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Details

Stereochemistry ACHIRAL
Molecular Formula 2C13H7Br3NO2.Zn
Molecular Weight 963.233
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIBROMSALAN ZINC

SMILES

[Zn++].[O-]C1=C(C=C(Br)C=C1Br)C(=O)NC2=CC=C(Br)C=C2.[O-]C3=C(C=C(Br)C=C3Br)C(=O)NC4=CC=C(Br)C=C4

InChI

InChIKey=FYDPELQJHOCRKA-UHFFFAOYSA-L
InChI=1S/2C13H8Br3NO2.Zn/c2*14-7-1-3-9(4-2-7)17-13(19)10-5-8(15)6-11(16)12(10)18;/h2*1-6,18H,(H,17,19);/q;;+2/p-2

HIDE SMILES / InChI

Molecular Formula Zn
Molecular Weight 65.409
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C13H7Br3NO2
Molecular Weight 448.912
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:08:14 GMT 2023
Edited
by admin
on Fri Dec 15 15:08:14 GMT 2023
Record UNII
R83418008N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIBROMSALAN ZINC
Common Name English
ZINC 3,4',5-TRIBROMOSALICYANILIDE
Systematic Name English
BENZAMIDE, 3,5-DIBROMO-N-(4-BROMOPHENYL)-2-HYDROXY-, ZINC SALT (2:1)
Systematic Name English
Code System Code Type Description
CAS
38934-24-6
Created by admin on Fri Dec 15 15:08:14 GMT 2023 , Edited by admin on Fri Dec 15 15:08:14 GMT 2023
PRIMARY
FDA UNII
R83418008N
Created by admin on Fri Dec 15 15:08:14 GMT 2023 , Edited by admin on Fri Dec 15 15:08:14 GMT 2023
PRIMARY
PUBCHEM
91617870
Created by admin on Fri Dec 15 15:08:14 GMT 2023 , Edited by admin on Fri Dec 15 15:08:14 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY