Dapsone hydroxylamine
Solid powder
Others
Dapsone hydroxylamine is a synthetic compound that has been used in various fields, including medical, environmental, and industrial research. It is a derivative of dapsone, which is an antibiotic used to treat leprosy and other skin conditions. Dapsone hydroxylamine has been found to have potent biological activity and has been studied extensively for its potential therapeutic and toxic effects.
264.3 g/mol
264.3 g/mol
Formulation:
264.3 g/mol
Source:
Usage:
Dapsone hydroxylamine
The product is for non-human research only. Not for therapeutic or veterinary use.
Catalog Number: BT-264449
CAS Number: 32695-27-5
Molecular Formula: C12H12N2O3S
Molecular Weight: 264.3 g/mol
| CAS Number | 32695-27-5 |
|---|---|
| Product Name | Dapsone hydroxylamine |
| Molecular Formula | C12H12N2O3S |
| Molecular Weight | 264.3 g/mol |
| Appearance | Solid powder |
| InChI | InChI=1S/C12H12N2O3S/c13-9-1-5-11(6-2-9)18(16,17)12-7-3-10(14-15)4-8-12/h1-8,14-15H,13H2 |
| InChI Key | IYDSJDWESCGRKW-UHFFFAOYSA-N |
| IUPAC Name | N-[4-(4-aminophenyl)sulfonylphenyl]hydroxylamine |
| Canonical SMILES | C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)NO |
| Description | Dapsone hydroxylamine is a synthetic compound that has been used in various fields, including medical, environmental, and industrial research. It is a derivative of dapsone, which is an antibiotic used to treat leprosy and other skin conditions. Dapsone hydroxylamine has been found to have potent biological activity and has been studied extensively for its potential therapeutic and toxic effects. |
| Method of Synthesis or Extraction | Dapsone hydroxylamine can be synthesized using various methods, including reduction of dapsone with sodium dithionite, sodium borohydride, or zinc dust. The efficiency and yield of each method vary depending on the reaction conditions and the purity of the starting materials. Environmental and safety considerations must also be taken into account when synthesizing dapsone hydroxylamine, as some of the reagents used can be hazardous. |
| Chemical Structure and Biological Activity | The chemical structure of dapsone hydroxylamine consists of a hydroxylamine group attached to the aromatic ring of dapsone. The mechanism of action of dapsone hydroxylamine is not fully understood, but it is believed to inhibit the activity of enzymes involved in the production of reactive oxygen species, which are involved in various cellular processes. Dapsone hydroxylamine has been found to have potent bioactivity and has been studied for its potential therapeutic effects in various diseases, including cancer, neurodegenerative disorders, and inflammatory conditions. |
| Biological Effects | Dapsone hydroxylamine has been found to have various effects on cell function and signal transduction. It has been shown to induce apoptosis, inhibit cell proliferation, and modulate the activity of various signaling pathways. Dapsone hydroxylamine has also been studied for its potential therapeutic and toxic effects in various diseases. It has been found to have anti-inflammatory, antioxidant, and neuroprotective effects, but it can also have toxic effects on certain cell types. |
| Applications | In medical research, dapsone hydroxylamine has been studied for its role in drug development. It has been found to have potential therapeutic effects in various diseases, including cancer, neurodegenerative disorders, and inflammatory conditions. Clinical trials have been conducted to evaluate the safety and efficacy of dapsone hydroxylamine in these diseases. Benefits and potential side effects of dapsone hydroxylamine in these diseases need to be further studied. In environmental research, dapsone hydroxylamine has been studied for its effects on ecosystems and its role in pollution management. It has been found to have potential applications in the treatment of wastewater and the removal of pollutants from the environment. Sustainability and environmental impact of dapsone hydroxylamine need to be further studied. In industrial research, dapsone hydroxylamine has been used in various manufacturing processes to improve product quality and efficiency. Health and safety considerations must be taken into account when using dapsone hydroxylamine in industrial applications. |
| Future Perspectives and Challenges | Current limitations in the use and study of dapsone hydroxylamine include its potential toxicity and the need for further studies to evaluate its safety and efficacy in various diseases. Possible solutions and improvements include the development of more selective and potent derivatives of dapsone hydroxylamine and the use of advanced technologies to study its mechanism of action and biological effects. Future trends and prospects in the application of dapsone hydroxylamine in scientific research include its potential use as a therapeutic agent in various diseases and its role in environmental and industrial applications. |
| Other CAS Number | 32695-27-5 |
| Shelf Life | >3 years if stored properly |
| SMILES | C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)NO |
| Solubility | Soluble in DMSO |
| Storage | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Synonyms | 4-amino-4'-hydroxylaminodiphenylsulfone 4-amino-4'-hydroxylaminodiphenylsulfone, T-labeled cpd 4-hydroxylamino-4'-aminophenyl sulfone dapsone hydroxylamine DDS-NOH HADS N-hydroxydapsone |
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PubMed PMID: 26284371; PubMed Central PMCID: PMC4540410. 4: Bordin L, Fiore C, Zen F, Coleman MD, Ragazzi E, Clari G. Dapsone hydroxylamine induces premature removal of human erythrocytes by membrane reorganization and antibody binding. Br J Pharmacol. 2010 Nov;161(5):1186-99. doi: 10.1111/j.1476-5381.2010.00962.x. PubMed PMID: 20662842; PubMed Central PMCID: PMC2998697. 5: Veggi LM, Pretto L, Ochoa EJ, Catania VA, Luquita MG, Taborda DR, Sánchez Pozzi EJ, Ikushiro S, Coleman MD, Roma MG, Mottino AD. Dapsone induces oxidative stress and impairs antioxidant defenses in rat liver. Life Sci. 2008 Aug 1;83(5-6):155-63. doi: 10.1016/j.lfs.2008.05.016. Epub 2008 Jun 18. PubMed PMID: 18602405. 6: Thiboutot DM, Willmer J, Sharata H, Halder R, Garrett S. Pharmacokinetics of dapsone gel, 5% for the treatment of acne vulgaris. Clin Pharmacokinet. 2007;46(8):697-712. PubMed PMID: 17655376. 7: Roychowdhury S, Cram AE, Aly A, Svensson CK. Detection of haptenated proteins in organotypic human skin explant cultures exposed to dapsone. Drug Metab Dispos. 2007 Sep;35(9):1463-5. Epub 2007 Jun 6. PubMed PMID: 17553916. 8: Roychowdhury S, Vyas PM, Svensson CK. Formation and uptake of arylhydroxylamine-haptenated proteins in human dendritic cells. Drug Metab Dispos. 2007 Apr;35(4):676-81. Epub 2007 Jan 12. PubMed PMID: 17220235. 9: McMillan DC, Powell CL, Bowman ZS, Morrow JD, Jollow DJ. Lipids versus proteins as major targets of pro-oxidant, direct-acting hemolytic agents. Toxicol Sci. 2005 Nov;88(1):274-83. Epub 2005 Aug 17. PubMed PMID: 16107547. 10: Clement B, Behrens D, Amschler J, Matschke K, Wolf S, Havemeyer A. Reduction of sulfamethoxazole and dapsone hydroxylamines by a microsomal enzyme system purified from pig liver and pig and human liver microsomes. Life Sci. 2005 May 27;77(2):205-19. Epub 2005 Feb 8. PubMed PMID: 15862605. 11: Roychowdhury S, Vyas PM, Reilly TP, Gaspari AA, Svensson CK. Characterization of the formation and localization of sulfamethoxazole and dapsone-associated drug-protein adducts in human epidermal keratinocytes. J Pharmacol Exp Ther. 2005 Jul;314(1):43-52. Epub 2005 Mar 22. PubMed PMID: 15784651. 12: Winter HR, Trapnell CB, Slattery JT, Jacobson M, Greenspan DL, Hooton TM, Unadkat JD. The effect of clarithromycin, fluconazole, and rifabutin on dapsone hydroxylamine formation in individuals with human immunodeficiency virus infection (AACTG 283). Clin Pharmacol Ther. 2004 Dec;76(6):579-87. PubMed PMID: 15592329. 13: Kurian JR, Bajad SU, Miller JL, Chin NA, Trepanier LA. NADH cytochrome b5 reductase and cytochrome b5 catalyze the microsomal reduction of xenobiotic hydroxylamines and amidoximes in humans. J Pharmacol Exp Ther. 2004 Dec;311(3):1171-8. Epub 2004 Aug 9. PubMed PMID: 15302896. 14: Coleman MD, Holden LJ. The methaemoglobin forming and GSH depleting effects of dapsone and monoacetyl dapsone hydroxylamines in human diabetic and non-diabetic erythrocytes in vitro. Environ Toxicol Pharmacol. 2004 May;17(1):55-9. doi: 10.1016/j.etap.2004.01.005. PubMed PMID: 21782713. 15: Coleman MD, Taylor CT. Effects of dihydrolipoic acid (DHLA), α-lipoic acid. N-acetyl cysteine and ascorbate on xenobiotic-mediated methaemoglobin formation in human erythrocytes in vitro. Environ Toxicol Pharmacol. 2003 Sep;14(3):121-7. doi: 10.1016/S1382-6689(03)00048-6. PubMed PMID: 21782671. 16: Coleman MD, Fernandes S, Khanderia L. A preliminary evaluation of a novel method to monitor a triple antioxidant combination (vitamins E, C and α-lipoic acid) in diabetic volunteers using in vitro methaemoglobin formation. Environ Toxicol Pharmacol. 2003 Jun;14(1-2):69-75. doi: 10.1016/S1382-6689(03)00027-9. PubMed PMID: 21782664. 17: Hutzler JM, Wienkers LC, Wahlstrom JL, Carlson TJ, Tracy TS. Activation of cytochrome P450 2C9-mediated metabolism: mechanistic evidence in support of kinetic observations. Arch Biochem Biophys. 2003 Feb 1;410(1):16-24. PubMed PMID: 12559973. 18: Jollow DJ, McMillan DC. Oxidative stress, glucose-6-phosphate dehydrogenase and the red cell. Adv Exp Med Biol. 2001;500:595-605. Review. PubMed PMID: 11765001. 19: Hutzler JM, Hauer MJ, Tracy TS. Dapsone activation of CYP2C9-mediated metabolism: evidence for activation of multiple substrates and a two-site model. Drug Metab Dispos. 2001 Jul;29(7):1029-34. Erratum in: Drug Metab Dispos 2001 Aug;29(8):1171. PubMed PMID: 11408370. 20: Coleman MD, Walker CL. Effects of oxidised alpha-lipoic acid and alpha-tocopherol on xenobiotic-mediated methaemoglobin formation in diabetic and non-diabetic human erythrocytes in-vitro. Environ Toxicol Pharmacol. 2000 Jan 1;8(2):127-132. PubMed PMID: 10867372. |
| PubChem Compound | Dapsone hydroxylamine |
| Last Modified | May 30 2023 |