TOLONIUM

US Previously Marketed

First approved in 1953

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H16N3S
Molecular Weight	270.373
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)C1=CC2=C(C=C1)N=C3C=C(C)C(N)=CC3=[S+]2

InChI

InChIKey=RQNADZJRELIICT-UHFFFAOYSA-N

InChI=1S/C15H16N3S/c1-9-6-13-15(8-11(9)16)19-14-7-10(18(2)3)4-5-12(14)17-13/h4-8H,16H2,1-3H3/q+1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22923899

Tolonium chloride (INN, also known as toluidine blue or TBO) is a phenothiazine that has been used as a hemostatic, a biological stain, and a dye for wool and silk. Tolonium chloride has also been used as a diagnostic aid for oral and gastric neoplasms and in the identification of the parathyroid gland in thyroid surgery. Toluidine blue has high affinity for acidic tissue components, thereby staining tissues rich in DNA and RNA. It has found wide applications both as vital staining in living tissues and as a special stain owing to its metachromatic property. Toluidine blue has been used in vivo to identify dysplasia and carcinoma of the oral cavity.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA or RNA 3 Target ID: DNA or RNA Sources: https://www.ncbi.nlm.nih.gov/pubmed/22923899	Binding Agent 1064

Conditions

Condition	Modality	Highest Phase	Product
Menorrhagia 4 Sources: https://www.drugs.com/international/tolonium-chloride.html	Primary	Approved 8429	Blutene Approved Use Treatment and prevention of excessive menstrual flow.
Keratosis (leucoplakia) 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10903660	Diagnostic	Not Provided 504	Unknown Approved Use Unknown
Oral cancer 13 Sources: https://clinicaltrials.gov/ct2/show/NCT00655421	Diagnostic	Phase III 656	Unknown Approved Use Unknown
Chronic periodontitis 4 Sources: https://clinicaltrials.gov/ct2/show/NCT01330082	Diagnostic	Phase III 656	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
2 mg/kg 1 times / day single, intravenous Studied dose Dose: 2 mg/kg, 1 times / day Route: intravenous Route: single Dose: 2 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30349973/	unhealthy, 27 years n = 1 Health Status: unhealthy Condition: Lipedema Age Group: 27 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/30349973/	Other AEs: Edema... Other AEs: Edema Sources: https://pubmed.ncbi.nlm.nih.gov/30349973/
4 mg/kg 1 times / day single, intravenous (mean) Studied dose Dose: 4 mg/kg, 1 times / day Route: intravenous Route: single Dose: 4 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4176446/	unhealthy, adult n = 27 Health Status: unhealthy Age Group: adult Population Size: 27 Sources: https://pubmed.ncbi.nlm.nih.gov/4176446/	Other AEs: Cardiac arrhythmia... Other AEs: Cardiac arrhythmia Sources: https://pubmed.ncbi.nlm.nih.gov/4176446/

AEs

AE	Significance	Dose	Population
Edema		2 mg/kg 1 times / day single, intravenous Studied dose Dose: 2 mg/kg, 1 times / day Route: intravenous Route: single Dose: 2 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30349973/	unhealthy, 27 years n = 1 Health Status: unhealthy Condition: Lipedema Age Group: 27 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/30349973/
Cardiac arrhythmia		4 mg/kg 1 times / day single, intravenous (mean) Studied dose Dose: 4 mg/kg, 1 times / day Route: intravenous Route: single Dose: 4 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4176446/	unhealthy, adult n = 27 Health Status: unhealthy Age Group: adult Population Size: 27 Sources: https://pubmed.ncbi.nlm.nih.gov/4176446/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:87648	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:87648
ZINC	ZINC000004217587	http://zinc15.docking.org/substances/ZINC000004217587

PubMed

Title	Date	PubMed
ABC of oral health. Swellings and red, white, and pigmented lesions.	2000 Jul 22	10903660
Toluidine blue: A review of its chemistry and clinical utility.	2012 May	22923899

Patents

Sample Use Guides

In Vivo Use Guide

Examination of the oral cavity after the local application of Toluidine Blue dye (tolonium chloride)

Route of Administration: Other

In Vitro Use Guide

Unknown

Name

Type

Language

TOLONIUM

Common Name

English

PHENOTHIAZIN-5-IUM, 3-AMINO-7-(DIMETHYLAMINO)-2-METHYL-

Systematic Name

English

TOLONIUM ION

Common Name

English

Tolonium [WHO-DD]

Common Name

English

TOLONIUM CATION

Common Name

English

Code System Code Type Description

FDA UNII

P3Y6XJA2D1