ADEFOVIR

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)

HIDE SMILES / InChI

Molecular Formula	C8H12N5O4P
Molecular Weight	273.1857
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Multidrug resistance-associated protein 4 14	Inhibitor 8,297	133.0 µM [IC50]
Bile salt export pump 15	Inhibitor 8,297	46.0 µM [IC50]
Canalicular multispecific organic anion transporter 1 21	Inhibitor 8,297	133.0 µM [IC50]
Canalicular multispecific organic anion transporter 2 8	Inhibitor 8,297	133.0 µM [IC50]
DNA polymerase/reverse transcriptase 10	Inhibitor 8,297	0.1 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic hepatitis B 16	Primary		Approved 8,429	HEPSERA

C_max

Value	Dose	Co-administered	Analyte	Population
18.4 ng/mL	10 mg single, oral		ADEFOVIR plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
220 ng × h/mL	10 mg single, oral		ADEFOVIR plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
7.48 h	10 mg single, oral		ADEFOVIR plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
96%	10 mg single, oral		ADEFOVIR plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
10 mg 1 times / day multiple, oral Recommended	unhealthy, 12 - 17 years	Other AEs: Rhinorrhea, Sneezing...
0.3 mg/kg 1 times / day multiple, oral Recommended	unhealthy, 2 - 6 years
0.3 mg/kg 1 times / day multiple, oral Recommended	unhealthy, 7 - 11 years	Other AEs: Headache, Vertigo...

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AEs

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AE	Significance	Dose	Population
Blister	1 patient	10 mg 1 times / day multiple, oral Recommended	unhealthy, 12 - 17 years
Rhinorrhea	1 patient	10 mg 1 times / day multiple, oral Recommended	unhealthy, 12 - 17 years
Sneezing	1 patient	10 mg 1 times / day multiple, oral Recommended	unhealthy, 12 - 17 years
Disorder eye	1 patient	0.3 mg/kg 1 times / day multiple, oral Recommended	unhealthy, 7 - 11 years
Disturbance in attention	1 patient	0.3 mg/kg 1 times / day multiple, oral Recommended	unhealthy, 7 - 11 years

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587 substrate 1,737	inhibitor 1,767 substrate 1,037	inhibitor 1,852 substrate 1,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2C19 1,478 P-gp 1,461	OAT1 326 OCT2 355 MRP4 77 CYP1A2 1,054 CYP2C19 991 P-gp 1,537	CYP 76

Drug as perpetrator

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Target	Modality	Activity
CYP 147	inducer 1,573	inconclusive
P-gp 1,650	inhibitor 3,277	inconclusive
CYP1A2 1,692	inhibitor 3,277	no
CYP2C19 1,553	inhibitor 3,277	no
CYP2C9 1,819	inhibitor 3,277	no

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Drug as victim

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Target	Modality	Activity
P-gp 1,537	substrate 3,367	inconclusive
CYP1A2 1,054	substrate 3,367	no
CYP2C19 991	substrate 3,367	no
CYP2C9 1,037	substrate 3,367	no
CYP2D6 1,217	substrate 3,367	no

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:2469	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2469
ChemicalBook	CB2698137	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2698137
eMolecules	901335	https://www.emolecules.com/cgi-bin/more?vid=901335
ZINC	ZINC000021297308	http://zinc15.docking.org/substances/ZINC000021297308

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PubMed

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Title	Date	PubMed
Herpes simplex virus-specified DNA polymerase is the target for the antiviral action of 9-(2-phosphonylmethoxyethyl)adenine.	1991 Jan 5	1845964
Chemotherapy of feline immunodeficiency virus infection.	1991 Nov 15	1666108
Synthesis and antiviral activity of methyl derivatives of 9-[2-(phosphonomethoxy)ethyl]guanine.	1992 Aug 7	1323678
In vitro selection and molecular characterization of human immunodeficiency virus-1 resistant to non-nucleoside inhibitors of reverse transcriptase.	1992 Mar	1372083
Synthesis and in vitro evaluation of a phosphonate prodrug: bis(pivaloyloxymethyl) 9-(2-phosphonylmethoxyethyl)adenine.	1992 Sep	1332606

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Patents

Sample Use Guides

In Vivo Use Guide

One tablet containing 10 mg adefovir dipivoxil once daily orally

Route of Administration: Oral

In Vitro Use Guide

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
Record UNII	6GQP90I798
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

ADEFOVIR

Official Name

English

adefovir [INN]

Common Name

English

ADEFOVIR [VANDF]

Common Name

English

GS0393

Code

English

ADEFOVIR [USAN]

Common Name

English

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Classification Tree

Code System

Code

Analogs/Derivatives

NDF-RT

N0000175459

Nucleosides

NDF-RT

N0000175459

Reverse Transcriptase Inhibitor

NCI_THESAURUS

C97452

Antiviral: HBV

LIVERTOX

NBK548633

Established Pharmacologic Class

NDF-RT

N0000175656

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Code System

Code

Type

Description

CHEBI

134512

PRIMARY

INN

7313

PRIMARY

ChEMBL

CHEMBL484

PRIMARY

NCI_THESAURUS

C61526

PRIMARY

MERCK INDEX

m1409

PRIMARY

Merck Index

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Related Record

Type

Details


					77H9EM77P7

HEPATITIS B VIRUS

TARGET ORGANISM->INHIBITOR

Amount:


					I81U7H57XI

OAT-1

TRANSPORTER -> SUBSTRATE


					BQG94QJ69I

ABCC-4

TRANSPORTER -> SUBSTRATE


					I81U7H57XI

OAT-1

TRANSPORTER -> INHIBITOR

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Show entries

Related Record

Type

Details


					U6Q8Z01514

ADEFOVIR DIPIVOXIL

PRODRUG -> METABOLITE ACTIVE

Amount:


					GZE85Q9Q61

PRADEFOVIR

PRODRUG -> METABOLITE ACTIVE

Amount:

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Related Record

Type

Details


					6GQP90I798

ADEFOVIR

ACTIVE MOIETY

Amount:

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator