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 |
---|---|---|
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 |
|
Ribavirin and mycophenolic acid potentiate the activity of guanine- and diaminopurine-based nucleoside analogues against hepatitis B virus. | 2000 Nov |
|
In vitro susceptibilities of wild-type or drug-resistant hepatitis B virus to (-)-beta-D-2,6-diaminopurine dioxolane and 2'-fluoro-5-methyl-beta-L-arabinofuranosyluracil. | 2001 Sep |
|
Inhibitory activity of dioxolane purine analogs on wild-type and lamivudine-resistant mutants of hepadnaviruses. | 2002 Sep |
|
[Antiretroviral therapy 2003. The current status]. | 2003 Apr 28 |
|
Dioxolane guanosine 5'-triphosphate, an alternative substrate inhibitor of wild-type and mutant HIV-1 reverse transcriptase. Steady state and pre-steady state kinetic analyses. | 2003 May 23 |
|
Anabolism of amdoxovir: phosphorylation of dioxolane guanosine and its 5'-phosphates by mammalian phosphotransferases. | 2004 Nov 1 |
|
New targets and new drugs in the treatment of HIV. | 2005 Jul |
|
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 |
|
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 |
|
Raltegravir is a potent inhibitor of XMRV, a virus implicated in prostate cancer and chronic fatigue syndrome. | 2010 Apr 1 |
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
Sun Dec 18 21:19:28 UTC 2022
by
admin
on
Sun Dec 18 21:19:28 UTC 2022
|
Record UNII |
54I81H0M9C
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C97452
Created by
admin on Sun Dec 18 21:19:28 UTC 2022 , Edited by admin on Sun Dec 18 21:19:28 UTC 2022
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
MM-19
Created by
admin on Sun Dec 18 21:19:28 UTC 2022 , Edited by admin on Sun Dec 18 21:19:28 UTC 2022
|
PRIMARY | |||
|
54I81H0M9C
Created by
admin on Sun Dec 18 21:19:28 UTC 2022 , Edited by admin on Sun Dec 18 21:19:28 UTC 2022
|
PRIMARY | |||
|
CHEMBL458876
Created by
admin on Sun Dec 18 21:19:28 UTC 2022 , Edited by admin on Sun Dec 18 21:19:28 UTC 2022
|
PRIMARY | |||
|
SUB20547
Created by
admin on Sun Dec 18 21:19:28 UTC 2022 , Edited by admin on Sun Dec 18 21:19:28 UTC 2022
|
PRIMARY | |||
|
8124
Created by
admin on Sun Dec 18 21:19:28 UTC 2022 , Edited by admin on Sun Dec 18 21:19:28 UTC 2022
|
PRIMARY | |||
|
C098393
Created by
admin on Sun Dec 18 21:19:28 UTC 2022 , Edited by admin on Sun Dec 18 21:19:28 UTC 2022
|
PRIMARY | |||
|
145514-04-1
Created by
admin on Sun Dec 18 21:19:28 UTC 2022 , Edited by admin on Sun Dec 18 21:19:28 UTC 2022
|
PRIMARY | |||
|
124088
Created by
admin on Sun Dec 18 21:19:28 UTC 2022 , Edited by admin on Sun Dec 18 21:19:28 UTC 2022
|
PRIMARY | |||
|
C76927
Created by
admin on Sun Dec 18 21:19:28 UTC 2022 , Edited by admin on Sun Dec 18 21:19:28 UTC 2022
|
PRIMARY | |||
|
DB06619
Created by
admin on Sun Dec 18 21:19:28 UTC 2022 , Edited by admin on Sun Dec 18 21:19:28 UTC 2022
|
PRIMARY | |||
|
DTXSID801027435
Created by
admin on Sun Dec 18 21:19:28 UTC 2022 , Edited by admin on Sun Dec 18 21:19:28 UTC 2022
|
PRIMARY | |||
|
AMDOXOVIR
Created by
admin on Sun Dec 18 21:19:28 UTC 2022 , Edited by admin on Sun Dec 18 21:19:28 UTC 2022
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
TARGET ORGANISM->INHIBITOR |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |