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MedKoo Cat#: 581356 | Name: Dapsone hydroxylamine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dapsone hydroxylamine is the hydroxylamine derivative of the antibacterial dapspone (sc-203023), which is most commonly used as part of a multidrug therapy for the treatment of leprosy and as propchylaxis against pneumocystis pneumonia (PCP) in HIV patients. Dapsone hydroxylamine is a toxic metabolite that is responsible for the hemolytic anemia seen in patients following dapsone therapy.

Chemical Structure

Dapsone hydroxylamine
Dapsone hydroxylamine
CAS#32695-27-5

Theoretical Analysis

MedKoo Cat#: 581356

Name: Dapsone hydroxylamine

CAS#: 32695-27-5

Chemical Formula: C12H12N2O3S

Exact Mass: 264.0569

Molecular Weight: 264.30

Elemental Analysis: C, 54.53; H, 4.58; N, 10.60; O, 18.16; S, 12.13

Price and Availability

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5mg USD 350.00 2 Weeks
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Synonym
Dapsone hydroxylamine; Dds-noh; HADS; N-Hydroxydapsone;
IUPAC/Chemical Name
4-Amino-4'-hydroxylaminodiphenylsulfone
InChi Key
IYDSJDWESCGRKW-UHFFFAOYSA-N
InChi Code
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
SMILES Code
O=S(C1=CC=C(N)C=C1)(C2=CC=C(NO)C=C2)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Dapsone hydroxylamine is the hydroxylamine derivative of the antibacterial dapspone (sc-203023) and is a toxic metabolite.
In vitro activity:
The action of DDS-NHOH was tested by incubating human erythrocytes with increasing concentrations of the hydroxylamine for 30 min. In these conditions, the membrane proteins, mainly band 3, exhibited Tyr-P, which increased concentration dependently up to 0.3 mM DDS-NHOH and drastically decreased to the control level at higher concentrations. DDS-NHOH induced band 3 Tyr-P which peaked after 30 min at 0.3 mM, and was completely reversed after 45 min of incubation. It was found that both Tyr-kinase and phosphatase activities were promptly inhibited by DDS-NHOH, both concentration- and time-dependently and total inactivation was reached in both after 60 min incubation with 0.15 and 0.3 mM. At 0.6 mM, DDS-NHOH treatment produced almost complete inhibition after only 15 min of incubation. In conclusion, DDS-NHOH was able to both induce methemoglobin formation in erythrocytes and DNA damage in lymphocytes, most likely through elevated intracellular ROS production. Reference: PLoS One. 2015; 10(8): e0134768. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4540410/
In vivo activity:
To determine whether the N-hydroxyarylamine metabolites of dapsone could be responsible for dapsone-induced hemolysis, dapsone, dapsone hydroxylamine (DDS-NOH) and monoacetyldapsone hydroxylamine were administered to rats which had previously received 51Cr-labeled red blood cells. All three compounds caused an increase in the rate of disappearance of radioactivity from the blood as compared with saline-treated controls. The amount of damage (as measured by decreased red cell survival in vivo) was proportional to both concentration and time of exposure to DDS-NOH. The area under the blood concentration vs. time curve for total arylhydroxylamines (DDS-NOH + monacetyldapsone hydroxylamine) in rats given a hemotoxic dose of dapsone was similar to that of rats given an equitoxic dose of DDS-NOH. Collectively, these data indicate that the hydroxylamine metabolites of dapsone are direct acting hemolytic agents that are formed from dapsone in sufficient amounts to account for their being the sole mediators of dapsoneinduced hemolytic anemia in the rat. Referemce: J Pharmacol Exp Ther. 1988 Jan;244(1):118-25. https://pubmed.ncbi.nlm.nih.gov/3335994/
Solvent mg/mL mM
Solubility
H2O 1.0 3.69
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 264.30 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. 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.14765381.2010.00962.x. PMID: 20662842; PMCID: PMC2998697. 2. Albuquerque RV, Malcher NS, Amado LL, Coleman MD, Dos Santos DC, Borges RS, Valente SA, Valente VC, Monteiro MC. In Vitro Protective Effect and Antioxidant Mechanism of Resveratrol Induced by Dapsone Hydroxylamine in Human 3. . Grossman SJ, Jollow DJ. Role of dapsone hydroxylamine in dapsone-induced hemolytic anemia. J Pharmacol Exp Ther. 1988 Jan;244(1):118-25. PMID: 3335994
In vitro protocol:
1. 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.14765381.2010.00962.x. PMID: 20662842; PMCID: PMC2998697. 2. Albuquerque RV, Malcher NS, Amado LL, Coleman MD, Dos Santos DC, Borges RS, Valente SA, Valente VC, Monteiro MC. In Vitro Protective Effect and Antioxidant Mechanism of Resveratrol Induced by Dapsone Hydroxylamine in Human
In vivo protocol:
1. Grossman SJ, Jollow DJ. Role of dapsone hydroxylamine in dapsone-induced hemolytic anemia. J Pharmacol Exp Ther. 1988 Jan;244(1):118-25. PMID: 3335994.
1: Andrisani A, Donà G, Sabbadin C, Dall'Acqua S, Tibaldi E, Roveri A, Bosello Travain V, Brunati AM, Ambrosini G, Ragazzi E, Armanini D, Bordin L. Dapsone hydroxylamine-mediated alterations in human red blood cells from endometriotic patients. Gynecol Endocrinol. 2017 Dec;33(12):928-932. doi: 10.1080/09513590.2017.1332177. Epub 2017 May 30. PubMed PMID: 28557604. 2: Jarratt MT, Jones TM, Chang-Lin JE, Tong W, Berk DR, Lin V, Kaoukhov A. Safety and Pharmacokinetics of Once-Daily Dapsone Gel, 7.5% in Patients With Moderate Acne Vulgaris. J Drugs Dermatol. 2016 Oct 1;15(10):1250-1259. PubMed PMID: 27741344. 3: Albuquerque RV, Malcher NS, Amado LL, Coleman MD, Dos Santos DC, Borges RS, Valente SA, Valente VC, Monteiro MC. In Vitro Protective Effect and Antioxidant Mechanism of Resveratrol Induced by Dapsone Hydroxylamine in Human Cells. PLoS One. 2015 Aug 18;10(8):e0134768. doi: 10.1371/journal.pone.0134768. eCollection 2015. 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.