BATIMASTAT

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H31N3O4S2
Molecular Weight	477.64
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(C)C)[C@H](CSC2=CC=CS2)C(=O)NO

InChI

InChIKey=XFILPEOLDIKJHX-QYZOEREBSA-N

InChI=1S/C23H31N3O4S2/c1-15(2)12-17(18(22(28)26-30)14-32-20-10-7-11-31-20)21(27)25-19(23(29)24-3)13-16-8-5-4-6-9-16/h4-11,15,17-19,30H,12-14H2,1-3H3,(H,24,29)(H,25,27)(H,26,28)/t17-,18+,19+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C23H31N3O4S2
Molecular Weight	477.64
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23370482
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9484924 | https://www.ncbi.nlm.nih.gov/pubmed/12877590 | https://www.ncbi.nlm.nih.gov/pubmed/8913840 | https://www.ncbi.nlm.nih.gov/pubmed/10100701 | https://www.ncbi.nlm.nih.gov/pubmed/9873712

Batimastat is a powerful broad spectrum hydroxamate-type matrix metalloproteinases inhibitor(MMPI), with potent anticancer activity. Batimastat inhibits the growth and spread of lung tumors, breast cancer regrowth, and human colon tumor growth and spread in mouse models. Batimastat reduces MMP-mediated vascular dysfunction and vessel wall damage and enhances the sealing ability and bond strength of dental adhesives. Batimastat was the first MMPIs evaluated in cancer patients and to be used in a clinical trial. Batimastat was administered by the intraperitoneal and intra-pleural route in clinical trials. The Phase I and II clinical trials of Batimastat, when administered intraperitoneally, did not show a good response. Due to its poor water solubility, it is not well accepted for cancer treatment.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Matrix metalloproteinase-1 8 Target ID: CHEMBL332 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12877590	Inhibitor 8297	0.99 nM [IC50]
Matrix metalloproteinase-2 13 Target ID: CHEMBL333 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12877590	Inhibitor 8297	0.73 nM [IC50]
Matrix metalloproteinase 3 13 Target ID: CHEMBL283 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12877590	Inhibitor 8297	0.56 nM [IC50]
Matrix metalloproteinase 7 3 Target ID: CHEMBL4073 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9873712	Inhibitor 8297	2.4 nM [IC50]
Matrix metalloproteinase 9 20 Target ID: CHEMBL321 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12877590	Inhibitor 8297	0.6 nM [IC50]
Matrix metalloproteinase 13 8 Target ID: CHEMBL280 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12877590	Inhibitor 8297	5.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Advanced cancer 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8913840	Primary		Phase I 428	Unknown Approved Use Unknown
Malignant pleural effusion 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10100701	Primary		Phase I 428	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Tyrosine phosphorylation and proteolysis. Pervanadate-induced, metalloprotease-dependent cleavage of the ErbB-4 receptor and amphiregulin.	1998 Aug 7	9685416
Decreased expression of membrane IL-5 receptor alpha on human eosinophils: II. IL-5 down-modulates its receptor via a proteinase-mediated process.	2002 Dec 1	12444155
Metalloproteinase-dependent transforming growth factor-alpha release mediates neurotensin-stimulated MAP kinase activation in human colonic epithelial cells.	2004 Oct 15	15247267
Metalloproteinases and transforming growth factor-alpha mediate substance P-induced mitogen-activated protein kinase activation and proliferation in human colonocytes.	2004 Oct 29	15319441
Elastin-derived peptides enhance angiogenesis by promoting endothelial cell migration and tubulogenesis through upregulation of MT1-MMP.	2005 Jan 15	15632106
Inhibition of estrogen-induced pituitary tumor growth and angiogenesis in Fischer 344 rats by the matrix metalloproteinase inhibitor batimastat.	2007 Mar	17235567

Patents

Sample Use Guides

In Vivo Use Guide

Batimastat was administered at 600, 1200 and 1800 mg/m^2 to consecutive groups of 3 patients once every 4 weeks

Route of Administration: Intravenous

In Vitro Use Guide

MCF-7 breast cancer cells were seeded in 24-well multidishes in growth medium and allowed to adhere for two days. When experiments were initiated (day 0), growth medium containing fulvestrant (0.1 μM), HER ligands (10 ng/ml), BB-94 (Batimastat, 10 μM) were added. The control cells were added similar amount of vehicle as the treated cells. Growth medium was replaced on day three, and cell number was deter¬mined on day five, using a crystal violet colorimetric assay. Batimastat shows potent anticancer activity.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 18:01:26 GMT 2023` Edited by `admin` on `Sat Dec 16 18:01:26 GMT 2023`
Record UNII	BK349F52C9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BATIMASTAT

Official Name

English

BB-94

Code

English

BATIMASTAT [MI]

Common Name

English

BATIMASTAT [USAN]

Common Name

English

BATIMASTAT [MART.]

Common Name

English

batimastat [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1970