Dapsone - CAS 80-08-0
Catalog number:
B0084-393435
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C12H12N2O2S
Molecular Weight:
248.3
COA:
Inquire
Targets:
Antibacterial
Description:
Dapsone is a sulfone active against a wide range of bacteria but mainly employed for its actions against mycobacterium leprae, which has anti-inflammatory and immunomodulatory effects. It is an antibacterial most commonly used in combination with rifampicin and clofazimine as multidrug therapy (MDT) for the treatment of Mycobacterium leprae infections (leprosy). It antagonized all of the I/R end points measured, showing a remarkable ability to decrease markers of damage through antioxidant, antiinflammatory, and anti-apoptotic effects. It also inhibits bacterial synthesis of dihydrofolic acid, via competition with para-aminobenzoate for the active site of dihydropteroate synthetase.
Ordering Information
Catalog Number Size Price Stock Quantity
B0084-393435 1 k g $168 In stock
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Brife Description:
anti-inflammatory agent, Mycobacterium leprae infections (leprosy)
Purity:
>98%
Synonyms:
4,4′-Diaminodiphenyl sulfone; 4,4′-Sulfonyldianiline; 4-Aminophenyl sulfone; Bis(4-aminophenyl) sulfone; DDS
Solubility:
>37.2 ug/mL
MSDS:
Inquire
Application:
anti-inflammatory agent
Melting Point:
175.5 °C
InChIKey:
MQJKPEGWNLWLTK-UHFFFAOYSA-N
InChI:
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
Canonical SMILES:
C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)N
1.Early Onset Dapsone-induced Photosensitive Dermatitis: A Rare Side Effect of a Common Drug.
Karjigi S, Murthy SC, Kallappa H, Kusuma MR, Reddy YN. Indian J Lepr. 2015 Jul-Sep;87(3):161-4.
Dapsone, a potent anti-inflammatory compound, is mainly used in the treatment of leprosy, dermatitis herpetiformis, erythema elevatum diutinum and other dermatoses. Cutaneous adverse reactions range from acneiform eruptions to toxic epidermal necrolysis. A 30-year-old, married women who was treated with paucibacillary multi drug therapy, developed itchy skin lesions over the both forearms, 'V ' area of the neck and upper back after one week of the drug administration which worsened on exposure to sunlights. A clinical diagnosis of dapsone-induced photosensitive dermatitis was confirmed by histopathology and recurrence of symptoms and signs after re-exposure to the drug. Photosensitivity due to dapsone is rare and very few reports are available in the literature. Our patient had an unusually early onset compared to the previously reported cases.
2.Sulfonate salts of the therapeutic agent dapsone: 4-[(4-aminophenyl)sulfonyl]anilinium benzenesulfonate monohydrate and 4-[(4-aminophenyl)sulfonyl]anilinium methanesulfonate monohydrate.
Gaytán-Barrientos NS1, Morales-Morales D2, Herrera-Ruiz D1, Reyes-Martínez R3, Rivera-Islas J1. Acta Crystallogr C Struct Chem. 2016 Apr 1;72(Pt 4):280-4. doi: 10.1107/S2053229616003284. Epub 2016 Mar 8.
Dapsone, formerly used to treat leprosy, now has wider therapeutic applications. As is the case for many therapeutic agents, low aqueous solubility and high toxicity are the main problems associated with its use. Derivatization of its amino groups has been widely explored but shows no significant therapeutic improvements. Cocrystals have been prepared to understand not only its structural properties, but also its solubility and dissolution rate. Few salts of dapsone have been described. The title salts, C12H13N2O2S(+)·C6H5O3S(-)·H2O and C12H13N2O2S(+)·CH3SO3(-)·H2O, crystallize as hydrates and both compounds exhibit the same space group (monoclinic, P21/n). The asymmetric unit of each salt consists of a 4-[(4-aminophenyl)sulfonyl]anilinium monocation, the corresponding sulfonate anion and a water molecule. The cation, anion and water molecule form hydrogen-bonded networks through N-H...O=S, N-H...Owater and Owater-H...O=S hydrogen bonds.
3.Discovery of a potential lead compound for treating leprosy with dapsone resistance mutation in M. leprae folP1.
Nisha J1, Ramanathan K1, Nawaz Khan F2, Dhanasekaran D3, Shanthi V1. Mol Biosyst. 2016 Apr 28. [Epub ahead of print]
Dapsone resistance is a serious impediment to the implementation of the present leprosy control strategies. In the recent past, many studies have been undertaken to address the antibiotic activity and binding pattern of dapsone against both native and mutant (Pro55Leu) folP1. Yet, there is no well-developed structural basis for understanding drug action and there is dire need for new antibacterial therapies. In the present study, molecular simulation techniques were employed alongside experimental strategies to address and overcome the mechanism of dapsone resistance. In essence, we report the identification of small molecule compounds to effectively and specifically inhibit the growth of M. leprae through targeting dihydropteroate synthase, encoded by folP1 which is involved in folic acid synthesis. Initially, ADME and toxicity studies were employed to screen the lead compounds, using dapsone as standard drug. Subsequently, molecular docking was employed to understand the binding efficiency of dapsone and its lead compounds against folP1.
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CAS 80-08-0 Dapsone

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