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
Molecular Formula | C9H12N6O3 |
Molecular Weight | 252.23 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/15351346Curator's Comment: description was created based on several sources, including:
http://adisinsight.springer.com/drugs/800004771
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15351346
Curator's Comment: description was created based on several sources, including:
http://adisinsight.springer.com/drugs/800004771
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2362994 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10760047 |
0.61 µM [IC50] | ||
Target ID: CHEMBL2966 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11120959 |
|||
0.019 µM [Ki] | |||
Target ID: CHEMBL2392 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11120959 |
32.0 µM [Ki] | ||
Target ID: CHEMBL1828 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11120959 |
78.0 µM [Ki] | ||
Target ID: CHEMBL2732 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11120959 |
4.3 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
499 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20038617 |
500 mg 2 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
AMDOXOVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1545 ng/mL |
500 mg 2 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
1,3-DIOXOLANE GUANOSINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1326 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20038617 |
500 mg 2 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
AMDOXOVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
6834 ng × h/mL |
500 mg 2 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
1,3-DIOXOLANE GUANOSINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20038617 |
500 mg 2 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
AMDOXOVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
17.6 h |
500 mg 2 times / day multiple, oral dose: 500 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
1,3-DIOXOLANE GUANOSINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
1,3-dioxolanylpurine nucleosides (2R,4R) and (2R,4S) with selective anti-HIV-1 activity in human lymphocytes. | 1993 Jan 8 |
|
Perspectives for the treatment of hepatitis B virus infections. | 1999 Jul |
|
Highlights in the development of new antiviral agents. | 2002 Apr |
|
Novel use of a guanosine prodrug approach to convert 2',3'-didehydro-2',3'-dideoxyguanosine into a viable antiviral agent. | 2002 Mar |
|
Gateways to clinical trials. March 2003. | 2003 Mar |
|
In vitro combination of amdoxovir and the inosine monophosphate dehydrogenase inhibitors mycophenolic acid and ribavirin demonstrates potent activity against wild-type and drug-resistant variants of human immunodeficiency virus type 1. | 2004 Nov |
|
Anabolism of amdoxovir: phosphorylation of dioxolane guanosine and its 5'-phosphates by mammalian phosphotransferases. | 2004 Nov 1 |
|
New nucleoside reverse transcriptase inhibitors for the treatment of HIV infections. | 2004 Oct |
|
New targets and new drugs in the treatment of HIV. | 2005 Jul |
|
Gateways to clinical trials. | 2005 Jun |
|
Emerging anti-HIV drugs. | 2005 May |
|
Mechanism of anti-human immunodeficiency virus activity of beta-D-6-cyclopropylamino-2',3'-didehydro-2',3'-dideoxyguanosine. | 2005 May |
|
Gateways to clinical trials. | 2007 Dec |
|
Determination of 19 antiretroviral agents in pharmaceuticals or suspected products with two methods using high-performance liquid chromatography. | 2007 May 1 |
|
The use of beta-D-2,6-diaminopurine dioxolane with or without mycophenolate mofetil in drug-resistant HIV infection. | 2007 Oct 1 |
|
Synthesis and anti-HIV activity of (-)-beta-D-(2R,4R)-1,3-dioxolane-2,6-diamino purine (DAPD) (amdoxovir) and (-)-beta-D-(2R,4R)-1,3-dioxolane guanosine (DXG) prodrugs. | 2007 Sep |
|
Simultaneous quantification of 9-(beta-D-1,3-dioxolan-4-yl)guanine, Amdoxovir and Zidovudine in human plasma by liquid chromatography-tandem mass spectrometric assay. | 2009 Nov 1 |
|
Antiviral activity and tolerability of amdoxovir with zidovudine in a randomized double-blind placebo-controlled study in HIV-1-infected individuals. | 2010 |
|
New trends in nucleoside biotechnology. | 2010 Jul |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16964830
300 mg twice daily
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10760047
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
Created
by
admin
on
Edited
Sat Dec 16 18:04:04 UTC 2023
by
admin
on
Sat Dec 16 18:04:04 UTC 2023
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Record UNII |
54I81H0M9C
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Record Status |
Validated (UNII)
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Record Version |
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-
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NCI_THESAURUS |
C97452
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MM-19
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54I81H0M9C
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CHEMBL458876
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SUB20547
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8124
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C098393
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100000085765
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145514-04-1
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124088
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C76927
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DB06619
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DTXSID801027435
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AMDOXOVIR
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Related Record | Type | Details | ||
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TARGET ORGANISM->INHIBITOR |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |