Prinomastat

Prinomastat Property

Melting point:

149.8°

Density 

1.377±0.06 g/cm3(Predicted)

storage temp. 

room temp

solubility 

H2O: soluble15mg/mL (clear solution)

form 

powder

pka

9.25±0.23(Predicted)

color 

white to beige

Water Solubility 

H2O: 15mg/mL (clear solution)

Safety

Hazard Codes 

T

Risk Statements 

60-61

Safety Statements 

53-45

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H360May damage fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P308+P313IF exposed or concerned: Get medical advice/attention.

Prinomastat Chemical Properties,Usage,Production

Uses

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

Uses

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.

Uses

Antineoplastic; antiangiogenic; treatment for retinal and subfoveal choroidal neovascularization (matrix metalloproteinase inhibitor).

Definition

ChEBI: Prinomastat is a hydroxamic acid that is (3S)-N-hydroxy-2,2-dimethylthiomorpholine-3-carboxamide in which the hydrogen attached to the thiomorpholine nitrogen has been replaced by a [4-(pyridin-4-yloxy)phenyl]sulfonyl group. It is a selective inhibitor with of matrix metalloproteinases (MMPs) 2, 3, 9, 13, and 14. It has a role as an antineoplastic agent, a matrix metalloproteinase inhibitor and an EC 3.4.24.35 (gelatinase B) inhibitor. It is a hydroxamic acid, a member of thiomorpholines, a sulfonamide, an aromatic ether and a member of pyridines. It is a conjugate base of a prinomastat(1+).

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.