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Adefovir Dipivoxil

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ACTIVE PHARMA INGREDIENTS

14 API Suppliers, 7 USDMF, 2 EU WC, 6 KDMF, 1 NDC API, 7 Listed Suppliers, $ API Reference Price

14 API Suppliers
7 USDMF
2 EU WC
6 KDMF
1 NDC API
7 Listed Suppliers
$ API Reference Price

FINISHED DOSAGE FORMULATIONS

12 FDF Dossiers, 3 FDA Orange Book, 3 Europe, 1 Canada, 5 Listed Dossiers

12 FDF Dossiers
3 FDA Orange Book
3 Europe
1 Canada
5 Listed Dossiers

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4 SPI Pharma, 1 DKSH, 4 Faran Shimi Pharmaceutical, 6 Boai NKY Pharmaceuticals Ltd, 11 Gangwal Healthcare, 1 Nanjing Well Pharmaceutical, 1 Aeon Procare, 2 Alcedo Pharmachem, 7 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 8 BASF, 6 DFE Pharma, 7 Gangwal Chemicals, 1 Huzhou Sunflower Pharmaceutical, 1 Ideal Cures Pvt Ltd, 3 Ingredion Pharma Solutions, 25 Kerry, 12 Microlex e.U, 2 Novo Excipients, 2 Pharmatrans-Sanaq, 4 Pluviaendo, 3 Prachin Chemical, 14 Roquette, 1 Seppic, 4 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 11 Sigachi Industries, 1 Ulanqab Kema New Material, 3 Vasa Pharmachem

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67 Fillers, Diluents & Binders
37 Direct Compression
29 Disintegrants & Superdisintegrants
19 Granulation
15 Thickeners and Stabilizers
15 Co-Processed Excipients
13 Lubricants & Glidants
8 Chewable & Orodispersible Aids
7 Film Formers & Plasticizers
7 Controlled & Modified Release
6 Coating Systems & Additives
6 Taste Masking
5 Solubilizers
3 Emulsifying Agents
2 Rheology Modifiers
1 Parenteral
1 API Stability Enhancers

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2 US Medicaid Prescriptions, 3 Finished Drug Prices

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2 US Medicaid Prescriptions
3 Finished Drug Prices

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4 APIs, 1 FDF Dossiers

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4 APIs
1 FDF Dossiers

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2 Health Canada Patents

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Synopsis

ACTIVE PHARMA INGREDIENTS

API Suppliers

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CEP/COS

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EU WC

KDMF

NDC API

VMF

Listed Suppliers

API REF. PRICE (USD/KG)

$ 200

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FDF Dossiers

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Europe

Canada

Australia

South Africa

Listed Dossiers

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DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

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US Patents

US Exclusivities

Health Canada Patents

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Finished Drug Prices

145 RELATED EXCIPIENT COMPANIES

241EXCIPIENTS BY APPLICATIONS

Chemistry

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Also known as: 142340-99-6, Hepsera, Preveon, Adefovir pivoxil, Bis-pom pmea, Gs-0840

Molecular Formula

C₂₀H₃₂N₅O₈P

Molecular Weight

501.5 g/mol

InChI Key

WOZSCQDILHKSGG-UHFFFAOYSA-N

FDA UNII

U6Q8Z01514

Adefovir Dipivoxil is a dipivoxil formulation of adefovir, a nucleoside reverse transcriptase inhibitor analog of adenosine with activity against hepatitis B virus (HBV), herpes virus, and human immunodeficiency virus (HIV).

1 2D Structure

Adefovir Dipivoxil

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[2-(6-aminopurin-9-yl)ethoxymethyl-(2,2-dimethylpropanoyloxymethoxy)phosphoryl]oxymethyl 2,2-dimethylpropanoate

2.1.2 InChI

InChI=1S/C20H32N5O8P/c1-19(2,3)17(26)30-11-32-34(28,33-12-31-18(27)20(4,5)6)13-29-8-7-25-10-24-14-15(21)22-9-23-16(14)25/h9-10H,7-8,11-13H2,1-6H3,(H2,21,22,23)

2.1.3 InChI Key

WOZSCQDILHKSGG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N=CN=C21)N)OCOC(=O)C(C)(C)C

2.2 Other Identifiers

2.2.1 UNII

U6Q8Z01514

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 9-(2-((-bis((pivaloyloxy)methoxy)phosphinyl)methoxy)ethyl)adenine

2. Adefovir Depivoxil

3. Gs 840

4. Gs-0840

5. Hepsera

6. Preveon

2.3.2 Depositor-Supplied Synonyms

1. 142340-99-6

2. Hepsera

3. Preveon

4. Adefovir Pivoxil

5. Bis-pom Pmea

6. Gs-0840

7. Gs 0840

8. Gs 840

9. Gs-840

10. [2-(6-aminopurin-9-yl)ethoxymethyl-(2,2-dimethylpropanoyloxymethoxy)phosphoryl]oxymethyl 2,2-dimethylpropanoate

11. Adefovir Dipivoxil [usan]

12. Adefovir Pivoxil (jan)

13. Adefovir Di(pivaloyloxymethyl) Ester

14. Adefovir Dipivoxil (usan)

15. 9-(2-((bis((pivaloyloxy)methoxy)phosphinyl)methoxy)ethyl)adenine

16. (((2-(6-amino-9h-purin-9-yl)ethoxy)methyl)phosphinylidene)bis(oxymethylene) 2,2-dimethylpropanoate

17. ((2-(6-amino-9h-purin-9-yl)ethoxy)methyl)phosphonic Acid, Diester With Hydroxymethyl Pivalate

18. Adefovir Dipivoxil (preveon, Hepsera)

19. U6q8z01514

20. Propanoic Acid, 2,2-dimethyl-, (((2-(6-amino-9h-purin-9-yl)ethoxy)methyl)phosphinylidene)bis(oxymethylene) Ester

21. Ncgc00164624-01

22. Adefovirdipivoxl

23. Dsstox_cid_26487

24. Dsstox_rid_81658

25. Dsstox_gsid_46487

26. ((((2-(6-amino-9h-purin-9-yl)ethoxy)methyl)phosphoryl)bis(oxy))bis(methylene) Bis(2,2-dimethylpropanoate)

27. Adefovir Pivoxil [jan]

28. 9-[2-[bis(pivaloyloxymethoxy)phosphorylmethoxy]ethyl]adenine

29. Youheding

30. Adefovir Dipivoxyl

31. [({[2-(6-amino-9h-purin-9-yl)ethoxy]methyl}({[(2,2-dimethylpropanoyl)oxy]methoxy})phosphoryl)oxy]methyl 2,2-dimethylpropanoate

32. Bis(pom)pmea

33. Smr002530072

34. Hepsera (tm)

35. Hepsera (tn)

36. Piv2pmea

37. Cas-142340-99-6

38. Bis(pom)-pmea

39. 9-(2-((-bis((pivaloyloxy)methoxy)phosphinyl)methoxy)ethyl)adenine

40. Unii-u6q8z01514

41. Adefovir-dipivoxil

42. Mfcd00869897

43. Adefovir Dipivoxil- Bio-x

44. Chembl922

45. Schembl29729

46. Mls003915635

47. Mls004774124

48. Dtxsid5046487

49. Chebi:31175

50. 9-(2[bis(pivaloyloxymethoxy)phosphorylmethoxy]ethyl)adenine

51. Bis(pivaloyloxymethyl)-9-(2-phosphonylmethoxyethyl)adenine

52. Adefovir Dipivoxil [vandf]

53. Bcpp000434

54. Hms3604f09

55. Hms3655i04

56. Adefovir Dipivoxil [mart.]

57. Adefovir Dipivoxil [who-dd]

58. Bcp22959

59. Hy-b0255

60. Zinc3930376

61. Tox21_112243

62. Bdbm50248359

63. S1718

64. Stl257088

65. Adefovir Dipivoxil [ema Epar]

66. Akos005145737

67. Tox21_112243_1

68. Ab07592

69. Ac-1693

70. Bcp9000232

71. Ccg-269700

72. Db00718

73. Gs-3604

74. Adefovir Dipivoxil [orange Book]

75. Ncgc00164624-02

76. Ncgc00164624-03

77. Ncgc00164624-11

78. Ba164139

79. Bcp0726000157

80. B2222

81. Ft-0631164

82. Sw219933-1

83. D01655

84. Ab01274706-01

85. Ab01274706_02

86. 340a996

87. A807894

88. Adefovir Di(pivaloyloxymethyl) Ester [mi]

89. Adefovir Dipivoxil 100 Microg/ml In Acetonitrile

90. Sr-01000931258

91. Q-101927

92. Sr-01000931258-2

93. Brd-k96159438-001-03-0

94. Adefovir Dipivoxil, Antibiotic For Culture Media Use Only

95. Bis(pivaloyloxymethyl)-9-[2-(phosphonomethoxy)ethyl]adenine

96. ((((2-(6-amino-9h-purin-9-yl)ethoxy)methyl)phosphoryl)-bis(oxy))bis(methylene) Bis(2,2-dimethylpropanoate)

97. (((2-(6-amino-9h-purin-9-yl)ethoxy)methyl)phosphoryl)bis(oxy)bis(methylene) Bis(2,2-dimethylpropanoate)

98. ({[2-(6-amino-9h-purin-9-yl)ethoxy]methyl}phosphoryl)bis(oxymethanediyl) Bis(2,2-dimethylpropanoate)

99. 2,2-dimethylpropanoic Acid [2-(6-aminopurin-9-yl)ethoxymethyl-[(2,2-dimethyl-1-oxopropoxy)methoxy]phosphoryl]oxymethyl Ester;adefovir Dipivoxyl

100. 3-{[2-(6-amino-9h-purin-9-yl)ethoxy]methyl}-8,8-dimethyl-3-oxido-7-oxo-2,4,6-trioxa-3?5-phosphanon-1-yl 2,2-dimethylpropanoate

101. 3-{[2-(6-amino-9h-purin-9-yl)ethoxy]methyl}-8,8-dimethyl-3-oxido-7-oxo-2,4,6-trioxa-3lambda~5~-phosphanon-1-yl 2,2-dimethylpropanoate

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₃₂N₅O₈P
Molecular Weight	501.5 g/mol
XLogP3	1.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	15
Exact Mass	501.19884999 g/mol
Monoisotopic Mass	501.19884999 g/mol
Topological Polar Surface Area	167 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	706
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Adefovir dipivoxil
PubMed Health	Adefovir Dipivoxil (By mouth)
Drug Classes	Antiviral
Drug Label	HEPSERA is the tradename for adefovir dipivoxil, a diester prodrug of adefovir. Adefovir is an acyclic nucleotide analog with activity against human hepatitis B virus (HBV). The chemical name of adefovir dipivoxil is 9-[2-[[bis[(pivaloyloxy)methoxy...
Active Ingredient	Adefovir dipivoxil
Dosage Form	Tablet
Route	Oral
Strength	10mg
Market Status	Prescription
Company	Sigmapharm Labs

2 of 4
Drug Name	Hepsera
PubMed Health	Adefovir Dipivoxil (By mouth)
Drug Classes	Antiviral
Drug Label	HEPSERA is the tradename for adefovir dipivoxil, a diester prodrug of adefovir. Adefovir is an acyclic nucleotide analog with activity against human hepatitis B virus (HBV). The chemical name of adefovir dipivoxil is 9-[2-[[bis[(pivaloyloxy)methoxy...
Active Ingredient	Adefovir dipivoxil
Dosage Form	Tablet
Route	Oral
Strength	10mg
Market Status	Prescription
Company	Gilead

3 of 4
Drug Name	Adefovir dipivoxil
PubMed Health	Adefovir Dipivoxil (By mouth)
Drug Classes	Antiviral
Drug Label	HEPSERA is the tradename for adefovir dipivoxil, a diester prodrug of adefovir. Adefovir is an acyclic nucleotide analog with activity against human hepatitis B virus (HBV). The chemical name of adefovir dipivoxil is 9-[2-[[bis[(pivaloyloxy)methoxy...
Active Ingredient	Adefovir dipivoxil
Dosage Form	Tablet
Route	Oral
Strength	10mg
Market Status	Prescription
Company	Sigmapharm Labs

4 of 4
Drug Name	Hepsera
PubMed Health	Adefovir Dipivoxil (By mouth)
Drug Classes	Antiviral
Drug Label	HEPSERA is the tradename for adefovir dipivoxil, a diester prodrug of adefovir. Adefovir is an acyclic nucleotide analog with activity against human hepatitis B virus (HBV). The chemical name of adefovir dipivoxil is 9-[2-[[bis[(pivaloyloxy)methoxy...
Active Ingredient	Adefovir dipivoxil
Dosage Form	Tablet
Route	Oral
Strength	10mg
Market Status	Prescription
Company	Gilead

4.2 Drug Indication

Indicated for the treatment of chronic hepatitis B in adult patients with evidence of active viral replication and either evidence of persistent elevations in serum aminotransferases (ALT or AST) or histologically active disease; this is based on histological, virological, biochemical, and serological responses in adult patients with HBeAg+ and HBeAg- chronic hepatitis B with compensated liver function, and in adult patients with clinical evidence of lamivudine-resistant hepatitis B virus with either compensated or decompensated liver function.

FDA Label

Hepsera is indicated for the treatment of chronic hepatitis B in adults with:

- compensated liver disease with evidence of active viral replication, persistently elevated serum-alanine-aminotransferase (ALT) levels and histological evidence of active liver inflammation and fibrosis. Initiation of Hepsera treatment should only be considered when the use of an alternative antiviral agent with a higher genetic barrier to resistance is not available or appropriate (see section 5. 1);

- decompensated liver disease in combination with a second agent without cross-resistance to Hepsera.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Adefovir dipivoxil a diester prodrug of adefovir. Adefovir is an acyclic nucleotide analog with activity against human hepatitis B virus (HBV). The concentration of adefovir that inhibited 50% of viral DNA synthesis (IC50) in vitro ranged from 0.2 to 2.5 μM in HBV transfected human hepatoma cell lines. The combination of adefovir with lamivudine showed additive anti-HBV activity.

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.)

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 Pharmacological Classes

Nucleoside Analog [EXT]; Nucleoside Reverse Transcriptase Inhibitors [MoA]; Hepatitis B Virus Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]

5.4 ATC Code

J05AF08

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AF - Nucleoside and nucleotide reverse transcriptase inhibitors

J05AF08 - Adefovir dipivoxil

5.5 Absorption, Distribution and Excretion

Absorption

The approximate oral bioavailability of adefovir from HEPSERA is 59%. When a single oral 10 mg dose is given to chronic hepatitis B patients, the peak plasma concentration (Cmax) of adefovir was 18.4 6.26 ng/mL. This occurred between 0.58 - 4 hours post dose (Tmax). The adefovir area under the plasma concentration-time curve (AUC0) was 220 70.0 ngh/mL. Food does not affect the exposure of adeforvir.

Route of Elimination

Adefovir is renally excreted by a combination of glomerular filtration and active tubular secretion.

Volume of Distribution

392 75 mL/kg [Vd at steady state, intravenous administration of 1.0 mg/kg/day]

352 9 mL/kg [Vd at steady state, intravenous administration of 3.0 mg/kg/day]

Clearance

469 99.0 mL/min [Patients with Unimpaired renal Function receiving a 10 mg single dose]

356 85.6 mL/min [Patients with mild renal impairement receiving a 10 mg single dose]

237 118 mL/min [Patients with moderate renal impairement receiving a 10 mg single dose]

91.7 51.3 mL/min [Patients with severe renal impairement receiving a 10 mg single dose]

5.6 Metabolism/Metabolites

Following oral administration, adefovir dipivoxil is rapidly converted to adefovir. 45% of the dose is recovered as adefovir in the urine over 24 hours at steady state following 10 mg oral doses. Adefovir is not a substrate of the cytochrome P450 enzymes.

5.7 Biological Half-Life

Plasma adefovir concentrations declined in a biexponential manner with a terminal elimination half-life of 7.48 1.65 hours.

5.8 Mechanism of Action

Adefovir dipivoxil is a prodrug of adefovir. Adefovir is an acyclic nucleotide analog of adenosine monophosphate which is phosphorylated to the active metabolite adefovir diphosphate by cellular kinases. Adefovir diphosphate inhibits HBV DNA polymerase (reverse transcriptase) by competing with the natural substrate deoxyadenosine triphosphate and by causing DNA chain termination after its incorporation into viral DNA. The inhibition constant (Ki) for adefovir diphosphate for HBV DNA polymerase was 0.1 μM. Adefovir diphosphate is a weak inhibitor of human DNA polymerases α and γ with Ki values of 1.18 μM and 0.97μM, respectively.

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