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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

Molecular Formula C13H8Br3NO2
Molecular Weight 449.92
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

ConditionModalityTargetsHighest PhaseProduct
Preventing
Polytar Soap

Doses

AEs

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Tox targets

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Soap Bar: Pine Tar 1%; Tribromsalan 0.3%
Route of Administration: Topical
In Vitro Use Guide
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
Record UNII
6MCE3VTF0O
Record Status Validated (UNII)
Record Version