All Photos(1)
Synonym(s):
4-(3′-(3″,5″-Dimethylphenyl)ureido)phenyl sulfamate, 4-[(3,5-Dimethylphenyl)ureido]phenyl sulfamate, 4-[[[(3,5-Dimethylphenyl)amino]carbonyl]amino]phenyl sulfamic acid ester
Empirical Formula (Hill Notation):
C15H17N3O4S
CAS Number:
Molecular Weight:
335.38
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77
Recommended Products
Assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 2 mg/mL, clear
shipped in
ambient
storage temp.
2-8°C
SMILES string
O=S(OC1=CC=C(NC(NC2=CC(C)=CC(C)=C2)=O)C=C1)(N)=O
Biochem/physiol Actions
S4 is a potent and selective inhibitor against sulfamate carbonic anhydrase (CA) subtypes CAIX & CAXII (Ki = 2, 7, 546, 5600 nM against human CA XII, IX, II, and I, respectively). S4 selectively inhibits migration upon anoxia/hypoxia-induced CAIX expression in cancer cultures (% inhibition/conc./cell line = 54%/100 μM/WRO, 65%/33 μM/MDA-MB-231), while exhibiting no inhibitory effects under normoxia or among non-CAIX-expressing cells (HCT116 & RT112). Daily intraperitoneal injection (10 mg/kg) is reported to reduce the metastatic tumor burden in lungs of mice bearing orthotopic eGFP-MDA-MB-231 tumors in vivo.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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Roben G Gieling et al.
Journal of medicinal chemistry, 55(11), 5591-5600 (2012-05-25)
A panel of compounds belonging to the underexposed sulfamate class of carbonic anhydrase (CA, EC 4.2.1.1) inhibitors was generated that displayed high specificity at nanomolar levels for the tumor-associated CA IX/XII isoforms. Three of the specific CA IX/XII inhibitors showed
Tineke W H Meijer et al.
PloS one, 9(9), e108068-e108068 (2014-09-17)
Carbonic anhydrase IX (CAIX) plays a pivotal role in pH homeostasis, which is essential for tumor cell survival. We examined the effect of the CAIX inhibitor 4-(3'(3",5"-dimethylphenyl)-ureido)phenyl sulfamate (S4) on the tumor microenvironment in a laryngeal tumor model by analyzing
Jean-Yves Winum et al.
Bioorganic & medicinal chemistry letters, 22(14), 4681-4685 (2012-06-23)
A series of 50 sulfamates were obtained by reacting 4-aminophenol with isocyanates followed by sulfamoylation. Most of the new compounds were nanomolar inhibitors of the tumor-associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms IX and XII, whereas they inhibited less cytosolic
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