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Merck
CN

PZ0416

PF-05480090

≥98% (HPLC)

Synonym(s):

(2R,3S)-2-(4-(But-2-ynyloxy)phenylsulfonamido)-N,3-dihydroxybutanamide, (2R,3S)-2-({[4-(2-Butynyloxy)phenyl]sulfonyl}amino)-N,3-dihydroxybutanamide, (2R,3S)-2-[[[4-(2-Butyn-1-yloxy)phenyl]sulfonyl]amino]-N,3-dihydroxybutanamide, PF 05480090, PF 548, PF 5480090, PF-548, PF-5480090, PF05480090, PF548, PF5480090, TMI 002, TMI 2, TMI-002, TMI-2, TMI002, TMI2, WAY 180022, WAY 18022, WAY-180022, WAY-18022, WAY180022, WAY18022

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About This Item

Empirical Formula (Hill Notation):
C14H18N2O6S
CAS Number:
287406-12-6
Molecular Weight:
342.37
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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InChI

1S/C14H18N2O6S/c1-3-4-9-22-11-5-7-12(8-6-11)23(20,21)16-13(10(2)17)14(18)15-19/h5-8,10,13,16-17,19H,9H2,1-2H3,(H,15,18)/t10-,13+/m0/s1

InChI key

VMOSDDURWLNMNG-GXFFZTMASA-N

SMILES string

C[C@@H]([C@H](C(NO)=O)NS(=O)(C1=CC=C(C=C1)OCC#CC)=O)O

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Biochem/physiol Actions

PF-05480090 (PF-5480090; TMI-2) is an orally active, potent TACE (ADAM17) inhibitor (IC50 = 2 nM) with good selectivity over ADAM10 (IC50 = 1.09 μM), MMP-1/7 (IC50 = 2.47/0.96 μM) and MMP-8/9/13/14 (IC50 =35/ 777/96/582 nM). TMI-2 inhibits LPS-induced TNF production in cultrues (RAW/THP-1 IC50 = 200/430 nM), ex vivo (human whole blood IC50 = 1 μM) and in vivo (ED50 = 3 mg/kg; TMI-2 p.o. 1 hr prior to 40 ng LPS/mouse i.v.). TMI-2 is efficacious in a rat model of adjuvant-induced arthritis (AIA; 30 and 100 mg/kg p.o. b.i.d.) and a murine model of collagen-induced arthritis (CIA; 100 mg/kg p.o. b.i.d.).

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000140831
0000140832
0000123182

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Marta Stolarczyk et al.
American journal of physiology. Lung cellular and molecular physiology, 314(4), L555-L568 (2018-01-20)
The EGF receptor (EGFR)/a disintegrin and metalloproteinase 17 (ADAM17) signaling pathway mediates the shedding of growth factors and secretion of cytokines and is involved in chronic inflammation and tissue remodeling. Since these are hallmarks of cystic fibrosis (CF) lung disease
Marta Stolarczyk et al.
Physiological reports, 4(16) (2016-08-27)
Aberrant activity of a disintegrin and metalloprotease 17 (ADAM17), also known as TACE, and epidermal growth factor receptor (EGFR) has been suggested to contribute to chronic obstructive pulmonary disease (COPD) development and progression. The aim of this study was to
Mengcheng Shen et al.
Circulation research, 123(3), 372-388 (2018-06-23)
ADAM17 (a disintegrin and metalloproteinase-17) is a membrane-bound enzyme that regulates bioavailability of multiple transmembrane proteins by proteolytic processing. ADAM17 has been linked to several pathologies, but its role in thoracic aortic aneurysm (TAA) has not been determined. The objective
Amy W Ku et al.
eLife, 5 (2016-12-09)
Myeloid-derived suppressor cells (MDSC) contribute to an immunosuppressive network that drives cancer escape by disabling T cell adaptive immunity. The prevailing view is that MDSC-mediated immunosuppression is restricted to tissues where MDSC co-mingle with T cells. Here we show that
Yuhua Zhang et al.
International immunopharmacology, 4(14), 1845-1857 (2004-11-09)
TNF-alpha converting enzyme (TACE) is a validated therapeutic target for the development of oral tumor necrosis factor-alpha (TNF-alpha) inhibitors. Here we report the pre-clinical results and characterization of a selective and potent TACE inhibitor, (2R, 3S)-2-([[4-(2-butynyloxy)phenyl]sulfonyl]amino)-N,3-dihydroxybutanamide (TMI-2), in various in
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