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

Molecular Formula	C11H10N2O2
Molecular Weight	202.2093
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:38:09 GMT 2023` Edited by `admin` on `Fri Dec 15 16:38:09 GMT 2023`
Record UNII	G6T5819NXM
Record Status	`Validated (UNII)`
Record Version

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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