1. 1 Chloro 2,4 Dinitrobenzene
2. 2,4 Dinitrochlorobenzene
3. 2,4-dinitrochlorobenzene
4. Benzene, 1-chloro-2,4-dinitro-
5. Chlorodinitrobenzene
6. Dinitrochlorobenzene
7. Dncb
1. 2,4-dinitrochlorobenzene
2. 97-00-7
3. Dinitrochlorobenzene
4. Dncb
5. Chlorodinitrobenzene
6. Cdnb
7. Benzene, 1-chloro-2,4-dinitro-
8. 4-chloro-1,3-dinitrobenzene
9. 2,4-dinitrophenyl Chloride
10. Dinitrochlorobenzol
11. 1,3-dinitro-4-chlorobenzene
12. 2,4-dinitro-1-chlorobenzene
13. 6-chloro-1,3-dinitrobenzene
14. 1-chloro-2,4-dinitrobenzol
15. Cldnb
16. Dnpcl
17. 1-chlor-2,4-dinitrobenzene
18. 1-cloro-2,4-dinitrobenzene
19. 1-chloor-2,4-dinitrobenzeen
20. 1-chloro-2,4-dinitro-benzene
21. Chebi:34718
22. Nsc 6292
23. Nsc-6292
24. Ge3ibt7bmn
25. 2,4-dinitro Chlorobenzene
26. Nsc6292
27. Dsstox_cid_278
28. Dsstox_rid_75481
29. Dsstox_gsid_20278
30. 1-chlor-2,4-dinitrobenzol
31. Caswell No. 389c
32. Dinitrochlorobenzene (van)
33. Cas-97-00-7
34. Smr000857169
35. Ccris 1799
36. Hsdb 5306
37. Unii-ge3ibt7bmn
38. Einecs 202-551-4
39. Chloro-2,4-dinitrobenzene
40. 1-chloor-2,4-dinitrobenzeen [dutch]
41. 1-chloro-2,4-dinitrobenzeen [dutch]
42. 1-chloro-2,4-dinitrobenzol [german]
43. Epa Pesticide Chemical Code 055102
44. 1-cloro-2,4-dinitrobenzene [italian]
45. 1-chloro-2,4-dinitrobenzeen
46. Ai3-01053
47. 2,4-dinitrochlorbenzene
48. Wln: Wnr Bg Enw
49. 2,4-dinitro-chlorobenzene
50. Epitope Id:110163
51. Ec 202-551-4
52. 2,4-dinitro-chloro-benzene
53. 2,4dinitro-1-chlorobenzene
54. Schembl39251
55. 2-chloro-1,5-dinitrobenzene
56. Mls001332459
57. Mls001332460
58. Bidd:er0694
59. 1-chloro-2,4-dinitro Benzene
60. Chembl292687
61. Dtxsid6020278
62. Hms2233o04
63. Bcp27853
64. Str01511
65. Zinc1540301
66. Tox21_201956
67. Tox21_302802
68. Bbl009322
69. Bdbm50458521
70. Mfcd00007075
71. Stk387094
72. 1-chloro-2,4-dinitrobenzene, 97%
73. Akos000118946
74. 1 - Chloro - 2,4 - Dinitrobenzene
75. 1-chloro-2,4-dinitrobenzene, ~95%
76. Db11831
77. 1-chloro-2,4-dinitrobenzene, >=99%
78. Ncgc00164061-01
79. Ncgc00164061-02
80. Ncgc00164061-03
81. Ncgc00256396-01
82. Ncgc00259505-01
83. 2,4-dinitrochlorobenzene [mart.]
84. 1-chloro-2,4-dinitrobenzene [mi]
85. Db-057658
86. 1-chloro-2,4-dinitrobenzene [hsdb]
87. Am20050502
88. 1-chloro-2,4-dinitrobenzene [who-dd]
89. Q209216
90. 1-chloro-2,4-dinitrobenzene, Technical Grade, 95%
91. W-100123
92. 1-chloro-2,4-dinitrobenzene 100 Microg/ml In Methanol
93. 3-(3-hydroxy-2-methyl-4-oxo-1-pyridyl)propanoic Acid
94. F1908-0126
| Molecular Weight | 202.55 g/mol |
|---|---|
| Molecular Formula | C6H3ClN2O4 |
| XLogP3 | 2.3 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 0 |
| Exact Mass | 201.9781343 g/mol |
| Monoisotopic Mass | 201.9781343 g/mol |
| Topological Polar Surface Area | 91.6 Ų |
| Heavy Atom Count | 13 |
| Formal Charge | 0 |
| Complexity | 224 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
2,4-Dinitrochlorobenzene is a potent sensitizer that has been applied topically in the evaluation of delayed hypersensitivity. It has also been used as an immunostimulant in various conditions including some forms of cancer, and in the treatment of alopecia and warts. It has also been investigated in HIV infection and leprosy.
Sweetman S.C. (ed.) Martindale-The Extra Pharmacopoeia. 36th ed. London: The Pharmaceutical Press, p.2294 (2009)
Irritants
Drugs that act locally on cutaneous or mucosal surfaces to produce inflammation; those that cause redness due to hyperemia are rubefacients; those that raise blisters are vesicants and those that penetrate sebaceous glands and cause abscesses are pustulants; tear gases and mustard gases are also irritants. (See all compounds classified as Irritants.)
Indicators and Reagents
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant and Hackh's Chemical Dictionary, 5th ed, p301, p499) (See all compounds classified as Indicators and Reagents.)
THE CONJUGATION OF DRUGS AND OTHER FOREIGN CMPD /SUCH AS 1-CHLORO-2,4-DINITROBENZENE/ WITH GLUTATHIONE LEADS TO THE FORMATION OF N-ACETYLCYSTEINE (OR MERCAPTURIC ACID) DERIVATIVES.
Testa, B. and P. Jenner. Drug Metabolism: Chemical & Biochemical Aspects. New York: Marcel Dekker, Inc., 1976., p. 325
YIELDS S-(4-CHLORO-3-NITROPHENYL)GLUTATHIONE IN TICKS, LOCUST, HOUSEFLIES, GRASS GRUBS AND PIGEONS /FROM TABLE/
Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. C-27
Metabolism studies have demonstrated that 1-chloro-2,4-dinitrobenzene depletes hepatic GSH levels by the biotransformation displacement of chlorine to yield 1-SG-2,4-dinitrobenzene.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 4:1053
1-chloro-2,4-dinitrobenzene has known human metabolites that include 2-amino-5-[[1-(carboxymethylamino)-3-(1-chloro-2,4-dinitrocyclohexa-2,5-dien-1-yl)sulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid and S-(2,4-dinitrophenyl)glutathione.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560
The Thioredoxin (Trx)/Thioredoxin reductase (TrxR)-system has emerged as a crucial component of many cellular functions particularly antioxidant defence. We investigated the effect of the selective TrxR inhibitor 1-chloro-2,4-dinitrobenzene (CDNB) on survival and redox status in neuronal cell lines. CDNB was found to cause apoptosis without depletion of glutathione or loss of mitochondrial complex I-activity. Cells treated with CDNB displayed an early increase of reactive oxygen species and rapid activation of stress inducible protein kinases c-Jun N-terminal kinase (JNK) and mitogen activated protein kinase kinase 4 (MKK4). Thus TrxR inhibition by CDNB results in generation of reactive oxygen species and subsequent activation of stress-inducible kinases without impairment of the cellular antioxidant status or mitochondrial function. Inhibition of the specific kinases involved in cell death triggered by Trx/TrxR dysfunction could represent a novel and selective therapeutic approach in neurodegenerative disorders.
PMID:17559804 Seyfried J, Wullner U; Biochem Biophys Res Commun 359 (3): 759-64 (2007)
Prolonged topical exposure of BALB/c mice to chemical contact and respiratory allergens stimulates, respectively, preferential Th1- and Th2-type responses with respect to serum Ab isotype and cytokine secretion phenotypes displayed by draining lymph node cells. ... Differential cytokine secretion patterns are induced rapidly in the skin following first exposure to the contact allergen 2,4-dinitrochlorobenzene and the respiratory sensitizer trimellitic anhydride. Trimellitic anhydride induced early expression of IL-10, a cytokine implicated in the negative regulation of Langerhans cell (LC) migration, whereas exposure to 2,4-dinitrochlorobenzene resulted in production of the proinflammatory cytokine IL-1beta. Associated with this, trimellitic anhydride provoked LC migration with delayed kinetics compared with 2,4-dinitrochlorobenzene, and local neutralization of IL-10 caused enhanced LC mobilization in response to trimellitic anhydride with concomitant up-regulation of cutaneous IL-1beta. ... These differential epidermal cytokine profiles contribute to the polarization of immune responses to chemical allergens via effects on the phenotype of activated dendritic cells arriving in the draining lymph node. Thus, trimellitic anhydride-exposed dendritic cells that have been conditioned in vivo with IL-10 (a potent inhibitor of the type 1-polarizing cytokine IL-12) are effective APCs for the development of a Th2-type response.
PMID:15972630 Cumberbatch M et al; J Immunol 175 (1): 43-50 (2005)
Repeated topical exposure of BALB/c strain mice to chemical contact and respiratory allergens results in preferential T helper (Th)1- and Th2-cell activation, respectively. In addition, it has been shown that respiratory allergens, such as trimellitic anhydride, stimulate epidermal Langerhans cell (LC) migration with delayed kinetics compared with contact allergens, such as 2, 4-dinitrochlorobenzene. Experiments using anti-interleukin (IL)-10 antibodies in vivo suggest that cutaneous IL-10 may contribute to the differential regulation of LC migration by these chemicals. To investigate further the mechanistic basis for the development of polarised immune responses, we have examined the production of epidermal cytokines provoked following a single topical application to BALB/c strain mice of 2, 4-dinitrochlorobenzene (1%), trimellitic anhydride (25%) or vehicle (acetone:olive oil, 4:1; AOO). Skin explants were excised from mice exposed on the dorsum of both ears for various periods (30min-6hr) to chemical and were cultured on medium prior to analysis of supernatants for the presence of tumour necrosis factor alpha (TNF-alpha), IL-1beta, IL-1alpha, IL-6, IL-10, IL-12p40, IL-12p70 and IL-17 using the Bio-PlexTM cytokine array system. Enhanced production of IL-1beta, a cytokine involved in the initiation of LC migration, was detected only following exposure to 2, 4-dinitrochlorobenzene, with 15- fold increases induced by 6hr of exposure. In addition, only exposure to 2, 4-dinitrochlorobenzene was associated with early (2 hr) secretion of IL-17. In contrast, up-regulation of IL- 10, a cytokine that inhibits LC mobilization, was evident only for trimellitic anhydride during the first 3 hr of exposure, with 2 to 3-fold increases in IL-10 release being induced. Small increases in IL-1alpha levels were apparent for both chemicals. No alterations in either IL-6, IL-12p40 or IL-12p70 secretion were recorded and TNF-alpha remained undetectable throughout. These data suggest that discrete epidermal cytokine secretion profiles induced following exposure to chemical contact and respiratory allergens might contribute to the polarization of immune responses, possibly through effects on LC function.
Cumberbatch M et al; Toxicologist 78 (1-S): 327 (2004)
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