergy including median-effect analysis, MacSynergyII and quantitative isobologram analysis. We demonstrated that the enhanced formation of dead-end complexes (DEC) by HIV-1 RT and TFV-terminated DNA in the presence of FTC-triphosphate (TP) could contribute to the synergy observed for the combination of TFV+FTC, possibly through reduced terminal NRTI excision. Furthermore, /researchers/ showed that EFV facilitated efficient formation of stable, DEC-like complexes by TFV- or FTC-monophosphate (MP)-terminated DNA and this can contribute to the synergistic inhibition of HIV-1 RT by TFV-diphosphate (DP)+EFV and FTC-TP+EFV combinations. This study demonstrated a clear correlation between the synergistic antiviral activities of TFV+FTC, TFV+EFV, FTC+EFV, and TFV+FTC+EFV combinations and synergistic HIV-1 RT inhibition at the enzymatic level. /Researchers/ propose the molecular mechanisms for the TFV+FTC+EFV synergy to be a combination of increased levels of the active metabolites TFV-DP and FTC-TP and enhanced DEC formation by a chain-terminated DNA and HIV-1 RT in the presence of the second and the third drug in the combination. This study furthers the understanding of the longstanding observations of synergistic anti-HIV-1 effects of many NRTI+NNRTI and certain NRTI+NRTI combinations in cell culture, and provides biochemical evidence that combinations of anti-HIV agents can increase the intracellular drug efficacy, without increasing the extracellular drug concentrations.

    PMID:19439089 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2693498 Feng JY et al; Retrovirology 6: 44 (2009)

    4.3 Drug Warning

    /BOXED WARNING/ WARNING: LACTIC ACIDOSIS/SEVERE HEPATOMEGALY WITH STEATOSIS and POST TREATMENT EXACERBATION OF HEPATITIS. Lactic acidosis and severe hepatomegaly with steatosis, including fatal cases, have been reported with the use of nucleoside analogs, including Viread, in combination with other antiretrovirals. Severe acute exacerbations of hepatitis have been reported in HBV-infected patients who have discontinued anti-hepatitis B therapy, including Viread. Hepatic function should be monitored closely with both clinical and laboratory follow-up for at least several months in patients who discontinue anti-hepatitis B therapy, including Viread. If appropriate, resumption of anti-hepatitis B therapy may be warranted.

    US Natl Inst Health; DailyMed. Current Medication Information for VIREAD (tenofovir disoproxil fumarate) tablet, coated VIREAD (tenofovir disoproxil fumarate) powder (November 2012). Available from, as of November 14, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=33fd6418-fbdc-42ca-a50d-ce2a476a5418

    Lactic acidosis and severe hepatomegaly with steatosis (sometimes fatal) have been reported rarely in patients receiving nucleoside reverse transcriptase inhibitors alone or in conjunction with other antiretroviral agents. Most reported cases have involved women; obesity and long-term therapy with a nucleoside reverse transcriptase inhibitor also may be risk factors. Caution should be observed when nucleoside analogs are used in patients with known risk factors for liver disease; however, lactic acidosis and severe hepatomegaly with steatosis have been reported in patients with no known risk factors. Tenofovir therapy should be interrupted in any patient with clinical or laboratory findings suggestive of lactic acidosis or pronounced hepatotoxicity (signs of hepatotoxicity include hepatomegaly and steatosis even in the absence of marked increases in serum aminotransferase concentrations).

    American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 749

    Redistribution or accumulation of body fat, including central obesity, dorsocervical fat enlargement (buffalo hump), peripheral wasting, facial wasting, breast enlargement, and general cushingoid appearance, has been reported with antiretroviral therapy.

    American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 750

    The most common adverse effects in HIV-infected patients receiving tenofovir disoproxil fumarate are rash, diarrhea, headache, pain, depression, asthenia, and nausea. The most common adverse effect in HIV-infected patients receiving tenofovir disoproxil fumarate is nausea.

    American Society of Health-System Pharmacists 2012; Drug Information 2012. Bethesda, MD. 2012, p. 750

    For more Drug Warnings (Complete) data for TENOFOVIR DISOPROXIL FUMARATE (14 total), please visit the HSDB record page.

    4.4 Drug Indication

    * HIV 1 infection:

    Viread 123 mg film coated tablets are indicated in combination with other antiretroviral medicinal products for the treatment of HIV 1 infected paediatric patients, with NRTI resistance or toxicities precluding the use of first line agents, aged 6 to < 12 years who weigh from 17 kg to less than 22 kg.

    The choice of Viread to treat antiretroviral experienced patients with HIV 1 infection should be based on individual viral resistance testing and/or treatment history of patients.

    * Hepatitis B infection:

    Viread 123 mg film coated tablets are indicated for the treatment of chronic hepatitis B in paediatric patients aged 6 to < 12 years who weigh from 17 kg to less than 22 kg, with

    compensated liver disease and evidence of immune active disease, i. e. active viral replication and persistently elevated serum ALT levels, or histological evidence of moderate to severe inflammation and/or fibrosis. With respect to the decision to initiate treatment in paediatric patients, see sections 4. 2, 4. 4, 4. 8 and 5. 1.

    * HIV 1 infection:

    Viread 163 mg film coated tablets are indicated in combination with other antiretroviral medicinal products for the treatment of HIV 1 infected paediatric patients, with NRTI resistance or toxicities precluding the use of first line agents, aged 6 to < 12 years who weigh from 22 kg to less than 28 kg.

    The choice of Viread to treat antiretroviral experienced patients with HIV 1 infection should be based on individual viral resistance testing and/or treatment history of patients.

    * Hepatitis B infection:

    Viread 163 mg film coated tablets are indicated for the treatment of chronic hepatitis B in paediatric patients aged 6 to < 12 years who weigh from 22 kg to less than 28 kg, with:

    compensated liver disease and evidence of immune active disease, i. e. active viral replication and persistently elevated serum ALT levels, or histological evidence of moderate to severe inflammation and/or fibrosis. With respect to the decision to initiate tre