VASICINONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H10N2O2
Molecular Weight	202.2093
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H]1CCN2C1=NC3=C(C=CC=C3)C2=O

InChI

InChIKey=SDIVYZXRQHWCKF-VIFPVBQESA-N

InChI=1S/C11H10N2O2/c14-9-5-6-13-10(9)12-8-4-2-1-3-7(8)11(13)15/h1-4,9,14H,5-6H2/t9-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23811445 | https://www.ncbi.nlm.nih.gov/pubmed/22557323
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/25059038

Vasicinone is a quinazoline alkaloid. Hepatoprotective activity of vasicinone has being shown in mice. Pre-treatment with vasicinone and silymarin (25 mg/kg/day for 7 days) significantly decreased CCl4-induced increase in SGOT, SGPT, ALP levels. Vasicinone has shown cytotoxic and antiproliferative activity in several tumor cell lines. Vasicinone, an oxidation product of vascinine is a potent bronchodialator. Vasicinone could be utilised in alternate anti asthmatic therapy, since it plays a vital role in scavenging Nitric oxide which could prevent the bronchial inflammation in asthmatic patients.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Jurkat 1 Target ID: CHEMBL397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23811445	Inhibitor 8297
Escherichia coli 82 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23357363	Inhibitor 8297
Acetylcholinesterase 207 Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19784581	Inhibitor 8297
nitric oxide biosynthetic process 17 Target ID: GO:0006809 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22557323	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22557323	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Invitro antioxidant activity of selected antiasthmatic herbal constituents.	2009 Apr	22557323
Antitussive, expectorant, and bronchodilating effects of quinazoline alkaloids (±)-vasicine, deoxyvasicine, and (±)-vasicinone from aerial parts of Peganum harmala L.	2015 Nov 15	26547531

Patents

Sample Use Guides

In Vivo Use Guide

Rats experimental arthritis model: maximum inhibition rate was observed of vasicinone (63.94%) atter dose of 10.0 mg/kg p.o at 4 days after CFA injection.

Route of Administration: Oral

In Vitro Use Guide

The concentration of vasicinone needed to inhibit the incorporation of {(3)H-TDR} in the DNA cells of Jurkat, E6-1 clone by 50% (IC50) were 8.60 ± 0.023 ug/mL

Name

Type

Language

VASICINONE

Common Name

English

VASICINONE (CONSTITUENT OF MALABAR NUT TREE, LEAF) [DSC]

Common Name

English

(-)-VASICINONE

Common Name

English

L-VASICINONE

Common Name

English

PYRROLO(2,1-.BETA.)QUINAZOLIN-9(1H)-ONE, 2,3-DIHYDRO-3-HYDROXY-, (3S)-

Systematic Name

English

Code System Code Type Description

FDA UNII

G6T5819NXM