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
Structure for Alanosine (DB05540)
- 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).
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism UAspartate carbamoyltransferase catalytic chain Not Available Escherichia coli (strain K12) UAdenylosuccinate synthetase isozyme 2 Not Available Humans UAdenylosuccinate synthetase isozyme 1 Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAmbroxol The risk or severity of methemoglobinemia can be increased when Alanosine is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Alanosine is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Alanosine is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Alanosine is combined with Benzyl alcohol. Bupivacaine The 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
- 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]
- 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]
- External Links
- PubChem Compound
- 22128
- PubChem Substance
- 8166290
- ChemSpider
- 20787
- ChEMBL
- CHEMBL452715
- ZINC
- ZINC000004214744
- PDBe Ligand
- AL0
- Wikipedia
- Alanosine
- PDB Entries
- 2air
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 2 Completed Treatment Lung Cancer / Malignant Pleural Mesothelioma (MPM) / Pancreatic Cancer / Sarcomas 1 1 Completed Treatment Brain and Central Nervous System Tumors 1
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
Property Value Source logP -3.6 Chemaxon pKa (Strongest Acidic) 1.5 Chemaxon pKa (Strongest Basic) 8.67 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 116.22 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 30.7 m3·mol-1 Chemaxon Polarizability 11.94 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.6523 Blood Brain Barrier - 0.6928 Caco-2 permeable - 0.6474 P-glycoprotein substrate Non-substrate 0.6806 P-glycoprotein inhibitor I Non-inhibitor 0.9116 P-glycoprotein inhibitor II Non-inhibitor 0.9908 Renal organic cation transporter Non-inhibitor 0.9589 CYP450 2C9 substrate Non-substrate 0.907 CYP450 2D6 substrate Non-substrate 0.8242 CYP450 3A4 substrate Non-substrate 0.6489 CYP450 1A2 substrate Non-inhibitor 0.8735 CYP450 2C9 inhibitor Non-inhibitor 0.8825 CYP450 2D6 inhibitor Non-inhibitor 0.937 CYP450 2C19 inhibitor Non-inhibitor 0.854 CYP450 3A4 inhibitor Non-inhibitor 0.9525 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9913 Ames test AMES toxic 0.804 Carcinogenicity Non-carcinogens 0.607 Biodegradation Not ready biodegradable 0.7679 Rat acute toxicity 2.1600 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9844 hERG inhibition (predictor II) Non-inhibitor 0.9319
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-002f-9100000000-f9d27b3b036b79ec3b58 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0gb9-1900000000-c37f1f9ad13678f8378e Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-9000000000-b52dbd1cf8e34c21d328 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00dr-9200000000-eb3d08c8f2ea11d52354 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-9000000000-35cef0617d6c8c57fae0 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-9000000000-e21a7ca30c1ef2ee26c3 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-9000000000-fd3d8cd915b2a14a71d7 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 127.5507552 predictedDarkChem Lite v0.1.0 [M-H]- 119.27154 predictedDeepCCS 1.0 (2019) [M+H]+ 129.0681552 predictedDarkChem Lite v0.1.0 [M+H]+ 123.13748 predictedDeepCCS 1.0 (2019) [M+Na]+ 128.6783552 predictedDarkChem Lite v0.1.0 [M+Na]+ 132.0743 predictedDeepCCS 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
- 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
- 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
- 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