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

Description

Prinomastat, also known as Ag3340, is a hydroxamic acid-based compound that chelates with zinc ions. It is a broad-spectrum matrix metalloproteinase (MMP) inhibitor, which plays a crucial role in various biological processes, including tumor growth, angiogenesis, and tissue remodeling.

Uses

Used in Anticancer Applications:
Prinomastat is used as an antineoplastic and antiangiogenic agent for the treatment of various types of cancer. It has been shown to significantly reduce tumor invasion and vascularization in HaCaT-ras A-5RT3 tumor xenografts when administered for 6 days. The compound also demonstrates its effectiveness as a MMP-2 inhibitor in HepG2 cells, which contributes to its potential use in cancer therapy.
Used in Ophthalmology:
In the field of ophthalmology, Prinomastat is used for the treatment of retinal and subfoveal choroidal neovascularization. As a matrix metalloproteinase inhibitor, it helps in managing the abnormal growth of new blood vessels in the eye, which can lead to vision loss.
Used in Drug Development:
Prinomastat has been utilized as an antagonist for metalloproteinases (MMPs) in Crotalus atrox venom samples and mouse embryo cultures. This application highlights its potential use in the development of drugs targeting MMPs, which are involved in various physiological and pathological processes.

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