MW 331.41 Da, Purity >98%. Potent matrix metalloproteinase inhibitor. Broad-spectrum inhibitor of all major MMPs. Prevents or reduces spread and growth of tumors.
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- Immunity 47:710-722.e62017Epidermal Growth Factor Receptor Expression Licenses Type-2 Helper T Cells to Function in a T Cell Receptor-Independent Fashion.Applications:Unspecified applicationReactive species:Unspecified reactive speciesCarlos M Minutti,Sebastian Drube,Natalie Blair,Christian Schwartz,Jame C McCrae,Andrew N McKenzie,Thomas Kamradt,Michal Mokry,Paul J Coffer,Maria Sibilia,Alice J Sijts,Padraic G Fallon,Rick M Maizels,Dietmar M ZaissPubMed 29045902
- Expert opinion on investigational drugs 9:2913-222000Marimastat: the clinical development of a matrix metalloproteinase inhibitor.Applications:Unspecified applicationReactive species:Unspecified reactive speciesW P Steward,A L ThomasPubMed 11093361
- Cancer chemotherapy and pharmacology 43 Suppl:S56-601999Marimastat (BB2516): current status of development.Applications:Unspecified applicationReactive species:Unspecified reactive speciesW P StewardPubMed 10357560
- Pharmacology & therapeutics 75:69-751997Matrix metalloproteinase inhibition as a novel anticancer strategy: a review with special focus on batimastat and marimastat.Applications:Unspecified applicationReactive species:Unspecified reactive speciesH S Rasmussen,P P McCannPubMed 9364582
Key facts
- CAS number
154039-60-8
- Purity
> 98%
- Form
Solid
- Molecular weight
331.41 Da
- Molecular formula
C15H29N3O5
- PubChem identifier
119031
- Nature
Synthetic
Target data
Alternative names
27 kDa interstitial collagenase, 72 kDa gelatinase, 72kD type IV collagenase, 82 kDa matrix metalloproteinase-9, 92 kDa gelatinase, 92 kDa type IV collagenase, A disintegrin and metalloprotease domain 10, A disintegrin and metalloproteinase domain 10, A disintegrin and metalloproteinase domain 17, A disintegrin and metalloproteinase domain 17 (tumor necrosis factor, alpha, converting enzyme), AD 10, AD18, ADA10_HUMAN, ADA17_HUMAN, ADAM 17, ADAM metallopeptidase domain 10, ADAM metallopeptidase domain 17, ADAM17 protein, APC1 protein, CD 156b, CD 156c, CD156b antigen, CD156c antigen, CDw156, CHDS6, CLG, CLG 1, CLG 3, CLG 4, CLG 4A, CLG 4B, CSVP, Cachectin, Collagenase 1, Collagenase 1 neutrophil, Collagenase 3, Collagenase Type 4 alpha, Collagenase Type 4 beta, Collagenase type IV 92 KD, Collagenase type IV A, DIF, Differentiation inducing factor, Disintegrin and metalloproteinase domain-containing protein 10, Disintegrin and metalloproteinase domain-containing protein 17, EC 3.4.24.35, EC 3.4.24.65, Fibroblast collagenase, GELB, Gelatinase 92 KD, Gelatinase A, Gelatinase B, Gelatinase alpha, Gelatinase beta, Gelatinase neutrophil, HME, HNC, HsT 18717, Interstitial collagenase, Kuz, Kuzbanian, Kuzbanian protein homolog, Kuzbanian, Drosophila, homolog of, MANDP1, MANDP2, ME, MGC126102, MGC126103, MGC126104, MGC138506, MGC71942, MME, MMP II, MMP-X1, MMP12_HUMAN, MMP13_HUMAN, MMP14_HUMAN, MMP1_HUMAN, MMP2_HUMAN, MMP3_HUMAN, MMP7_HUMAN, MMP8_HUMAN, MMP9_HUMAN, MONA, MPSL1, MT-MMP 1, MT1-MMP, Macrophage cytotoxic factor, Macrophage elastase, Macrophage gelatinase, Macrophage metalloelastase, Macrophage metaloelastase, Mammalian disintegrin-metalloprotease, Matrilysin, Matrin, Matrix Metalloproteinase 9, Matrix metallopeptidase 1 (interstitial collagenase), Matrix metallopeptidase 12 (macrophage elastase), Matrix metallopeptidase 13 (collagenase 3), Matrix metallopeptidase 14 (membrane inserted), Matrix metallopeptidase 2 gelatinase A 72kDa gelatinase 72kDa type IV collagenase, Matrix metallopeptidase 8 (neutrophil collagenase), Matrix metallopeptidase 9 (gelatinase B, 92kDa gelatinase, 92kDa type IV collagenase), Matrix metalloprotease 1, Matrix metalloprotease 12, Matrix metalloprotease 8, Matrix metalloproteinase 2 (gelatinase A, 72kDa gelatinase, 72kDa type IV collagenase), Matrix metalloproteinase 3 preproprotein, Matrix metalloproteinase II, Matrix metalloproteinase-1, Matrix metalloproteinase-12, Matrix metalloproteinase-13, Matrix metalloproteinase-14, Matrix metalloproteinase-2, Matrix metalloproteinase-3, Matrix metalloproteinase-7, Matrix metalloproteinase-8, Membrane type 1 metalloprotease, Membrane-type matrix metalloproteinase 1, Membrane-type-1 matrix metalloproteinase, NISBD, NISBD1, Neutrophil collagenase, Neutrophil gelatinase, OTTHUMP00000045866, PEX, PMNL collagenase, PMNL-CL, PUMP 1, Proteoglycanase, Pump-1 protease, RAK, SL-1, STMY, STMY1, Snake venom-like protease, Stromelisin 1, Stromelysin 1 progelatinase, Stromelysin-1, TACE, TBE-1, TNF superfamily member 2, TNF, macrophage derived, TNF, monocyte derived, TNF-alpha, TNF-alpha convertase, TNF-alpha-converting enzyme, TNFA_HUMAN, TNFSF2, Tnf, Transin-1, Tumor Necrosis Factor Alpha Converting Enzyme, Tumor Necrosis Factor, Membrane Form, Tumor necrosis factor, Tumor necrosis factor (TNF superfamily member 2), Tumor necrosis factor alpha, Tumor necrosis factor ligand superfamily member 2, Tumor necrosis factor, soluble form, Type V collagenase, Uterine matrilysin, Uterine metalloproteinase, collagenase, fibroblast, collagenase, interstitial
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MW 331.41 Da, Purity >98%. Potent matrix metalloproteinase inhibitor. Broad-spectrum inhibitor of all major MMPs. Prevents or reduces spread and growth of tumors.
Key facts
- CAS number
154039-60-8
- Purity
> 98%
- Form
Solid
- Molecular weight
331.41 Da
- Molecular formula
C15H29N3O5
- PubChem identifier
119031
- Nature
Synthetic
- Solubility
Soluble in DMSO to 100 mM. Soluble in ethanol to 50 mM.
- Biochemical name
Marimastat
- Biological description
Potent matrix metalloproteinase inhibitor. Broad-spectrum inhibitor of all major MMPs. Prevents or reduces spread and growth of tumors.
- Canonical SMILES
CC(C)CC(C(C(=O)NO)O)C(=O)NC(C(=O)NC)C(C)(C)C
- Isomeric SMILES
CC(C)C[C@H]([C@@H](C(=O)NO)O)C(=O)N[C@H](C(=O)NC)C(C)(C)C
- InChI
InChI=1S/C15H29N3O5/c1-8(2)7-9(10(19)13(21)18-23)12(20)17-11(14(22)16-6)15(3,4)5/h8-11,19,23H,7H2,1-6H3,(H,16,22)(H,17,20)(H,18,21)/t9-,10+,11-/m1/s1
- InChIKey
OCSMOTCMPXTDND-OUAUKWLOSA-N
- IUPAC name
(2R,3S)-N-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-N',3-dihydroxy-2-(2-methylpropyl)butanediamide
Storage
- Shipped at conditions
Ambient - Can Ship with Ice
- Appropriate short-term storage conditions
-20°C
- Appropriate long-term storage conditions
-20°C
- Storage information
Store under desiccating conditions, The product can be stored for up to 12 months
Supplementary info
This supplementary information is collated from multiple sources and compiled automatically.
- Activity summary
MMPs (Matrix Metalloproteinases) are zinc-dependent endopeptidases essential for the breakdown of extracellular matrix components. The most well-studied members include MMP1 MMP2 MMP3 MMP7 MMP8 MMP9 MMP12 MMP13 and MMP14 each serving different mechanical functions. MMP9 also known as gelatinase B weighs approximately 92 kDa. These proteases are widely expressed in tissues such as connective tissues and immune cells including fibroblasts and macrophages where they aid in cellular migration tissue remodeling and inflammation. MMP14 known as MT1-MMP holds special relevance due to its role in pericellular proteolysis and its function as a membrane-bound enzyme.
- Biological function summary
MMPs participate in remodeling tissues during various physiological processes like wound healing angiogenesis and normal tissue maintenance. These proteases do not act alone; they often form complexes with other proteins facilitating processes like the activation of latent forms of MMPs. ADAM (A Disintegrin and Metalloproteinase) family members such as ADAM10 and ADAM17 act alongside MMPs especially in activities related to cell signaling and shedding of membrane proteins. TNF alpha a pro-inflammatory cytokine often interacts with MMPs modulating their activity during inflammatory responses.
- Pathways
These metalloproteases embed themselves within significant systems notably the Wnt signaling and TGF-beta pathways. In these pathways MMPs work in tandem with proteins such as integrins and growth factors to regulate cellular behavior and extracellular matrix composition. MMP inhibitors chemical compounds like marimastat restrain MMP activity demonstrating importance in research and potential therapeutic applications for conditions involving excessive matrix degradation.
- Associated diseases and disorders
Dysregulated MMP activity associates closely with cancer progression and arthritis. In cancer overexpression of MMPs contributes to metastasis by degrading basement membranes with MMP2 and MMP9 being particularly implicated. Similarly rheumatic diseases involve excessive activity of MMP13 leading to cartilage breakdown. MMP inhibitors and related molecules like ADAM10 help tailor treatments for these conditions offering insights into moderating the destructive impacts these proteases can exert when unregulated.
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Chemical Structure - Marimastat, Matrix metalloprotease (MMP) inhibitor (ab141276)
2D chemical structure image of ab141276, Marimastat, Matrix metalloprotease (MMP) inhibitor
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