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[CAS NO. 106941-25-7] Adefovir

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Catalog:	HY-B1826
Brand:	MCE
CAS:	106941-25-7

Overview

MDL	MFCD00866943
Molecular Weight	273.19
Molecular Formula	C8H12N5O4P
SMILES	NC1=C2N=CN(CCOCP(O)(O)=O)C2=NC=N1

For research use only. We do not sell to patients.

1 Publications Citing Use of MCE

[1]Molecules. 2022 May 18;27(10):3223.

Summary

Adefovir (GS-0393) is an adenosine monophosphate analog antiviral agent that after intracellular conversion to Adefovir diphosphate inhibits HBV DNA polymerase . Adefovir has an IC ₅₀ of 0.7 μM against HBV in the HepG2.2.15 cell line. Adefovir has good antiviral activity against several viruses, including HBV and herpesviruses ^[1] ^[2] ^[3] .

IC50 & Target

HBV ^[1] ^[2] ^[3] ;
DNA polymerase ^[1] ^[2]

In Vitro

Studies to elucidate the mechanism of action of Adefovir against herpesvirus replication reveals that the phosphorylation of Adefovir occurred intracellularly and is carried out by host cellular enzymes. The diphosphorylated derivatives of Adefovir targeted the viral DNA polymerase and also acted as DNA chain terminators. Adenylate kinase is shown to be responsible for the first phosphorylation, which was followed by ADP kinase and creatine kinase, forming Adefovir diphosphate ^[1] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Unaffected by food, Adefovir achieves 60% oral bioavailability. Its half-life is 12-30 hours and Adefovir undergoes renal excretion without significant metabolites. Adefovir does not substantially affect the cytochrome P450 system ^[3] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Clinical Trial

NCT Number	Sponsor	Condition	Start Date	Phase
NCT01300234	GlaxoSmithKline	Hepatitis B	March 30, 2011	Phase 3
NCT00986778	Bristol-Myers Squibb	Hepatitis B, Chronic	December 2009	Phase 4
NCT00002326	Gilead Sciences\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 1
NCT01834508	Nanfang Hospital of Southern Medical University\|Major Science and Technology Special Project of China 12th Five-year	Chronic Hepatitis B	March 2013	Phase 4
NCT01732367	Keimyung University Dongsan Medical Center\|Kyungpook National University Hospital\|Daegu Catholic University Medical Center\|DongGuk University\|Pusan National University Hospital\|Yeungnam University Hospital	Chronic Hepatitis B	November 2012	Phase 4
NCT02743260	University of Cologne\|Umm Al-Qura University\|Institute for Biomedical and Pharmaceutical Research (IBMP), Nürnberg-Heroldsberg, Germany	Healthy	April 2016	Phase 4
NCT01436539	Jun Cheng\|Sanofi\|Fujian Cosunter Pharmaceutical Co. Ltd\|Capital Medical University	Chronic Hepatitis B	September 2011	Phase 4
NCT00441974	GlaxoSmithKline	Chronic Hepatitis B	December 2006	Phase 4
NCT00002346	Gilead Sciences\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 1
NCT02075294	Ying-Jie Ji\|Beijing 302 Hospital	Hepatitis B, Chronic	January 2010
NCT00513968	Genexine, Inc.	Chronic Hepatitis B	July 2007	Phase 1
NCT00371761	Merck Sharp & Dohme LLC	Hepatitis B, Chronic (CHB)	September 2006	Phase 3
NCT00071201	Gilead Sciences	Chronic Hepatitis B	June 2003	Phase 3
NCT00051077	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections\|Hepatitis B\|Hepatitis C		Phase 2
NCT00605384	Bristol-Myers Squibb	Chronic Hepatitis B	August 2008	Phase 3
NCT02560649	Ruijin Hospital	Chronic Hepatitis B	May 2015	Phase 4
NCT03236584	Uijeongbu St. Mary Hospital	Proportion of Patients With a Sustained Virological Response (Serum HBV DNA <20 IU+mL) at Week 48	September 1, 2015	Phase 3
NCT01264133	Bukwang Pharmaceutical	Chronic Hepatitis B	September 2009	Phase 4
NCT00065507	Bristol-Myers Squibb	Hepatitis B	August 2003	Phase 3
NCT01720238	Beijing Friendship Hospital\|Peking University First Hospital\|Peking University People´s Hospital\|Beijing YouAn Hospital\|Beijing Tiantan Hospital\|Beijing Ditan Hospital\|Peking Union Medical College Hospital\|Beijing 302 Hospital	Liver Cirrhosis\|Hepatitis B	March 2012
NCT00208728	Emory University	Pediatric\|Cardiac Surgery	May 2003	Not Applicable
NCT01863589	GlaxoSmithKline	Hepatitis B	February 2005
NCT01146808	Columbia University\|Gilead Sciences	Hepatitis B\|Liver Transplantation	March 2006	Phase 1\|Phase 2
NCT01799486	Lin Bingliang\|Novartis\|Sun Yat-sen University	HBV-related Liver Cirrhosis	February 2013	Phase 4
NCT00002206	Gilead Sciences\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 1
NCT00002184	Gilead Sciences\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 2
NCT00661076	Hoffmann-La Roche	Hepatitis B, Chronic	August 2008	Phase 3
NCT00641082	Bukwang Pharmaceutical	HBeAg(-) Chronic Hepatitis B With Compensated Liver Function	February 2008	Phase 4
NCT00023153	National Institute of Allergy and Infectious Diseases (NIAID)\|National Institutes of Health Clinical Center (CC)	HIV Infections\|Chronic Hepatitis B	August 2001	Phase 3
NCT00753467	Huntington Medical Research Institutes\|InterMune	Hepatitis B	September 2008	Phase 2
NCT00187746	University of California, San Francisco	Other Conditions That May Be A Focus of Clinical Attention	August 2005	Phase 4
NCT00960518	Tongji University\|Interventional Radiology Research Group, Shanghai Radiology Society	Hepatitis B Virus\|Hepatocellular Carcinoma	August 2009	Phase 2
NCT00496158	Pharmasset	Chronic Hepatitis\|Hepatitis B	August 2007	Phase 3
NCT00115245	Novartis\|Novartis Pharmaceuticals	Chronic Hepatitis B	November 2004	Phase 3
NCT02366208	Jiangsu Hansoh Pharmaceutical Co., Ltd.\|Nanjing Medical University	Hepatitis B, Chronic	May 2011	Phase 2
NCT00810524	Sun Yat-sen University	Hepatitis B, Chronic	January 2007	Phase 4
NCT03801759	Akebia Therapeutics	Drug Interaction Potentiation	July 20, 2018	Phase 1
NCT00455091	National Health Research Institutes, Taiwan\|National Taiwan University Hospital\|Chang Gung Memorial Hospital\|Taipei Veterans General Hospital, Taiwan\|Mackay Memorial Hospital\|Taichung Veterans General Hospital\|Changhua Christian Hospital\|National Cheng-Kung University Hospital\|Kaohsiung Veterans General Hospital.\|Kaohsiung Medical University	Hepatocellular Carcinoma	May 2007
NCT00042393	Gilead Sciences	Chronic Hepatitis B
NCT00002234	Gilead Sciences\|Bristol-Myers Squibb\|Glaxo Wellcome\|Dupont Applied Biosciences	HIV Infections		Phase 2
NCT00410202	Bristol-Myers Squibb	Hepatitis B, Chronic	March 2008	Phase 3
NCT01581242	Bukwang Pharmaceutical	Healthy	April 2012	Phase 1
NCT01192854	Eisai Co., Ltd.\|Eisai Inc.	Chronic Hepatitis B	February 2010	Phase 3
NCT00376259	Novartis	Hepatitis B	January 2007	Phase 3
NCT00230490	Bausch Health Americas, Inc.	Hepatitis B, Chronic	June 2005	Phase 2
NCT00922207	Hoffmann-La Roche	Hepatitis B, Chronic	May 7, 2010	Phase 4
NCT00002220	Merck Sharp & Dohme LLC\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 3
NCT01693679	Shao-quan Zhang\|Sun Yat-sen University	HBV-related Liver Cirrhosis	September 2012	Phase 4
NCT01329419	GlaxoSmithKline	Hepatitis B	August 2004
NCT00002128	Gilead Sciences\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 1
NCT00000912	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00307242	Thomas Jefferson University	Chronic Hepatitis B	June 17, 2005	Phase 4
NCT00230503	Bausch Health Americas, Inc.	Hepatitis B, Chronic	June 2004	Phase 2
NCT02598063	Hoffmann-La Roche	Hepatitis B, Chronic	October 2005	Phase 4
NCT00000892	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Not Applicable
NCT00409019	Novartis Pharmaceuticals\|Novartis	Chronic Hepatitis B		Phase 4
NCT00001082	National Institute of Allergy and Infectious Diseases (NIAID)	Cytomegalovirus Infections\|HIV Infections	December 1996	Phase 3
NCT02965859	Guangzhou Yipinhong Pharmaceutical CO.,LTD	Chronic Hepatitis B	December 2012	Phase 2
NCT01353742	GlaxoSmithKline	Hepatitis B, Chronic	February 21, 2011	Phase 1
NCT01086085	Hoffmann-La Roche\|Major Science and Technology Special Project of China Eleventh Five-year	Hepatitis B, Chronic	April 2010	Phase 4
NCT00002379	Gilead Sciences\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 2
NCT00403585	GlaxoSmithKline	Hepatitis B, Chronic\|Chronic Hepatitis B	July 2006	Phase 4
NCT02327416	Tongji Hospital\|Xiamen Amoytop Biotech Co., Ltd.	Hepatitis B, Chronic	October 2014	Phase 3
NCT00645294	Gilead Sciences	Hepatitis B	February 2003	Phase 1\|Phase 2
NCT01341743	Nanfang Hospital of Southern Medical University\|JiangSu Chia-Tai Tianqin Pharmacy Co.Ltd	Hepatitis B	December 2010	Phase 4
NCT02482272	Asan Medical Center	Hepatitis B, Chronic	May 2015	Phase 4
NCT02366247	Jiangsu Hansoh Pharmaceutical Co., Ltd.\|Nanjing Medical University	Hepatitis B, Chronic	August 2013	Phase 3
NCT00640588	Novartis Pharmaceuticals\|Novartis	Hepatitis B, Chronic	March 2008	Phase 3
NCT00023309	National Institute of Diabetes and Digestive and Kidney Diseases (NIDDK)\|National Institutes of Health Clinical Center (CC)	HBV (Hepatitis B Virus)\|Hepatitis B\|Hepatitis	August 2001	Phase 2
NCT00000885	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00001087	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 2
NCT00033163	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections\|Hepatitis B		Phase 2
NCT00798460	Inje University\|Bukwang Pharmaceutical	Chronic Hepatitis B	December 2008	Phase 4
NCT00347009	GlaxoSmithKline	Hepatitis B, Chronic\|Cirrhosis\|Fibrosis\|Chronic Hepatitis B	May 2005	Phase 4
NCT00973219	Academisch Medisch Centrum - Universiteit van Amsterdam (AMC-UvA)	Chronic Hepatitis B	September 2009	Not Applicable
NCT01521975	Third Affiliated Hospital, Sun Yat-Sen University\|Guangdong Provincial People´s Hospital\|Guangzhou 8th People´s Hospital	Hepatitis B, Chronic	January 1, 2011	Phase 4
NCT00644761	Gilead Sciences	Hepatitis B	February 2004	Phase 2
NCT01088009	Nanfang Hospital of Southern Medical University\|Major Science and Technology Special Project of China Eleventh Five-year\|GlaxoSmithKline	Compensated Chronic Hepatitis B	March 2010	Phase 4
NCT00002161	Gilead Sciences\|NIH AIDS Clinical Trials Information Service	HIV Infections		Not Applicable
NCT01829685	Nanfang Hospital of Southern Medical University\|Major Science and Technology Special Project of China Eleventh Five-year	Chronic Hepatitis B\|Inadequate Response\|Nucleos(t)Ide Analogues Treatment	March 2013	Phase 4
NCT00095121	Gilead Sciences	Chronic Hepatitis B	June 2004	Phase 3
NCT02826070	Nanfang Hospital of Southern Medical University\|Major Science and Technology Special Project of China Twelfth-Five-Year Project\|Novartis	Hepatitis B, Chronic	April 2015	Phase 4
NCT00013702	National Institute of Allergy and Infectious Diseases (NIAID)\|National Institutes of Health Clinical Center (CC)	Hepatitis B\|HIV Infection	March 2001	Phase 2
NCT00000843	National Institute of Allergy and Infectious Diseases (NIAID)	HIV Infections		Phase 1
NCT00672867	Bukwang Pharmaceutical	Patients With LC-B	December 2007	Phase 3
NCT00002219	Gilead Sciences\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 2
NCT02327689	Asian-Pacific Alliance of Liver Disease, Beijing\|Beijing Ditan Hospital\|Hebei Medical University Pharmaceutical Factory\|National Health and Family Planning Commission, P.R.China	Hepatitis B, Chronic\|Fibrosis	January 2015	Phase 4
NCT00002115	Gilead Sciences\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 1
NCT01139203	Shanghai Jiao Tong University School of Medicine\|Zhejiang University	Liver Transplantation\|Hepatitis B	August 2009	Not Applicable
NCT01023217	Asan Medical Center	Hepatitis B, Chronic	November 2009	Phase 4
NCT00002398	Gilead Sciences\|NIH AIDS Clinical Trials Information Service	HIV Infections		Not Applicable
NCT00096785	Bristol-Myers Squibb	Hepatitis B\|Chronic Disease	December 2004	Phase 3
NCT00324961	GlaxoSmithKline	Chronic Hepatitis B	January 2006	Phase 4
NCT01491295	Taipei Veterans General Hospital, Taiwan\|Kaohsiung Medical University Chung-Ho Memorial Hospital\|China Medical University Hospital\|Chi Mei Medical Hospital\|Chiayi Christian Hospital	Chronic Hepatitis B	September 2012	Phase 4
NCT01263002	Bukwang Pharmaceutical	Hepatitis B Associated Hepatocellular Carcinoma	June 2010	Phase 4
NCT01804387	Korea University	Chronic Hepatitis B	May 2011	Phase 4
NCT00002419	Gilead Sciences\|Glaxo Wellcome\|Dupont Applied Biosciences\|NIH AIDS Clinical Trials Information Service	HIV Infections		Phase 2
NCT00496002	Pharmasset	Chronic Hepatitis\|Hepatitis B	August 2007	Phase 3
NCT00489151	Hospital Authority, Hong Kong\|The University of Hong Kong	Hepatitis B	June 2005	Not Applicable
NCT00606099	Novartis	Chronic Hepatitis B	November 2007	Phase 4
NCT01595633	Yonsei University	Chronic Hepatitis B	March 2012	Phase 4
NCT00002426	Gilead Sciences\|NIH AIDS Clinical Trials Information Service	HIV Infections		Not Applicable

Appearance

Solid

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvent & Solubility

In Vitro:

0.1 M NaOH : 10 mg/mL ( 36.60 mM ; ultrasonic and adjust pH to 10 with NaOH)

H ₂ O : 1 mg/mL ( 3.66 mM ; ultrasonic and warming and heat to 60°C)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	3.6605 mL	18.3023 mL	36.6046 mL
5 mM	0.7321 mL	3.6605 mL	7.3209 mL
10 mM	0.3660 mL	1.8302 mL	3.6605 mL

* Please refer to the solubility information to select the appropriate solvent.

References

[1] X.-X.Zhou, et al. 7.11 - Deoxyribonucleic Acid Viruses: Antivirals for Herpesviruses and Hepatitis B Virus. Comprehensive Medicinal Chemistry II. Volume 7, 2007, Pages 295-327.
[2] Marcellin P, et al. Adefovir dipivoxil for the treatment of hepatitis B e antigen-positive chronic hepatitis B. N Engl J Med. 2003 Feb 27;348(9):808-16.
[3] Leah A.Burke, et al. 155 - Drugs to Treat Viral Hepatitis. Infectious Diseases. Volume 2, 2017, Pages 1327-1332.

Synonyms

Phosphonic acid, P-[[2-(6-amino-9H-purin-9-yl)ethoxy]methyl]-

Phosphonic acid, [[2-(6-amino-9H-purin-9-yl)ethoxy]methyl]-

P-[[2-(6-Amino-9H-purin-9-yl)ethoxy]methyl]phosphonic acid

9-(2-Phosphonylmethoxyethyl)adenine

PMEA

9-[2-(Phosphonomethoxy)ethyl]adenine

GS 0393

Adefovir

((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)phosphonicacid

[[2-(6-Amino-9H-purin-9-yl)ethoxy]methyl]phosphonic acid

2-(6-Aminopurin-9-yl)ethoxymethylphosphonic acid

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