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(Br)C=C(Br)C=C1C(=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)
| Molecular Formula | C13H8Br3NO2 |
| Molecular Weight | 449.92 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
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 |
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 |
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 |
|
| 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 |
|
| 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 |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
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 |
|---|---|---|
| Determination of bithionol, bromophen, nitroxynil, oxyclozanide, and tribromsalan in milk with liquid chromatography coupled with tandem mass spectrometry. | 2010-10-07 |
|
| Identification of known drugs that act as inhibitors of NF-kappaB signaling and their mechanism of action. | 2010-05-01 |
|
| Increased expression of IRE1alpha and stress-related signal transduction proteins in ischemia-reperfusion injured retina. | 2008-12 |
|
| Identification of halosalicylamide derivatives as a novel class of allosteric inhibitors of HCV NS5B polymerase. | 2008-06-01 |
|
| [Concentration in plasma and excretion in milk of lactating cows after oral administration of tribromsalan, oxyclozanide and bromofenofos]. | 2006-12 |
|
| Spectrum of cross-photosensitization in 18 consecutive patients with contact photoallergy to ketoprofen: associated photoallergies to non-benzophenone-containing molecules. | 2003-03 |
|
| A new animal model for contact dermatitis: the hairless guinea pig. | 1992-03 |
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:45:09 GMT 2025
by
admin
on
Mon Mar 31 17:45:09 GMT 2025
|
| Record UNII |
6MCE3VTF0O
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
CFR |
21 CFR 310.502
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
||
|
CFR |
21 CFR 216.24
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
||
|
EPA PESTICIDE CODE |
77404
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
||
|
NCI_THESAURUS |
C28394
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
||
|
CFR |
21 CFR 700.15
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
DTXSID4026181
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
PRIMARY | |||
|
SUB11261MIG
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
PRIMARY | |||
|
C004361
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
PRIMARY | |||
|
m11048
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
PRIMARY | Merck Index | ||
|
14868
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
PRIMARY | |||
|
6MCE3VTF0O
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
PRIMARY | |||
|
1623
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
PRIMARY | |||
|
87-10-5
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
PRIMARY | |||
|
20526
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
PRIMARY | |||
|
201-723-6
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
PRIMARY | |||
|
127105
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
PRIMARY | |||
|
100000077533
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
PRIMARY | |||
|
C47768
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
PRIMARY | |||
|
CHEMBL24944
Created by
admin on Mon Mar 31 17:45:09 GMT 2025 , Edited by admin on Mon Mar 31 17:45:09 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
SALT/SOLVATE -> PARENT |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |