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

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
Structure of AMDOXOVIR

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 TargetPharmacologyConditionPotency
0.61 µM [IC50]
0.019 µM [Ki]
32.0 µM [Ki]
78.0 µM [Ki]
4.3 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
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

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

PubMed

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