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2D Structure
Also known as: 147127-20-6, (r)-9-(2-phosphonomethoxypropyl)adenine, Truvada, (r)-pmpa, Tenofovir (anhydrous), Pmpa gel
Molecular Formula
C9H14N5O4P
Molecular Weight
287.21  g/mol
InChI Key
SGOIRFVFHAKUTI-ZCFIWIBFSA-N
FDA UNII
W4HFE001U5

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.
Tenofovir anhydrous is a Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor and Hepatitis B Virus Nucleoside Analog Reverse Transcriptase Inhibitor. The mechanism of action of tenofovir anhydrous is as a Nucleoside Reverse Transcriptase Inhibitor.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethylphosphonic acid
2.1.2 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
2.1.3 InChI Key
SGOIRFVFHAKUTI-ZCFIWIBFSA-N
2.1.4 Canonical SMILES
CC(CN1C=NC2=C(N=CN=C21)N)OCP(=O)(O)O
2.1.5 Isomeric SMILES
C[C@H](CN1C=NC2=C(N=CN=C21)N)OCP(=O)(O)O
2.2 Other Identifiers
2.2.1 UNII
W4HFE001U5
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 Disoproxil

12. Tenofovir Disoproxil Fumarate

13. Viread

2.3.2 Depositor-Supplied Synonyms

1. 147127-20-6

2. (r)-9-(2-phosphonomethoxypropyl)adenine

3. Truvada

4. (r)-pmpa

5. Tenofovir (anhydrous)

6. Pmpa Gel

7. (r)-(((1-(6-amino-9h-purin-9-yl)propan-2-yl)oxy)methyl)phosphonic Acid

8. Apropovir

9. Gs-1275

10. Anhydrous Tenofovir

11. Tenofovir Anhydrous

12. Tenofovir (anh.)

13. Chebi:63625

14. Pmp-a

15. [(2r)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethylphosphonic Acid

16. ({[(2r)-1-(6-amino-9h-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic Acid

17. W4hfe001u5

18. (r)-(1-(6-amino-9h-purin-9-yl)propan-2-yloxy)methylphosphonic Acid

19. 147127-20-6 (tenofovir)

20. Gs-1278

21. 9-[(r)-2-(phosphonomethoxy)propyl]adenine

22. Phosphonic Acid, P-[[(1r)-2-(6-amino-9h-purin-9-yl)-1-methylethoxy]methyl]-

23. D,l-tenofovir

24. Tenofovir Gel

25. [(1r)-2-(6-aminopurin-9-yl)-1-methyl-ethoxy]methylphosphonic Acid

26. (((1r)-2-(6-amino-9h-purin-9-yl)-1-methylethoxy)methyl)phosphonic Acid

27. (r)-[[2-(6-amino-9h-purin-9-yl)-1-methylethoxy]methyl]phosphonic Acid

28. {[(1r)-2-(6-amino-9h-purin-9-yl)-1-methylethoxy]methyl}phosphonic Acid

29. Gna & Tenofovir

30. Hha & Tenofovir

31. Tfv Gel

32. Gs 1275

33. Pmpa-(r)

34. Unii-w4hfe001u5

35. Tenofovir [usan:inn:ban]

36. Rac Tenofovir

37. Anh. Tenofovir

38. Viread (prodrug For Tenofovir)

39. Phosphonic Acid, (((1r)-2-(6-amino-9h-purin-9-yl)-1-methylethoxy)methyl)-

40. Phosphonic Acid, [[(1r)-2-(6-amino-9h-purin-9-yl)-1-methylethoxy]methyl]-

41. Phosphonic Acid, P-(((1r)-2-(6-amino-9h-purin-9-yl)-1-methylethoxy)methyl)-

42. Tenofovir- Bio-x

43. Tenofovir (viread)

44. (r)-9-(phosphonomethoxypropyl)adenine

45. Gs 1278

46. Ks-5021

47. Tenofovir [inn]

48. Tenofovir [mi]

49. 9-pmpa

50. Chembl483

51. Ec 604-571-2

52. Tenofovir [who-dd]

53. Schembl39724

54. Tenofovir Gel (gs-1278)

55. Dtxsid9040132

56. Tenofovir, >=98% (hplc)

57. Gtpl10948

58. Bcpp000049

59. Hms3264h05

60. Zinc1543475

61. Ac-760

62. Bdbm50450813

63. Mfcd00943794

64. Akos015856701

65. Akos015894941

66. Ccg-267345

67. Cs-1609

68. Db14126

69. Phosphonic Acid, ((2-(6-amino-9h-purin-9-yl)-1-methylethoxy)methyl)-, (r)-

70. Ncgc00167535-16

71. Bt164455

72. Hy-13910

73. (r)-9-(2-phosphonoylmethoxypropyl)adenine

74. Am20090678

75. T3006

76. (r)-9-[2-(phosphonomethoxy) Propyl] Adenine

77. C17407

78. Ab01274787-01

79. Ab01274787_02

80. Ab01274787_03

81. 127t206

82. A808613

83. Q155954

84. Sr-01000883934

85. Q-201787

86. Sr-01000883934-1

87. Brd-k15891719-001-02-8

88. [(2r)-3-(6-aminopurin-9-yl)-2-methyl-propyl] Dihydrogen Phosphate

89. [[(1r)-2(6-amino-9h-purin-9-yl)-1-methylethoxy]methyl]phosphonic Acid

90. [2-(6-amino-9h-purin-9-yl)-1-methylethoxy]methylphosphonic Acid

91. Phosphonic Acid, [[(1r)-2-(6-amino-9h-purin-9-yl)-1-methylethoxy]methyl]- & Galanthus Nivalis Agglutinin (gna)

92. Phosphonic Acid, [[(1r)-2-(6-amino-9h-purin-9-yl)-1-methylethoxy]methyl]- & Hippeastrum Hybrid Agglutinin( Hha)

2.4 Create Date
2005-08-01
3 Chemical and Physical Properties
Molecular Weight 287.21 g/mol
Molecular Formula C9H14N5O4P
XLogP3-1.6
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count5
Exact Mass287.07834094 g/mol
Monoisotopic Mass287.07834094 g/mol
Topological Polar Surface Area136 Ų
Heavy Atom Count19
Formal Charge0
Complexity354
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Tenofovir has been shown to be effective against HIV, herpes simplex virus-2, and hepatitis B virus. To know more about the specific product indications, please visit the information in the orally available forms of tenofovir, [tenofovir alafenamide] and [tenofovir disoproxil].


Treatment of HIV-1 infection:

- Truvada is indicated in antiretroviral combination therapy for the treatment of HIV-1 infected adults.

- Truvada is also indicated for the treatment of HIV-1 infected adolescents, with NRTI resistance or toxicities precluding the use of first line agents, aged 12 to < 18 years.

Pre-exposure prophylaxis (PrEP):

- Truvada is indicated in combination with safer sex practices for pre-exposure prophylaxis to reduce the risk of sexually acquired HIV-1 infection in adults at high risk.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Tenofovir has been shown to be highly effective in patients that have never had an antiretroviral therapy and it seemed to have lower toxicity than other antivirals such as [stavudine]. In phase 3 clinical trials, tenofovir presented a similar efficacy than [efavirenz] in treatment-naive HIV patients. In hepatitis B infected patients, after one year of tenofovir treatment, the viral DNA levels were undetectable.


5.2 MeSH Pharmacological Classification

Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)


Anti-HIV Agents

Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)


Reverse Transcriptase Inhibitors

Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template. (See all compounds classified as Reverse Transcriptase Inhibitors.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
TENOFOVIR ANHYDROUS
5.3.2 FDA UNII
W4HFE001U5
5.3.3 Pharmacological Classes
Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]; Nucleoside Reverse Transcriptase Inhibitors [MoA]; Nucleosides [CS]; Hepatitis B Virus Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]
5.4 ATC Code

J05AR03


5.5 Absorption, Distribution and Excretion

Absorption

Tenofovir as the active moiety presents a very low bioavailability when orally administered. Hence, the administration of this active agent is required to be under its two prodrug forms, [tenofovir disoproxil] and [tenofovir alafenamide]. This reduced absorption is suggested to be related to the presence of two negative charges among its structure. This negative charge limits its cellular penetration, and its passive diffusion across cellular membranes and intestinal mucosa hindering its availability for oral administration. Intravenous tenofovir has been shown to produce a maximum plasma concentration of 2500 ng/ml with an AUC of 4800 ng.h/ml.


Route of Elimination

Tenofovir is eliminated in the urine by tubular secretion and glomerular filtration. The elimination of this compound is driven by the activity of the human organic anion transporters 1 and 3 and its secretion is mainly ruled by the activity of the multidrug resistance-associated protein 4.


Volume of Distribution

Accumulation of tenofovir in plasma is related to the presence of nephrotoxic effects. It is reported that tenofovir presents a volume of distribution of 0.813 L/kg.


Clearance

The clearance of tenofovir is highly dependent on the patient renal stage and hence the clearance rate in patients with renal impairment is reported to be of 134 ml/min while in patients with normal function the clearance rate can be of 210 ml/min.


5.6 Metabolism/Metabolites

Tenofovir activation is performed by a bi-phosphorylation which in order forms the biologically active compound, tenofovir biphosphate. This metabolic activation has been shown to be performed in hepG2 cells and human hepatocytes.


5.7 Biological Half-Life

The reported half-life of tenofovir is of 32 hours.


5.8 Mechanism of Action

Once tenofovir is activated by a bi-phosphorylation it acts as an antiviral acyclic nucleoside phosphonate. It is a potent inhibitor of the viral reverse transcriptase with an inhibitory constant of approximately 0.022 micromolar. Once activated, tenofovir acts with different mechanisms including the inhibition of viral polymerase causing chain termination and the inhibition of viral synthesis. All these activities are attained by its competition with deoxyadenosine 5'-triphosphate in the generation of new viral DNA. Once tenofovir is incorporated in the chain, it induces a chain termination which in order inhibits viral replication. The safety of tenofovir relies on its low affinity towards the cellular DNA polymerase including the mitochondrial DNA polymerase gamma.