Synonym
Diaphenylsulfone; Bis(4-aminophenyl) Sulfone; 4,4'-Diaminodiphenyl sulfone; NSC 6091; NSC-6091; NSC6091;
IUPAC/Chemical Name
4-(4-aminophenyl)sulfonylaniline
InChi Key
MQJKPEGWNLWLTK-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H12N2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H,13-14H2
SMILES Code
C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)N
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, not in water
Shelf Life
>2 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
2934.99.9001
Biological target:
Dapsone (4,4′-Diaminodiphenyl sulfone) is an orally active and blood-brain penetrant sulfonamide antibiotic with bacteriostatic, antimycobacterial and antiprotozoal activities that also exerts effective antileprosy activity and inhibits folate synthesis in cell extracts of M. leprae.
In vitro activity:
The present study investigated the anti-inflammatory effects of dapsone on bone marrow cells (BMs), especially upon exposure to lipopolysaccharide (LPS). BMs were treated with LPS and dapsone, and the treated cells underwent cellular activity assay, flow cytometry analysis, cytokine production assessment, and reactive oxygen species assay. Interestingly, dapsone modulated the inflammatory cells, including granulocytes in LPS-treated BMs, by inducing cell death. While the percentage of Gr-1 positive cells was 57% in control cells, LPS increased that to 75%, and LPS plus dapsone decreased it to 64%. Furthermore, dapsone decreased the mitochondrial membrane potential of LPS-treated BMs. At a low concentration (25 μg/mL), dapsone significantly decreased the production of TNF-α in LPS-treated BMs by 54%. This study confirmed that dapsone has anti-inflammatory effects on LPS-mediated inflammation via modulation of the number and function of inflammatory cells, providing new and useful information for clinicians and researchers.
Reference: J Vet Sci. 2018 Nov 30;19(6):744-749. https://pubmed.ncbi.nlm.nih.gov/30304888/
In vivo activity:
To determine whether DDS has protective effects on brain microvessels, the cortical microvascular permeability for tetramethylrhodamine (TMR)-dextran (40 kDa) was examined with multiphoton microscopy in a live optical study. Intact microvessel networks were shown in control mice. Administration of DDS significantly attenuated HFD-induced microvessel leakage (Fig. 1a), and the relative fluorescence intensity decreased (Fig. 1c, p = 0.0001, n = 6). There was no significant difference between control and HFD + DDS group (p = 0.2039). The amount of Evans blue in brain parenchyma was detected in the following experiment. Consistently, the content of dye into brain from HFD + DDS group was lower than HFD group (Fig. 1d, F = 9.964, R2 = 0.6242, p = 0.041, n = 5). These data indicated that DDS protects brain microvascular integrity during HFD in vivo.
Reference: Cell Death Dis. 2018 Jun; 9(6): 683. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5992187/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
75.0 |
302.05 |
| Ethanol |
10.0 |
40.27 |
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
248.30
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.
| 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. Kwon MJ, Joo HG. Dapsone modulates lipopolysaccharide-activated bone marrow cells by inducing cell death and down-regulating tumor necrosis factor-α production. J Vet Sci. 2018 Nov 30;19(6):744-749. doi: 10.4142/jvs.2018.19.6.744. PMID: 30304888; PMCID: PMC6265590. 2. Zhan R, Zhao M, Zhou T, Chen Y, Yu W, Zhao L, Zhang T, Wang H, Yang H, Jin Y, He Q, Yang X, Guo X, Willard B, Pan B, Huang Y, Chen Y, Chui D, Zheng L. Dapsone protects brain microvascular integrity from high-fat diet induced LDL oxidation. Cell Death Dis. 2018 Jun 7;9(6):683. doi: 10.1038/s41419-018-0739-y. PMID: 29880899; PMCID: PMC5992187.
In vitro protocol:
1. Kwon MJ, Joo HG. Dapsone modulates lipopolysaccharide-activated bone marrow cells by inducing cell death and down-regulating tumor necrosis factor-α production. J Vet Sci. 2018 Nov 30;19(6):744-749. doi: 10.4142/jvs.2018.19.6.744. PMID: 30304888; PMCID: PMC6265590. 2. Zhan R, Zhao M, Zhou T, Chen Y, Yu W, Zhao L, Zhang T, Wang H, Yang H, Jin Y, He Q, Yang X, Guo X, Willard B, Pan B, Huang Y, Chen Y, Chui D, Zheng L. Dapsone protects brain microvascular integrity from high-fat diet induced LDL oxidation. Cell Death Dis. 2018 Jun 7;9(6):683. doi: 10.1038/s41419-018-0739-y. PMID: 29880899; PMCID: PMC5992187.
In vivo protocol:
1. Zhan R, Zhao M, Zhou T, Chen Y, Yu W, Zhao L, Zhang T, Wang H, Yang H, Jin Y, He Q, Yang X, Guo X, Willard B, Pan B, Huang Y, Chen Y, Chui D, Zheng L. Dapsone protects brain microvascular integrity from high-fat diet induced LDL oxidation. Cell Death Dis. 2018 Jun 7;9(6):683. doi: 10.1038/s41419-018-0739-y. PMID: 29880899; PMCID: PMC5992187.
1: Schulkes KJ, Tervaert JW, Rijken F, Haas LE. Dapsone hypersensitivity syndrome not related to G6PD deficiency. BMJ Case Rep. 2015 Dec 18;2015. pii: bcr2015212742. doi: 10.1136/bcr-2015-212742. PubMed PMID: 26682839.
2: Klebes M, Wutte N, Aberer E. Dapsone as Second-Line Treatment for Cutaneous Lupus Erythematosus? A Retrospective Analysis of 34 Patients and a Review of the Literature. Dermatology. 2015 Nov 26. [Epub ahead of print] PubMed PMID: 26606129.
3: Poirot E, Vittinghoff E, Ishengoma D, Alifrangis M, Carneiro I, Hashim R, Baraka V, Mosha J, Gesase S, Chandramohan D, Gosling R. Risks of Hemolysis in Glucose-6-Phosphate Dehydrogenase Deficient Infants Exposed to Chlorproguanil-Dapsone, Mefloquine and Sulfadoxine-Pyrimethamine as Part of Intermittent Presumptive Treatment of Malaria in Infants. PLoS One. 2015 Nov 23;10(11):e0142414. doi: 10.1371/journal.pone.0142414. eCollection 2015. PubMed PMID: 26599634; PubMed Central PMCID: PMC4658078.
4: Kast RE. Erlotinib augmentation with dapsone for rash mitigation and increased anti-cancer effectiveness. Springerplus. 2015 Oct 23;4:638. doi: 10.1186/s40064-015-1441-5. eCollection 2015. PubMed PMID: 26543772; PubMed Central PMCID: PMC4628020.
5: Ferreira AO, Polonini HC, Silva SL, Patrício FB, Brandão MA, Raposo NR. Feasibility of amlodipine besylate, chloroquine phosphate, dapsone, phenytoin, pyridoxine hydrochloride, sulfadiazine, sulfasalazine, tetracycline hydrochloride, trimethoprim and zonisamide in SyrSpend(®) SF PH4 oral suspensions. J Pharm Biomed Anal. 2016 Jan 25;118:105-12. doi: 10.1016/j.jpba.2015.10.032. Epub 2015 Oct 27. PubMed PMID: 26540625.
6: Gavilanes MC, Palacio AL, Chellini PR, Nery JA, Rego JG. Dapsone hypersensitivity syndrome in a lepromatous leprosy patient--A Case Report. Lepr Rev. 2015 Jun;86(2):186-90. PubMed PMID: 26502691.
7: Sunilkumar MN, Ajith TA, Parvathy VK. Acute dapsone poisoning in a 3-year-old child: Case report with review of literature. World J Clin Cases. 2015 Oct 16;3(10):911-4. doi: 10.12998/wjcc.v3.i10.911. PubMed PMID: 26488029; PubMed Central PMCID: PMC4607811.
8: Sheu JS, Divito SJ, Enamandram M, Merola JF. Dapsone Therapy for Pustular Psoriasis: Case Series and Review of the Literature. Dermatology. 2015 Oct 15. [Epub ahead of print] PubMed PMID: 26465742.
9: Kocaturk E, Memet B, Topal IO, Yuksel T, Ulkumen PK, Kızıltac U. A Case of Erythema Elevatum Diutinum With Pancytopenia: Focus on Dapsone-Induced Hematologic Side Effects and Colchicine as a Safe Treatment Option. J Drugs Dermatol. 2015 Oct 1;14(10):1090-2. PubMed PMID: 26461818.
10: Mancano MA. Methemoglobinemia Caused by Topical Dapsone Gel; Renal Tubular Acidosis After Topiramate Administration; Diabetic Ketoacidosis Following Epidural Steroid Injection in a Nondiabetic Patient; Galactorrhea Associated with Bupropion Therapy; Telaprevir-Induced Acquired Perforating Dermatosis; Manic Episodes Associated with Tramadol Use. Hosp Pharm. 2015 Apr;50(4):264-8. doi: 10.1310/hpj5004-264. Epub 2015 Apr 8. PubMed PMID: 26448655; PubMed Central PMCID: PMC4589886.
