NAV

Irosustat

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
3D
Similar Structures
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
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USteryl-sulfatase
inhibitor
Humans
UCarbonic anhydrase 2Not 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.
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
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
PhaseStatusPurposeConditionsCount
2CompletedTreatmentEndometrial Cancer1
2CompletedTreatmentLocally Advanced Breast Cancer (LABC) / Metastatic Breast Cancer1
2TerminatedBasic ScienceBreast Cancer1
2TerminatedTreatmentBreast Neoplasms1
2TerminatedTreatmentEndometrial Cancer1

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
Water Solubility0.0967 mg/mLALOGPS
logP2.76ALOGPS
logP1.99Chemaxon
logS-3.5ALOGPS
pKa (Strongest Acidic)10.65Chemaxon
pKa (Strongest Basic)-6Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area95.69 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity75.7 m3·mol-1Chemaxon
Polarizability30.67 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9963
Blood Brain Barrier+0.953
Caco-2 permeable-0.6178
P-glycoprotein substrateNon-substrate0.721
P-glycoprotein inhibitor INon-inhibitor0.7208
P-glycoprotein inhibitor IINon-inhibitor0.9485
Renal organic cation transporterNon-inhibitor0.865
CYP450 2C9 substrateNon-substrate0.8853
CYP450 2D6 substrateNon-substrate0.81
CYP450 3A4 substrateNon-substrate0.5582
CYP450 1A2 substrateNon-inhibitor0.5336
CYP450 2C9 inhibitorNon-inhibitor0.6732
CYP450 2D6 inhibitorNon-inhibitor0.8703
CYP450 2C19 inhibitorNon-inhibitor0.5966
CYP450 3A4 inhibitorNon-inhibitor0.8664
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8239
Ames testNon AMES toxic0.5347
CarcinogenicityNon-carcinogens0.6975
BiodegradationNot ready biodegradable0.8294
Rat acute toxicity2.4709 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7388
hERG inhibition (predictor II)Non-inhibitor0.6542
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0009000000-8bd2b83e4c73dbee431c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-056r-9007000000-4db6f96413e7e7933d90
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01qc-0091000000-83406ef2b359fae83649
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bt9-4079000000-56f9030d37e22e5ee359
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0hji-0290000000-ff3cf2807cf1bd413d46
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ta-9260000000-be7d7eaeb57b4a85e7a3
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]-179.4393547
predicted
DarkChem Lite v0.1.0
[M-H]-160.12953
predicted
DeepCCS 1.0 (2019)
[M+H]+181.0614547
predicted
DarkChem Lite v0.1.0
[M+H]+162.48753
predicted
DeepCCS 1.0 (2019)
[M+Na]+179.4301547
predicted
DarkChem Lite v0.1.0
[M+Na]+168.93593
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Steryl-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
  1. 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]
Details2. Carbonic 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
  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 February 21, 2021 18:51