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
Correction of an in vitro immunoregulatory defect in atopic subjects by the immunostimulating drug fanetizole mesylate (CP-48,810).	1984	6233230
How do immunomodulators affect host defense in the burn patient?	1984 Sep	6384529
Inhibition of neutrophil superoxide production by fanetizole.	1985 Sep	2995253

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