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MolPort-001-757-383
Also known as: 2,4-dinitrochlorobenzene, 97-00-7, Dinitrochlorobenzene, Dncb, Chlorodinitrobenzene, Cdnb
Molecular Formula
C6H3ClN2O4
Molecular Weight
202.55  g/mol
InChI Key
VYZAHLCBVHPDDF-UHFFFAOYSA-N
FDA UNII
GE3IBT7BMN

A skin irritant that may cause dermatitis of both primary and allergic types. Contact sensitization with DNCB has been used as a measure of cellular immunity. DNCB is also used as a reagent for the detection and determination of pyridine compounds.
1 2D Structure

MolPort-001-757-383

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-chloro-2,4-dinitrobenzene
2.1.2 InChI
InChI=1S/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H
2.1.3 InChI Key
VYZAHLCBVHPDDF-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=C(C=C1[N+](=O)[O-])[N+](=O)[O-])Cl
2.2 Other Identifiers
2.2.1 UNII
GE3IBT7BMN
2.3 Synonyms
2.3.1 MeSH Synonyms

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

2.3.2 Depositor-Supplied Synonyms

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

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 202.55 g/mol
Molecular Formula C6H3ClN2O4
XLogP32.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count0
Exact Mass201.9781343 g/mol
Monoisotopic Mass201.9781343 g/mol
Topological Polar Surface Area91.6 Ų
Heavy Atom Count13
Formal Charge0
Complexity224
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

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)


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

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.)


5.2 Metabolism/Metabolites

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


5.3 Mechanism of Action

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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