FANETIZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H16N2S
Molecular Weight	280.387
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C(CC1=CC=CC=C1)NC2=NC(=CS2)C3=CC=CC=C3

InChI

InChIKey=WEEYMMXMBFJUAI-UHFFFAOYSA-N

InChI=1S/C17H16N2S/c1-3-7-14(8-4-1)11-12-18-17-19-16(13-20-17)15-9-5-2-6-10-15/h1-10,13H,11-12H2,(H,18,19)

HIDE SMILES / InChI

Molecular Formula	C17H16N2S
Molecular Weight	280.387
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/2995253 | https://www.ncbi.nlm.nih.gov/pubmed/6233230 | DOI: 10.1016/0091-6749(83)90328-7

Fanetizole is a derivative of 2-aminothiazole. It is an anti-inflammatory agent. This drug is reported to have some cyclooxygenase inhibiting activity. Production of superoxide in response to the chemotactic factor formyl-methionyl-leucyl-phenylalanine (f-Met-Leu-Phe) was markedly inhibited by fanetizole. Suppression of neutrophil production of toxic oxygen metabolites may partially explain the antiarthritic effect of fanetizole. Fanetizole was shown to restore depressed E-rosetting activity in adult thymectomized mice, as well as enhance in in vitro proliferation of murine thymic cells to mitogen and synergistically acted with the monokine interleukin-1. It displays anti-arthritic activity in viva in the rat adjuvant arthritis model, inhibiting the development of disease in the non-infected foot. This drug has less side effects than levamisole in animals.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
superoxide anion generation 11 Target ID: GO:0042554 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2995253	Inhibitor 8297
Cyclooxygenase 89 Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6233230	Inhibitor 8297
IgE production 2 Target ID: IgE production Sources: https://www.ncbi.nlm.nih.gov/pubmed/6233230	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rheumatoid arthritis 316 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6233230 Wirth, T. (2008) Microreactors in Organic Synthesis and Catalysis, page 65, retrieved from: https://books.google.ru/books?id=gmZnSM3DGM8C	Palliative		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

B cells from 16 atopic subjects without eczema produced de novo a mean of 516 pg/ml of IgE without the drug and 196 pg/ml in the presence of 2.5 x 10(-4) M drug. B cells from 6 atopic subjects with eczema synthesized a mean of 1984 pg/ml of IgE in the absence of the drug and 1486 pg/ml in the presence of 2.5 x 10(-4) M drug.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:17:27 GMT 2023` Edited by `admin` on `Fri Dec 15 16:17:27 GMT 2023`
Record UNII	BH48F620JA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FANETIZOLE

Official Name

English

2-(PHENETHYLAMINO)-4-PHENYLTHIAZOLE

Systematic Name

English

fanetizole [INN]

Common Name

English

2-THIAZOLAMINE, 4-PHENYL-N-(2-PHENYLETHYL)-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C257