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
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)
DescriptionCurator'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
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
Doses
Dose | Population | Adverse 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... |
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... |
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... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical 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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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[Concentration in plasma and excretion in milk of lactating cows after oral administration of tribromsalan, oxyclozanide and bromofenofos]. | 2006 Dec |
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Increased expression of IRE1alpha and stress-related signal transduction proteins in ischemia-reperfusion injured retina. | 2008 Dec |
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Identification of halosalicylamide derivatives as a novel class of allosteric inhibitors of HCV NS5B polymerase. | 2008 Jun 1 |
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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
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20067776
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.
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 310.502
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EPA PESTICIDE CODE |
77404
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NCI_THESAURUS |
C28394
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CFR |
21 CFR 700.15
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SUB11261MIG
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C004361
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m11048
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14868
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C47768
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CHEMBL24944
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)