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SML1543

Sigma-Aldrich

Apratastat

≥98% (HPLC)

Synonym(s):

(3S)-N-Hydroxy-4-[[4-[(4-hydroxy-2-butyn-1-yl)oxy]phenyl]sulfonyl]-2,2-dimethyl-3-thiomorpholinecarboxamide, (3S)-N-Hydroxy-4-[[4-[(4-hydroxy-2-butynyl)oxy]phenyl]sulfonyl]-2,2-dimethyl-3-thiomorpholinecarboxamide, TMI 005, TMI-005

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About This Item

Empirical Formula (Hill Notation):
C17H22N2O6S2
CAS Number:
287405-51-0
Molecular Weight:
414.50
MDL number:
MFCD13152357
UNSPSC Code:
12352200
PubChem Substance ID:
329825953

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=S(N1CCSC(C)(C)[C@@H]1C(NO)=O)(C2=CC=C(OCC#CCO)C=C2)=O

InChI

1S/C17H22N2O6S2/c1-17(2)15(16(21)18-22)19(9-12-26-17)27(23,24)14-7-5-13(6-8-14)25-11-4-3-10-20/h5-8,15,20,22H,9-12H2,1-2H3,(H,18,21)/t15-/m0/s1

InChI key

MAVDNGWEBZTACC-HNNXBMFYSA-N

General description

Apratastat is one of the thiomorpholine sulfonamide hydroxymate selective inhibitors of ADAM17 (a disintegrin and metalloproteinase).

Biochem/physiol Actions

Apratastat (TMI-005) is an orally active, potent and selective dual inhibitor of disintegrin metalloenzyme 17 (ADAM17/ TACE) and matrix metalloprotease (MMP).

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Pharmacokinetic-pharmacodynamic modeling of apratastat: a population-based approach.
Shu C et al
Journal of Clinical Pharmacology, 51(4), 472-481 (2011)
Bridget M Ford et al.
American journal of physiology. Renal physiology, 305(3), F323-F332 (2013-05-17)
Matrix protein accumulation is a prominent feature of diabetic nephropathy that contributes to renal fibrosis and decline in renal function. The pathogenic mechanisms of matrix accumulation are incompletely characterized. We investigated if the matrix metalloprotease a disintegrin and metalloprotease1 7

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