AMDOXOVIR

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H12N6O3
Molecular Weight	252.23
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

NC1=NC2=C(N=CN2[C@H]3CO[C@@H](CO)O3)C(N)=N1

InChI

InChIKey=RLAHNGKRJJEIJL-RFZPGFLSSA-N

InChI=1S/C9H12N6O3/c10-7-6-8(14-9(11)13-7)15(3-12-6)4-2-17-5(1-16)18-4/h3-5,16H,1-2H2,(H4,10,11,13,14)/t4-,5-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C9H12N6O3
Molecular Weight	252.23
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Amdoxovir is a guanosine analogue nucleoside reverse transcriptase inhibitor that is active in vitro against both HIV-1 and HBV. It is deaminated intracellularly by adenosine deaminase to dioxolane guanine (DXG). DXG-triphosphate, the active form of the drug, has greater activity than DAPD-triphosphate. Amdoxovir is under development (phase II study) for the treatment of HIV infection. Five subjects demonstrated lens opacities during the study, although baseline evaluations were not performed. Clinical studies of amdoxovir are currently on hold pending additional safety data.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
DNA polymerase/reverse transcriptase 10	Inhibitor 8,297	0.61 µM [IC50]
Adenosine deaminase 13	Substrate 661
Human immunodeficiency virus type 1 reverse transcriptase 67	Inhibitor 8,297	0.019 µM [Ki]
DNA polymerase beta 5	Inhibitor 8,297	32.0 µM [Ki]
DNA polymerase alpha subunit 9	Inhibitor 8,297	78.0 µM [Ki]
DNA polymerase gamma subunit 1 2	Inhibitor 8,297	4.3 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 151	Primary		Phase II 1,132	Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
499 ng/mL	500 mg 2 times / day multiple, oral		AMDOXOVIR plasma	Homo sapiens
1545 ng/mL	500 mg 2 times / day multiple, oral		1,3-DIOXOLANE GUANOSINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
1326 ng × h/mL	500 mg 2 times / day multiple, oral		AMDOXOVIR plasma	Homo sapiens
6834 ng × h/mL	500 mg 2 times / day multiple, oral		1,3-DIOXOLANE GUANOSINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.4 h	500 mg 2 times / day multiple, oral		AMDOXOVIR plasma	Homo sapiens
17.6 h	500 mg 2 times / day multiple, oral		1,3-DIOXOLANE GUANOSINE plasma	Homo sapiens

Doses

Doses

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Dose	Population	Adverse events
500 mg 2 times / day multiple, oral (unknown) Highest studied dose	unhealthy n = 8

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
BOC Sciences	145514-04-1	http://www.bocsci.com/description.asp?cas=145514-04-1
Compound Cloud	124088
MuseChem	M091480	https://www.musechem.com/product/M091480.html
eMolecules	109867526	https://orderbb.emolecules.com/search/#?query=109867526
eMolecules	76746369	https://orderbb.emolecules.com/search/#?query=76746369

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PubMed

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Title	Date	PubMed
1,3-dioxolanylpurine nucleosides (2R,4R) and (2R,4S) with selective anti-HIV-1 activity in human lymphocytes.	1993 Jan 8	8421287
Anti-HIV-1 activities of 1,3-dioxolane guanine and 2,6-diaminopurine dioxolane.	1999 Apr-May	10432704
Mechanism of action and in vitro activity of 1',3'-dioxolanylpurine nucleoside analogues against sensitive and drug-resistant human immunodeficiency virus type 1 variants.	1999 Oct	10508010
In vitro selection of mutations in the human immunodeficiency virus type 1 reverse transcriptase that decrease susceptibility to (-)-beta-D-dioxolane-guanosine and suppress resistance to 3'-azido-3'-deoxythymidine.	2000 Jul	10858331
Ribavirin and mycophenolic acid potentiate the activity of guanine- and diaminopurine-based nucleoside analogues against hepatitis B virus.	2000 Nov	11114413

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Patents

Sample Use Guides

In Vivo Use Guide

300 mg twice daily

Route of Administration: Oral

In Vitro Use Guide

Amdoxovir proved equipotent at inhibiting HBV replication in HepG2 2.2.15, HepAD79 and HepAD38 cells with EC50 13, 16 and 14 ug/ml respectively.

Substance Class	Chemical
Record UNII	54I81H0M9C
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

AMDOXOVIR

Official Name

English

(-)-DAPD

Common Name

English

amdoxovir [INN]

Common Name

English

DAPD

Code

English

AMDOXOVIR [USAN]

Common Name

English

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Classification Tree

Code System

Code

Reverse Transcriptase Inhibitor

NCI_THESAURUS

C97452

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Code System

Code

Type

Description

USAN

MM-19

PRIMARY

FDA UNII

54I81H0M9C

PRIMARY

ChEMBL

CHEMBL458876

PRIMARY

EVMPD

SUB20547

PRIMARY

INN

8124

PRIMARY

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Related Record

Type

Details


					859A956UY8

HUMAN IMMUNODEFICIENCY VIRUS TYPE 1

TARGET ORGANISM->INHIBITOR

Amount:

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Related Record

Type

Details


					54I81H0M9C

AMDOXOVIR

ACTIVE MOIETY

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SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2