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Adefovir dipivoxil

CAT: 0804-HY-B0255-01Size: 50 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-B0255-01Size:50 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Adefovir dipivoxil is an orally active adenosine analog and Adefovir prodrug. Adefovir dipivoxil inhibits DNA synthesis, activates the ATR signaling pathway, and disrupts the KCTD12-CDK1 interaction. Adefovir dipivoxil has antiviral activity against PRV, HBV, and orthopoxviruses. Adefovir dipivoxil has inhibitory effects on both lamivudine-resistant and wild-type strains. Adefovir dipivoxil has antitumor activity against lung and colon cancer[1][2][3][4][5][6][7][8][9][10][11].
CAS Number
142340-99-6
Product Name Alternative
GS 0840
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
ATM/ATR; CDK; DNA/RNA Synthesis; HBV; HSV; Orthopoxvirus
Type
Reference compound
Related Pathways
Anti-infection; Cell Cycle/DNA Damage; PI3K/Akt/mTOR
Applications
COVID-19-anti-virus
Field of Research
Infection; Cancer
Assay Protocol
https://www.medchemexpress.com/Adefovir-dipivoxil.html
Purity
99.03
Solubility
DMSO : ≥ 100 mg/mL|H2O : 0.67 mg/mL (ultrasonic)
Smiles
NC1=C2N=CN(CCOCP(OCOC(C(C)(C)C)=O)(OCOC(C(C)(C)C)=O)=O)C2=NC=N1
Molecular Formula
C20H32N5O8P
Molecular Weight
501.47
Precautions
H302, H315, H319, H335
References & Citations
[1]Noble S, et al. Adefovir dipivoxil. Drugs. 1999;58 (3) :479-489.|[2]Buti M, et al. Adefovir dipivoxil. Drugs Today (Barc) . 2003;39 (2) :127-135.|[3]Mark N Prichard, et al. Orthopoxvirus targets for the development of antiviral therapies. Curr Drug Targets Infect Disord. 2005 Mar;5 (1) :17-28. |[4]Patel A, et al. Adefovir dipivoxil induces DNA replication stress and augments ATR inhibitor-related cytotoxicity. Int J Cancer. 2020 Sep 1;147 (5) :1474-1484.|[5]Maeng HJ, et al. Effects of 1α,25-dihydroxyvitamin D3 on transport and metabolism of adefovir dipivoxil and its metabolites in Caco-2 cells. Eur J Pharm Sci. 2012 Jun 14;46 (3) :149-66. |[6]Annaert P, et al. In vitro, ex vivo, and in situ intestinal absorption characteristics of the antiviral ester prodrug adefovir dipivoxil. J Pharm Sci. 2000 Aug;89 (8) :1054-62.|[7]Wang G, et al. Adefovir dipivoxil efficiently inhibits the proliferation of pseudorabies virus in vitro and in vivo. Antiviral Res. 2021 Feb;186:105014.|[8]Yang J, et al. Adefovir dipivoxil sensitizes colon cancer cells to vemurafenib by disrupting the KCTD12-CDK1 interaction. Cancer Lett. 2019 Jun 1;451:79-91.|[9]Julander JG, et al. Characterizing antiviral activity of adefovir dipivoxil in transgenic mice expressing hepatitis B virus. Antiviral Res. 2002 Jul;55 (1) :27-40. |[10]Cundy KC, et al. Oral formulations of adefovir dipivoxil: in vitro dissolution and in vivo bioavailability in dogs. J Pharm Sci. 1997 Dec;86 (12) :1334-8.|[11]Qaqish RB, et al. Adefovir dipivoxil: a new antiviral agent for the treatment of hepatitis B virus infection. Clin Ther. 2003 Dec;25 (12) :3084-99.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Adefovir Dipivoxil

Adefovir pivoxil is an organic phosphonate that is the dipivoxil ester of adefovir. A prodrug for adefovir, an HIV-1 reverse transcriptase inhibitor, adefovir pivoxil is used to treat chronic hepatitis B viral infection. It has a role as an antiviral drug, a prodrug, a nephrotoxic agent, a HIV-1 reverse transcriptase inhibitor and a DNA synthesis inhibitor. It is a member of 6-aminopurines, an ether, an organic phosphonate and a carbonate ester. It is functionally related to an adefovir.

CAS Number142340-99-6
PubChem CID60871
IUPAC Name[2-(6-aminopurin-9-yl)ethoxymethyl-(2,2-dimethylpropanoyloxymethoxy)phosphoryl]oxymethyl 2,2-dimethylpropanoate
Molecular FormulaC20H32N5O8P
Molecular Weight501.5
XLogP1.8
Topological Polar Surface Area167
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count12
Rotatable Bond Count15
Heavy Atom Count34
Formal Charge0
Complexity705
SMILES
CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N=CN=C21)N)OCOC(=O)C(C)(C)C
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)
InChIKey
WOZSCQDILHKSGG-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Adefovir Dipivoxil
CAS: 142340-99-6
CID: 60871
Formula: C20H32N5O8P
MW: 501.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight501.5
XLogP31.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count12
Rotatable Bond Count15
Exact Mass501.19884999
Monoisotopic Mass501.19884999
Topological Polar Surface Area167 Ų
Heavy Atom Count34
Formal Charge0
Complexity705
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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