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PZ0198

Sigma-Aldrich

Prinomastat hydrochloride

≥95% (HPLC)

Synonym(s):

(S)-2,2-Dimethyl-4-((p-(4-pyridyloxy)phenyl)sulfonyl)-3-thiomorpholinecarbohydroxamic acid hydrochloride, AG 3340 hydrochloride, AG-3340 hydrochloride, AG3340 hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C18H21N3O5S2 · HCl
CAS Number:
192329-42-3
Molecular Weight:
459.97
UNSPSC Code:
12352200
PubChem Substance ID:
329823770
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 15 mg/mL (clear solution)

storage temp.

room temp

SMILES string

Cl.CC1(C)SCCN([C@H]1C(=O)NO)S(=O)(=O)c2ccc(Oc3ccncc3)cc2

InChI

1S/C18H21N3O5S2.ClH/c1-18(2)16(17(22)20-23)21(11-12-27-18)28(24,25)15-5-3-13(4-6-15)26-14-7-9-19-10-8-14;/h3-10,16,23H,11-12H2,1-2H3,(H,20,22);1H/t16-;/m0./s1

InChI key

UQGWXXLNXBRNBU-NTISSMGPSA-N

General description

Prinomastat comprises hydroxamic acid group and chelates with zinc ion.

Application

Prinomastat hydrochloride has been used as an antagonist for metalloproteinases (MMPs) in Crotalus atrox venom samples and mouse embryo cultures. It may be used as a MMP-2 inhibitor in HepG2 cells.

Biochem/physiol Actions

Prinomastat is a matrix metalloprotease (MMP) inhibitor with selectivity for MMPs 2, 3, 9, 13, and 14. Inhibition of these MMPs has been postulated to block tumor invasion and metastasis. It is extremely potent at MMP-3 and MMP-2 with IC50s, 30 pM & 50 pM, respectively.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360

Hazard Classifications

Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

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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Devin W McBride et al.
Journal of neuroscience research, 98(1), 191-200 (2018-09-23)
Hemorrhagic transformation after ischemic stroke is an independent predictor for poor outcome and is characterized by blood vessel rupture leading to brain edema. To date, no therapies for preventing hemorrhagic transformation exist. Disintegrins from the venom of Crotalus atrox have
Anamika Dayal et al.
Nature communications, 8(1), 475-475 (2017-09-09)
Skeletal muscle excitation-contraction (EC) coupling is initiated by sarcolemmal depolarization, which is translated into a conformational change of the dihydropyridine receptor (DHPR), which in turn activates sarcoplasmic reticulum (SR) Ca2+ release to trigger muscle contraction. During EC coupling, the mammalian
A F Dulhunty et al.
Progress in biophysics and molecular biology, 79(1-3), 45-75 (2002-09-13)
Excitation-contraction coupling in both skeletal and cardiac muscle depends on structural and functional interactions between the voltage-sensing dihydropyridine receptor L-type Ca(2+) channels in the surface/transverse tubular membrane and ryanodine receptor Ca(2+) release channels in the sarcoplasmic reticulum membrane. The channels
Abhinandan Chowdhury et al.
Toxicology letters, 340, 77-88 (2021-01-08)
Species within the viperid genus Macrovipera are some of the most dangerous snakes in the Eurasian region, injecting copious amounts of potent venom. Despite their medical importance, the pathophysiological actions of their venoms have been neglected. Particularly poorly known are
Hongli Hu et al.
Scientific reports, 5, 8370-8370 (2015-02-11)
Dihydropyridine receptor (DHPR), an L-type Ca(2+) channel complex, plays an essential role in muscle contraction, secretion, integration of synaptic input in neurons and synaptic transmission. The molecular architecture of DHPR complex remains elusive. Here we present a 15-Å resolution cryo-electron
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