Dapsona
Descripción general
Descripción
Mecanismo De Acción
Target of Action
Dapsone, also known as 4,4’-diaminodiphenyl sulfone (DDS), is a sulfone drug that primarily targets a wide range of bacteria, but is mainly employed for its actions against Mycobacterium leprae .
Mode of Action
Dapsone acts against bacteria and protozoa in the same way as sulphonamides, that is by inhibiting the synthesis of dihydrofolic acid. This inhibition occurs through competition with para-amino-benzoate for the active site of dihydropteroate synthetase . This interaction with its targets leads to the inhibition of bacterial growth .
Biochemical Pathways
Dapsone’s anti-inflammatory properties are triggered by inhibiting reactive oxygen species (ROS) production, reducing the effect of eosinophil peroxidase on mast cells, and downregulating neutrophil-mediated inflammatory responses . These actions affect various biochemical pathways and result in multiple antioxidant, anti-inflammatory, and anti-apoptotic functions .
Pharmacokinetics
Dapsone is absorbed rapidly and nearly completely from the gastrointestinal tract . After oral administration, the drug is slowly absorbed, reaching the maximum concentration in plasma at about 4 hours, with an absorption half-life of about 1.1 hours . The elimination half-life of dapsone is about 30 hours . The drug shows linear pharmacokinetics within the therapeutic range and the time-course after oral administration fits a 2-compartment model .
Result of Action
The molecular and cellular effects of Dapsone’s action are multifaceted. Its antibacterial effects lead to the inhibition of bacterial growth . Its anti-inflammatory properties result in the inhibition of ROS production, reduction of the effect of eosinophil peroxidase on mast cells, and downregulation of neutrophil-mediated inflammatory responses . These actions result in multiple antioxidant, anti-inflammatory, and anti-apoptotic functions .
Action Environment
The action, efficacy, and stability of Dapsone can be influenced by various environmental factors. For instance, coeliac disease and dermatitis herpetiformis may delay its oral absorption . Severe leprosy has been reported to affect the extent of absorption . Rifampicin increases the rate of elimination of dapsone; pyrimethamine increases the volume of distribution and probenecid decreases the renal clearance of dapsone .
Aplicaciones Científicas De Investigación
Dapsone has a wide range of scientific research applications:
Chemistry: Used as a reagent in organic synthesis and as a standard in analytical chemistry.
Biology: Studied for its effects on cellular processes and its role in inhibiting bacterial growth.
Medicine: Extensively used in the treatment of leprosy, dermatitis herpetiformis, and other bacterial infections. .
Industry: Used in the production of certain polymers and as an additive in some industrial processes.
Análisis Bioquímico
Biochemical Properties
Dapsone acts against bacteria and protozoa in the same way as sulphonamides, by inhibiting the synthesis of dihydrofolic acid through competition with para-amino-benzoate for the active site of dihydropteroate synthetase . This inhibition of folic acid synthesis in susceptible organisms leads to the prevention of bacterial growth .
Cellular Effects
Dapsone has been shown to possess anti-inflammatory activity in a variety of animal models . It possesses oral anti-oedema activity especially pronounced in novel models of acute inflammation . Dapsone can cause haematological effects, increases in organ weights, degeneration of liver and spleen, and hyperreactivity . Toxic effects of dapsone in humans indicate haemolytic anemia, leucopenia, gastro-intestinal and neurologic effects .
Molecular Mechanism
The molecular mechanism of Dapsone involves the inhibition of folic acid synthesis in bacteria, which is achieved by competing with para-amino-benzoate for the active site of dihydropteroate synthetase . This results in the prevention of bacterial growth . In addition, Dapsone’s anti-inflammatory properties are triggered by inhibiting reactive oxygen species (ROS) production, reducing the effect of eosinophil peroxidase on mast cells, and downregulating neutrophil-mediated inflammatory responses .
Temporal Effects in Laboratory Settings
Dapsone treatment requires careful laboratory monitoring . It is important to have a blood test to make sure your blood counts, liver, and kidney functions are normal before starting Dapsone . Blood tests will take place frequently after first starting Dapsone and can be reduced to every three months when the dose is stabilised .
Dosage Effects in Animal Models
Dapsone has been shown to possess anti-inflammatory activity in a variety of animal models . It is effective in chronic models such as adjuvant arthritis and the cotton pellet granuloma although multiple administration may also produce cyanosis . Antipyretic and analgesic effects for Dapsone have been demonstrated and are similar to those produced by phenylbutazone .
Metabolic Pathways
Dapsone is metabolized mainly through acetylation by -acetyltransferase enzyme to monoacteyldapsone (MADDS) and through hydroxylation by cytochrome P-450 enzymes (including CYP2E1, CYP2C9, and CYP3A4), resulting in the creation of dapsone hydroxylamine (DDS-NOH) .
Transport and Distribution
Dapsone is distributed throughout total body water and is present in all tissues . It tends to be retained in skin and muscle and especially in the liver and kidney: traces of the drug are present in these organs up to 3 weeks after therapy cessation .
Métodos De Preparación
Synthetic Routes and Reaction Conditions
Dapsone can be synthesized using various methods. One common method involves the reaction of chlorobenzene with sulfuric acid to produce dichlorodiphenyl sulfone. This intermediate is then subjected to ammoniation to yield dapsone . The reaction conditions typically involve the use of dilute sulfuric acid as a solvent, and sodium hydrosulfite as a reducing agent to improve yield and quality .
Industrial Production Methods
In industrial settings, dapsone is produced through a similar synthetic route but on a larger scale. The process involves careful control of reaction conditions to ensure high purity and yield. The use of continuous flow reactors and advanced purification techniques helps in achieving the desired product quality .
Análisis De Reacciones Químicas
Types of Reactions
Dapsone undergoes various chemical reactions, including:
Oxidation: Dapsone can be oxidized to form hydroxylamine derivatives.
Reduction: It can be reduced to form amine derivatives.
Substitution: Dapsone can participate in nucleophilic substitution reactions, particularly at the sulfone group.
Common Reagents and Conditions
Oxidation: Common oxidizing agents include hydrogen peroxide and potassium permanganate.
Reduction: Reducing agents such as sodium borohydride and lithium aluminum hydride are used.
Substitution: Nucleophiles like amines and thiols can be used under basic conditions.
Major Products
Oxidation: Hydroxylamine derivatives.
Reduction: Amine derivatives.
Substitution: Various substituted sulfone derivatives.
Comparación Con Compuestos Similares
Similar Compounds
Sulfonamides: Similar to dapsone in their mechanism of action, inhibiting dihydrofolic acid synthesis.
Prednisone: Used for its anti-inflammatory properties but differs in its mechanism of action.
Dexamethasone: Another anti-inflammatory agent with a different mechanism of action compared to dapsone.
Uniqueness
Dapsone is unique in its dual role as an antibacterial and anti-inflammatory agent. Its ability to inhibit dihydrofolic acid synthesis while also reducing inflammation makes it particularly effective in treating conditions like leprosy and dermatitis herpetiformis .
Propiedades
IUPAC Name |
4-(4-aminophenyl)sulfonylaniline |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
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 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
MQJKPEGWNLWLTK-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C12H12N2O2S |
Source
|
| Record name | 4,4'-SULFONYLDIANILINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/21054 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID4020371 |
Source
|
| Record name | Dapsone | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID4020371 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
248.30 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
4,4'-sulfonyldianiline appears as odorless white or creamy white crystalline powder. Slightly bitter taste. (NTP, 1992), Odorless white or creamy white crystalline powder; [CAMEO], Solid |
Source
|
| Record name | 4,4'-SULFONYLDIANILINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/21054 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Dapsone | |
| Source | Haz-Map, Information on Hazardous Chemicals and Occupational Diseases | |
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| Record name | Dapsone | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014395 | |
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Flash Point |
greater than 320 °F (NTP, 1992), Flash point > 320 °F |
Source
|
| Record name | 4,4'-SULFONYLDIANILINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/21054 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Dapsone | |
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| Description | Haz-Map® is an occupational health database designed for health and safety professionals and for consumers seeking information about the adverse effects of workplace exposures to chemical and biological agents. | |
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Solubility |
>37.2 [ug/mL] (The mean of the results at pH 7.4), less than 1 mg/mL at 68 °F (NTP, 1992), In water, 380 mg/L at 37 °C, Soluble in alcohol, methanol, acetone, dilute hydrochloric acid. Practically insoluble in water., Insoluble in fixed and vegetable oils., Slightly soluble in deuterated dimethyl sulfoxide., 2.84e-01 g/L |
Source
|
| Record name | SID855979 | |
| Source | Burnham Center for Chemical Genomics | |
| URL | https://pubchem.ncbi.nlm.nih.gov/bioassay/1996#section=Data-Table | |
| Description | Aqueous solubility in buffer at pH 7.4 | |
| Record name | 4,4'-SULFONYLDIANILINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/21054 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Dapsone | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00250 | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/5073 | |
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| Record name | Dapsone | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014395 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Density |
1.33 at 77 °F (NTP, 1992) - Denser than water; will sink |
Source
|
| Record name | 4,4'-SULFONYLDIANILINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/21054 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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Vapor Density |
8.3 (NTP, 1992) - Heavier than air; will sink (Relative to Air), 8.3 (Air = 1) |
Source
|
| Record name | 4,4'-SULFONYLDIANILINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/21054 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | DAPSONE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/5073 | |
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Vapor Pressure |
0.00000003 [mmHg] |
Source
|
| Record name | Dapsone | |
| Source | Haz-Map, Information on Hazardous Chemicals and Occupational Diseases | |
| URL | https://haz-map.com/Agents/1170 | |
| Description | Haz-Map® is an occupational health database designed for health and safety professionals and for consumers seeking information about the adverse effects of workplace exposures to chemical and biological agents. | |
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Mechanism of Action |
Dapsone acts against bacteria and protozoa in the same way as sulphonamides, that is by inhibiting the synthesis of dihydrofolic acid through competition with para-amino-benzoate for the active site of dihydropteroate synthetase. The anti-inflammatory action of the drug is unrelated to its antibacterial action and is still not fully understood., Dapsone is a structural analog of para-aminobenzoic acid (PABA) and a competitive inhibitor of dihydropteroate synthase (folP1P2) in the folate pathway ... The effect on this evolutionarily conserved pathway also explains why dapsone is a broad-spectrum agent with antibacterial, anti-protozoal, and antifungal effects. The anti-inflammatory effects of dapsone occur via inhibition of tissue damage by neutrophils. First, dapsone inhibits neutrophil myeloperoxidase activity and respiratory burst. Second, it inhibits activity of neutrophil lysosomal enzymes. Third, it may also act as a free radical scavenger, counteracting the effect of free radicals generated by neutrophils. Fourth, dapsone may also inhibit migration of neutrophils to inflammatory lesions., 1-30 Ug/mL dapsone interfered with myeloperoxidase-H2O2-halide-mediated cytotoxic system in polymorphonuclear leukocytes. Kinetic studies revealed competitive inhibition of myeloperoxidase. Its action in dermatitis herpetiformis may be explained by effect on this system. |
Source
|
| Record name | Dapsone | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00250 | |
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Impurities |
Three contaminants commonly found in commercial dapsone, 2,4-sulfonylbis(benzeneamine); 4-(phenylsulfonyl)benzeneamine; & 4-(4'-chlorophenylsulfonyl)benzeneamine, were identified by NMR & unambiguous synth of each compd. |
Source
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| Record name | DAPSONE | |
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Color/Form |
Crystals from 95% ethanol, White or creamy white crystalline powder | |
CAS No. |
80-08-0 |
Source
|
| Record name | 4,4'-SULFONYLDIANILINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/21054 | |
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| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Melting Point |
347 to 349 °F (NTP, 1992), 175-176 °C (also a higher melting form, MP 180.5 °C), There are extraordinarily complicated polymorphism conditions in the drugs dapsone and ethambutol chloride. In both cases, four modifications were detected, and in the case of dapsone there exists a hydrate in addition. The dapsone anhydrate is present as enantiotropic Mod. III, which transforms into Mod. II at 80 °C. This form is mostly stable up to its melting point. Mod. I, which crystallizes from the melt, is likewise enantiotropic with Mod. II. In addition, there is enantiotropy between Mod. I and Mod. III. The transformation of Mod. III /between/ Mod. II takes place continuously and independently from nuclei, so that the melting point of Mod. III cannot be determined. In Mod. IV, no enantiotropy with another crystal form could be detected. ..., 175.5 °C |
Source
|
| Record name | 4,4'-SULFONYLDIANILINE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/21054 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | Dapsone | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00250 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | DAPSONE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/5073 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Dapsone | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014395 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Synthesis routes and methods I
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Synthesis routes and methods II
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Synthesis routes and methods III
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Retrosynthesis Analysis
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