U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

Molecular Formula C14H15NO5S
Molecular Weight 309.338
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.0 nM [IC50]
Conditions
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
10.44 ng/mL
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IROSUSTAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
159.4 ng/mL
80 mg 1 times / day steady-state, oral
dose: 80 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IROSUSTAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
1.94 ng/mL
1 mg 1 times / day steady-state, oral
dose: 1 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IROSUSTAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
33.31 ng/mL
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IROSUSTAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
72.3 ng/mL
40 mg 1 times / day steady-state, oral
dose: 40 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IROSUSTAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
121 ng × h/mL
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IROSUSTAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
1229 ng × h/mL
80 mg 1 times / day steady-state, oral
dose: 80 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IROSUSTAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
26.86 ng × h/mL
1 mg 1 times / day steady-state, oral
dose: 1 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IROSUSTAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
432.2 ng × h/mL
20 mg 1 times / day steady-state, oral
dose: 20 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IROSUSTAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
681.2 ng × h/mL
40 mg 1 times / day steady-state, oral
dose: 40 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IROSUSTAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Inhibition of MCF-7 breast cancer cell proliferation and in vivo steroid sulphatase activity by 2-methoxyoestradiol-bis-sulphamate.
2003 Feb
Patents

Sample Use Guides

40 mg per day
Route of Administration: Oral
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:41:29 GMT 2023
Edited
by admin
on Fri Dec 15 17:41:29 GMT 2023
Record UNII
366037O6O7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IROSUSTAT
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
667 COUMATE
Code English
BN-83495
Code English
STX64
Code English
IROSUSTAT [USAN]
Common Name English
6-Oxo-6,7,8,9,10,11-hexahydrocyclohepta[c][1]benzopyran-3-yl sulfamate
Systematic Name English
667-COUMATE
Code English
irosustat [INN]
Common Name English
SULFAMIC ACID, 6,7,8,9,10,11-HEXAHYDRO-6-OXOBENZO(B)CYCLOHEPTA(D)PYRAN-3-YL ESTER
Common Name English
Irosustat [WHO-DD]
Common Name English
STX-64
Code English
BN83495
Code English
Classification Tree Code System Code
NCI_THESAURUS C471
Created by admin on Fri Dec 15 17:41:29 GMT 2023 , Edited by admin on Fri Dec 15 17:41:29 GMT 2023
NCI_THESAURUS C1742
Created by admin on Fri Dec 15 17:41:29 GMT 2023 , Edited by admin on Fri Dec 15 17:41:29 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL286738
Created by admin on Fri Dec 15 17:41:29 GMT 2023 , Edited by admin on Fri Dec 15 17:41:29 GMT 2023
PRIMARY
USAN
WW-92
Created by admin on Fri Dec 15 17:41:29 GMT 2023 , Edited by admin on Fri Dec 15 17:41:29 GMT 2023
PRIMARY
WIKIPEDIA
Irosustat
Created by admin on Fri Dec 15 17:41:29 GMT 2023 , Edited by admin on Fri Dec 15 17:41:29 GMT 2023
PRIMARY
NCI_THESAURUS
C79827
Created by admin on Fri Dec 15 17:41:29 GMT 2023 , Edited by admin on Fri Dec 15 17:41:29 GMT 2023
PRIMARY
INN
9281
Created by admin on Fri Dec 15 17:41:29 GMT 2023 , Edited by admin on Fri Dec 15 17:41:29 GMT 2023
PRIMARY
SMS_ID
100000175158
Created by admin on Fri Dec 15 17:41:29 GMT 2023 , Edited by admin on Fri Dec 15 17:41:29 GMT 2023
PRIMARY
DRUG BANK
DB02292
Created by admin on Fri Dec 15 17:41:29 GMT 2023 , Edited by admin on Fri Dec 15 17:41:29 GMT 2023
PRIMARY
FDA UNII
366037O6O7
Created by admin on Fri Dec 15 17:41:29 GMT 2023 , Edited by admin on Fri Dec 15 17:41:29 GMT 2023
PRIMARY
EPA CompTox
DTXSID50183059
Created by admin on Fri Dec 15 17:41:29 GMT 2023 , Edited by admin on Fri Dec 15 17:41:29 GMT 2023
PRIMARY
CAS
288628-05-7
Created by admin on Fri Dec 15 17:41:29 GMT 2023 , Edited by admin on Fri Dec 15 17:41:29 GMT 2023
PRIMARY
PUBCHEM
5287541
Created by admin on Fri Dec 15 17:41:29 GMT 2023 , Edited by admin on Fri Dec 15 17:41:29 GMT 2023
PRIMARY
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