Identification

Generic Name
Nebularine
DrugBank Accession Number
DB04440
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 252.2267
Monoisotopic: 252.085854892
Chemical Formula
C10H12N4O4
Synonyms
  • N-D-Ribosylpurine
  • Purine nucleoside
  • Purine riboside

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAdenosine deaminaseNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Darbepoetin alfaThe risk or severity of Thrombosis can be increased when Darbepoetin alfa is combined with Nebularine.
ErythropoietinThe risk or severity of Thrombosis can be increased when Erythropoietin is combined with Nebularine.
Methoxy polyethylene glycol-epoetin betaThe risk or severity of Thrombosis can be increased when Methoxy polyethylene glycol-epoetin beta is combined with Nebularine.
PeginesatideThe risk or severity of Thrombosis can be increased when Peginesatide is combined with Nebularine.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleosides
Sub Class
Not Available
Direct Parent
Purine nucleosides
Alternative Parents
Glycosylamines / Pentoses / Purines and purine derivatives / Pyrimidines and pyrimidine derivatives / N-substituted imidazoles / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Oxacyclic compounds / Azacyclic compounds
show 4 more
Substituents
Alcohol / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Imidazopyrimidine / Monosaccharide
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
purine ribonucleoside (CHEBI:18255)
Affected organisms
Not Available

Chemical Identifiers

UNII
B8B604PS4P
CAS number
550-33-4
InChI Key
MRWXACSTFXYYMV-FDDDBJFASA-N
InChI
InChI=1S/C10H12N4O4/c15-2-6-7(16)8(17)10(18-6)14-4-13-5-1-11-3-12-9(5)14/h1,3-4,6-8,10,15-17H,2H2/t6-,7-,8-,10-/m1/s1
IUPAC Name
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(9H-purin-9-yl)oxolane-3,4-diol
SMILES
[H][C@]1(CO)O[C@@]([H])(N2C=NC3=CN=CN=C23)[C@]([H])(O)[C@]1([H])O

References

General References
Not Available
KEGG Compound
C01736
PubChem Compound
68368
PubChem Substance
46507074
ChemSpider
61656
BindingDB
50335291
ChEBI
18255
ChEMBL
CHEMBL1399702
ZINC
ZINC000003814314
PDBe Ligand
PUR

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2TerminatedTreatmentAcute Myeloid Leukemia (AML)1
Not AvailableCompletedNot AvailableMelanoma, Malignant1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)181 °CPhysProp
water solubility1E+005 mg/LMERCK (1989)
Predicted Properties
PropertyValueSource
Water Solubility16.8 mg/mLALOGPS
logP-0.99ALOGPS
logP-1.9ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)3.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.52 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.18 m3·mol-1ChemAxon
Polarizability23.51 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5193
Blood Brain Barrier+0.8419
Caco-2 permeable-0.87
P-glycoprotein substrateNon-substrate0.7028
P-glycoprotein inhibitor INon-inhibitor0.9767
P-glycoprotein inhibitor IINon-inhibitor0.9111
Renal organic cation transporterNon-inhibitor0.9415
CYP450 2C9 substrateNon-substrate0.812
CYP450 2D6 substrateNon-substrate0.8277
CYP450 3A4 substrateNon-substrate0.5748
CYP450 1A2 substrateNon-inhibitor0.8872
CYP450 2C9 inhibitorNon-inhibitor0.9628
CYP450 2D6 inhibitorNon-inhibitor0.967
CYP450 2C19 inhibitorNon-inhibitor0.9469
CYP450 3A4 inhibitorNon-inhibitor0.9882
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9683
Ames testNon AMES toxic0.876
CarcinogenicityNon-carcinogens0.93
BiodegradationNot ready biodegradable0.5979
Rat acute toxicity2.1732 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9802
hERG inhibition (predictor II)Non-inhibitor0.8942
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0gba-0960000000-02588b36be524da1fbdb
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0940000000-558c13580fe37e7be7cc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-1900000000-c0a60904cd95924d259f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dl-8900000000-dece14475c7e39a2463e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uxr-0790000000-52cdec17cf806f6a8d60
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0900000000-825da67e9ee8ead415d1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014l-9800000000-eeb587fff62d67752a0c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0uk9-0690000000-3132e9cf975c9d333807
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0900000000-30611d46c742b20458a6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0900000000-bf687a37f1a8fdee4b9f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0900000000-1ca445719eb772d826e5
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-2900000000-d4186191baed33ece266
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-00di-0900000000-fe942a1442dc2ba58705

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, an...
Gene Name
ADA
Uniprot ID
P00813
Uniprot Name
Adenosine deaminase
Molecular Weight
40764.13 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52