Alanosine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Alanosine
DrugBank Accession Number
DB05540
Background

An amino acid analogue and antibiotic derived from the bacterium Streptomyces alanosinicus with antimetabolite and potential antineoplastic activities.

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 149.1054
Monoisotopic: 149.043655727
Chemical Formula
C3H7N3O4
Synonyms
  • Alanosina
  • Alanosine
  • Alanosinum
  • L-Alanosine
External IDs
  • SDX-102

Pharmacology

Indication

Investigated for use/treatment in brain cancer and cancer/tumors (unspecified).

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

L-alanosine inhibits adenylosuccinate synthetase, which converts inosine monophospate (IMP) into adenylosuccinate, an intermediate in purine metabolism. L-alanosine-induced disruption of de novo purine biosynthesis is potentiated by methylthioadenosine phosphorylase (MTAP) deficiency.

TargetActionsOrganism
UAspartate carbamoyltransferase catalytic chainNot AvailableEscherichia coli (strain K12)
UAdenylosuccinate synthetase isozyme 2Not AvailableHumans
UAdenylosuccinate synthetase isozyme 1Not 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
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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
AmbroxolThe risk or severity of methemoglobinemia can be increased when Alanosine is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Alanosine is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Alanosine is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Alanosine is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Alanosine is combined with Bupivacaine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-alpha-amino acids
Alternative Parents
Organic N-nitroso compounds / Amino acids / N-organohydroxylamines / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Amine / Amino acid / Carbonyl group / Carboxylic acid / Hydrocarbon derivative / L-alpha-amino acid / Monocarboxylic acid or derivatives / N-organohydroxylamine / Organic n-nitroso compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
2CNI71214Y
CAS number
5854-93-3
InChI Key
MLFKVJCWGUZWNV-REOHCLBHSA-N
InChI
InChI=1S/C3H7N3O4/c4-2(3(7)8)1-6(10)5-9/h2,10H,1,4H2,(H,7,8)/t2-/m0/s1
IUPAC Name
(2S)-2-amino-3-[hydroxy(nitroso)amino]propanoic acid
SMILES
N[C@@H](CN(O)N=O)C(O)=O

References

General References
  1. Kindler HL, Burris HA 3rd, Sandler AB, Oliff IA: A phase II multicenter study of L-alanosine, a potent inhibitor of adenine biosynthesis, in patients with MTAP-deficient cancer. Invest New Drugs. 2009 Feb;27(1):75-81. doi: 10.1007/s10637-008-9160-1. Epub 2008 Jul 11. [Article]
  2. Huang Y, Dai Z, Barbacioru C, Sadee W: Cystine-glutamate transporter SLC7A11 in cancer chemosensitivity and chemoresistance. Cancer Res. 2005 Aug 15;65(16):7446-54. [Article]
PubChem Compound
22128
PubChem Substance
8166290
ChemSpider
20787
ChEMBL
CHEMBL452715
ZINC
ZINC000004214744
PDBe Ligand
AL0
Wikipedia
Alanosine
PDB Entries
2air

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
2CompletedTreatmentLung Cancer / Malignant Pleural Mesothelioma (MPM) / Pancreatic Cancer / Sarcomas1somestatusstop reasonjust information to hide
1CompletedTreatmentBrain and Central Nervous System Tumors1somestatusstop reasonjust information to hide

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
logP-3.6Chemaxon
pKa (Strongest Acidic)1.5Chemaxon
pKa (Strongest Basic)8.67Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area116.22 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity30.7 m3·mol-1Chemaxon
Polarizability11.94 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6523
Blood Brain Barrier-0.6928
Caco-2 permeable-0.6474
P-glycoprotein substrateNon-substrate0.6806
P-glycoprotein inhibitor INon-inhibitor0.9116
P-glycoprotein inhibitor IINon-inhibitor0.9908
Renal organic cation transporterNon-inhibitor0.9589
CYP450 2C9 substrateNon-substrate0.907
CYP450 2D6 substrateNon-substrate0.8242
CYP450 3A4 substrateNon-substrate0.6489
CYP450 1A2 substrateNon-inhibitor0.8735
CYP450 2C9 inhibitorNon-inhibitor0.8825
CYP450 2D6 inhibitorNon-inhibitor0.937
CYP450 2C19 inhibitorNon-inhibitor0.854
CYP450 3A4 inhibitorNon-inhibitor0.9525
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9913
Ames testAMES toxic0.804
CarcinogenicityNon-carcinogens0.607
BiodegradationNot ready biodegradable0.7679
Rat acute toxicity2.1600 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9844
hERG inhibition (predictor II)Non-inhibitor0.9319
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
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-002f-9100000000-f9d27b3b036b79ec3b58
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gb9-1900000000-c37f1f9ad13678f8378e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-9000000000-b52dbd1cf8e34c21d328
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dr-9200000000-eb3d08c8f2ea11d52354
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-9000000000-35cef0617d6c8c57fae0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-9000000000-e21a7ca30c1ef2ee26c3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-fd3d8cd915b2a14a71d7
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-127.5507552
predicted
DarkChem Lite v0.1.0
[M-H]-119.27154
predicted
DeepCCS 1.0 (2019)
[M+H]+129.0681552
predicted
DarkChem Lite v0.1.0
[M+H]+123.13748
predicted
DeepCCS 1.0 (2019)
[M+Na]+128.6783552
predicted
DarkChem Lite v0.1.0
[M+Na]+132.0743
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Amino acid binding
Gene Name
pyrB
Uniprot ID
P0A786
Uniprot Name
Aspartate carbamoyltransferase catalytic subunit
Molecular Weight
34427.02 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Phosphate ion binding
Specific Function
Plays an important role in the de novo pathway and in the salvage pathway of purine nucleotide biosynthesis. Catalyzes the first committed step in the biosynthesis of AMP from IMP.
Gene Name
ADSS
Uniprot ID
P30520
Uniprot Name
Adenylosuccinate synthetase isozyme 2
Molecular Weight
50097.075 Da
References
  1. Datta SK, Guicherit OM, Kellems RE: Adenylosuccinate synthetase: a dominant amplifiable genetic marker in mammalian cells. Somat Cell Mol Genet. 1994 Sep;20(5):381-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Phosphate ion binding
Specific Function
Component of the purine nucleotide cycle (PNC), which interconverts IMP and AMP to regulate the nucleotide levels in various tissues, and which contributes to glycolysis and ammoniagenesis. Catalyz...
Gene Name
ADSSL1
Uniprot ID
Q8N142
Uniprot Name
Adenylosuccinate synthetase isozyme 1
Molecular Weight
50208.16 Da
References
  1. Datta SK, Guicherit OM, Kellems RE: Adenylosuccinate synthetase: a dominant amplifiable genetic marker in mammalian cells. Somat Cell Mol Genet. 1994 Sep;20(5):381-9. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Cystine:glutamate antiporter activity
Specific Function
Sodium-independent, high-affinity exchange of anionic amino acids with high specificity for anionic form of cystine and glutamate.
Gene Name
SLC7A11
Uniprot ID
Q9UPY5
Uniprot Name
Cystine/glutamate transporter
Molecular Weight
55422.44 Da
References
  1. Huang Y, Dai Z, Barbacioru C, Sadee W: Cystine-glutamate transporter SLC7A11 in cancer chemosensitivity and chemoresistance. Cancer Res. 2005 Aug 15;65(16):7446-54. [Article]

Drug created at November 18, 2007 18:25 / Updated at February 21, 2021 18:51