Dapsone is a sulfone-class drug that has been used clinically since the 1940s and is on the WHO List of Essential Medicines (WHO, 2023).
According to the FDA-approved label, G6PD deficiency testing is mandatory before starting Dapsone to prevent severe hemolytic anemia (FDA, 2024).
Dapsone is the primary treatment for dermatitis herpetiformis, often relieving symptoms within 24-48 hours (NIH, 2023).
The World Health Organization recommends Dapsone as a key component of multidrug therapy for leprosy to prevent antibiotic resistance (WHO, 2022).
Methemoglobinemia is a common side effect of Dapsone, occurring to some degree in nearly all patients taking systemic doses (DailyMed, 2024).
Dapsone Hypersensitivity Syndrome is a rare but life-threatening reaction that typically occurs within the first 8 weeks of treatment (PubMed, 2023).
A study published in the Journal of the American Academy of Dermatology noted that Dapsone's anti-inflammatory effects are due to its inhibition of neutrophil myeloperoxidase (JAAD, 2022).
Dapsone can cause falsely low Hemoglobin A1c readings in diabetic patients due to its effect on red blood cell lifespan (ADA, 2024).
This page is for informational purposes only and does not replace medical advice. Before using any prescription or over-the-counter medication for Aczone, you must consult a qualified healthcare professional.
Clinical Information
Detailed information about Aczone
ℹ️Overview
Dapsone is a potent sulfone-class medication used primarily for the treatment of leprosy and dermatitis herpetiformis. It possesses both antibacterial and significant anti-inflammatory properties by inhibiting folate synthesis and neutrophil activity.
💊Usage & Dosage
Adult Dosage
Dosage for Dapsone is highly individualized and depends on the condition being treated, the patient's response, and their tolerance for potential side effects.
Dermatitis Herpetiformis: The typical starting dose for adults is 50 mg daily. If the condition is not controlled, your healthcare provider may increase the dose to 100 mg or higher. Some patients may require up to 300 mg per day, though the goal is always to find the minimum effective dose to maintain control of skin symptoms. Once the lesions are cleared, the dose is often tapered down.
Leprosy: In the treatment of leprosy, Dapsone is almost always used as part of a multidrug regimen. The standard adult dose is 100 mg once daily. The duration of treatment can range from 6 months to 2 years, depending on whether the infection is paucibacillary (fewer bacteria) or multibacillary (more bacteria).
Pneumocystis jirovecii Prophylaxis: The standard dose is typically 100 mg once daily or 50 mg twice daily.
Pediatric Dosage
Dapsone is used in children, but dosing must be calculated carefully, usually based on body weight.
Leprosy: For children, the WHO recommends a dose of approximately 2 mg/kg of body weight once daily, not to exceed the adult dose of 100 mg.
Pneumocystis Prophylaxis: In infants and children older than 1 month, the dose is generally 2 mg/kg once daily (maximum 100 mg/day).
Dosage Adjustments
Renal Impairment
Because Dapsone and its metabolites are primarily excreted by the kidneys, patients with impaired renal function may require lower doses or more frequent monitoring. There are no specific GFR-based formulas, but clinical caution is advised to prevent drug accumulation.
Hepatic Impairment
Since Dapsone is extensively metabolized in the liver, patients with liver disease are at an increased risk of toxicity. Healthcare providers may perform frequent liver function tests and adjust the dosage if enzymes become elevated.
Elderly Patients
Elderly patients should generally start at the lower end of the dosing range. This population is more likely to have decreased renal or hepatic function and may be more susceptible to the hematologic side effects of the drug.
How to Take Dapsone
Administration: Dapsone tablets should be swallowed whole with a full glass of water. It can be taken with or without food. If you experience stomach upset, taking the medication with a meal may help.
Consistency: It is important to take Dapsone at the same time every day to maintain a steady level of the drug in your bloodstream.
Dietary Considerations: For patients with dermatitis herpetiformis, Dapsone treats the symptoms, but a strict gluten-free diet is often necessary to address the underlying cause and may eventually allow for a reduction in medication dose.
Storage: Store the medication at room temperature (68°F to 77°F or 20°C to 25°C), away from moisture, heat, and direct light.
Missed Dose
If you miss a dose of Dapsone, take it as soon as you remember. However, if it is almost time for your next scheduled dose, skip the missed dose and resume your regular schedule. Do not double the dose to catch up, as this increases the risk of serious hematologic side effects.
Overdose
An overdose of Dapsone can be life-threatening. Symptoms of overdose include:
Nausea and vomiting
Intense cyanosis (bluish skin or lips due to lack of oxygen)
Extreme fatigue or weakness
Shortness of breath
Seizures
Coma
Emergency Action: If an overdose is suspected, contact emergency medical services or a poison control center immediately. Treatment usually involves gastric lavage (stomach pumping) and the administration of methylene blue if methemoglobinemia is severe.
> Important: Follow your healthcare provider's dosing instructions exactly. Do not adjust your dose or stop taking the medication without medical guidance, as this can cause a relapse of your condition.
⚠️Side Effects
Common Side Effects (>1 in 10)
Most patients taking Dapsone will experience some degree of hematologic (blood-related) changes, though they may not always cause noticeable symptoms.
Hemolysis: This is the breakdown of red blood cells. Patients may feel slightly more tired than usual. In most healthy individuals, the body can compensate for this loss, but it is more pronounced in certain populations.
Methemoglobinemia: This occurs when the iron in hemoglobin is oxidized, making it unable to carry oxygen effectively. A slight bluish tint to the fingernails or lips (cyanosis) is common and usually not dangerous unless levels exceed 15-20%.
Gastrointestinal Distress: Nausea, vomiting, and loss of appetite are frequently reported, especially when starting the medication.
Less Common Side Effects (1 in 100 to 1 in 10)
🔴Warnings
Important Safety Information
Dapsone is a high-alert medication due to its narrow therapeutic index and potential for severe blood-related toxicity. Patients must be under the strict supervision of a healthcare provider familiar with the drug’s profile. The most critical safety concern is the drug's effect on red blood cells, which can be life-threatening in patients with certain genetic predispositions.
Black Box Warnings
No FDA black box warnings for Dapsone. However, the absence of a black box warning does not imply the drug is without risk; the warnings for hemolysis and hypersensitivity are severe and require clinical diligence.
Major Precautions
G6PD Deficiency: This is the most critical precaution. Glucose-6-phosphate dehydrogenase (G6PD) is an enzyme that protects red blood cells. Individuals with a deficiency in this enzyme are at an extremely high risk of severe, life-threatening hemolytic anemia when taking Dapsone. Testing for G6PD deficiency is mandatory before starting Dapsone.
🔄Interactions
Contraindicated Combinations (Do Not Use Together)
There are few absolute contraindications, but certain combinations are avoided due to extreme risk:
Live Vaccines (e.g., Typhoid Vaccine): Dapsone may diminish the therapeutic effect of live bacterial vaccines. It is generally recommended to avoid live vaccinations while on systemic antibiotic therapy.
Serious Interactions (Monitor Closely)
Trimethoprim: When taken with Dapsone, the levels of both drugs may increase in the blood. This significantly raises the risk of methemoglobinemia and other toxicities. If used together, frequent blood monitoring is required.
Rifampin: This is a potent enzyme inducer. It can increase the metabolism of Dapsone, lowering its concentration in the blood by as much as 70-100%. While used together in leprosy treatment, the dose of Dapsone may need to be carefully managed to ensure efficacy.
🚫Contraindications
Absolute Contraindications
There are specific scenarios where Dapsone must NEVER be used because the risks far outweigh any potential benefits:
Hypersensitivity to Dapsone or Sulfones: If a patient has had a previous severe allergic reaction to Dapsone or related sulfone drugs, they must not take it. The reaction can be fatal upon re-exposure.
Severe Anemia: Patients with very low hemoglobin levels (e.g., less than 7-8 g/dL) should not start Dapsone, as the drug's inherent hemolytic effect will further deplete red blood cells to dangerous levels.
Known G6PD Deficiency: In many clinical guidelines, a known deficiency in G6PD is considered an absolute contraindication for standard doses due to the high risk of fulminant (sudden and severe) hemolytic anemia.
Relative Contraindications
👥Special Populations
Pregnancy
Dapsone is classified as FDA Pregnancy Category C. This means that animal studies have shown an adverse effect on the fetus, but there are no adequate and well-controlled studies in humans. However, Dapsone has been used for decades in pregnant women with leprosy without a clear increase in birth defects.
Risks: The primary concern during pregnancy is the risk of hemolytic anemia in both the mother and the fetus. If Dapsone is used during the third trimester, there is a theoretical risk of neonatal hyperbilirubinemia (jaundice in the newborn).
Clinical Decision: Dapsone should only be used during pregnancy if the potential benefit justifies the potential risk to the fetus. In cases of leprosy, the WHO generally recommends continuing MDT (including Dapsone) during pregnancy.
Breastfeeding
Dapsone is excreted into breast milk in significant quantities. There have been reports of hemolytic anemia in nursing infants whose mothers were taking Dapsone.
🧬Pharmacology
Mechanism of Action
Dapsone (4,4'-diaminodiphenyl sulfone) exerts its effects through two primary pathways:
1Antimicrobial: It acts as a competitive inhibitor of the enzyme dihydropteroate synthase. By mimicking para-aminobenzoic acid (PABA), it prevents the synthesis of dihydropteroic acid, a crucial step in the microbial production of dihydrofolate. This depletion of folate inhibits DNA synthesis in susceptible organisms like Mycobacterium leprae and Pneumocystis jirovecii.
2Anti-inflammatory: Dapsone suppresses the inflammatory response by inhibiting the lysosomal enzymes of neutrophils and reducing the production of toxic oxygen radicals. It specifically inhibits myeloperoxidase-mediated halogenation, which prevents the tissue damage typically seen in bullous (blistering) skin diseases.
Pharmacodynamics
Frequently Asked Questions
Common questions about Aczone
What is Dapsone used for?
Dapsone is primarily used to treat leprosy (Hansen's disease) and a chronic skin condition called dermatitis herpetiformis. It is also frequently prescribed to prevent or treat Pneumocystis jirovecii pneumonia (PCP) in patients with weakened immune systems. Because it has both antibiotic and anti-inflammatory properties, it is effective against certain bacteria and inflammatory skin reactions. Your doctor may also prescribe it off-label for other conditions like vasculitis or brown recluse spider bites. It is a potent medication that requires close medical supervision.
What are the most common side effects of Dapsone?
The most common side effects of Dapsone involve the blood, specifically a breakdown of red blood cells called hemolysis and a condition called methemoglobinemia, which reduces the blood's ability to carry oxygen. Patients often experience mild anemia, which can cause fatigue or pale skin. Other frequent side effects include nausea, vomiting, headache, and dizziness. Some patients may notice a slight bluish tint to their lips or fingernails. Most of these effects are dose-related and are monitored closely by healthcare providers through regular blood tests.
Can I drink alcohol while taking Dapsone?
It is generally advised to avoid or strictly limit alcohol consumption while taking Dapsone. Alcohol can increase the risk of liver toxicity, which is a potential side effect of the medication. Additionally, both Dapsone and alcohol can cause dizziness and fatigue, and combining them may worsen these effects. Chronic alcohol use can also interfere with folate levels in the body, potentially making Dapsone-induced anemia more severe. Always consult your doctor about your alcohol intake before starting this treatment.
Is Dapsone safe during pregnancy?
Dapsone is classified as Pregnancy Category C, meaning its safety has not been fully established in human clinical trials. While it has been used for decades to treat leprosy in pregnant women without a confirmed link to birth defects, risks still exist. The main concern is the potential for hemolytic anemia in both the mother and the developing fetus. Healthcare providers typically only prescribe Dapsone during pregnancy if the benefits to the mother clearly outweigh the risks to the baby. If you are pregnant or planning to become pregnant, a detailed discussion with your doctor is necessary.
How long does it take for Dapsone to work?
The time it takes for Dapsone to work depends on the condition being treated. For dermatitis herpetiformis, patients often feel a significant reduction in itching and skin pain within 24 to 48 hours of starting the medication. However, for leprosy, the process is much slower; it may take several months of consistent use to see visible improvements in skin lesions or nerve symptoms. It is vital to continue taking the medication exactly as prescribed, even if you do not see immediate results, to ensure the infection is fully treated.
Can I stop taking Dapsone suddenly?
You should never stop taking Dapsone suddenly without consulting your healthcare provider. For those being treated for leprosy, stopping the medication early can lead to the bacteria becoming resistant to the drug, making the disease much harder to treat later. For patients with dermatitis herpetiformis, stopping Dapsone abruptly usually causes a rapid and severe flare-up of itchy skin blisters. If the medication needs to be stopped due to side effects, your doctor will provide a specific plan to safely transition you off the drug.
What should I do if I miss a dose of Dapsone?
If you miss a dose of Dapsone, you should take it as soon as you remember. However, if it is almost time for your next scheduled dose, skip the missed dose and simply take your next one at the regular time. Do not take two doses at once to make up for a missed one, as this significantly increases the risk of toxic effects on your red blood cells. Maintaining a consistent level of the drug in your system is important for its effectiveness, so try using a pill organizer or alarm to help you remember.
Does Dapsone cause weight gain?
Weight gain is not a commonly reported side effect of Dapsone. Most patients do not experience significant changes in weight while taking this medication. In fact, some patients report a loss of appetite or nausea, which could potentially lead to minor weight loss. If you notice rapid or unusual weight gain while taking Dapsone, it is important to contact your doctor, as it could be a sign of a different underlying issue, such as fluid retention or a reaction affecting your kidneys or heart.
Can Dapsone be taken with other medications?
Dapsone can interact with several other medications, so it is crucial to inform your doctor of everything you are taking. For example, taking Dapsone with rifampin can lower Dapsone's effectiveness, while taking it with trimethoprim can increase the levels of both drugs and raise the risk of side effects. Other drugs that affect the blood or liver can also interact poorly with Dapsone. Your healthcare provider will review your current medications to ensure there are no dangerous interactions before starting your Dapsone therapy.
Is Dapsone available as a generic?
Yes, Dapsone is available as a generic medication in tablet form, which is typically much more affordable than brand-name versions. Generic Dapsone is required by the FDA to have the same active ingredient, strength, and effectiveness as the brand-name drug. It is widely available at most pharmacies. If you are prescribed Dapsone, you can ask your pharmacist if a generic version is available to help manage your treatment costs while ensuring you receive the same clinical benefits.
Similar Medications
Other drugs with the same active ingredient (Dapsone)
Dizziness and Vertigo: A feeling of spinning or lightheadedness.
Headache: Persistent or dull headaches may occur during the first few weeks of therapy.
Insomnia: Difficulty falling or staying asleep.
Tinnitus: Ringing in the ears.
Rare Side Effects (less than 1 in 100)
Peripheral Neuropathy: This involves damage to the nerves, usually manifesting as motor weakness in the hands or feet. It is often reversible upon discontinuation of the drug.
Albuminuria: The presence of protein in the urine, indicating potential kidney stress.
Psychosis: Rare reports of mental confusion, hallucinations, or extreme agitation.
Serious Side Effects — Seek Immediate Medical Attention
> Warning: Stop taking Dapsone and call your doctor immediately if you experience any of the following serious symptoms:
Severe Hypersensitivity (Dapsone Syndrome): This is a potentially fatal multi-organ reaction. Symptoms include a high fever, a widespread skin rash, and jaundice (yellowing of the eyes or skin). It typically occurs 2 to 8 weeks after starting the drug.
Agranulocytosis: A severe drop in white blood cell count, which makes you extremely vulnerable to infection. Seek help for a sudden fever, sore throat, or chills.
Toxic Epidermal Necrolysis (TEN) / Stevens-Johnson Syndrome (SJS): Rare but life-threatening skin reactions characterized by painful rashes, blistering, and peeling skin.
Severe Hemolytic Anemia: Symptoms include extreme pallor, dark-colored urine, rapid heart rate, and severe shortness of breath.
Hepatotoxicity: Signs of liver damage, such as dark urine, clay-colored stools, or severe abdominal pain.
Long-Term Side Effects
Prolonged use of Dapsone requires constant vigilance. Long-term effects can include:
Chronic Anemia: Persistent low red blood cell counts can lead to heart strain over time.
Optic Atrophy: Rare cases of damage to the optic nerve have been reported with long-term, high-dose therapy.
Male Infertility: Some studies suggest Dapsone may temporarily reduce sperm count and motility, though this is typically reversible after stopping the drug.
Black Box Warnings
Currently, Dapsone does not carry a formal FDA Black Box Warning. However, the FDA-approved labeling contains prominent "Warnings" regarding the risk of serious blood disorders (hemolysis and methemoglobinemia) and the "Dapsone Syndrome" hypersensitivity reaction. These risks are considered significant enough that they are often the first thing a pharmacist or doctor will discuss with a patient.
Report any unusual symptoms, especially changes in skin color, sudden fatigue, or fever, to your healthcare provider immediately.
Methemoglobinemia: Dapsone causes the formation of methemoglobin. While low levels are tolerated, high levels prevent oxygen from reaching tissues. Patients with pre-existing heart or lung disease are at much higher risk of complications from this effect.
Dapsone Hypersensitivity Syndrome (DHS): This is a severe reaction characterized by the triad of fever, eruption (rash), and internal organ involvement (usually the liver). If DHS is suspected, the drug must be discontinued immediately and never restarted.
Hepatotoxicity and Nephrotoxicity: Dapsone can cause toxic hepatitis and albuminuria. Regular monitoring of liver and kidney function is required.
Sulfonamide Allergy: While Dapsone is a sulfone, not a sulfonamide, there is a possibility of cross-sensitivity. Patients allergic to "sulfa drugs" should use Dapsone with extreme caution.
Monitoring Requirements
Because of the risks mentioned above, patients on Dapsone require a rigorous laboratory monitoring schedule:
Baseline Tests: Complete Blood Count (CBC) with differential, G6PD enzyme levels, liver function tests (LFTs), and renal function tests (creatinine/BUN).
Initial Monitoring: CBCs are typically performed weekly for the first month of treatment to catch rapid drops in hemoglobin or white blood cells.
Ongoing Monitoring: CBCs and LFTs are usually performed monthly for the first six months, and then every 3 to 6 months thereafter for the duration of therapy.
Driving and Operating Machinery
Dapsone may cause dizziness, blurred vision, or significant fatigue due to anemia. Patients should determine how they react to the medication before driving or operating heavy machinery.
Alcohol Use
Alcohol should be avoided or strictly limited while taking Dapsone. Alcohol can increase the risk of liver toxicity and may worsen the dizziness or sedative effects of the medication. Additionally, chronic alcohol use can deplete folate levels, potentially worsening Dapsone-induced anemia.
Discontinuation
Do not stop taking Dapsone suddenly unless you are experiencing a severe allergic reaction. For conditions like leprosy, stopping early can lead to antibiotic resistance. For dermatitis herpetiformis, stopping abruptly will likely result in a rapid and painful return of skin lesions. Your doctor will provide a tapering schedule if the drug needs to be discontinued.
> Important: Discuss all your medical conditions, especially any history of anemia or liver disease, with your healthcare provider before starting Dapsone.
Prilocaine: This local anesthetic can also cause methemoglobinemia. Using it alongside Dapsone creates an additive effect that can lead to dangerously high methemoglobin levels.
Moderate Interactions
Cimetidine: This heartburn medication can actually be beneficial. It inhibits the N-hydroxylation of Dapsone, which may reduce the levels of the toxic metabolite responsible for methemoglobinemia without affecting the therapeutic levels of the drug.
Folic Acid Antagonists (e.g., Methotrexate): Since Dapsone interferes with folate metabolism, taking it with other folate antagonists can increase the risk of bone marrow suppression and anemia.
Anticonvulsants (e.g., Phenytoin, Phenobarbital): These drugs may induce hepatic enzymes, potentially reducing the effectiveness of Dapsone.
Food Interactions
High-Fat Meals: While food doesn't stop absorption, a very high-fat meal might slightly delay the time it takes for the drug to reach peak levels. Generally, Dapsone can be taken with or without food.
Grapefruit Juice: Grapefruit is a known inhibitor of CYP3A4. Since CYP3A4 is involved in Dapsone metabolism, consuming large amounts of grapefruit juice could theoretically increase Dapsone levels and toxicity risks.
Herbal/Supplement Interactions
St. John’s Wort: This herbal supplement is a potent inducer of CYP3A4. It may lower the levels of Dapsone in the blood, making the treatment less effective.
Iron Supplements: While Dapsone causes anemia, taking iron should only be done under medical supervision, as the anemia is caused by cell destruction (hemolysis), not necessarily iron deficiency.
Lab Test Interactions
Hemoglobin A1c: Dapsone-induced hemolysis shortens the lifespan of red blood cells. This can lead to falsely low HbA1c readings in diabetic patients, making their blood sugar control appear better than it actually is.
Bilirubin: Dapsone can cause elevations in serum bilirubin due to the breakdown of red blood cells, which may interfere with liver function assessments.
For each major interaction, the mechanism usually involves the CYP450 enzyme system or additive pharmacodynamic effects on red blood cells. The clinical consequence is typically either reduced efficacy of the antibiotic or increased risk of life-threatening blood disorders.
> Important: Tell your doctor about ALL medications, supplements, and herbal products you are taking, as well as any changes in your diet.
These are conditions where Dapsone may be used, but only with extreme caution and intensive monitoring:
Liver Disease: Because the liver is the primary site of Dapsone metabolism, patients with hepatitis or cirrhosis are at higher risk for drug accumulation and hepatotoxicity.
Renal Impairment: Decreased kidney function can slow the excretion of Dapsone metabolites, increasing the risk of side effects.
Cardiopulmonary Disease: Patients with heart failure or chronic obstructive pulmonary disease (COPD) are less able to tolerate the reduction in oxygen-carrying capacity caused by methemoglobinemia.
Porphyria: Dapsone has been linked to the triggering of acute attacks in patients with certain types of porphyria (a group of rare genetic blood disorders).
Cross-Sensitivity
Sulfonamides: Although Dapsone is a sulfone, there is a structural similarity to sulfonamide antibiotics (sulfa drugs). While most patients with a sulfa allergy can tolerate Dapsone, a small percentage may experience cross-reactivity. Healthcare providers will typically monitor these patients very closely during the first few weeks of therapy.
> Important: Your healthcare provider will evaluate your complete medical history, including genetic testing for G6PD, before prescribing Dapsone to ensure it is safe for you.
Recommendation: Because of the potential for serious adverse reactions in nursing infants, a decision should be made whether to discontinue nursing or discontinue the drug, taking into account the importance of the drug to the mother. If breastfeeding continues, the infant must be monitored closely for signs of jaundice or anemia.
Pediatric Use
Dapsone is approved for use in children for the treatment of leprosy and PCP prophylaxis.
Safety: The safety profile in children is generally similar to that in adults. However, children may be more sensitive to the effects of methemoglobinemia.
Dosing: Dosing must be weight-based (typically 2 mg/kg). Dapsone is not generally used for dermatitis herpetiformis in very young children, as the condition is rarer in this age group.
Geriatric Use
Clinical studies of Dapsone did not include sufficient numbers of subjects aged 65 and over to determine if they respond differently than younger subjects.
Pharmacokinetics: Older adults are more likely to have decreased renal and hepatic function, which can lead to higher blood levels of the drug.
Comorbidities: The elderly are more likely to have underlying heart disease, making them much more vulnerable to the effects of methemoglobinemia and anemia. Lower starting doses and frequent monitoring are strongly recommended.
Renal Impairment
In patients with kidney disease, the excretion of Dapsone and its metabolites is delayed. While there are no specific dosage adjustment tables, healthcare providers often reduce the dose or increase the interval between doses if the GFR is significantly low. Regular monitoring of CBC and renal function is essential.
Hepatic Impairment
Since Dapsone is metabolized by the liver, hepatic impairment increases the risk of toxicity. In patients with significant liver damage (Child-Pugh Class B or C), Dapsone should be used with extreme caution. If liver enzymes (ALT/AST) rise to more than 2-3 times the upper limit of normal, the drug is usually discontinued.
> Important: Special populations require individualized medical assessment and more frequent laboratory monitoring to ensure safety.
Onset of Action: In dermatitis herpetiformis, the anti-inflammatory effect is rapid, with itching often subsiding within 24 hours. For leprosy, the antibacterial effect is slow, and clinical improvement may take months.
Duration: The effects of a single dose can persist for several days due to the drug's long half-life and tissue binding.
Tolerance: There is no evidence of pharmacological tolerance developing to the anti-inflammatory effects of Dapsone over time.
Pharmacokinetics
| Parameter | Value |
|---|---|
| Bioavailability | >85% (Rapidly absorbed) |
| Protein Binding | 70% to 90% (Primarily to albumin) |
| Half-life | 20 to 30 hours (Average) |
| Tmax (Time to Peak) | 2 to 8 hours |
| Metabolism | Hepatic (N-acetylation and N-hydroxylation) |
Solubility: Very slightly soluble in water; soluble in alcohol.
Structure: Dapsone consists of two benzene rings linked by a sulfone group, with amino groups in the para positions. This symmetrical structure is key to its interaction with bacterial enzymes.
Drug Class
Dapsone is the prototypical member of the sulfone class of drugs. While chemically related to sulfonamides, its unique structure allows for its specific anti-inflammatory applications that standard sulfa antibiotics lack. It remains the most clinically significant sulfone in modern medicine.