U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C8H12N5O4P
Molecular Weight 273.1861
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ADEFOVIR

SMILES

C(COCP(=O)(O)O)n1cnc2c(N)ncnc21

InChI

InChIKey=SUPKOOSCJHTBAH-UHFFFAOYSA-N
InChI=1S/C8H12N5O4P/c9-7-6-8(11-3-10-7)13(4-12-6)1-2-17-5-18(14,15)16/h3-4H,1-2,5H2,(H2,9,10,11)(H2,14,15,16)

HIDE SMILES / InChI

Molecular Formula C8H12N5O4P
Molecular Weight 273.1861
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: http://link.springer.com/chapter/10.1007%2F978-0-387-49785-3_33

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. Oral adefovir dipivoxil is effective and generally well tolerated in HBeAg-positive and -negative patients chronically infected with wild-type or lamivudine-resistant HBV.

Originator

Curator's Comment:: (De Clercq et al., 1986, 1987; Holý et al., 1999, 2002)

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
HEPSERA

Approved Use

HEPSERA is indicated for the treatment of chronic hepatitis B in patients 12 years of age and older with evidence of active viral replication and either evidence of persistent elevations in serum aminotransferases (ALT or AST) or histologically active disease. This indication is based on histological, virological, biochemical, and serological responses in adult patients with HBeAg+ and HBeAg- chronic hepatitis B with compensated liver function, and with clinical evidence of lamivudine-resistant hepatitis B virus with either compensated or decompensated liver function. For patients 12 to <18 years of age, the indication is based on virological and biochemical responses in patients with HBeAg+ chronic hepatitis B virus infection with compensated liver function. HEPSERA is a nucleotide analogue indicated for the treatment of chronic hepatitis B in patients ≥12 years of age. (1)

Launch Date

1032480000000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
18.4 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ADEFOVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
220 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ADEFOVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.48 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ADEFOVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
96%
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ADEFOVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 12 - 17 years
Health Status: unhealthy
Age Group: 12 - 17 years
Sex: M+F
Sources:
Other AEs: Rhinorrhea, Sneezing...
Other AEs:
Rhinorrhea (1 patient)
Sneezing (1 patient)
Blister (1 patient)
Sources:
0.3 mg/kg 1 times / day multiple, oral
Recommended
Dose: 0.3 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 0.3 mg/kg, 1 times / day
Sources:
unhealthy, 2 - 6 years
Health Status: unhealthy
Age Group: 2 - 6 years
Sex: M+F
Sources:
0.3 mg/kg 1 times / day multiple, oral
Recommended
Dose: 0.3 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 0.3 mg/kg, 1 times / day
Sources:
unhealthy, 7 - 11 years
Health Status: unhealthy
Age Group: 7 - 11 years
Sex: M+F
Sources:
Other AEs: Headache, Vertigo...
Other AEs:
Headache (1 patient)
Vertigo (1 patient)
Disturbance in attention (1 patient)
Disorder eye (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Blister 1 patient
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 12 - 17 years
Health Status: unhealthy
Age Group: 12 - 17 years
Sex: M+F
Sources:
Rhinorrhea 1 patient
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 12 - 17 years
Health Status: unhealthy
Age Group: 12 - 17 years
Sex: M+F
Sources:
Sneezing 1 patient
10 mg 1 times / day multiple, oral
Recommended
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, 12 - 17 years
Health Status: unhealthy
Age Group: 12 - 17 years
Sex: M+F
Sources:
Disorder eye 1 patient
0.3 mg/kg 1 times / day multiple, oral
Recommended
Dose: 0.3 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 0.3 mg/kg, 1 times / day
Sources:
unhealthy, 7 - 11 years
Health Status: unhealthy
Age Group: 7 - 11 years
Sex: M+F
Sources:
Disturbance in attention 1 patient
0.3 mg/kg 1 times / day multiple, oral
Recommended
Dose: 0.3 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 0.3 mg/kg, 1 times / day
Sources:
unhealthy, 7 - 11 years
Health Status: unhealthy
Age Group: 7 - 11 years
Sex: M+F
Sources:
Headache 1 patient
0.3 mg/kg 1 times / day multiple, oral
Recommended
Dose: 0.3 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 0.3 mg/kg, 1 times / day
Sources:
unhealthy, 7 - 11 years
Health Status: unhealthy
Age Group: 7 - 11 years
Sex: M+F
Sources:
Vertigo 1 patient
0.3 mg/kg 1 times / day multiple, oral
Recommended
Dose: 0.3 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 0.3 mg/kg, 1 times / day
Sources:
unhealthy, 7 - 11 years
Health Status: unhealthy
Age Group: 7 - 11 years
Sex: M+F
Sources:
Overview

OverviewOther

Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Intracellular metabolism and mechanism of anti-retrovirus action of 9-(2-phosphonylmethoxyethyl)adenine, a potent anti-human immunodeficiency virus compound.
1991 Feb 15
Early therapy of feline leukemia virus infection (FeLV-FAIDS) with 9-(2-phosphonylmethoxyethyl)adenine (PMEA).
1991 Jul
9-[(2RS)-3-fluoro-2-phosphonylmethoxypropyl] derivatives of purines: a class of highly selective antiretroviral agents in vitro and in vivo.
1991 Jun 1
In vitro selection and molecular characterization of human immunodeficiency virus-1 resistant to non-nucleoside inhibitors of reverse transcriptase.
1992 Mar
Synthesis and in vitro evaluation of a phosphonate prodrug: bis(pivaloyloxymethyl) 9-(2-phosphonylmethoxyethyl)adenine.
1992 Sep
Selective activity of various antiviral compounds against HHV-7 infection.
1999 Aug
Hydroxyurea potentiates the antiherpesvirus activities of purine and pyrimidine nucleoside and nucleoside phosphonate analogs.
1999 Dec
Sensitivity of L-(-)2,3-dideoxythiacytidine resistant hepatitis B virus to other antiviral nucleoside analogues.
1999 Jun 15
Lamivudine, adefovir and tenofovir exhibit long-lasting anti-hepatitis B virus activity in cell culture.
2000 Jan
Drug resistance and drug combination features of the human immunodeficiency virus inhibitor, BCH-10652 [(+/-)-2'-deoxy-3'-oxa-4'-thiocytidine, dOTC].
2000 Jul
A new acyclic heterodinucleotide active against human immunodeficiency virus and herpes simplex virus.
2000 Sep
Antiviral agents active against human herpesviruses HHV-6, HHV-7 and HHV-8.
2001 Nov-Dec
Raman spectroscopy study of acid-base and structural properties of 9-[2-(phosphonomethoxy)ethyl]adenine in aqueous solutions.
2002
Novel nucleoside analogue MCC-478 (LY582563) is effective against wild-type or lamivudine-resistant hepatitis B virus.
2002 Aug
Fanconi syndrome and renal failure induced by tenofovir: a first case report.
2002 Dec
Dioxolane guanosine, the active form of the prodrug diaminopurine dioxolane, is a potent inhibitor of drug-resistant HIV-1 isolates from patients for whom standard nucleoside therapy fails.
2002 Jan 1
Antiretrovirus activity of a novel class of acyclic pyrimidine nucleoside phosphonates.
2002 Jul
Antivaccinia activities of acyclic nucleoside phosphonate derivatives in epithelial cells and organotypic cultures.
2002 Nov
Inhibitory activity of dioxolane purine analogs on wild-type and lamivudine-resistant mutants of hepadnaviruses.
2002 Sep
Antiviral activities of MCC-478, a novel and specific inhibitor of hepatitis B virus.
2002 Sep
In vitro activity of potential anti-poxvirus agents.
2003 Jan
Nickel(II), copper(II) and zinc(II) complexes of 9-[2- (phosphonomethoxy)ethyl]-8-azaadenine (9,8aPMEA), the 8-aza derivative of the antiviral nucleotide analogue 9-[2-(phosphonomethoxy)ethyl] adenine (PMEA). Quantification of four isomeric species in aqueous solution.
2004
Quantification of isomeric equilibria formed by metal ion complexes of 8-[2-(phosphonomethoxy)ethyl]-8-azaadenine (8,8aPMEA) and 9-[2-(phosphonomethoxy)ethyl]-8-azaadenine (9,8aPMEA). Derivatives of the antiviral nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA).
2004 Dec
Phosphorothioate di- and trinucleotides as a novel class of anti-hepatitis B virus agents.
2004 Jun
Synthesis and antiviral activity of 2,4-diamino-5-cyano-6-[2-(phosphonomethoxy)ethoxy]pyrimidine and related compounds.
2004 Jun 15
In vitro selection of drug-resistant varicella-zoster virus (VZV) mutants (OKA strain): differences between acyclovir and penciclovir?
2004 Mar
A novel class of phosphonate nucleosides. 9-[(1-phosphonomethoxycyclopropyl)methyl]guanine as a potent and selective anti-HBV agent.
2004 May 20
Combinations of adefovir with nucleoside analogs produce additive antiviral effects against hepatitis B virus in vitro.
2004 Oct
Cross-resistance testing of next-generation nucleoside and nucleotide analogues against lamivudine-resistant HBV.
2005
Introduction to chronic hepatitis B infection.
2006
Cellular and virological mechanisms of HBV drug resistance.
2006 Feb
Virologic response and resistance to adefovir in patients with chronic hepatitis B.
2006 Feb
In vivo effects of antiviral acyclic nucleoside phosphonate 9-[2-(phosphonomethoxy)ethyl]adenine (adefovir) on cytochrome P450 system of rat liver microsomes.
2006 May
Improved outcome of chronic hepatitis B after heart transplantation by long-term antiviral therapy.
2006 Nov
Favorable outcome of liver transplantation despite a high hepatitis B virus replication: beyond the limits?
2006 Sep
Pronounced in vitro and in vivo antiretroviral activity of 5-substituted 2,4-diamino-6-[2-(phosphonomethoxy)ethoxy] pyrimidines.
2007 Jan
Design and synthesis of novel bis(L-amino acid) ester prodrugs of 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) with improved anti-HBV activity.
2007 Jan 15
Side-effects of cidofovir in the treatment of recurrent respiratory papillomatosis.
2008 Aug
Living donor liver transplantation for hepatitis B associated liver diseases: a 10-year experience in a single center.
2008 Jul-Aug
The human multidrug resistance protein 4 (MRP4, ABCC4): functional analysis of a highly polymorphic gene.
2008 Jun
Permeation enhancer dodecyl 6-(dimethylamino)hexanoate increases transdermal and topical delivery of adefovir: influence of pH, ion-pairing and skin species.
2008 Nov
Gene induction for the treatment of methylmalonic aciduria.
2009 Apr
Telbivudine, a nucleoside analog inhibitor of HBV polymerase, has a different in vitro cross-resistance profile than the nucleotide analog inhibitors adefovir and tenofovir.
2009 Feb
Renal side effects of adefovir in hepatitis B virus-(HBV) positive kidney allograft recipients.
2009 Jan
Association of lamivudine-resistant mutational patterns with the antiviral effect of adefovir in patients with chronic hepatitis B.
2009 Mar
Patents

Sample Use Guides

One tablet containing 10 mg adefovir dipivoxil once daily orally
Route of Administration: Oral
The concentration of adefovir that inhibited 50% of viral DNA synthesis (EC50) in HBV transfected human hepatoma cell lines ranged from 0.2 to 2.5 uM.
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:01:50 UTC 2021
Edited
by admin
on Sat Jun 26 03:01:50 UTC 2021
Record UNII
6GQP90I798
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ADEFOVIR
INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
ADEFOVIR [INN]
Common Name English
ADEFOVIR [VANDF]
Common Name English
GS 0393
Code English
ADEFOVIR [USAN]
Common Name English
((2-(6-AMINO-9H-PURIN-9-YL)ETHOXY)METHYL)PHOSPHONIC ACID
Systematic Name English
PHOSPHONIC ACID, ((2-(6-AMINO-9H-PURIN-9-YL)ETHOXY)METHYL)-
Common Name English
PMEA
Common Name English
GS-0393
Code English
9-(2-(PHOSPHONOMETHOXY)ETHYL)ADENINE
Systematic Name English
ADEFOVIR [MI]
Common Name English
ADEFOVIR [WHO-DD]
Common Name English
9-(2-PHOSPHONYLMETHOXYETHYL)ADENINE
Common Name English
ADEFOVIR [MART.]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175459
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
NDF-RT N0000175459
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
NCI_THESAURUS C97452
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
LIVERTOX 16
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
NDF-RT N0000175656
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
NDF-RT N0000009947
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
NDF-RT N0000175459
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
Code System Code Type Description
INN
7313
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
PRIMARY
ChEMBL
CHEMBL484
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
PRIMARY
NCI_THESAURUS
C61526
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
PRIMARY
MERCK INDEX
M1409
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
PRIMARY Merck Index
FDA UNII
6GQP90I798
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
PRIMARY
EPA CompTox
106941-25-7
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
PRIMARY
CAS
106941-25-7
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
PRIMARY
RXCUI
16521
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
PRIMARY RxNorm
MESH
C053001
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
PRIMARY
LACTMED
Adefovir
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
PRIMARY
PUBCHEM
60172
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
PRIMARY
EVMPD
SUB05264MIG
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
PRIMARY
WIKIPEDIA
Adefovir
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
PRIMARY
DRUG BANK
DB13868
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
PRIMARY
HSDB
8079
Created by admin on Sat Jun 26 03:01:50 UTC 2021 , Edited by admin on Sat Jun 26 03:01:50 UTC 2021
PRIMARY
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