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Compound Detail

CHEMBL515914

AZARIBINE
💊 Approved Drug
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💊 Approved Drug
CC(=O)OC[C@H]1O[C@@H](n2ncc(=O)[nH]c2=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL515914
Name AZARIBINE
Phase Approved
Structure Type MOL
InChI Key QQOBRRFOVWGIMD-OJAKKHQRSA-N

Known Names

6-azauridine 2',3',5'-triacetate Azaribina Azaribine CB 304 CB-304 NSC-67239 Triazure
1
Targets
1
Activities
1
Assay Types
0
PK Parameters
20
Publications
7
Known Names
1
Mechanisms

Molecular Properties

371.3
MW (Da)
-1.74
ALogP
11
HBA
1
HBD
155.9
PSA (Ų)
0.47
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Single Enantiomer

Flags

Withdrawn Natural Product
USAN Stem -ribine
USAN Year 1968

Extended Properties

Molecular Formula C14H17N3O9
MW 371.30
Aromatic Rings 1
Heavy Atoms 26
NP-Likeness 0.70

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Uridine 5'-monophosphate synthase inhibitor INHIBITOR Uridine 5'-monophosphate synthase ✓ ✓

Drug Warnings

Withdrawn
vascular toxicity
Thromboembolism
Country: United States; Mauritius; Saudi Arabia   Year: 1976
Withdrawn
General Warning
Adverse effect
Country: United States; Mauritius; Saudi Arabia   Year: 1976

Activity Summary

IC50 1 meas. best 5.01

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 5.01 5.01 9792.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 9792.0 nM 5.01 PUBCHEM_BIOASSAY: Anti-Viral Drugs Against Arbovirus Infections, a Confirmatory ... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 214
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
37468498 10.1038/s41467-023-40064-9 Acetylcholinesterase 1
37468498 10.1038/s41467-023-40064-9 cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A 1
37468498 10.1038/s41467-023-40064-9 Vascular endothelial growth factor receptor 2 1
37468498 10.1038/s41467-023-40064-9 Amine oxidase [flavin-containing] A 1
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 1
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent serotonin transporter 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent noradrenaline transporter 1
18834112 10.1021/jm800656v Amine oxidase [flavin-containing] A 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent dopamine transporter 1
37468498 10.1038/s41467-023-40064-9 Voltage-gated inwardly rectifying potassium channel KCNH2 1
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 1
- 10.1101/2020.04.03.023846 SARS-CoV-2 1
20020916 10.1080/15376510701857262 Phospholipidosis 1

Data from ChEMBL 36 via Core Engine