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Marimastat

Marimastat structure

CAS No:
154039-60-8
Formula:
C15H29N3O5
Chemical Name:
Marimastat
Synonyms:
Butanediamide,N4-[(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-N1,2-dihydroxy-3-(2-methylpropyl)-,(2S,3R)-;Butanediamide,N4-[2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-N1,2-dihydroxy-3-(2-methylpropyl)-,[2S-[N4(R*),2R*,3S*]]-;(2S,3R)-N4-[(1S)-2,2-Dimethyl-1-[(methylamino)carbonyl]propyl]-N1,2-dihydroxy-3-(2-methylpropyl)butanediamide;BB 2516;Marimastat;GI 5712;TA 2516;KB-R 8898
Categories:
Biochemical Engineering > Inhibitors

Description

Marimastat is a broad spectrum inhibitor of MMPs with IC50 values of 3, 5, 6, 9 and 13 nM for MMP-9, MMP-1, MMP-2, MMP-14 and MMP-7, respectively.

Solid

Marimastat is a secondary carboxamide resulting from the foraml condensation of the carboxy group of (2R)-2-[(1S)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoic acid with the alpha-amino group of N,3-dimethyl-L-valinamide. It has a role as an antineoplastic agent and a matrix metalloproteinase inhibitor. It is a secondary carboxamide and a hydroxamic acid.|Used in the treatment of cancer, Marmiastat is an angiogenesis and metastasis inhibitor. As an angiogenesis inhibitor it limits the growth and production of blood vessels. As an antimetatstatic agent it prevents malignant cells from breaching the basement membranes.|Marimastat is an orally-active synthetic hydroxamate with potential antineoplastic activity. Marimastat covalently binds to the zinc(II) ion in the active site of matrix metalloproteinases (MMPs), thereby inhibiting the action of MMPs, inducing extracellular matrix degradation, and inhibiting angiogenesis, tumor growth and invasion, and metastasis. This agent may also inhibit tumor necrosis factor-alpha converting enzyme (TACE), an enzyme involved in tumor necrosis factor alpha (TNF-alpha) production that may play a role in some malignancies as well as in the development of arthritis and sepsis. (NCI04)

Marimastat Basic Attributes

Molecular Weight：

331.41

Exact Mass：

331.41

UNII：

D5EQV23TDS

NSC Number：

719333|689451

DSSTox ID：

DTXSID20165524

NCI Thesaurus Code：

C1652

HScode：

29241990

Characteristics

PSA：

128

XLogP3：

0.5

Density：

1.140±0.06 g/cm3(Predicted)

Melting Point：

148℃

Refractive Index：

1.499

Water Solubility：

DMSO: ≥20mg/mL

Storage Conditions：

Store at -20°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

RTECS Number：

EJ6665000

Drug Information

Drug Indication：

For the treatment of various cancers

Pharmacology：

Used in the treatment of cancer, it is an angiogenesis and metastasis inhibitor. As an angiogenesis inhibitor it limits the growth and production of blood vessels. As an antimetatstatic agent it prevents malignant cells from breaching the basement membranes.

MeSH：

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

Mechanism of Action：

Marimastat is a broad spectrum matrix metalloprotease inhibitor. It mimics the peptide structure of natural MMP substrates and binds to matrix metalloproteases, thereby preventing the degradation of the basement membrane by these proteases. This antiprotease action prevents the migration of endothelial cells needed to form new blood vessels. Inhibition of MMPs also prevents the entry and exit of tumor cells into existing blood cells, thereby preventing metastasis.

MeSH Entry Terms：

BB-2516

Marimastat Use and Manufacturing

Antineoplastic (matrix metalloproteinase inhibitor).Broad spectrum inhibitor of matrix metalloprotease (MMP) (IC 50 values are 3, 5, 6, 9 and 13 nM for MMP-9, MMP-1, MMP-2, MMP-14 and MMP-7 respectively). In vivo inhibits peritoneal dissemination of human gastric cancer cells through inhibition of tumor angiogenesis.

Computed Properties

Molecular Weight:331.41
XLogP3:0.5
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:8
Exact Mass:331.21072103
Monoisotopic Mass:331.21072103
Topological Polar Surface Area:128
Heavy Atom Count:23
Complexity:431
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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