Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H11N5O4 |
Molecular Weight | 253.2147 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H]1O[C@H](C[C@@H]1N=[N+]=[N-])N2C=CC(=O)NC2=O
InChI
InChIKey=ZSNNBSPEFVIUDS-SHYZEUOFSA-N
InChI=1S/C9H11N5O4/c10-13-12-5-3-8(18-6(5)4-15)14-2-1-7(16)11-9(14)17/h1-2,5-6,8,15H,3-4H2,(H,11,16,17)/t5-,6+,8+/m0/s1
Molecular Formula | C9H11N5O4 |
Molecular Weight | 253.2147 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 1 |
Optical Activity | UNSPECIFIED |
Navuridine (AzddU) is a nucleoside analogue which demonstrated significant anti-HIV activity and low toxicity in preclinical studies. The drug was originally developed by University of Georgia. Navuridine is a dideoxyuridine inhibitor of HIV reverse transcriptase that is related to zidovudine. Navuridine exhibits a relatively short half-life and incomplete oral bioavailability and has not been developed into a clinical drug.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2328158
Curator's Comment: Navuridine (AzddU) and AZT penetrated the cerebrospinal fluid (CSF) with concentration ratios in CSF:serum ranging from 0.05 to 0.25 one hour after drug administration in rhesus monkeys.
Originator
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Replication of human immunodeficiency virus in monocytes. Granulocyte/macrophage colony-stimulating factor (GM-CSF) potentiates viral production yet enhances the antiviral effect mediated by 3'-azido-2'3'-dideoxythymidine (AZT) and other dideoxynucleoside congeners of thymidine. | 1989 Mar 1 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2328158
Rhesus monkeys: Oral absorption of Navuridine (AzddU) was virtually complete after 60 mg/kg. However, bioavailability of both nucleosides was markedly lower (less than 50%) after 200 mg/kg.
Young adult male rhesus monkeys weighing 5-6 kg were used for all intravenous and oral studies.
Each monkey received a single dose of AzddU or AZT. AzddU, 60 mg/kg, was administered intravenously (20 ml) as a bolus to three monkeys (563D, AP21, and RJN2) and 60 mg/kg AZT was similarly
administered to one monkey (N785). For oral bioavailability studies, each of two monkeys received
60 mg/kg (AP19 and RKOl) or 200 mg/kg (634D and N854) AzddU in 50 ml water by gastric
intubation. One monkey received 60 mg/kg (RFL1) AZT orally and two monkeys were given 200
mg/kg (231D and AP17) AZT orally.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2480079
Navuridine (AzddU) inhibited HIV-1 replication in human peripheral blood mononuclear (PBM) cells in the 0.18 to 0.46 uM range.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:32:52 GMT 2023
by
admin
on
Fri Dec 15 15:32:52 GMT 2023
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Record UNII |
PS28W65479
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Record Status |
Validated (UNII)
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Record Version |
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FDA ORPHAN DRUG |
39889
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NCI_THESAURUS |
C1557
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NCI_THESAURUS |
C97452
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DTXSID901004737
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84472-85-5
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C058803
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380882
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55262
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PS28W65479
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8002
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CHEMBL591804
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C83920
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300000034237
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