BENZANTHRONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H10O
Molecular Weight	230.2607
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1C2=CC=CC=C2C3=CC=CC4=CC=CC1=C34

InChI

InChIKey=HUKPVYBUJRAUAG-UHFFFAOYSA-N

InChI=1S/C17H10O/c18-17-14-8-2-1-7-12(14)13-9-3-5-11-6-4-10-15(17)16(11)13/h1-10H

HIDE SMILES / InChI

Molecular Formula	C17H10O
Molecular Weight	230.2607
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25454808 | https://www.ncbi.nlm.nih.gov/pubmed/28495615

Benzanthrone (BA) is an important dye used in the manufacturing of several polycyclic vats and disperse dyes in textile industries. In several clinical studies, it has been shown that workers exposed to BA developed itching, burning sensation, erythema and hyperpigmentation of the skin, which could be an outcome of the dysregulated immune response. Chronically exposed workers complained loss of appetite, intolerance to fatty food, fatigue, weight loss, weakness and decrease in sexual activity. Recently was discovered, that benzanthrone binds to a critical component in the regulation of the BA-induced inflammation, Toll-like receptor 4, TLR4.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Toll-like receptor 4 6 Target ID: O00206\|\|\|Q5VZI8 Gene ID: 7099.0 Gene Symbol: TLR4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28495615	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Role of biological antioxidants in benzanthrone toxicity.	2001 Jun	11482520
Comparative effect of benzanthrone and 3-bromobenzanthrone on hepatic xenobiotic metabolism and anti-oxidative defense system in guinea pigs.	2003 Feb	12590361
Identification of estrogenic compounds emitted from the combustion of computer printed circuit boards in electronic waste.	2007 Dec 15	18200886
Biochemical parameters of liver function in artisans occupationally exposed to "vat dyes".	2007 May	21938220
Concentration of oxygenated polycyclic aromatic hydrocarbons and oxygen free radical formation from urban particulate matter.	2007 Nov	17934959
Correlation of altered blood albumin characteristics and lymphocyte populations to tumor stage in gastrointestinal cancer patients.	2010	21178267
Ligand-Specific Transcriptional Mechanisms Underlie Aryl Hydrocarbon Receptor-Mediated Developmental Toxicity of Oxygenated PAHs.	2015 Oct	26141390

Patents

Sample Use Guides

In Vivo Use Guide

immunotoxicity in Balb/c mice: benzanthrone (7.5mg/kgb.w. and 15mg/kgb.w.) for one week

Route of Administration: Intraperitoneal

In Vitro Use Guide

In vitro addition of benzanthrone caused a spectral change with oxidized microsomal cytochrome P450 (P450) and concentration-dependent reduction in the carbon monoxide spectrum of dithionite-reduced P450. The addition of benzanthrone to hepatic microsomes prepared from phenobarbital-treated rats resulted in spectral changes characterized by an absorbance maximum at 397 nm indicative of type I binding. In vitro addition of benzanthrone showed a concentration-dependent inhibition of hepatic aminopyrine N-demethylase (APD) and ethoxyresorufin-O-deethylase (ERD) activities with respective I50 values of 9.5 x 10(-4) and 8.0 x 10(-5) M. However, the inhibition of aryl hydrocarbon hydroxylase (AHH) even at the highest concentration of benzanthrone (10(-2) M), was of the order of only 29%.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:10:41 GMT 2023` Edited by `admin` on `Fri Dec 15 17:10:41 GMT 2023`
Record UNII	LP5P3RR8QN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENZANTHRONE

Systematic Name

English

BENZ(DE)ANTHRACEN-7-ONE

Systematic Name

English

7H-BENZ(DE)ANTHRACEN-7-ONE

Systematic Name

English

BENZANTHRONE [MI]

Common Name

English

NSC-5189

Code

English

BENZANTHRONE [HSDB]

Common Name

English

NSC-631641

Code

English

Code System Code Type Description

NSC

631641