Irosustat
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Identification
- Generic Name
- Irosustat
- DrugBank Accession Number
- DB02292
- Background
Irosustat has been investigated for the treatment of Metastatic Breast Cancer and Locally Advanced Breast Cancer.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 309.338
Monoisotopic: 309.067093285 - Chemical Formula
- C14H15NO5S
- Synonyms
- 6-Oxo-8,9,10,11-Tetrahydro-7h-Cyclohepta[C][1]Benzopyran-3-O-Sulfamate
- Irosustat
- External IDs
- 667 COUMATE
- 667-COUMATE
- BN 83495
- BN-83495
- BN83495
- STX 64
- STX-64
- STX64
Pharmacology
- Indication
Not Available
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
- Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.
- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism USteryl-sulfatase inhibitorHumans UCarbonic anhydrase 2 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.Improve decision support & research outcomes with our structured adverse effects data.
- 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.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cycloheptapyrans. These are organic heterocyclic compounds containing a cycloheptane derivative fused to a pyran. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Cycloheptapyrans
- Sub Class
- Not Available
- Direct Parent
- Cycloheptapyrans
- Alternative Parents
- Coumarins and derivatives / 1-benzopyrans / Pyranones and derivatives / Benzenoids / Organic sulfuric acids and derivatives / Heteroaromatic compounds / Lactones / Oxacyclic compounds / Organooxygen compounds / Organic oxides show 2 more
- Substituents
- 1-benzopyran / Aromatic heteropolycyclic compound / Benzenoid / Benzopyran / Coumarin / Cycloheptapyran / Heteroaromatic compound / Hydrocarbon derivative / Lactone / Organic nitrogen compound show 7 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 366037O6O7
- CAS number
- 288628-05-7
- InChI Key
- DSLPMJSGSBLWRE-UHFFFAOYSA-N
- InChI
- InChI=1S/C14H15NO5S/c15-21(17,18)20-9-6-7-11-10-4-2-1-3-5-12(10)14(16)19-13(11)8-9/h6-8H,1-5H2,(H2,15,17,18)
- IUPAC Name
- 6-oxo-6H,7H,8H,9H,10H,11H-cyclohepta[c]chromen-3-yl sulfamate
- SMILES
- NS(=O)(=O)OC1=CC=C2C3=C(CCCCC3)C(=O)OC2=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 5287541
- PubChem Substance
- 46507132
- ChemSpider
- 4449897
- BindingDB
- 13058
- ChEMBL
- CHEMBL286738
- ZINC
- ZINC000001549366
- PDBe Ligand
- 667
- Wikipedia
- Irosustat
- PDB Entries
- 1ttm
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Endometrial Cancer 1 2 Completed Treatment Locally Advanced Breast Cancer (LABC) / Metastatic Breast Cancer 1 2 Terminated Basic Science Breast Cancer 1 2 Terminated Treatment Breast Neoplasms 1 2 Terminated Treatment Endometrial Cancer 1 1 Completed Treatment Breast Cancer 1 1 Completed Treatment Prostate Cancer 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 Water Solubility 0.0967 mg/mL ALOGPS logP 2.76 ALOGPS logP 1.99 Chemaxon logS -3.5 ALOGPS pKa (Strongest Acidic) 10.65 Chemaxon pKa (Strongest Basic) -6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 95.69 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 75.7 m3·mol-1 Chemaxon Polarizability 30.67 Å3 Chemaxon Number of Rings 3 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
Property Value Probability Human Intestinal Absorption + 0.9963 Blood Brain Barrier + 0.953 Caco-2 permeable - 0.6178 P-glycoprotein substrate Non-substrate 0.721 P-glycoprotein inhibitor I Non-inhibitor 0.7208 P-glycoprotein inhibitor II Non-inhibitor 0.9485 Renal organic cation transporter Non-inhibitor 0.865 CYP450 2C9 substrate Non-substrate 0.8853 CYP450 2D6 substrate Non-substrate 0.81 CYP450 3A4 substrate Non-substrate 0.5582 CYP450 1A2 substrate Non-inhibitor 0.5336 CYP450 2C9 inhibitor Non-inhibitor 0.6732 CYP450 2D6 inhibitor Non-inhibitor 0.8703 CYP450 2C19 inhibitor Non-inhibitor 0.5966 CYP450 3A4 inhibitor Non-inhibitor 0.8664 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8239 Ames test Non AMES toxic 0.5347 Carcinogenicity Non-carcinogens 0.6975 Biodegradation Not ready biodegradable 0.8294 Rat acute toxicity 2.4709 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7388 hERG inhibition (predictor II) Non-inhibitor 0.6542
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

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1. DetailsSteryl-sulfatase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sulfuric ester hydrolase activity
- Specific Function
- Conversion of sulfated steroid precursors to estrogens during pregnancy.
- Gene Name
- STS
- Uniprot ID
- P08842
- Uniprot Name
- Steryl-sulfatase
- Molecular Weight
- 65491.72 Da
References
- Purohit A, Woo LW, Potter BV, Reed MJ: In vivo inhibition of estrone sulfatase activity and growth of nitrosomethylurea-induced mammary tumors by 667 COUMATE. Cancer Res. 2000 Jul 1;60(13):3394-6. [Article]
2. DetailsCarbonic anhydrase 2
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion in...
- Gene Name
- CA2
- Uniprot ID
- P00918
- Uniprot Name
- Carbonic anhydrase 2
- Molecular Weight
- 29245.895 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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 February 21, 2021 18:51