U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C14H15NO5S
Molecular Weight 309.338
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IROSUSTAT

SMILES

NS(=O)(=O)OC1=CC=C2C(OC(=O)C3=C2CCCCC3)=C1

InChI

InChIKey=DSLPMJSGSBLWRE-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description

Irosustat is a first-generation, orally active, irreversible steroid sulfatase inhibitor. It did not stimulate the growth of estrogen-sensitive MCF-7 breast cells in vitro. Irosustat was in phase II clinical trials for the treatment of breast cancer and endometrial cancer and phase I clinical trial for the treatment of prostate cancer. However, this research has been discontinued.

Originator

Purohit, A. et al.
1

Approval Year

Unknown
149,124

Targets

Primary TargetPharmacologyConditionPotency
Steryl-sulfatase
33
Inhibitor
8,504
 8.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Endometrial cancer
44
 Primary
Phase II
1,147
Unknown
Breast cancer
432
 Primary
Phase II
1,147
Unknown
Prostate cancer
186
 Primary
Phase I
438
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
10.44 ng/mL
5 mg 1 times / day steady-state, oral
 IROSUSTAT plasma
Homo sapiens
72.3 ng/mL
40 mg 1 times / day steady-state, oral
 IROSUSTAT plasma
Homo sapiens
159.4 ng/mL
80 mg 1 times / day steady-state, oral
 IROSUSTAT plasma
Homo sapiens
1.94 ng/mL
1 mg 1 times / day steady-state, oral
 IROSUSTAT plasma
Homo sapiens
33.31 ng/mL
20 mg 1 times / day steady-state, oral
 IROSUSTAT plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
16323 ng × h/mL
20 mg single, oral
 IROSUSTAT plasma
Homo sapiens
121 ng × h/mL
5 mg 1 times / day steady-state, oral
 IROSUSTAT plasma
Homo sapiens
681.2 ng × h/mL
40 mg 1 times / day steady-state, oral
 IROSUSTAT plasma
Homo sapiens
1229 ng × h/mL
80 mg 1 times / day steady-state, oral
 IROSUSTAT plasma
Homo sapiens
26.86 ng × h/mL
1 mg 1 times / day steady-state, oral
 IROSUSTAT plasma
Homo sapiens
432.2 ng × h/mL
20 mg 1 times / day steady-state, oral
 IROSUSTAT plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
28.5 h
20 mg single, oral
 IROSUSTAT plasma
Homo sapiens

PubMed

Patents

20050154050
1
20070021492
1
20070105886
1
20070112009
1
20070173531
1

Sample Use Guides

In Vivo Use Guide
40 mg per day
Route of Administration: Oral
In Vitro Use Guide
The ER+ MCF-7 breast cancer cell line was used to test in vitro whether the Irosustat possessed any estrogenic properties. Irosustat over the range from 10(−11) to 10(−5) M had no significant effect on the proliferation of MCF-7 cells.
ACTIVE MOIETY
Structure of IROSUSTAT
METABOLITE (PARENT)
Structure of 10-HYDROXY 667-COUMARIN
METABOLITE (PARENT)
Structure of 667-COUMARIN
METABOLITE (PARENT)
Structure of 8-HYDROXY IROSUSTAT
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966