178606-66-1

Basic information

• Product Name: Carbonic Anhydrase IX/XII Inhibitor II(U-104)
• Synonyms: Carbonic Anhydrase IX/XII Inhibitor II(U-104);U-104;MST-104 ;4-[[[(4-Fluorophenyl)amino]carbonyl]amino]benzenesulfonamide;NSC 213841;4-[[[(4-Fluorophenyl)aMino]carbonyl]aMino]-benzenesulfonaMide, NSC 213841;Benzenesulfonamide, 4-[[[(4-fluorophenyl)amino]carbonyl]amino]-;4-(3-(4-fluorophenyl)ureido)benzenesulfonamide
• CAS NO: 178606-66-1
• Molecular Formula: C₁₃H₁₂FN₃O₃S
• Molecular Weight: 309.3160832
• Product Categories: Inhibitor;Inhibitors
• Mol File: 178606-66-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 242-243℃
• Appearance: white to beige/
• Density: 1.523±0.06 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: 2-8°C
• Solubility: DMSO: >15mg/mL
• PKA: 9.94±0.12(Predicted)
• CAS DataBase Reference: Carbonic Anhydrase IX/XII Inhibitor II(U-104)(CAS DataBase Reference)
• NIST Chemistry Reference: Carbonic Anhydrase IX/XII Inhibitor II(U-104)(178606-66-1)
• EPA Substance Registry System: Carbonic Anhydrase IX/XII Inhibitor II(U-104)(178606-66-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 178606-66-1(Hazardous Substances Data)

Usage

Uses

U 104 targets hypoxia-induced carbonic anhydrase IX, which inhibits tumor growth and metastasis.

Biological Activity

u-104 is a novel ureido-sulfonamide inhibitor of carbonic anhydrase ix (caix). tumor volume measurements show important inhibition of primary tumor growth in the mice treated with the u-104 compound compared with vehicle controls. it also has ability to inhibit metastasis formation in the 4t1 experimental metastasis model.yuanmei lou, paul c. mcdonald, arusha oloumi, stephen chia, christina ostlund, ardalan ahmadi, alastair kyle, ulrich auf dem keller, samuel leung, david huntsman, blaise clarke, brent w. sutherland, dawn waterhouse, marcel bally, calvin roskelley, christopher m. overall, andrew minchinton, fabio pacchiano, fabrizio carta, andrea scozzafava, nadia touisni, jean-yves winum, claudiu t. supuran, shoukat dedhar. targeting tumor hypoxia: suppression of breast tumor growth and metastasis by novel carbonic anhydrase ix inhibitors. cancer research may 1, 2011 71; 3364

Biochem/physiol Actions

U-104 is an inhibitor of CA IX that binds only to CA IX under hypoxic conditions in vivo. The binding results in significant inhibition of tumor growth and metastasis formation in both spontaneous and experimental models of metastasis. U-104 reduces the medium acidity by inhibiting the catalytic activity of the CA IX. It binds specifically only to hypoxic cells expressing CA IX.

Upstream product

• 1195-45-5 para-fluorophenyl isocyanate 
• 63-74-1 sulfanilamide 
• 459-25-6 N-(4-fluorophenyl)formamide 

Relevant articles and documents

Structural Insights into Schistosoma mansoni Carbonic Anhydrase (SmCA) Inhibition by Selenoureido-Substituted Benzenesulfonamides

Tegumental carbonic anhydrase from the wormSchistosomamansoni(SmCA) is considered a new anti-parasitic target because suppressing its expression interferes with schistosome metabolism and virulence. Here, we present the inhibition profiles of selenoureido

Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis

A series of ureido-substituted benzenesulfonamides was prepared that showed a very interesting profile for the inhibition of several human carbonic anhydrases (hCAs, EC 4.2.1.1), such as hCAs I and II (cytosolic isoforms) and hCAs IX and XII (transmembrane, tumor-associated enzymes). Excellent inhibition of all these isoforms has been observed with various members of the series, depending on the substitution pattern of the urea moiety. Several low nanomolar CA IX/XII inhibitors also showing good selectivity for the transmembrane over the cytosolic isoforms have been discovered. One of them, 4-{[(3′- nirophenyl)carbamoyl]amino}benzenesulfonamide, significantly inhibited the formation of metastases by the highly aggressive 4T1 mammary tumor cells at pharmacologic concentrations of 45 mg/kg, constituting an interesting candidate for the development of conceptually novel antimetastatic drugs.

Selective hydrophobic pocket binding observed within the carbonic anhydrase II active site accommodate different 4-substituted-ureido-benzenesulfonamides and correlate to inhibitor potency

4-Substituted-ureido benzenesulfonamides showing inhibitory activity against carbonic anhydrase (CA, EC 4.2.1.1) II between 3.3-226 nM were crystallized in complex with the enzyme. Hydrophobic interactions between the scaffold of the inhibitors in differe