IROSUSTAT

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10910045 | https://www.ncbi.nlm.nih.gov/pubmed/11165021 | http://adisinsight.springer.com/drugs/800020388

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Steryl-sulfatase 33 Target ID: CHEMBL3531 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10910045	Inhibitor 8297		8.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Endometrial cancer 43 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27870712	Primary	Phase II 1132	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25355461 https://www.ncbi.nlm.nih.gov/pubmed/17695445 https://www.ncbi.nlm.nih.gov/pubmed/16533785	Primary	Phase II 1132	Unknown Approved Use Unknown
Prostate cancer 178 Sources: http://www.pharmatimes.com/news/ipsen_to_take_combo_route_with_irosustat_after_trial_failures_980921	Primary	Phase I 428	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
10.44 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23797179	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23797179	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23797179	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23797179	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23797179	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

Value	Dose	Analyte	Population
121 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23797179	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23797179	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23797179	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23797179	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23797179	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

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P002XCK	https://www.1pchem.com/search?query=1P002XCK
AOBIOUS INC	AOB5998	http://aobious.com/aobious/search?search_query=AOB5998
Axon MedChem	2892	https://www.axonmedchem.com/product/2892
BOC Sciences	288628-05-7	http://www.bocsci.com/description.asp?cas=288628-05-7
Chem Scene	CS-0003463	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0003463
Lab Network	LN01346276	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01346276
MedChem Express	HY-14586	https://www.medchemexpress.com/search.html?q=HY-14586&ft=&fa=&fp=
MolPort	MolPort-006-168-285	https://www.molport.com/shop/molecule-link/MolPort-006-168-285
Molnova	M18370	https://www.molnova.com/en/serch-list.html?keywords=M18370
MuseChem	I007362	https://www.musechem.com/product/I007362.html
Selleck Chemicals	S6558	http://www.selleckchem.com/search.html?searchDTO.searchParam=S6558
TargetMol	T4464	https://www.targetmol.com/search?keyword=T4464
Toronto Research Chemicals	S687208	https://www.trc-canada.com/product-detail/?CatNum=S687208
Wonderchem	WD05SXQ	http://www.wonder-chem.com/search.html?text=WD05SXQ
eMolecules	6755127	https://orderbb.emolecules.com/search/#?query=6755127

PubMed

Title	Date	PubMed
Inhibition of MCF-7 breast cancer cell proliferation and in vivo steroid sulphatase activity by 2-methoxyoestradiol-bis-sulphamate.	2003 Feb	12711022
Steroid sulphatase inhibitors for breast cancer therapy.	2003 Sep	14623540
The use of steroid sulfatase inhibitors as a novel therapeutic strategy against hormone-dependent endometrial cancer.	2008 Aug	18450955

Patents

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.

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

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Name

Type

Language

IROSUSTAT

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