Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H7Cl4NO2 |
| Molecular Weight | 351.012 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=C(C=CC(Cl)=C1Cl)C(=O)NC2=CC(Cl)=CC(Cl)=C2
InChI
InChIKey=ZJIQNOMMMRNUEM-UHFFFAOYSA-N
InChI=1S/C13H7Cl4NO2/c14-6-3-7(15)5-8(4-6)18-13(20)9-1-2-10(16)11(17)12(9)19/h1-5,19H,(H,18,20)
| Molecular Formula | C13H7Cl4NO2 |
| Molecular Weight | 351.012 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/22159739 | https://www.ncbi.nlm.nih.gov/pubmed/2971665 | https://www.ncbi.nlm.nih.gov/pubmed/6320920 | https://www.drugfuture.com/chemdata/3-3-4-5-Tetrachlorosalicylanilide.html | https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=700.15https://pubmed.ncbi.nlm.nih.gov/33477039 | https://pubmed.ncbi.nlm.nih.gov/4951805
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22159739 | https://www.ncbi.nlm.nih.gov/pubmed/2971665 | https://www.ncbi.nlm.nih.gov/pubmed/6320920 | https://www.drugfuture.com/chemdata/3-3-4-5-Tetrachlorosalicylanilide.html | https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=700.15https://pubmed.ncbi.nlm.nih.gov/33477039 | https://pubmed.ncbi.nlm.nih.gov/4951805
3,3′,4′,5-Tetrachlorosalicylanilide (TCSA) is an apoptosis-inducing photosensitizer for keratinocytes. It was studied as a causative agent of photo contact dermatitis and drug photosensitivity. TCSA was used as a metabolic uncoupler in activated sludge biological wastewater treatment systems to reduce the amount of the produced sludge.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011-07-14 |
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| Periodic assessment of plasma sFlt-1 and PlGF concentrations and its association with placental morphometry in gestational hypertension (GH) - a prospective follow-up study. | 2010-09-28 |
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| Role of the osmotic stress regulatory pathway in morphogenesis and secondary metabolism in filamentous fungi. | 2010-04 |
|
| Energy uncoupling inhibits aerobic granulation. | 2010-01 |
|
| Differential expression of proteins in Listeria monocytogenes under thermotolerance-inducing, heat shock, and prolonged heat shock conditions. | 2009-11 |
|
| Bone and muscle development during puberty in girls: a seven-year longitudinal study. | 2009-10 |
|
| Comparison of four chemical uncouplers for excess sludge reduction. | 2009-06 |
|
| [Effect of 2-aminophenol and 3,3',4',5-tetrachlorosalicylanilide on biomass yield of activated sludge]. | 2009-05-15 |
|
| In vivo transcriptional profiling of Listeria monocytogenes and mutagenesis identify new virulence factors involved in infection. | 2009-05 |
|
| Characterization and regulation of basal calcium influx in human peripheral blood lymphocytes. | 2008-12 |
|
| Total colonic aganglionosis with or without small bowel involvement: a 30-year retrospective nationwide survey in Japan. | 2008-12 |
|
| Evaluation of photoallergic potential of chemicals using THP-1 cells. | 2008-11 |
|
| Skeletal effects of estrogen and mechanical loading are structurally distinct. | 2008-10 |
|
| The information highways of a biotechnological workhorse--signal transduction in Hypocrea jecorina. | 2008-09-20 |
|
| Pathogenesis of age-related osteoporosis: impaired mechano-responsiveness of bone is not the culprit. | 2008-07-02 |
|
| Correlation between high-resolution computed tomography features and patients' characteristics in chronic obstructive pulmonary disease. | 2008-07 |
|
| The histidine kinase AHK5 integrates endogenous and environmental signals in Arabidopsis guard cells. | 2008-06-18 |
|
| Identification of halosalicylamide derivatives as a novel class of allosteric inhibitors of HCV NS5B polymerase. | 2008-06-01 |
|
| Metabolic uncoupling of Shewanella oneidensis MR-1, under the influence of excess substrate and 3, 3', 4', 5-tetrachlorosalicylanilide (TCS). | 2008-04-15 |
|
| Hirschsprung disease: do risk factors of poor surgical outcome exist? | 2008-04 |
|
| Topical cyclosporine A in the prevention of pterygium recurrence. | 2008 |
|
| Effect of 3,3',4',5-tetrachlorosalicylanilide on reduction of excess sludge and nitrogen removal in biological wastewater treatment process. | 2007-07 |
|
| Isolation and characterization of an amiloride-resistant mutant of Methanothermobacter thermautotrophicus possessing a defective Na+/H+ antiport. | 2007-04 |
|
| Effect of acidic pH on the ability of Clostridium sporogenes MD1 to take up and retain intracellular potassium. | 2007-02 |
|
| Induction of keratinocyte apoptosis by photosensitizing chemicals plus UVA. | 2007-02 |
|
| Crop load affects maximum daily trunk shrinkage of plum trees. | 2007-01 |
|
| The Sinorhizobium medicae WSM419 lpiA gene is transcriptionally activated by FsrR and required to enhance survival in lethal acid conditions. | 2006-10 |
|
| Correlates of bone quality in older persons. | 2006-10 |
|
| Successful resection of Hypothalamic Hamartoma with intractable gelastic seizures--by transcallosal subchoroidal approach. | 2006-08 |
|
| Efficacy of commercially available topical cyclosporine A 0.05% in the treatment of meibomian gland dysfunction. | 2006-02 |
|
| Structural adaptations to bone loss in aging men and women. | 2006-01 |
|
| Study of Trichoderma viride metabolism under conditions of the restriction of oxidative processes. | 2005-10 |
|
| The impact of topical cyclosporine A emulsion 0.05% on the outcomes of patients with keratoconjunctivitis sicca. | 2005-07 |
|
| Reduction of excess sludge production by 3,3',4', 5-tetrachlorosalicylanilide in an activated sludge process. | 2005-04 |
|
| [Bacteriological sampling of surfaces: importance of the step of enrichment and the choice of the culture media]. | 2005-03-18 |
|
| Biochemical characteristics of a mutant of the methanoarchaeon Methanothermobacter thermautotrophicus resistant to the protonophoric uncoupler TCS. | 2004 |
|
| Biochemical analysis of neomycin-resistance in the methanoarchaeon Methanothermobacter thermautotrophicus and some implications for energetic processes in this strain. | 2003-02 |
|
| Altered permeability and disordered cutaneous immunoregulatory function in mice with acute barrier disruption. | 1997-08 |
|
| Spontaneous hair follicle cycling may influence the development of murine contact photosensitivity by modulating keratinocyte cytokine production. | 1997-06-15 |
|
| A new animal model for contact dermatitis: the hairless guinea pig. | 1992-03 |
|
| Genetic control of contact photosensitivity to tetrachlorosalicylanilide. II. Igh complex controls the sensitivity induced by photohapten-modified spleen cells but not epidermal cells. | 1991-06 |
|
| In vitro activation of immune lymph node cell proliferation by photohapten-modified cells in murine contact photosensitivity. | 1991 |
|
| Ultraviolet-induced suppressor T cells and factor(s) in murine contact photosensitivity. III. Mode of action of T-cell-suppressor factor(s) and interaction with cytokines. | 1990-11 |
|
| Genetic control of contact photosensitivity to tetrachlorosalicylanilide. I. Preferential activation of suppressor T cells in low responder H-2k mice. | 1990-04 |
|
| An optimized lymphocyte blastogenesis assay for detecting the response of contact sensitized or photosensitized lymphocytes to hapten or photohapten modified antigen presenting cells. | 1990 |
|
| Ultraviolet-induced suppressor T cells and factor(s) in murine contact photosensitivity. II. Igh-V restriction of T-cell-suppressor factor. | 1989-04 |
|
| Induction of contact photosensitivity to TCSA using photohapten-modified syngeneic spleen cells. | 1988 |
|
| Induction of photoallergy in guinea-pigs by injection of photoallergen-protein conjugates. | 1987 |
|
| Mechanisms of contact photosensitivity in mice. VI. Oxygen intermediates are involved in contact photosensitization but not in ordinary contact sensitization. | 1986-01 |
|
| Mechanisms of contact photosensitivity in mice: I. T cell regulation of contact photosensitivity to tetrachlorosalicylanilide under the genetic restrictions of the major histocompatibility complex. | 1982-08 |
Patents
Sample Use Guides
BALB/c mice were painted with 5 uL of 0.1% TCSA on the earlobes and irradiated with 16 J/cm2 (at 365 nm) of UVA.
Route of Administration:
Topical
In Vitro Use Guide
Curator's Comment: Without UVA, caspase-3 was not activated. TCSA was identified as apoptosis-inducing photosensitizers for keratinocytes.
HaCaT keratinocytes were incubated with 3,3',4',5-tetrachlorosalicylanilide (TCSA), bithionol, diphenylhydramine, chlorpromazine, 6-methylcoumarin, sparfloxacin, and enoxacin at 10(-7) to 10(-4)M and irradiated with UVA at 4J/cm(2). In a comparison with non-irradiated cells, significant apoptosis was found in TCSA, bithionol, chlorpromazine, sparfloxacin and enoxacin at 10(-4) or 10(-5)M as well as 8-MOP as assessed by both annexin V and active caspase-3 stainings, while necrosis occurred in most of these chemicals at 10(-4)M.
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
4H8SC2479J
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| Record Status |
Validated (UNII)
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| Record Version |
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Systematic Name | English | ||
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Preferred Name | English | ||
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Systematic Name | English |
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CFR |
21 CFR 700.15
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CFR |
21 CFR 310.502
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4H8SC2479J
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34262-92-5
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22561456
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