192329-42-3

Basic information

• Product Name: Prinomastat
• Synonyms: (S)-2,2-DIMETHYL-N-HYDROXY-4-[4-(4-PYRIDYLOXY)PHENYLSULFONYL]-1,4-THIAZINANE-3-CARBOXAMIDE;2-[(hydroxyamino)methyl]-5,6-dimethyl-4-(4-pyridin-4-yloxyphenyl)sulfonyl-morpholine-3-thione;(S)-2-[(Hydroxyamino)methyl]-5,6-dimethyl-4-(4-pyridin-4-yloxyphenyl)sulfonylmorpholine-3-thione;Prinomastat;3-Thiomorpholinecarboxamide, N-hydroxy-2,2-dimethyl-4-((4-(4-pyridinyloxy)phenyl)sulfonyl)-, (S)-;Ag 3340;Ag3340;Ag-3340
• CAS NO: 192329-42-3
• Molecular Formula: C18H21N3O5S2
• Molecular Weight: 423.51
• Mol File: 192329-42-3.mol
• Article Data: 0

Chemical Properties

• Melting Point: 149.8°
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: white to beige/
• Density: 1.377g/cm³
• Refractive Index: 1.615
• Storage Temp.: room temp
• Solubility: H2O: soluble15mg/mL (clear solution)
• CAS DataBase Reference: Prinomastat(CAS DataBase Reference)
• NIST Chemistry Reference: Prinomastat(192329-42-3)
• EPA Substance Registry System: Prinomastat(192329-42-3)

Safety Data

• Hazard Codes: T
• Statements: 60-61
• Safety Statements: 53-45
• WGK Germany: 3
• Hazardous Substances Data: 192329-42-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 192329-42-3 differently. You can refer to the following data:
1. Treatment of HaCaT-ras A-5RT3 tumor xenografts with Prinomastat (Ag3340) for 6 days strongly reduces tumor invasion and vascularization. Prinomastat is also a broad spectrum MMP inhibitor
2. 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.
3. Antineoplastic; antiangiogenic; treatment for retinal and subfoveal choroidal neovascularization (matrix metalloproteinase inhibitor).

General Description

Prinomastat comprises hydroxamic acid group and chelates with zinc ion.

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.

Enzyme inhibitor

C113282), also known as AG3340, inhibits a number of matrix metalloproteinases, including collagenase-3 (Ki = 38 pM), gelatinase A (Ki = 83 pM), stromelysin 1 (Ki = 0.27 nM), and interstitial collagenase (Ki = 8.2 nM). Note that both the 3- and 4-pyridyl structures have been reported for prinomastat; however, the 4-analogue is the original structure reported for this inhibitor. Target(s): ADAM 17 endopeptidase, or tumor necrosis factor-a converting enzyme, or TACE; ADAMTS-4 endopeptidase, or aggrecanase; collagenase-3; gelatinase A; gelatinase B; interstitial collagenase; matrilysin; membrane-type matrix metalloproteinase-1, or matrix metalloproteinase 14; and stromelysin 1.

InChI:InChI=1/C18H21N3O5S2/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)/t16-/m0/s1