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MedKoo Cat#: 200550 | Name: Irosustat
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Irosustat, also known as STX64, BN83495 and 667 coumate, is a potent, irreversible inhibitor of steroid sulfatase. Inhibition of steroid sulfatase (STS), the enzyme responsible for the hydrolysis of steroid sulfates, represents a potential novel treatment for postmenopausal women with hormone-dependent breast cancer. Estrone and DHEA are formed by this sulfatase pathway and can be converted to steroids (estradiol and androstenediol, respectively), which have potent estrogenic properties. STX64 (667 coumate) is a potent tricylic coumarin-based sulfamate that irreversibly inhibits STS activity (IC50 = 8 nM in a placental microsomal assay system). Estrone sulfamate (EMATE) is also a potent STS inhibitor, but has estrogenic activity.

Chemical Structure

Irosustat
Irosustat
CAS#288628-05-7

Theoretical Analysis

MedKoo Cat#: 200550

Name: Irosustat

CAS#: 288628-05-7

Chemical Formula: C14H15NO5S

Exact Mass: 309.0671

Molecular Weight: 309.34

Elemental Analysis: C, 54.36; H, 4.89; N, 4.53; O, 25.86; S, 10.37

Price and Availability

Size Price Availability Quantity
50mg USD 450.00 2 Weeks
100mg USD 750.00 2 Weeks
200mg USD 1,250.00 2 Weeks
500mg USD 1,950.00 2 Weeks
1g USD 2,950.00 2 Weeks
2g USD 5,250.00 2 Weeks
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Related CAS #
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Synonym
STX64; STX-64; STX 64; BN83495; BN-83495; BN 83495; STX 64667; STX64667; ST-64667; COUMATE. Irosustat.
IUPAC/Chemical Name
6-oxo-6,7,8,9,10,11-hexahydrocyclohepta[c]chromen-3-yl sulfamate.
InChi Key
DSLPMJSGSBLWRE-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=S(OC1=CC(O2)=C(C=C1)C(CCCCC3)=C3C2=O)(N)=O
Appearance
Solid powder
Purity
>98%
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>5 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
   
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#S8G03M13
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Irosustat is a potent steroid sulfatase inhibitor, with an IC50 of 8 nM, and exhibits anti-breast cancer activity.
In vitro activity:
In comparison, 10 nM concentration Irosustat led to a 12.9% residual enzymatic action. The experiment at a 1 nM inhibitor concentration showed a notable STS residual activity of 13.6% after incubation with 5l, even lower than the 16.8% produced by reference Irosustat. Relevantly, 4a, 4b, 5e, 5g, and 5l demonstrated STS inhibitory potency comparable to or greater than that of Irosustat. In fact, 4a, 4b, 5e, and 5g showed IC50 values of 1.90, 1.71, 2.95, and 1.69 nM, respectively, that are comparable to that of 1.06 nM detected for Irosustat. Reference: J Med Chem. 2022 Mar 24;65(6):5044-5056. https://pubmed.ncbi.nlm.nih.gov/35235747/
In vivo activity:
In this study the ability of the STS inhibitor STX64 (BN83495) and its N,N-dimethyl analogue (STX289) to inhibit liver and skin STS when applied orally or topically to nude mice was examined. It is concluded that both STX64 and STX289 are not only effective inhibitors of skin STS, but also liver STS when applied topically. Reference: Anticancer Res. 2008 May-Jun;28(3A):1517-23. https://pubmed.ncbi.nlm.nih.gov/18630506/
Solvent mg/mL mM
Solubility
DMF 30.0 96.98
DMSO 53.2 175.09
Ethanol 9.1 29.24
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 309.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Biernacki K, Ciupak O, Daśko M, Rachon J, Kozak W, Rak J, Kubiński K, Masłyk M, Martyna A, Śliwka-Kaszyńska M, Wietrzyk J, Świtalska M, Nocentini A, Supuran CT, Demkowicz S. Development of Sulfamoylated 4-(1-Phenyl-1H-1,2,3-triazol-4-yl)phenol Derivatives as Potent Steroid Sulfatase Inhibitors for Efficient Treatment of Breast Cancer. J Med Chem. 2022 Mar 24;65(6):5044-5056. doi: 10.1021/acs.jmedchem.1c02220. Epub 2022 Mar 2. PMID: 35235747; PMCID: PMC8958511. 2. Woo LW, Ganeshapillai D, Thomas MP, Sutcliffe OB, Malini B, Mahon MF, Purohit A, Potter BV. Structure-activity relationship for the first-in-class clinical steroid sulfatase inhibitor Irosustat (STX64, BN83495). ChemMedChem. 2011 Nov 4;6(11):2019-34. doi: 10.1002/cmdc.201100288. Epub 2011 Aug 25. PMID: 21990014; PMCID: PMC3262147. 3. Purohit A, Chander SK, Woo LW, Parsons MF, Jhalli R, Potter BV, Reed MJ. Inhibition of steroid sulphatase activity via the percutaneous route: a new option for breast cancer therapy. Anticancer Res. 2008 May-Jun;28(3A):1517-23. PMID: 18630506. 4. Foster PA, Woo LW, Potter BV, Reed MJ, Purohit A. The use of steroid sulfatase inhibitors as a novel therapeutic strategy against hormone-dependent endometrial cancer. Endocrinology. 2008 Aug;149(8):4035-42. doi: 10.1210/en.2008-0223. Epub 2008 May 1. PMID: 18450955; PMCID: PMC2488239.
In vitro protocol:
1. Biernacki K, Ciupak O, Daśko M, Rachon J, Kozak W, Rak J, Kubiński K, Masłyk M, Martyna A, Śliwka-Kaszyńska M, Wietrzyk J, Świtalska M, Nocentini A, Supuran CT, Demkowicz S. Development of Sulfamoylated 4-(1-Phenyl-1H-1,2,3-triazol-4-yl)phenol Derivatives as Potent Steroid Sulfatase Inhibitors for Efficient Treatment of Breast Cancer. J Med Chem. 2022 Mar 24;65(6):5044-5056. doi: 10.1021/acs.jmedchem.1c02220. Epub 2022 Mar 2. PMID: 35235747; PMCID: PMC8958511. 2. Woo LW, Ganeshapillai D, Thomas MP, Sutcliffe OB, Malini B, Mahon MF, Purohit A, Potter BV. Structure-activity relationship for the first-in-class clinical steroid sulfatase inhibitor Irosustat (STX64, BN83495). ChemMedChem. 2011 Nov 4;6(11):2019-34. doi: 10.1002/cmdc.201100288. Epub 2011 Aug 25. PMID: 21990014; PMCID: PMC3262147.
In vivo protocol:
1. Purohit A, Chander SK, Woo LW, Parsons MF, Jhalli R, Potter BV, Reed MJ. Inhibition of steroid sulphatase activity via the percutaneous route: a new option for breast cancer therapy. Anticancer Res. 2008 May-Jun;28(3A):1517-23. PMID: 18630506. 2. Foster PA, Woo LW, Potter BV, Reed MJ, Purohit A. The use of steroid sulfatase inhibitors as a novel therapeutic strategy against hormone-dependent endometrial cancer. Endocrinology. 2008 Aug;149(8):4035-42. doi: 10.1210/en.2008-0223. Epub 2008 May 1. PMID: 18450955; PMCID: PMC2488239.
1: Lawrence Woo LW, Leblond B, Purohit A, Potter BV. Synthesis and evaluation of analogues of estrone-3-O-sulfamate as potent steroid sulfatase inhibitors. Bioorg Med Chem. 2012 Apr 15;20(8):2506-19. Epub 2012 Mar 8. PubMed PMID: 22455789. 2: Ventura V, Solà J, Peraire C, Brée F, Obach R. In vitro evaluation of the interaction potential of irosustat with drug-metabolizing enzymes. Drug Metab Dispos. 2012 Jul;40(7):1268-78. Epub 2012 Mar 26. PubMed PMID: 22451700. 3: Woo LW, Ganeshapillai D, Thomas MP, Sutcliffe OB, Malini B, Mahon MF, Purohit A, Potter BV. Structure-activity relationship for the first-in-class clinical steroid sulfatase inhibitor Irosustat (STX64, BN83495). ChemMedChem. 2011 Nov 4;6(11):2019-34. doi: 10.1002/cmdc.201100288. Epub 2011 Aug 25. PubMed PMID: 21990014; PubMed Central PMCID: PMC3262147. 4: Purohit A, Woo LW, Potter BV. Steroid sulfatase: a pivotal player in estrogen synthesis and metabolism. Mol Cell Endocrinol. 2011 Jul 4;340(2):154-60. Epub 2011 Jun 30. Review. PubMed PMID: 21693170. 5: Ventura V, Solà J, Celma C, Peraire C, Obach R. In vitro metabolism of irosustat, a novel steroid sulfatase inhibitor: interspecies comparison, metabolite identification, and metabolic enzyme identification. Drug Metab Dispos. 2011 Jul;39(7):1235-46. Epub 2011 Apr 4. PubMed PMID: 21464173. 6: Palmieri C, Januszewski A, Stanway S, Coombes RC. Irosustat: a first-generation steroid sulfatase inhibitor in breast cancer. Expert Rev Anticancer Ther. 2011 Feb;11(2):179-83. Review. Erratum in: Expert Rev Anticancer Ther. 2011 Sep;11(9):1472. PubMed PMID: 21342037. 7: Woo LW, Purohit A, Potter BV. Development of steroid sulfatase inhibitors. Mol Cell Endocrinol. 2011 Jul 4;340(2):175-85. Epub 2011 Jan 14. Review. PubMed PMID: 21238537. 8: Fusi L, Purohit A, Brosens J, Woo LW, Potter BV, Reed MJ. Inhibition of steroid sulfatase activity in endometriotic implants by STX64 (667Coumate): a potential new therapy. ScientificWorldJournal. 2008 Dec 25;8:1325-7. PubMed PMID: 19112542. 9: Purohit A, Chander SK, Woo LW, Parsons MF, Jhalli R, Potter BV, Reed MJ. Inhibition of steroid sulphatase activity via the percutaneous route: a new option for breast cancer therapy. Anticancer Res. 2008 May-Jun;28(3A):1517-23. PubMed PMID: 18630506. 10: Foster PA, Chander SK, Parsons MF, Newman SP, Woo LW, Potter BV, Reed MJ, Purohit A. Efficacy of three potent steroid sulfatase inhibitors: pre-clinical investigations for their use in the treatment of hormone-dependent breast cancer. Breast Cancer Res Treat. 2008 Sep;111(1):129-38. Epub 2007 Oct 4. PubMed PMID: 17914670. 11: Stanway SJ, Delavault P, Purohit A, Woo LW, Thurieau C, Potter BV, Reed MJ. Steroid sulfatase: a new target for the endocrine therapy of breast cancer. Oncologist. 2007 Apr;12(4):370-4. Review. PubMed PMID: 17470679.