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A9730

Sigma-Aldrich

Adefovir dipivoxil

Synonym(s):

9-(2[bis(Pivaloyloxymethoxy)phosphorylmethoxy]ethyl)adenine

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About This Item

Empirical Formula (Hill Notation):
C20H32N5O8P
CAS Number:
142340-99-6
Molecular Weight:
501.47
MDL number:
MFCD00869897
UNSPSC Code:
51102829
PubChem Substance ID:
329771057
NACRES:
NA.76

biological source

synthetic

assay

≥98% (HPLC)

form

solid

solubility

ethanol: 50 mg/mL

antibiotic activity spectrum

viruses

mode of action

enzyme | inhibits

storage temp.

−20°C

SMILES string

CC(C)(C)C(=O)OCOP(=O)(COCCn1cnc2c(N)ncnc12)OCOC(=O)C(C)(C)C

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)

InChI key

WOZSCQDILHKSGG-UHFFFAOYSA-N

Biochem/physiol Actions

Adefovir is an antiviral acyclic nucleoside phosphonate (ANP) analog that works by blocking reverse transcriptase. It is an inhibitor of duck hepatitis B virus (DHBV) replication that inhibits covalently closed circular DNA (CCC DNA) amplification. Cytotxicity is induced by Human Renal Organic Anion Transporter 1 (hOAT1). Adefovir is an Inhibitor of edema factor (EF)-induced cAMP accumulation and changes in cytokine production in mouse primary macrophages .

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Julien Delmas et al.
Antimicrobial agents and chemotherapy, 46(2), 425-433 (2002-01-18)
The elimination of viral covalently closed circular DNA (CCC DNA) from the nucleus of infected hepatocytes is an obstacle to achieving sustained viral clearance during antiviral therapy of chronic hepatitis B virus (HBV) infection. The aim of our study was
A Takeda et al.
Journal of viral hepatitis, 14(2), 75-88 (2007-01-25)
Standard treatments for chronic hepatitis B (CHB) include interferon-alpha (IFN-alpha) and lamivudine (LAM), but these are associated with adverse effects and viral resistance, respectively. The aim of this systematic review and economic evaluation was to assess the clinical effectiveness and
M Danta et al.
International journal of clinical practice, 58(9), 877-886 (2004-11-09)
Adefovir dipivoxil (ADF) is a novel acyclic nucleoside analogue that has recently been approved for the treatment of chronic hepatitis B virus (HBV). Adefovir was initially assessed at higher doses for the treatment of human immunodeficiency virus (HIV) infection. However
Andrea Puhar et al.
PloS one, 3(10), e3564-e3564 (2008-10-30)
Anthrax edema toxin (EdTx) is an adenylate cyclase which operates in the perinuclear region of host cells. However, the action of EdTx is poorly understood, especially at molecular level. The ability of EdTx to modulate cAMP-dependent signaling was studied in
Selective inhibition of anthrax edema factor by adefovir, a drug for chronic hepatitis B virus infection.
Yuequan Shen, Natalia L. Zhukovskaya, et. Al
Proceedings of the National Academy of Sciences of the USA, 101, 3234-3247 (2004)
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