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MedKoo Cat#: 317160 | Name: Adefovir Dipivoxil
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Adefovir dipivoxil (trade names Preveon and Hepsera) is an antiviral acyclic nucleoside phosphonate (ANP) analog. It 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). It is an orally-administered acyclic nucleotide analog reverse transcriptase inhibitor (ntRTI) that works by blocking reverse transcriptase for the treatment of hepatitis B. Adefovir dipivoxil is not effective against HIV-1.

Chemical Structure

Adefovir Dipivoxil
Adefovir Dipivoxil
CAS#142340-99-6 (dipivoxil)

Theoretical Analysis

MedKoo Cat#: 317160

Name: Adefovir Dipivoxil

CAS#: 142340-99-6 (dipivoxil)

Chemical Formula: C20H32N5O8P

Exact Mass: 501.1989

Molecular Weight: 501.48

Elemental Analysis: C, 47.90; H, 6.43; N, 13.97; O, 25.52; P, 6.18

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
2g USD 400.00 2 Weeks
5g USD 850.00 2 Weeks
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Related CAS #
142340-99-6 (dipivoxil) 106941-25-7 (free acid) 129556-87-2 (monophosphate)
Synonym
9-(2-((-bis((pivaloyloxy)methoxy)phosphinyl)methoxy)ethyl)adenine, GS 840, GS-0840, Hepsera; Preveon.
IUPAC/Chemical Name
[2-(6-aminopurin-9-yl)ethoxymethyl-(2,2-dimethylpropanoyloxymethoxy)phosphoryl]oxymethyl 2,2-dimethylpropanoate
InChi Key
WOZSCQDILHKSGG-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C1N=CN=C2N)OCOC(=O)C(C)(C)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Adefovir dipivoxil, an adenosine analogue, is an oral prodrug of the nucleoside reverse transcriptase inhibitor Adefovir.
In vitro activity:
The cell supernatants of various concentrations of drugs were detected by PFU assays (Fig. 5C). According to the virus titer, this study found that these 4 kinds of drugs can strongly inhibit the proliferation of PRV in vitro. Adefovir dipivoxil showed the strongest activity to restrain the proliferation of viruses. The mechanism of adefovir dipivoxil against PRV may be associated with virus assembly, release, or chain terminator. Reference: Antiviral Res. 2021 Feb;186:105014. https://pubmed.ncbi.nlm.nih.gov/33422610/
In vivo activity:
Adefovir dipivoxil treatment reduced the pathological lesions of the PRV-infected mice (Fig. S1A). There were significantly fewer PRV particles in the major organs of the mice treated with adefovir dipivoxil than in the mice in the PBS treatment group (Fig. S1B). The body weight curves and survival curves demonstrated that two of six mice survived after adefovir dipivoxil treatment. All six mice in the PBS treatment group died at 5 days post PRV infection (Fig. 7C and D). These results suggested that adefovir dipivoxil had late therapeutic activity against PRV. Reference: Antiviral Res. 2021 Feb;186:105014. https://pubmed.ncbi.nlm.nih.gov/33422610/
Solvent mg/mL mM
Solubility
DMSO 76.7 152.89
DMF 30.0 59.82
Ethanol 65.0 129.62
Water 0.7 1.34
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 501.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Wang G, Chen R, Huang P, Hong J, Cao J, Wu Q, Zheng W, Lin L, Han Q, Chen Y, Xia N. Adefovir dipivoxil efficiently inhibits the proliferation of pseudorabies virus in vitro and in vivo. Antiviral Res. 2021 Feb;186:105014. doi: 10.1016/j.antiviral.2021.105014. Epub 2021 Jan 7. PMID: 33422610.
In vitro protocol:
1. Wang G, Chen R, Huang P, Hong J, Cao J, Wu Q, Zheng W, Lin L, Han Q, Chen Y, Xia N. Adefovir dipivoxil efficiently inhibits the proliferation of pseudorabies virus in vitro and in vivo. Antiviral Res. 2021 Feb;186:105014. doi: 10.1016/j.antiviral.2021.105014. Epub 2021 Jan 7. PMID: 33422610.
In vivo protocol:
1. Wang G, Chen R, Huang P, Hong J, Cao J, Wu Q, Zheng W, Lin L, Han Q, Chen Y, Xia N. Adefovir dipivoxil efficiently inhibits the proliferation of pseudorabies virus in vitro and in vivo. Antiviral Res. 2021 Feb;186:105014. doi: 10.1016/j.antiviral.2021.105014. Epub 2021 Jan 7. PMID: 33422610.
1: Lin RZ, Sun PJ, Tao Q, Yao J, Chen JM, Lu TB. Mechanism study on stability enhancement of adefovir dipivoxil by cocrystallization: Degradation kinetics and structure-stability correlation. Eur J Pharm Sci. 2015 Oct 10. pii: S0928-0987(15)30035-X. doi: 10.1016/j.ejps.2015.10.006. [Epub ahead of print] PubMed PMID: 26462447. 2: Ning HB, Li K, Li W, Ding GQ, Xiao EH, Mao ZS, Kang Y, Shang J. [Adefovir dipivoxil effects on and related factors of blood phosphorus metabolism in patients with chronic hepatitis B]. Zhonghua Gan Zang Bing Za Zhi. 2015 Aug 20;23(8):590-3. doi: 10.3760/cma.j.issn.1007-3418.2015.08.007. Chinese. PubMed PMID: 26447622. 3: Gu J, Sun R, Shen S, Yu Z. The curative effect of adefovir dipivoxil treating HBeAg negative chronic hepatitis B and treating HBeAg positive chronic hepatitis B combining interferon α-2b. Pak J Pharm Sci. 2015 Jul;28(4 Suppl):1493-7. PubMed PMID: 26431662. 4: Zhu H, Yuan X, Tang L, Hu P, Cai D, Ren F, Huang W. [Clinical analysis of Fanconi syndrome induced by adefovir dipivoxil]. Zhonghua Gan Zang Bing Za Zhi. 2015 Apr;23(4):302-3. Chinese. PubMed PMID: 26427083. 5: Chen Z, Ma X, Zhao Y, Wang J, Zhang Y, Zhu Y, Wang L, Chen C, Wei S, Yang Z, Gong M, Shen H, Bai Z, Guo Y, Niu M, Xiao X. Kushenin Combined with Nucleos(t)ide Analogues for Chronic Hepatitis B: A Systematic Review and Meta-Analysis. Evid Based Complement Alternat Med. 2015;2015:529636. doi: 10.1155/2015/529636. Epub 2015 Aug 11. Review. PubMed PMID: 26347789; PubMed Central PMCID: PMC4548141. 6: De Clercq E. Current treatment of hepatitis B virus infections. Rev Med Virol. 2015 Jul 23. doi: 10.1002/rmv.1849. [Epub ahead of print] PubMed PMID: 26205627. 7: Česnek M, Jansa P, Šmídková M, Mertlíková-Kaiserová H, Dračínský M, Brust TF, Pávek P, Trejtnar F, Watts VJ, Janeba Z. Bisamidate Prodrugs of 2-Substituted 9-[2-(Phosphonomethoxy)ethyl]adenine (PMEA, adefovir) as Selective Inhibitors of Adenylate Cyclase Toxin from Bordetella pertussis. ChemMedChem. 2015 Aug;10(8):1351-64. doi: 10.1002/cmdc.201500183. Epub 2015 Jul 1. PubMed PMID: 26136378. 8: Yao N, Wang C, Yu Z, Zhao K, Kang W, Liu Q, Dang B, Sun Y. [Efficacy and safety of telbivudine alone and combined with adefovir for the treatment of nucleos(t)ide-naive chronic hepatitis B in patients with high-level hepatitis B virus load]. Zhonghua Gan Zang Bing Za Zhi. 2015 Apr;23(4):250-3. doi: 10.3760/cma.j.issn.1007-3418.2015.04.004. Chinese. PubMed PMID: 26133814. 9: Wang Y, Shan X, Liang Z, Shan Y, Huang W, Zhang D, Zen A, Zhou X, Zhao Y, Gong X, Xu G, Zhang X, Chen J, Huang A. Deep sequencing analysis of HBV genotype shift and correlation with antiviral efficiency during adefovir dipivoxil therapy. PLoS One. 2015 Jun 25;10(6):e0131337. doi: 10.1371/journal.pone.0131337. eCollection 2015. PubMed PMID: 26110616; PubMed Central PMCID: PMC4482366. 10: Yang J, Chen G, Chen X, Zhang H, Jiang D, Yang G. Initial combination anti-viral therapy with lamivudine and adefovir dipivoxil decreases short-term fatality rate of hepatitis-B-virus-related acute-on-chronic liver failure. Virol J. 2015 Jun 24;12:97. doi: 10.1186/s12985-015-0323-3. PubMed PMID: 26104153; PubMed Central PMCID: PMC4501091.

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