Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H12N5O4P |
Molecular Weight | 273.1857 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC=NC2=C1N=CN2CCOCP(O)(O)=O
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)
Molecular Formula | C8H12N5O4P |
Molecular Weight | 273.1857 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: Description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/14498759
http://link.springer.com/chapter/10.1007%2F978-0-387-49785-3_33
Curator's Comment: Description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/14498759
http://link.springer.com/chapter/10.1007%2F978-0-387-49785-3_33
The potential antiviral effect of adefovir, an acyclic nucleoside phosphonate analog of 2′-deoxyadenosine monophosphate, was first studied by Holý and De Clercq in 1980s.
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1743128 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23956101 |
133.0 µM [IC50] | ||
Target ID: CHEMBL6020 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23956101 |
46.0 µM [IC50] | ||
Target ID: CHEMBL5748 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23956101 |
133.0 µM [IC50] | ||
Target ID: CHEMBL5918 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23956101 |
133.0 µM [IC50] | ||
Target ID: CHEMBL2362994 |
0.1 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | HEPSERA Approved UseHEPSERA 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 Date2002 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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 n = 15 Health Status: unhealthy Condition: chronic hepatitis B Age Group: 12 - 17 years Sex: M+F Population Size: 15 Sources: |
Other AEs: Rhinorrhea, Sneezing... Other AEs: Rhinorrhea (1 patient) Sources: Sneezing (1 patient) Blister (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, 2 - 6 years n = 13 Health Status: unhealthy Condition: chronic hepatitis B Age Group: 2 - 6 years Sex: M+F Population Size: 13 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 n = 19 Health Status: unhealthy Condition: chronic hepatitis B Age Group: 7 - 11 years Sex: M+F Population Size: 19 Sources: |
Other AEs: Headache, Vertigo... Other AEs: Headache (1 patient) Sources: Vertigo (1 patient) Disturbance in attention (1 patient) Disorder eye (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 n = 15 Health Status: unhealthy Condition: chronic hepatitis B Age Group: 12 - 17 years Sex: M+F Population Size: 15 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 n = 15 Health Status: unhealthy Condition: chronic hepatitis B Age Group: 12 - 17 years Sex: M+F Population Size: 15 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 n = 15 Health Status: unhealthy Condition: chronic hepatitis B Age Group: 12 - 17 years Sex: M+F Population Size: 15 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 n = 19 Health Status: unhealthy Condition: chronic hepatitis B Age Group: 7 - 11 years Sex: M+F Population Size: 19 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 n = 19 Health Status: unhealthy Condition: chronic hepatitis B Age Group: 7 - 11 years Sex: M+F Population Size: 19 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 n = 19 Health Status: unhealthy Condition: chronic hepatitis B Age Group: 7 - 11 years Sex: M+F Population Size: 19 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 n = 19 Health Status: unhealthy Condition: chronic hepatitis B Age Group: 7 - 11 years Sex: M+F Population Size: 19 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-449_Hepsera_biopharmr_P1.pdf Page: 6, 16 |
inconclusive | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-449_Hepsera_biopharmr_P2.pdf Page: 26.0 |
inconclusive | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-449_Hepsera_biopharmr_P1.pdf Page: 15.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-449_Hepsera_biopharmr_P1.pdf Page: 15.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-449_Hepsera_biopharmr_P1.pdf Page: 15.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-449_Hepsera_biopharmr_P1.pdf Page: 15.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-449_Hepsera_biopharmr_P1.pdf Page: 15.0 |
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-449_Hepsera_biopharmr_P2.pdf Page: 26.0 |
inconclusive | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-449_Hepsera_biopharmr_P1.pdf Page: 15.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-449_Hepsera_biopharmr_P1.pdf Page: 15.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-449_Hepsera_biopharmr_P1.pdf Page: 15.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-449_Hepsera_biopharmr_P1.pdf Page: 15.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-449_Hepsera_biopharmr_P1.pdf Page: 15.0 |
no | |||
no | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Intracellular metabolism and mechanism of anti-retrovirus action of 9-(2-phosphonylmethoxyethyl)adenine, a potent anti-human immunodeficiency virus compound. | 1991 Feb 15 |
|
Herpes simplex virus-specified DNA polymerase is the target for the antiviral action of 9-(2-phosphonylmethoxyethyl)adenine. | 1991 Jan 5 |
|
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 |
|
Chemotherapy of feline immunodeficiency virus infection. | 1991 Nov 15 |
|
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 |
|
6-[2-phosphonomethoxy)alkoxy]-2,4-diaminopyrimidines: a new class of acyclic pyrimidine nucleoside phosphonates with antiviral activity. | 2004 Oct |
|
Antiviral potential of a new generation of acyclic nucleoside phosphonates, the 6-[2-(phosphonomethoxy)alkoxy]-2,4-diaminopyrimidines. | 2005 |
|
Cross-resistance testing of next-generation nucleoside and nucleotide analogues against lamivudine-resistant HBV. | 2005 |
|
Deoxythreosyl phosphonate nucleosides as selective anti-HIV agents. | 2005 Apr 13 |
|
cycloSal-PMEA and cycloAmb-PMEA: potentially new phosphonate prodrugs based on the cycloSal-pronucleotide approach. | 2005 Dec 15 |
|
Acid-base and metal-ion-binding properties of 9-[2-(2-phosphonoethoxy)ethyl]adenine (PEEA), a relative of the antiviral nucleotide analogue 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA). An exercise on the quantification of isomeric complex equilibria in solution. | 2005 Jul 11 |
|
Novel acyclic nucleoside phosphonate analogues with potent anti-hepatitis B virus activities. | 2005 Mar |
|
In vitro activity of structurally diverse nucleoside analogs against human immunodeficiency virus type 1 with the K65R mutation in reverse transcriptase. | 2005 Mar |
|
Susceptibilities of several clinical varicella-zoster virus (VZV) isolates and drug-resistant VZV strains to bicyclic furano pyrimidine nucleosides. | 2005 Mar |
|
Spectrum of antiviral activity of o-(acetoxyphenyl)hept-2-ynyl sulphide (APHS). | 2005 May |
|
Introduction to chronic hepatitis B infection. | 2006 |
|
In vitro comparison of antiviral drugs against feline herpesvirus 1. | 2006 Apr 26 |
|
Inhibition of human liver microsomal cytochrome P450 activities by adefovir and tenofovir. | 2006 Dec |
|
The flounder organic anion transporter fOat has sequence, function, and substrate specificity similarity to both mammalian Oat1 and Oat3. | 2006 Dec |
|
Synthesis, in vitro antiviral evaluation, and stability studies of novel alpha-borano-nucleotide analogues of 9-[2-(phosphonomethoxy)ethyl]adenine and (R)-9-[2-(phosphonomethoxy)propyl]adenine. | 2006 Dec 28 |
|
Cellular and virological mechanisms of HBV drug resistance. | 2006 Feb |
|
Virologic response and resistance to adefovir in patients with chronic hepatitis B. | 2006 Feb |
|
Purine P1 receptor-dependent immunostimulatory effects of antiviral acyclic analogues of adenine and 2,6-diaminopurine. | 2006 Jan 13 |
|
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 |
|
Synthesis and antiviral evaluation of alkoxyalkyl esters of acyclic purine and pyrimidine nucleoside phosphonates against HIV-1 in vitro. | 2006 Oct |
|
Favorable outcome of liver transplantation despite a high hepatitis B virus replication: beyond the limits? | 2006 Sep |
|
Decompensated lamivudine-resistant hepatitis B virus-related cirrhosis treated successfully with adefovir dipivoxil allowing surgery for hepatocellular carcinoma. | 2007 |
|
Sequential emergence and clinical implications of viral mutants with K70E and K65R mutation in reverse transcriptase during prolonged tenofovir monotherapy in rhesus macaques with chronic RT-SHIV infection. | 2007 Apr 6 |
|
Successful treatment of an entecavir-resistant hepatitis B virus variant. | 2007 Dec |
|
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 |
|
Substrate overlap between Mrp4 and Abcg2/Bcrp affects purine analogue drug cytotoxicity and tissue distribution. | 2007 Jul 15 |
|
Redetection of HBV lamivudine-resistant mutations in a patient under entecavir therapy, who had been treated sequentially with nucleos(t)ide analogues. | 2007 Nov |
|
Some new acyclic nucleotide analogues as antiviral prodrugs: synthesis and bioactivities in vitro. | 2007 Nov 15 |
|
Secretion of antiretroviral chemokines by human cells cultured with acyclic nucleoside phosphonates. | 2007 Nov 21 |
|
In vitro drug susceptibility analysis of hepatitis B virus clinical quasispecies populations. | 2007 Oct |
|
Combination therapy in liver transplant recipients with hepatitis B virus without hepatitis B immune globulin. | 2007 Oct |
|
Side-effects of cidofovir in the treatment of recurrent respiratory papillomatosis. | 2008 Aug |
|
Prophylaxsis against recurrance of hepatitis B virus after liver transplantation: a retrospective analysis spanning 20 years. | 2008 Jan |
|
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 |
|
[Factors affecting initial virologic response and emergence of resistant mutants after adefovir treatment in lamivudine-resistant chronic hepatitis B patients]. | 2008 Mar |
|
Short-term overlap lamivudine treatment with adefovir dipivoxil in patients with lamivudine-resistant chronic hepatitis B. | 2008 Mar 21 |
|
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:53:18 GMT 2023
by
admin
on
Sat Dec 16 17:53:18 GMT 2023
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Record UNII |
6GQP90I798
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000175459
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NDF-RT |
N0000175459
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NCI_THESAURUS |
C97452
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LIVERTOX |
NBK548633
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N0000175656
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N0000009947
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NDF-RT |
N0000175459
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134512
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7313
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CHEMBL484
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C61526
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m1409
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6GQP90I798
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6GQP90I798
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16521
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C053001
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Adefovir
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Adefovir
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DB13868
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2469
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TARGET ORGANISM->INHIBITOR |
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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PRODRUG -> METABOLITE ACTIVE |
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PRODRUG -> METABOLITE ACTIVE |
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ACTIVE MOIETY |
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