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| | Prinomastat Basic information |
| Product Name: | Prinomastat | | Synonyms: | (S)-2,2-DIMETHYL-N-HYDROXY-4-[4-(4-PYRIDYLOXY)PHENYLSULFONYL]-1,4-THIAZINANE-3-CARBOXAMIDE;3-Thiomorpholinecarboxamide, N-hydroxy-2,2-dimethyl-4-((4-(4-pyridinyloxy)phenyl)sulfonyl)-, (S)-;Ag 3340;Ag-3340;KB-R 9896;(S)-2,2-Dimethyl-4-((p-(4-pyridyloxy)phenyl)sulfonyl)-3-thiomorpholinecarbohydroxamic acid hydrochloride;AG 3340 hydrochloride;AG3340 hydrochloride | | CAS: | 192329-42-3 | | MF: | C18H21N3O5S2 | | MW: | 423.51 | | EINECS: | | | Product Categories: | | | Mol File: | 192329-42-3.mol |  |
| | Prinomastat Chemical Properties |
| 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) | | 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 | | InChIKey | UQGWXXLNXBRNBU-NTISSMGPSA-N | | SMILES | Cl.CC1(C)SCCN([C@H]1C(=O)NO)S(=O)(=O)c2ccc(Oc3ccncc3)cc2 |
| Hazard Codes | T | | Risk Statements | 60-61 | | Safety Statements | 53-45 | | WGK Germany | 3 | | Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | | Hazard Classifications | Repr. 1B |
| | Prinomastat Usage And Synthesis |
| Uses | Antineoplastic; antiangiogenic; treatment for retinal and subfoveal choroidal neovascularization (matrix metalloproteinase inhibitor). | | 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. | | 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in which the hydrogen attached to the thiomorpholine nitrogen has been replaced by a [4-(pyridin-4-yloxy)phenyl]sulfonyl group.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. |
| | Prinomastat Preparation Products And Raw materials |
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