Adefovir Dipivoxil

Adefovir Dipivoxil is a acyclic nucleotide analog reverse transcriptase inhibitor (ntRTI). It 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.

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CAT No: 10-101-107

CAS No: 142340-99-6

Synonyms/Alias: Adefovir di(pivaloyloxymethyl) ester;Bis(POM)PMEA; GS-0840; Piv2PMEA;9-[2-(Bis[(pivaloyloxy)-methoxy]phosphinylmethoxy)ethyl]adenine

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

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M.F/FormulaC20H32N5O8P
M.W/Mr.501.48
Sequenceno
Labeling TargetDNA polymerase/reverse transcriptase
ApplicationFor treatment of hepatitis B and herpes simplex virus infection
AppearanceSolid powder
Purity>98% (or refer to the Certificate of Analysis)
Biological ActivityAdefovir 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).
Areas of InterestInfection
FunctionsRna-dna hybrid ribonuclease activity
TargetHBV
Source#Synthetic
Long-term Storage ConditionsSoluble in DMSO
Shipping ConditionShipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Short-term Storage ConditionsDry, dark and at 0 - 4 °C
Solubility-20 °C
OrganismHBV-D
InChIInChI=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)
InChI KeyWOZSCQDILHKSGG-UHFFFAOYSA-N
Canonical SMILESCC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N=CN=C21)N)OCOC(=O)C(C)(C)C
BoilingPoint641.0±65.0 °C at 760 mmHg
ShelfLife>2 years if stored properly
References

Tenofovir disoproxil fumarate (DF) is a nucleotide analogue and a potent inhibitor of human immunodeficiency virus type 1 reverse transcriptase and hepatitis B virus (HBV) polymerase.

Marcellin P, Heathcote E J, Buti M, et al. Tenofovir disoproxil fumarate versus adefovir dipivoxil for chronic hepatitis B[J]. New England Journal of Medicine, 2008, 359(23): 2442-2455.

Adefovir dipivoxil possesses potent in vitro and in vivo antiviral activity in wild-type hepatitis B. This study assessed the safety and efficacy of adefovir dipivoxil alone and in combination with lamivudine compared with ongoing lamivudine therapy in patients with chronic hepatitis B with compensated liver disease and lamivudine-resistant hepatitis B virus (HBV).

Peters M G, Hann H W, Martin P, et al. Adefovir dipivoxil alone or in combination with lamivudine in patients with lamivudine-resistant chronic hepatitis B[J]. Gastroenterology, 2004, 126(1): 91-101.

Adefovir dipivoxil effectively inhibits both hepatitis B virus (HBV) replication and disease activity in patients with chronic hepatitis B. Resistance to treatment was not observed in 2 recent large placebo-controlled 48-week studies with this drug. The aim of this study was to characterize adefovir resistance in a patient who developed clinical and virologic evidence of breakthrough during a 96-week course of treatment.

Angus P, Vaughan R, Xiong S, et al. Resistance to adefovir dipivoxil therapy associated with the selection of a novel mutation in the HBV polymerase[J]. Gastroenterology, 2003, 125(2): 292-297.

Oral adefovir dipivoxil is effective and generally well tolerated in HBeAg-positive and -negative patients chronically infected with wild-type or lamivudine-resistant HBV. Few resistant HBV mutants have emerged to date. Data from ongoing long-term studies are awaited with interest. Existing treatment options for patients with chronic hepatitis B are limited in both number and effectiveness; the proven efficacy, good tolerability profile and apparently low potential for resistance of adefovir dipivoxil make it a promising new option in the management of this disease.

Dando T M, Plosker G L. Adefovir dipivoxil: a review of its use in chronic hepatitis B[J]. Drugs, 2003, 63(20): 2215-2235.

Melting Point98-102ºC
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