NM-3

Investigational

Details

Stereochemistry	EPIMERIC
Molecular Formula	C13H12O6
Molecular Weight	264.2308
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(O)=C2C(=O)OC(=CC2=C1)C(C)C(O)=O

InChI

InChIKey=BPZCXUROMKDLGX-UHFFFAOYSA-N

InChI=1S/C13H12O6/c1-6(12(15)16)10-4-7-3-8(18-2)5-9(14)11(7)13(17)19-10/h3-6,14H,1-2H3,(H,15,16)

HIDE SMILES / InChI

Molecular Formula	C13H12O6
Molecular Weight	264.2308
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug/def/nm-3 | https://adisinsight.springer.com/drugs/800012816 | https://www.ncbi.nlm.nih.gov/pubmed/12467237

1H-2-BENZOPYRAN-3-ACETIC ACID, 8-HYDROXY-6-METHOXY-Α-METHYL-1-OXO- (NM-3) is an orally bioavailable antiangiogenic isocoumarin with potential antineoplastic activity. NM-3 inhibits vascular endothelial growth factor (VEGF), a pro-angiogenic growth factor, thereby inhibiting endothelial cell proliferation. NM-3 induces apoptosis by a mechanism involving reactive oxygen species. In human MCF-7 and ZR-75-1 breast cancer cells, NM-3 induces the p21 cyclin-dependent kinase inhibitor, cell cycle arrest at G1-S-phase, and necrotic cell death. NM-3 has been used in trials studying the treatment of solid tumours.

Originator

Approval Year

PubMed

Title	Date	PubMed
The novel isocoumarin 2-(8-hydroxy-6-methoxy-1-oxo-1H-2-benzopyran-3-yl) propionic acid (NM-3) induces lethality of human carcinoma cells by generation of reactive oxygen species.	2001 Nov	12467237
Effect of 2-(8-hydroxy-6-methoxy-1-oxo-1H-2-benzopyran-3-yl) propionic acid in combination with carboplatin on gastric carcinoma growth in vivo.	2007 Jan 28	17278215
Synergistic effect of oxymatrine and angiogenesis inhibitor NM-3 on modulating apoptosis in human gastric cancer cells.	2007 Mar 28	17465467

Sample Use Guides

In Vivo Use Guide

Mice: NM-3 was injected peritoneally at the dose of 10 mg/kg, 20 mg/kg or 40 mg/kg every other day for 5 wk, combined with carboplatin (5 mg/kg) every third day for 4 wk. As controls of combined treatment, another 4 groups of mice were injected with either NM-3 at 10 mg/kg, 20 mg/kg or 40 mg/kg, or with carboplatin alone (5 mg/kg).

Route of Administration: Intraperitoneal

In Vitro Use Guide

To assess the effects of NM-3 on cell proliferation and survival, MCF-7 breast carcinoma cells were treated with 100–400 ug/ml NM-3 for 24 and 48 h. The results demonstrate adose- and time-dependent inhibition of cell growth. o determine whether NM-3 affects clono-genic survival, cells were treated for 48 h and then culturedfor 10–14 days. Assessment of colonies demonstrated that NM-3 decreases clonogenicity of MCF-7 cells with an IC50 of 180 ug/ml. Similar results were found for ZR-75-1cells (IC50, 180 ug/ml).

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:00:57 GMT 2023` Edited by `admin` on `Sat Dec 16 05:00:57 GMT 2023`
Record UNII	5797K23F95
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NM-3

Common Name

English

1H-2-BENZOPYRAN-3-ACETIC ACID, 8-HYDROXY-6-METHOXY-.ALPHA.-METHYL-1-OXO-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1971