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Details

Stereochemistry ACHIRAL
Molecular Formula C13H8Br3NO2
Molecular Weight 449.92
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIBROMSALAN

SMILES

OC1=C(C=C(Br)C=C1Br)C(=O)NC2=CC=C(Br)C=C2

InChI

InChIKey=KVSKGMLNBAPGKH-UHFFFAOYSA-N
InChI=1S/C13H8Br3NO2/c14-7-1-3-9(4-2-7)17-13(19)10-5-8(15)6-11(16)12(10)18/h1-6,18H,(H,17,19)

HIDE SMILES / InChI

Description
Curator's Comment: Description was created using several sources including: PMID:20067776 https://www.ncbi.nlm.nih.gov/pubmed/20067776; http://www.fda.gov/downloads/aboutfda/centersoffices/officeofmedicalproductsandtobacco/cder/ucm135607.pdf; https://www.ncbi.nlm.nih.gov/pubmed/12755728; https://www.federalregister.gov/documents/2016/09/06/2016-21337/safety-and-effectiveness-of-consumer-antiseptics-topical-antimicrobial-drug-products-for

Tribromsalan (trade name Temasept IV) is a member of brominated salicylanilides chemical family. Was initially registered in 1964 manufactured by Hexcel Corporation, Sherwin Williams Chemicals. It is a pesticide type with antimicrobial and preservative features found its application in hard surfaces, laundry, textiles, and manufactured products. Types of tribromsalan formulations include solid, solutions, and sprays and its usual carrier is soap. Limited exposure is possible based on the registered uses of these products as disinfectants, laundry additives, textile preservatives, and manufactured products and do not include direct application to a food or feed crop. In 1974 FDA directed the removal of tribromsalan drug products from the market because it was found to make skin extrasensitive to light. For the same reason it was forbidden in Europe since the 1970s. Since 1982 the OTC topical antimicrobial drug products rulemaking was reopened and included tribromsalan in a list of antimicrobial OTC Drug Products. At present tribromsalan is considered an antiseptic active ingredient eligible for the OTC use as a consumer antiseptic hand and body wash drug product. It was reported that tribromsalan, inhibits NF-kappaB signaling via inhibition of IkappaBalpha phosphorylation with IC50 of 7.9 uM. This finding provides new information on activities and mechanisms of action that may suggest mechanisms of potential novel applications in cancer treatment of such drugs as tribromsalan.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Polytar Soap

Approved Use

Marketed as hand and body wash soap for human use. Approval information unknown
Doses

Doses

DosePopulationAdverse events​
1 % 1 times / day single, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: single
Dose: 1 %, 1 times / day
Sources:
unhealthy, 47 years
n = 1
Health Status: unhealthy
Condition: Photoallergic contact dermatitis
Age Group: 47 years
Sex: M
Population Size: 1
Sources:
Other AEs: Photosensitivity...
Other AEs:
Photosensitivity
Sources:
1 % 1 times / day single, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: single
Dose: 1 %, 1 times / day
Sources:
unhealthy, 60 years
n = 1
Health Status: unhealthy
Condition: atopic dermatitis
Age Group: 60 years
Sex: M
Population Size: 1
Sources:
Other AEs: Photosensitivity...
Other AEs:
Photosensitivity
Sources:
0.5 % 1 times / day single, topical
Dose: 0.5 %, 1 times / day
Route: topical
Route: single
Dose: 0.5 %, 1 times / day
Sources:
healthy, adult
n = 10
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 10
Sources:
Other AEs: Photosensitivity...
Other AEs:
Photosensitivity
Sources:
AEs

AEs

AESignificanceDosePopulation
Photosensitivity
1 % 1 times / day single, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: single
Dose: 1 %, 1 times / day
Sources:
unhealthy, 47 years
n = 1
Health Status: unhealthy
Condition: Photoallergic contact dermatitis
Age Group: 47 years
Sex: M
Population Size: 1
Sources:
Photosensitivity
1 % 1 times / day single, topical
Studied dose
Dose: 1 %, 1 times / day
Route: topical
Route: single
Dose: 1 %, 1 times / day
Sources:
unhealthy, 60 years
n = 1
Health Status: unhealthy
Condition: atopic dermatitis
Age Group: 60 years
Sex: M
Population Size: 1
Sources:
Photosensitivity
0.5 % 1 times / day single, topical
Dose: 0.5 %, 1 times / day
Route: topical
Route: single
Dose: 0.5 %, 1 times / day
Sources:
healthy, adult
n = 10
Health Status: healthy
Age Group: adult
Sex: M
Population Size: 10
Sources:
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
yes [IC50 2 uM]
yes [IC50 2 uM]
Tox targets
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
A new animal model for contact dermatitis: the hairless guinea pig.
1992 Mar
Spectrum of cross-photosensitization in 18 consecutive patients with contact photoallergy to ketoprofen: associated photoallergies to non-benzophenone-containing molecules.
2003 Mar
[Concentration in plasma and excretion in milk of lactating cows after oral administration of tribromsalan, oxyclozanide and bromofenofos].
2006 Dec
Increased expression of IRE1alpha and stress-related signal transduction proteins in ischemia-reperfusion injured retina.
2008 Dec
Identification of halosalicylamide derivatives as a novel class of allosteric inhibitors of HCV NS5B polymerase.
2008 Jun 1
Determination of bithionol, bromophen, nitroxynil, oxyclozanide, and tribromsalan in milk with liquid chromatography coupled with tandem mass spectrometry.
2010 Jul-Aug
Identification of known drugs that act as inhibitors of NF-kappaB signaling and their mechanism of action.
2010 May 1
Patents

Patents

Sample Use Guides

Soap Bar: Pine Tar 1%; Tribromsalan 0.3%
Route of Administration: Topical
For measurement of phosphorylation of GFP-IκBα in IκBα GripTite cells, cells were incubated with 0.5 nM to 38 uM of tribromsalan followed by addition of either assay buffer with or without 1 ng/ml TNFα. The assay plates were incubated for 30 min at 37°C. Tribromsalan inhibited NF-kappaB signaling via inhibition of IkappaBalpha phosphorylation with IC50 of 7.9 uM.
Name Type Language
TRIBROMSALAN
INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
TRIBROMSALAN [MI]
Common Name English
TUASOL 100
Brand Name English
Tribromsalan [WHO-DD]
Common Name English
BENZAMIDE, 3,5-DIBROMO-N-(4-BROMOPHENYL)-2-HYDROXY-
Systematic Name English
NSC-20526
Code English
TRIBROMSALAN [MART.]
Common Name English
3,4',5-TRIBROMOSALICYLANILIDE
Systematic Name English
tribromsalan [INN]
Common Name English
TRIBROMSALAN [USAN]
Common Name English
ET-394
Code English
WR-34912
Code English
TEMASEPT IV
Brand Name English
Classification Tree Code System Code
CFR 21 CFR 310.502
Created by admin on Fri Dec 15 15:03:58 GMT 2023 , Edited by admin on Fri Dec 15 15:03:58 GMT 2023
EPA PESTICIDE CODE 77404
Created by admin on Fri Dec 15 15:03:58 GMT 2023 , Edited by admin on Fri Dec 15 15:03:58 GMT 2023
NCI_THESAURUS C28394
Created by admin on Fri Dec 15 15:03:58 GMT 2023 , Edited by admin on Fri Dec 15 15:03:58 GMT 2023
CFR 21 CFR 700.15
Created by admin on Fri Dec 15 15:03:58 GMT 2023 , Edited by admin on Fri Dec 15 15:03:58 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID4026181
Created by admin on Fri Dec 15 15:03:58 GMT 2023 , Edited by admin on Fri Dec 15 15:03:58 GMT 2023
PRIMARY
EVMPD
SUB11261MIG
Created by admin on Fri Dec 15 15:03:58 GMT 2023 , Edited by admin on Fri Dec 15 15:03:58 GMT 2023
PRIMARY
MESH
C004361
Created by admin on Fri Dec 15 15:03:58 GMT 2023 , Edited by admin on Fri Dec 15 15:03:58 GMT 2023
PRIMARY
MERCK INDEX
m11048
Created by admin on Fri Dec 15 15:03:58 GMT 2023 , Edited by admin on Fri Dec 15 15:03:58 GMT 2023
PRIMARY Merck Index
PUBCHEM
14868
Created by admin on Fri Dec 15 15:03:58 GMT 2023 , Edited by admin on Fri Dec 15 15:03:58 GMT 2023
PRIMARY
FDA UNII
6MCE3VTF0O
Created by admin on Fri Dec 15 15:03:58 GMT 2023 , Edited by admin on Fri Dec 15 15:03:58 GMT 2023
PRIMARY
INN
1623
Created by admin on Fri Dec 15 15:03:58 GMT 2023 , Edited by admin on Fri Dec 15 15:03:58 GMT 2023
PRIMARY
CAS
87-10-5
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PRIMARY
NSC
20526
Created by admin on Fri Dec 15 15:03:58 GMT 2023 , Edited by admin on Fri Dec 15 15:03:58 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-723-6
Created by admin on Fri Dec 15 15:03:58 GMT 2023 , Edited by admin on Fri Dec 15 15:03:58 GMT 2023
PRIMARY
CHEBI
127105
Created by admin on Fri Dec 15 15:03:58 GMT 2023 , Edited by admin on Fri Dec 15 15:03:58 GMT 2023
PRIMARY
SMS_ID
100000077533
Created by admin on Fri Dec 15 15:03:58 GMT 2023 , Edited by admin on Fri Dec 15 15:03:58 GMT 2023
PRIMARY
NCI_THESAURUS
C47768
Created by admin on Fri Dec 15 15:03:58 GMT 2023 , Edited by admin on Fri Dec 15 15:03:58 GMT 2023
PRIMARY
ChEMBL
CHEMBL24944
Created by admin on Fri Dec 15 15:03:58 GMT 2023 , Edited by admin on Fri Dec 15 15:03:58 GMT 2023
PRIMARY