Drug General Information
Drug ID
D05VZE
Former ID
DCL000005
Drug Name
Marimastat
Synonyms
Marimastat [USAN]; BB 2516; BB-2516; Marimastat (USAN/INN); (2R,3S)-N-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-N',3-dihydroxy-2-(2-methylpropyl)butanediamide; (2S,3R)-3-(((1S)-2,2-Dimethyl-1-(methylcarbamoxy)propyl)carboyl)-2-hydroxy-5-methylhexanohydroxamic acid; (2S,3R)-3-(((1S)-2,2-Dimethyl-1-(methylcarbamoyl)propyl)carbamoyl)-2-hydroxy-5-methylhexanohydroxamic acid; (2S,3R)-N(4)-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-N(1),2-dihydroxy-3-(2-methylpropyl)butanediamide
Drug Type
Small molecular drug
Indication Pancreatic cancer [ICD9: 140-199, 140-229, 157, 210-229; ICD10:C25] Phase 3 [468274], [527314]
Pancreatic cancer; Lung cancer [ICD9: 140-229, 157, 162; ICD10:C25, C33-C34] Discontinued in Phase 3 [468274], [536223]
Therapeutic Class
Anticancer Agents
Company
British Biotech plc; Schering-Plough
Structure
Download
2D MOL

3D MOL

Formula
C15H29N3O5
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
CAS Number
CAS 154039-60-8
PubChem Compound ID
PubChem Substance ID
Target and Pathway
Target(s) Matrilysin Target Info Inhibitor [528049], [536340], [537040], [538064]
Interstitial collagenase Target Info Inhibitor [528049], [536340], [537040], [538064]
72 kDa type IV collagenase Target Info Inhibitor [528049], [536340], [537040], [538064]
KEGG Pathway Wnt signaling pathwayhsa03320:PPAR signaling pathway
Pathways in cancer
Bladder cancer
Rheumatoid arthritishsa04670:Leukocyte transendothelial migration
GnRH signaling pathway
Estrogen signaling pathway
Proteoglycans in cancer
NetPath Pathway Wnt Signaling PathwayNetPath_13:IL1 Signaling Pathway
EGFR1 Signaling Pathway
TWEAK Signaling Pathway
Wnt Signaling PathwayNetPath_22:Leptin Signaling Pathway
TCR Signaling Pathway
ID Signaling Pathway
PANTHER Pathway Alzheimer disease-presenilin pathway
Wnt signaling pathway
CCKR signaling map STP00004:Alzheimer disease-presenilin pathway
Plasminogen activating cascadeP00004:Alzheimer disease-presenilin pathway
Pathway Interaction Database Posttranslational regulation of adherens junction stability and dissassembly
p75(NTR)-mediated signaling
Syndecan-1-mediated signaling eventsendothelinpathway:Endothelins
Validated transcriptional targets of AP1 family members Fra1 and Fra2
Glucocorticoid receptor regulatory network
AP-1 transcription factor network
Syndecan-1-mediated signaling eventslysophospholipid_pathway:LPA receptor mediated events
Plasma membrane estrogen receptor signaling
Osteopontin-mediated events
Angiopoietin receptor Tie2-mediated signaling
Direct p53 effectors
amb2 Integrin signaling
ATF-2 transcription factor network
FOXM1 transcription factor network
Regulation of nuclear beta catenin signaling and target gene transcription
Syndecan-2-mediated signaling events
Reactome Collagen degradation
Degradation of the extracellular matrix
Activation of Matrix Metalloproteinases
Assembly of collagen fibrils and other multimeric structuresR-HSA-1442490:Collagen degradation
Basigin interactions
Regulation of Insulin-like Growth Factor (IGF) transport and uptake by Insulin-like Growth Factor Binding Proteins (IGFBPs)R-HSA-1442490:Collagen degradation
Regulation of Insulin-like Growth Factor (IGF) transport and uptake by Insulin-like Growth Factor Binding Proteins (IGFBPs)
EPH-ephrin mediated repulsion of cells
WikiPathways Wnt Signaling Pathway and Pluripotency
Activation of Matrix Metalloproteinases
AGE/RAGE pathway
Matrix MetalloproteinasesWP366:TGF beta Signaling Pathway
Bladder Cancer
Degradation of collagen
Quercetin and Nf-kB/ AP-1 Induced Cell Apoptosis
Oncostatin M Signaling Pathway
Prostate Cancer
Integrated Breast Cancer Pathway
Integrated Cancer pathway
Cell surface interactions at the vascular wall
Matrix MetalloproteinasesWP2769:Activation of Matrix Metalloproteinases
Matrix Metalloproteinases
References
Ref 468274(http://www.guidetopharmacology.org/) Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5220).
Ref 527314Randomized phase III trial of marimastat versus placebo in patients with metastatic breast cancer who have responding or stable disease after first-line chemotherapy: Eastern Cooperative Oncology Group trial E2196. J Clin Oncol. 2004 Dec 1;22(23):4683-90.
Ref 536223Emerging drugs for the treatment of chronic obstructive pulmonary disease. Expert Opin Emerg Drugs. 2006 May;11(2):275-91.
Ref 528049Tumour microenvironment - opinion: validating matrix metalloproteinases as drug targets and anti-targets for cancer therapy. Nat Rev Cancer. 2006 Mar;6(3):227-39.
Ref 536340Metalloelastase (MMP-12) induced inflammatory response in mice airways: effects of dexamethasone, rolipram and marimastat. Eur J Pharmacol. 2007 Mar 15;559(1):75-81. Epub 2006 Dec 12.
Ref 537040Matrix metalloproteinase-2 involvement in breast cancer progression: a mini-review. Med Sci Monit. 2009 Feb;15(2):RA32-40.
Ref 538064Matrix metalloproteinase inhibition as a novel anticancer strategy: a review with special focus on batimastat and marimastat. Pharmacol Ther. 1997;75(1):69-75.

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