Tosedostat
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Name
- Tosedostat
- Accession Number
- DB11781
- Description
Tosedostat has been used in trials studying the treatment and supportive care of AML, Leukemia, Pancreas Cancer, Multiple Myeloma, and Pancreatic Cancer, among others.
Tosedostat is an inhibitor of the M1 family of aminopeptidases, in particular PuSA, and LTA4 hydrolase. It has demonstrated anti-tumour activity in a number of models of cancer, both as a single agent and in synergy with cytotoxic agents such as carboplatin and paclitaxel. It entered the clinical trial in patients with haematological malignancies.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Tosedostat (DB11781)
- Weight
- Average: 406.479
Monoisotopic: 406.210386694 - Chemical Formula
- C21H30N2O6
- Synonyms
- Not Available
- External IDs
- CHR 2797
- CHR-2797
Pharmacology
- Indication
- Not Available
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Tosedostat has pleiotropic effects against a range of human tumor cell lines originating from diverse tumor types in vitro and in vivo.
- Mechanism of action
Tosedostat is anti-proliferative agent which induces apoptosis in leukemic cell lines in vitro. The mechanism underlying these anti-cancer actions is unclear, particularly since normal cells are much less sensitive to the agents than transformed cells. It exerts potent anti-proliferative, pro-apoptotic and anti-angiogenic effects in vitro and shows selectivity for transformed over non-transformed cells. It inhibits a number of M1 aminopeptidase enzyme family members in vitro (eg puromycin-sensitive aminopeptidase (PSA), leukotriene A4 hydrolase (LTA4H)).
Target Actions Organism UPuromycin-sensitive aminopeptidase Not Available Humans ULeukotriene A-4 hydrolase 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- 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.Not Available
- Food Interactions
- Not Available
Products
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- N-acyl-alpha amino acids and derivatives
- Alternative Parents
- Alpha amino acid esters / N-acyl amines / Monosaccharides / Benzene and substituted derivatives / Secondary carboxylic acid amides / Secondary alcohols / Hydroxamic acids / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organopnictogen compounds show 4 more
- Substituents
- Alcohol / Alpha-amino acid ester / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid ester / Fatty acyl / Fatty amide / Hydrocarbon derivative show 14 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- KZK563J2UW
- CAS number
- 238750-77-1
- InChI Key
- FWFGIHPGRQZWIW-SQNIBIBYSA-N
- InChI
- InChI=1S/C21H30N2O6/c1-13(2)12-16(18(24)20(26)23-28)19(25)22-17(14-8-4-3-5-9-14)21(27)29-15-10-6-7-11-15/h3-5,8-9,13,15-18,24,28H,6-7,10-12H2,1-2H3,(H,22,25)(H,23,26)/t16-,17+,18+/m1/s1
- IUPAC Name
- cyclopentyl (2S)-2-[(2R,3S)-3-hydroxy-3-(hydroxycarbamoyl)-2-(2-methylpropyl)propanamido]-2-phenylacetate
- SMILES
- CC(C)C[[email protected]]([[email protected]](O)C(=O)NO)C(=O)N[[email protected]](C(=O)OC1CCCC1)C1=CC=CC=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 15547703
- PubChem Substance
- 347828131
- ChemSpider
- 24606030
- ChEBI
- 95044
- ChEMBL
- CHEMBL2103847
- ZINC
- ZINC000013914293
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.092 mg/mL ALOGPS logP 1.9 ALOGPS logP 2.13 ChemAxon logS -3.6 ALOGPS pKa (Strongest Acidic) 8.61 ChemAxon pKa (Strongest Basic) -2.2 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 4 ChemAxon Polar Surface Area 124.96 Å2 ChemAxon Rotatable Bond Count 10 ChemAxon Refractivity 105.13 m3·mol-1 ChemAxon Polarizability 42.88 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Aminopeptidase with broad substrate specificity for several peptides. Involved in proteolytic events essential for cell growth and viability. May act as regulator of neuropeptide activity. Plays a ...
- Gene Name
- NPEPPS
- Uniprot ID
- P55786
- Uniprot Name
- Puromycin-sensitive aminopeptidase
- Molecular Weight
- 103275.36 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Epoxide hydrolase that catalyzes the final step in the biosynthesis of the proinflammatory mediator leukotriene B4. Has also aminopeptidase activity.
- Gene Name
- LTA4H
- Uniprot ID
- P09960
- Uniprot Name
- Leukotriene A-4 hydrolase
- Molecular Weight
- 69284.64 Da
Drug created on October 20, 2016 14:47 / Updated on June 12, 2020 10:53
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