SALICYLANILIDE

US Previously Marketed

First approved in 1946

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H11NO2
Molecular Weight	213.2319
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=C(C=CC=C1)C(=O)NC2=CC=CC=C2

InChI

InChIKey=WKEDVNSFRWHDNR-UHFFFAOYSA-N

InChI=1S/C13H11NO2/c15-12-9-5-4-8-11(12)13(16)14-10-6-2-1-3-7-10/h1-9,15H,(H,14,16)

HIDE SMILES / InChI

Molecular Formula	C13H11NO2
Molecular Weight	213.2319
Charge	0
Count

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

Description
Sources: https://books.google.ru/books?id=QkmF7rcBaRIC&pg=PA258&lpg=PA258&dq=Salinidol retrieved from Synthetic Drugs By Rajbir Singh, p.258 | http://www.abcam.com/salicylanilide-ab145794.html

Salicylanilide (Salinidol). It is anilide of salicylic acid. It is an antifungal agent useful in the treatment of tinea capitis. Due to its inritant action on the skin, the concentration used should be 5 per cent or less. Salicylanilide is an oxidative phosphorylation uncoupler. Salicylanilide inhibits mycobacterial isocitrate lyase. Shows antifungal, antimycobacterial and antihelmitic effects in vivo.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Isocitrate lyase 2 Target ID: CHEMBL1667699 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23506018 \| http://www.abcam.com/salicylanilide-ab145794.html	Inhibitor 8297
Mycobacterium tuberculosis H37Rv 11 Target ID: CHEMBL2111188 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24953953	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tinea capitis 4 Sources: Singh, R. () Synthetic Drugs, page 258, retrieved from: https://books.google.ru/books?id=QkmF7rcBaRIC	Primary		Approved 8429	Salinidol Approved Use Tinea capitis Launch Date -7.5746882E11

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:239133	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:239133
ChemicalBook	CB9124965	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9124965
MolPort	MolPort-001-781-621	https://www.molport.com/shop/molecule-link/MolPort-001-781-621
Selleck Chemicals	salicylanilide	http://www.selleckchem.com/products/salicylanilide.html
ZINC	ZINC000000002057	http://zinc15.docking.org/substances/ZINC000000002057
eMolecules	480609	https://www.emolecules.com/cgi-bin/more?vid=480609

PubMed

Title	Date	PubMed
Relationship between the structure and antimycobacterial activity of substituted salicylanilides.	2003 Mar	12666254
Small molecules with antimicrobial activity against E. coli and P. aeruginosa identified by high-throughput screening.	2006 Nov	16981005
Myelin vacuolation, optic neuropathy and retinal degeneration after closantel overdosage in sheep and in a goat.	2007 Feb-Apr	17270202
Salicylanilide acetates: synthesis and antibacterial evaluation.	2007 Jan 1	17693949
Protein and Peptide drug delivery: oral approaches.	2008 May-Jun	20046732
Salicylanilides: selective inhibitors of interleukin-12p40 production.	2008 Sep 15	18715785
2-Hydr-oxy-3-nitro-N-phenyl-benzamide.	2009 Apr 18	21583861
Salicylanilide esters of N-protected amino acids as novel antimicrobial agents.	2009 Jan 15	19081718
Drug discovery for schistosomiasis: hit and lead compounds identified in a library of known drugs by medium-throughput phenotypic screening.	2009 Jul 14	19597541
Multi-residue determination of phenolic and salicylanilide anthelmintics and related compounds in bovine kidney by liquid chromatography-tandem mass spectrometry.	2009 Nov 13	19426989
Salicylanilide carbamates: antitubercular agents active against multidrug-resistant Mycobacterium tuberculosis strains.	2010 Feb	20060303
Polioencephalomalacia associated with closantel overdosage in a goat.	2010 Jun	21247019
Salicylanilide derivatives block Mycobacterium tuberculosis through inhibition of isocitrate lyase and methionine aminopeptidase.	2012 Sep	22765970

Patents

Sample Use Guides

In Vivo Use Guide

Tinea capitis treatment: the concentration used should be 5 per cent or less.

Route of Administration: Topical

In Vitro Use Guide

Salicylanilide inhibited Mycobacterium tuberculosis H37Rv 331/88 (assessed as complete growth inhibition after 14 days) with MIC 32uM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:03:59 UTC 2023` Edited by `admin` on `Fri Dec 15 15:03:59 UTC 2023`
Record UNII	LHP8NEY345
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SALICYLANILIDE

Systematic Name

English

SALICYLANILIDE [MI]

Common Name

English

N-PHENYLSALICYLAMIDE

Systematic Name

English

2-HYDROXY-N-PHENYLBENZAMIDE

Systematic Name

English

NSC-14881

Code

English

SALINIDOL

Brand Name

English

Salicylanilide [WHO-DD]

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

77407