What are sulfonamides. How do sulfonamides work. What conditions do sulfonamides treat. Are there different types of sulfonamides. What are the common side effects of sulfonamides. How to use sulfonamides safely.

The History and Evolution of Sulfonamides in Medicine

Sulfonamides, commonly known as sulfa drugs, revolutionized the field of medicine in the 1930s. Their discovery marked the beginning of a new era in treating bacterial infections. The journey began with a German scientist isolating a sulfonamide called Prontosil, which he used to save his daughter’s arm from amputation.

This breakthrough led to the development of other effective sulfonamides:

• Sulfapyridine: Effective against pneumonia
• Sulfacetamide: Used for urinary tract infections
• Sulfathiazole: Treated gastrointestinal tract infections and was widely used during World War II to prevent infection in soldiers’ wounds

As research progressed, scientists discovered that sulfonamides could do more than just fight infections. Today, these drugs are used to treat a wide range of conditions, including diabetes, inflammatory diseases, HIV-1, epilepsy, high blood pressure, and certain skin conditions.

Understanding Sulfonamides: Chemical Structure and Classification

Sulfonamides are synthetic, man-made medicines that share a common chemical structure. They are broadly classified into two main groups based on their therapeutic activity:

1. Antibacterial sulfonamides: Used to treat infections
2. Non-antibacterial sulfonamides: Used to treat various other illnesses

This classification helps healthcare providers and patients understand the primary purpose of each sulfonamide drug. For instance, Bactrim (sulfamethoxazole-trimethoprim) is an antibacterial sulfonamide, while Amaryl (glimepiride) is a non-antibacterial sulfonamide used to treat diabetes.

How do sulfonamides function in the body?

The mechanism of action varies depending on the type of sulfonamide:

• Antibacterial sulfonamides: These drugs bind to and inhibit a specific enzyme, preventing bacteria from reproducing. This action is bacteriostatic, meaning it stops bacterial growth rather than killing the bacteria directly.
• Non-antibacterial sulfonamides: While their exact mechanisms are less understood, they are believed to have anti-inflammatory properties and effects on the immune system. For example, in treating Type 2 diabetes, sulfonamides stimulate pancreatic beta cells to release insulin.

The Versatility of Sulfonamides: Treatment Applications

Sulfonamides are used to treat a wide range of medical conditions. Here’s a comprehensive list of their applications:

Bacterial Infections

• Bactrim (sulfamethoxazole-trimethoprim)
• Bactrim DS (sulfamethoxazole-trimethoprim double strength)
• Sulfatrim Pediatric (sulfamethoxazole-trimethoprim)

Type 2 Diabetes

• Amaryl (glimepiride)
• Glucotrol (glipizide)
• Glynase PresTab (glyburide micronized)
• Tolbutamide

High Blood Pressure

• Acetazolamide
• Bumetanide
• Chlorthalidone
• Lasix (furosemide)
• Hydrochlorothiazide
• Indapamide
• Metolazone

Other Medical Conditions

• Glaucoma: Methazolamide, Azopt (brinzolamide), Trusopt (dorzolamide HCl)
• Gout: Probenecid
• Inflammatory diseases: Celebrex (celecoxib)
• HIV-1: Lexiva (fosamprenavir calcium)
• Epilepsy: Zonegran (zonisamide)
• Irregular heartbeat: Tikosyn (dofetilide), Betapace (sotalol HCl)
• Benign prostatic hyperplasia (BPH): Flomax (tamsulosin HCl)
• Migraine headaches: Imitrex (sumatriptan succinate)

Sulfonamides in Topical and Ophthalmic Applications

Sulfonamides are not limited to oral medications. They are also used in topical and ophthalmic applications:

Topical Sulfonamides

• Silvadene (silver sulfadiazine)
• Aczone (dapsone)
• Klaron (sodium sulfacetamide)
• Sulfamylon (mafenide acetate)

These topical medications are often used to treat skin conditions or prevent infections in burn wounds.

Ophthalmic Sulfonamides

• Azopt (brinzolamide)
• Bleph-10 (sulfacetamide sodium)
• Trusopt (dorzolamide HCl)

Ophthalmic sulfonamides are primarily used to treat glaucoma by reducing intraocular pressure.

The Mechanism of Action: How Sulfonamides Work in Different Conditions

The versatility of sulfonamides is reflected in their varied mechanisms of action across different medical conditions:

In Bacterial Infections

Antibacterial sulfonamides work by inhibiting the synthesis of folic acid in bacteria. They compete with para-aminobenzoic acid (PABA), a substrate necessary for bacterial growth, thereby preventing bacterial reproduction.

In Diabetes

Sulfonamide drugs used in diabetes treatment, such as glimepiride and glipizide, stimulate the pancreatic beta cells to release more insulin. This helps lower blood glucose levels in patients with Type 2 diabetes.

In Hypertension

Sulfonamide diuretics, like hydrochlorothiazide, work by increasing the excretion of water and sodium through urine. This reduces blood volume and, consequently, blood pressure.

In Inflammatory Conditions

Sulfonamide derivatives with anti-inflammatory properties, such as celecoxib, work by inhibiting cyclooxygenase-2 (COX-2) enzymes. This action reduces the production of prostaglandins, which are responsible for pain and inflammation.

In HIV Treatment

Sulfonamide drugs used in HIV treatment, like fosamprenavir, act as protease inhibitors. They block the action of protease enzymes, which are crucial for the replication of the HIV virus.

Safety Considerations and Side Effects of Sulfonamides

While sulfonamides are effective in treating various conditions, they can cause side effects and may not be suitable for everyone. It’s crucial to understand the potential risks associated with these medications.

Common Side Effects

• Nausea and vomiting
• Diarrhea
• Loss of appetite
• Skin rash
• Headache
• Dizziness

Serious Side Effects

• Allergic reactions (including anaphylaxis)
• Stevens-Johnson syndrome
• Toxic epidermal necrolysis
• Blood disorders (such as agranulocytosis)
• Liver damage
• Kidney problems

It’s important to note that some people may be allergic to sulfonamides. If you’ve had an allergic reaction to one sulfonamide drug, you may be allergic to others in the same class.

Who should avoid sulfonamides?

Certain groups of people should use sulfonamides with caution or avoid them altogether:

• Pregnant women: Some sulfonamides can cross the placenta and may cause harm to the developing fetus.
• Breastfeeding mothers: Sulfonamides can be passed through breast milk.
• People with liver or kidney disease: These conditions may affect how the body processes sulfonamides.
• Individuals with G6PD deficiency: Sulfonamides can trigger hemolytic anemia in these patients.
• People with porphyria: Sulfonamides may exacerbate this condition.

Always consult with a healthcare provider before starting or stopping any medication, including sulfonamides.

Drug Interactions and Precautions with Sulfonamides

Sulfonamides can interact with various medications and substances, potentially altering their effectiveness or increasing the risk of side effects. It’s crucial to inform your healthcare provider about all medications, supplements, and herbal products you’re taking.

Common Drug Interactions

• Warfarin: Sulfonamides may increase the anticoagulant effect of warfarin, increasing the risk of bleeding.
• Methotrexate: Sulfonamides can increase methotrexate levels, potentially leading to toxicity.
• Cyclosporine: Some sulfonamides may decrease cyclosporine levels, reducing its effectiveness.
• Phenytoin: Sulfonamides can increase phenytoin levels, potentially leading to toxicity.
• Oral hypoglycemics: Sulfonamides may enhance the effect of these drugs, potentially causing hypoglycemia.

Precautions When Using Sulfonamides

1. Sun sensitivity: Some sulfonamides can make your skin more sensitive to sunlight. Use sunscreen and protective clothing when outdoors.
2. Hydration: Drink plenty of water when taking sulfonamides, especially those used as diuretics, to prevent dehydration and kidney problems.
3. Regular monitoring: If you’re on long-term sulfonamide therapy, your doctor may recommend regular blood tests to monitor liver and kidney function.
4. Alcohol: Avoid or limit alcohol consumption while taking sulfonamides, as it may increase the risk of side effects.
5. Pregnancy and breastfeeding: Always consult your healthcare provider about the risks and benefits of using sulfonamides during pregnancy or while breastfeeding.

The Future of Sulfonamides in Medical Treatment

Despite being one of the oldest classes of antibiotics, sulfonamides continue to play a crucial role in modern medicine. Researchers are exploring new applications and modifications to improve their efficacy and reduce side effects.

Current Research and Development

• Novel sulfonamide derivatives: Scientists are developing new sulfonamide compounds with enhanced antibacterial properties and fewer side effects.
• Combination therapies: Researchers are exploring the potential of combining sulfonamides with other drugs to enhance their effectiveness and combat antibiotic resistance.
• Targeted delivery systems: New technologies are being developed to deliver sulfonamides more precisely to affected areas, potentially reducing systemic side effects.
• Applications in cancer treatment: Some studies suggest that certain sulfonamide derivatives may have anti-cancer properties, opening up new avenues for research.

Challenges and Opportunities

While sulfonamides have proven their worth over decades, they face several challenges:

• Antibiotic resistance: As with many antibiotics, some bacteria have developed resistance to sulfonamides. Researchers are working on strategies to overcome this resistance.
• Side effect profile: Efforts are ongoing to develop sulfonamides with fewer adverse effects, particularly for patients with allergies or sensitivities.
• New indications: Scientists are exploring the potential of sulfonamides in treating emerging diseases and conditions beyond their current applications.

The future of sulfonamides looks promising, with ongoing research aiming to harness their full potential while addressing current limitations. As our understanding of these drugs grows, we can expect to see new and improved sulfonamide-based treatments in the coming years.

Practical Advice for Patients Taking Sulfonamides

If you’ve been prescribed a sulfonamide medication, following these guidelines can help ensure safe and effective use:

Tips for Taking Sulfonamides

1. Follow instructions: Take the medication exactly as prescribed by your healthcare provider. Don’t alter the dosage or duration without consulting them first.
2. Complete the course: If you’re taking an antibacterial sulfonamide, complete the entire course of treatment, even if you start feeling better. This helps prevent antibiotic resistance.
3. Stay hydrated: Drink plenty of water, especially if you’re taking a sulfonamide diuretic.
4. Monitor for side effects: Be aware of potential side effects and report any unusual symptoms to your healthcare provider promptly.
5. Avoid sun exposure: If your medication increases sun sensitivity, use sunscreen and protective clothing when outdoors.
6. Inform healthcare providers: Always tell your doctors, dentists, and pharmacists that you’re taking a sulfonamide medication.
7. Store properly: Keep your medication in a cool, dry place, away from direct sunlight and out of reach of children.

When to Seek Medical Attention

Contact your healthcare provider immediately if you experience:

• Severe skin rash or blistering
• Difficulty breathing or swallowing
• Unusual bleeding or bruising
• Yellowing of the skin or eyes
• Severe diarrhea
• Signs of an allergic reaction (hives, swelling of face or throat, rapid heartbeat)

Remember, while this information provides a comprehensive overview of sulfonamides, it’s not a substitute for professional medical advice. Always consult with your healthcare provider for personalized guidance on using sulfonamide medications.

Uses, common brands, and safety information

Sulfonamides, also commonly known as sulfa drugs, were first discovered to have antibacterial properties in the 1930s. A German scientist isolated a sulfonamide called Prontosil and, ironically, treated his own daughter with it, saving her arm from being amputated. The discovery of Prontosil led to a new era in medicine, as sulfonamides were the first broadly effective drugs to treat bacterial infections. Prontosil led the way to the discoveries of other antibacterial sulfonamides: sulfapyridine, which was effective against pneumonia, sulfacetamide, which was effective against urinary tract infections, and sulfathiazole, which was effective against gastrointestinal (GI) tract infections. Sulfathiazole was also commonly used in pill and powder form during World War II to treat soldiers’ wounds to prevent infection. 

The chemical activity of sulfonamides provides for more than just anti-infective properties. There are many other disease states that drugs in the sulfonamide class are used for including diabetes, inflammatory diseases, HIV-1, epilepsy, high blood pressure, and topically for certain skin conditions. The table below lists common sulfonamide medicines followed by information on how they work, what conditions they treat, safety, and cost.

Other sulfonamides

Topicals

• Silvadene (silver sulfadiazine)
• Aczone (dapsone)
• Klaron (sodium sulfacetamide)
• Sulfamylon (mafenide acetate)

Ophthalmics

• Azopt (brinzolamide)
• Bleph-10 (sulfacetamide sodium) 
• Trusopt (dorzolamide HCl)

What are sulfonamides?

Sulfonamides are synthetic, or man-made, medicines that all share a common chemical structure. Sulfonamides treat a variety of disorders and illnesses and, based on their therapeutic activity, are divided into one of two general groups: the antibacterial sulfonamides that are used to treat infections and the non-antibacterial sulfonamides that are used to treat a variety of other illnesses including diabetes, inflammatory diseases, HIV-1, epilepsy, high blood pressure, glaucoma, and certain skin conditions.

How do sulfonamides work?

Antibacterial sulfonamide drugs work by binding to and stopping a specific enzyme, or protein, from carrying out its normal function of helping provide nutrients to the infectious bacteria cell. Sulfonamides don’t kill bacteria, but instead, they stop the reproduction of infectious bacteria. This action is called “bacteriostatic,” meaning it prevents the growth of bacteria. 

Less is known about how the non-antibacterial sulfonamide drugs work, although they are thought to have anti-inflammatory activity and effects on the body’s immune system. Examples: 

• In treating Type 2 diabetes, sulfonamide drugs increase the release of insulin by stimulating the pancreatic beta cells. 
• For treating high blood pressure, sulfonamide drugs act as diuretics and increase the amount of water and salt, or sodium, eliminated from the body by increasing urination frequency and amount. 
• Sulfonamide derivatives act as anti-inflammatory medicines by blocking the hormones in the body responsible for causing pain and inflammation.  
• In HIV patients, sulfonamide drugs act to block protease enzymes and stop the virus from multiplying. 

What are sulfonamides used for?

• Bacterial infections
  • Bactrim (sulfamethoxazole-trimethoprim)
  • Bactrim DS (sulfamethoxazole-trimethoprim double strength)
  • Sulfatrim Pediatric (sulfamethoxazole-trimethoprim)
• Type 2 diabetes
  • Amaryl (glimepiride)
  • Glucotrol (glipizide)
  • Glynase PresTab (glyburide micronized)
  • Tolbutamide
• High blood pressure
  • Acetazolamide 
  • Bumetanide
  • Chlorthalidone
  • Lasix (furosemide)
  • Hydrochlorothiazide
  • Indapamide
  • Metolazone
• Glaucoma
  • Methazolamide
  • Azopt (brinzolamide)
  • Trusopt (dorzolamide HCl)
• Gout
  • Probenecid 
• Inflammatory diseases (e. g., rheumatoid arthritis, Crohn’s disease)
  • Celebrex (celecoxib)
• Human immunodeficiency virus type 1 (HIV-1)
  • Lexiva (fosamprenavir calcium)
• Epilepsy
  • Zonegran (zonisamide)
• Irregular heartbeat
  • Tikosyn (dofetilide)
  • Betapace (sotalol HCl)
• Benign prostatic hyperplasia (BPH)
  • Flomax (tamsulosin HCl)
• Migraine headaches
  • Imitrex (sumatriptan succinate)

Types of sulfonamides

Sulfonamides are divided into one of two general groups: the antibacterial sulfonamides, used to treat infections, and the non-antibacterial sulfonamides that treat a variety of different diseases.

Antibacterial sulfonamides

• Bactrim (sulfamethoxazole/trimethoprim)
• Sulfatrim Pediatric (sulfamethoxazole/trimethoprim)

Non-antibacterial sulfonamides

• Azulfidine (sulfasalazine)
• Amaryl (glimepiride)
• Glucotrol (glipizide)
• Glynase PresTab (glyburide micronized)
• Chlorthalidone
• Lasix (furosemide)
• Hydrochlorothiazide
• Zonegran (zonisamide)
• Lexiva (fosamprenavir calcium)
• Celebrex (celecoxib)
• Tikosyn (dofetilide)
• Betapace (sotalol HCl)
• Flomax (tamsulosin HCl)
• Probenecid 
• Imitrex (sumatriptan succinate)

Who can take sulfonamides?

Adult men and women can take sulfonamides. However, they should also be used with extreme care in patients with liver problems, kidney problems, and certain types of anemia.

Pregnancy and breastfeeding

In general, animal studies have shown that some sulfonamides cause birth defects. Sulfonamides are not recommended for use if you’re pregnant or might become pregnant. Sulfonamides enter into breast milk and therefore they are not recommended for use while breastfeeding. A woman’s healthcare provider is the best source of information when managing sulfonamide treatment before becoming pregnant, during pregnancy, or while breastfeeding.

Children

The most common use for sulfonamides in children is the treatment of infections. Sulfisoxazole, in combination with the antibiotic erythromycin, is commonly used for the treatment and prevention of ear infections and prevention of meningococcal infections. Sulfasalazine is used in children 4 years and older to treat ulcerative colitis and inflammatory bowel disease. Sulfonamides should never be used in infants younger than 2 months old.

Seniors

In general, older adults can take sulfonamides. Older patients may be more sensitive to the adverse effects of sulfonamides, e.g., severe skin and blood problems may be more likely to occur in seniors, especially when complicating conditions exist such as impaired kidney or liver function, or use of other drugs concurrently.

Are sulfonamides safe?

Because all sulfonamides share a common chemical structure, if you have an allergy to one sulfonamide or sulfa drug, you may be allergic to other sulfonamide drugs—even across the two general groups. According to a recent SingleCare survey, 10% of survey respondents with a drug allergy were reportedly allergic to sulfa drugs. Talk to your healthcare professional if you have any type of drug allergy or if you have had a hypersensitivity reaction to any sulfonamide.

Anaphylaxis, or anaphylactic shock, is a severe allergic reaction that may occur if you are hypersensitive to a sulfonamide, or sulfa drug, that requires immediate medical care. Symptoms of an anaphylactic reaction may include:

• Skin rash
• Nausea
• Vomiting
• Difficulty breathing
• Shock

Stevens-Johnson syndrome is a rare but severe form of a sulfonamide allergy that requires immediate medical care. Symptoms may include:

• Flu-like symptoms
• Painful red blisters around the mouth, throat, eyes, or genitals
• Red or purple skin rash
• Peeling skin
• Fatigue
• Diarrhea
• Nausea and vomiting
• Fever

Recalls

• Accord Healthcare Inc. issues voluntary nationwide recall of hydrochlorothiazide tablets USP 12.5 mg due to labeling mix-up, March 2020

Restrictions

You should not take sulfonamide medicines if you are allergic to sulfa drugs. The presence of other medical problems and conditions may affect the use of sulfonamides. You should not use sulfonamides or they should be used cautiously if you have any of the following conditions:

• Porphyria (a group of disorders that result from a buildup of natural chemicals that produce porphyrin in your body)
• Certain types of anemia (e.g., from low blood levels of folic acid or from pyruvate kinase and glucose-6-phosphate dehydrogenase [G6PD] deficiencies) 
• Impaired or decreased liver or kidney function

Drug-drug interactions

Using sulfonamide medicines with any of the following is not recommended: 

• Coumadin (warfarin)
• Toradol (ketorolac)
• Orlaam (levomethadyl)
• Hiprex (methenamine)

This is not a complete list of drugs that may interact with sulfonamides. Talk to your healthcare professional before starting a sulfonamide about any other prescription or over-the-counter medicines you may take.

Are sulfonamides controlled substances?

Sulfonamides are not controlled substances.

Common sulfonamides side effects

The following are potential common side effects when taking sulfonamides. This is not an exhaustive list and you should always talk to your healthcare professional and seek medical advice about what adverse reactions to expect and how to address them.

• Skin rash
• Itching
• Headache
• Dizziness
• Diarrhea
• Tiredness
• Nausea or vomiting
• Pale skin
• Joint pain
• Sensitivity to light

How much do sulfonamides cost?

Sulfonamides have a wide price range depending on the specific drug, quantity, and dosage. Almost all Medicare and insurance plans will cover sulfonamides. Since most sulfonamides are available in generic formulations, they are much less expensive than their brand-name counterpart. A SingleCare discount card could reduce prescription costs up to 80% at participating pharmacies.

Sulfonamide (medicine) – wikidoc

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

There are several sulphonamide-based groups of drugs. The original antibacterial sulfonamides (sometimes called simply sulfa drugs) are synthetic antimicrobial agents that contain the sulfonamide group. Some sulfonamides are also devoid of antibacterial activity, e.g., the anticonvulsant sultiame. The sulfonylureas (main article: sulfonylureas) and thiazide diuretics (main article thiazide) are newer drug groups based on the antibacterial sulfonamides.

Sulfa allergies are common, hence medications containing sulfonamides are prescribed carefully.

Contents

• 1 Function
• 2 History
• 3 Preparation
• 4 List of Sulfonamides
• 5 Side effects
• 6 See also
• 7 External links

Function

In bacteria, antibacterial sulfonamides act as competitive inhibitors of the enzyme dihydropteroate synthetase, DHPS. DHPS catalyses the conversion of PABA (para-aminobenzoate) to dihydropteroate, a key step in folate synthesis. Folate is necessary for the cell to synthesize nucleic acids (nucleic acids are essential building blocks of DNA and RNA), and in its absence cells will be unable to divide. Hence the sulfonamide antibacterials exhibit a bacteriostatic rather than bactericidal effect.

Folate is not synthesized in mammalian cells, but is instead a dietary requirement. This explains the selective toxicity to bacterial cells of these drugs.

History

Sulfonamide drugs (known widely as “sulfa drugs”) were the first antimicrobial drugs, and paved the way for the antibiotic revolution in medicine. The first sulfonamide was trade named Prontosil, which is a prodrug. Experiments with Prontosil began in 1932 in the laboratories of Bayer AG, at that time a component of the huge German chemical trust IG Farben. The dye-based drug was synthesized by Bayer chemist Josef Klarer and tested in animals under the direction of physician/researcher Gerhard Domagk. Domagk quickly won the 1939 Nobel Prize in Medicine and Physiology, an honor that Adolf Hitler forbade him to accept (Hitler was incensed at the awarding of a Nobel Peace Prize a few years earlier to an anti-Nazi activist). Domagk’s prize also caused some bad feeling between him and Klarer. The discovery was in fact a team effort in which Domagk played a central role, operating under the general direction of Heinrich Hoerlein, a Farben executive later tried (and acquitted) at Nuremberg. The first official communication about the breakthrough discovery was not published until 1935, more than two years after the drug was patented by Klarer and his research partner Fritz Mietzsch. Prontosil was the first medicine ever discovered that could effectively treat a range of bacterial infections inside the body. It had a strong protective action against infections caused by streptococci, including blood infections, childbed fever, and erysipelas, and a lesser effect on infections caused by other cocci. Perplexingly, it had no effect at all in the test tube, exerting its antibacterial action only in live animals. Later it was discovered by a French research team at the Pasteur Institute that the drug was metabolized into two pieces inside the body, releasing from the inactive dye portion a smaller, colorless, active compound called sulfanilamide. The discovery helped establish the concept of “bioactivation” and dashed the German corporation’s dreams of enormous profit; the active molecule sulfanilamide (or sulfa) had first been synthesized in 1906 and was widely used in the dye-making industry; its patent had since expired and the drug was available to anyone.

The result was a sulfa craze. For several years in the late 1930s hundreds of manufacturers produced tens of thousands of tons of myriad forms of sulfa. This and nonexistent testing requirements lead to the Elixir Sulfanilamide disaster in the fall of 1937, wherein at least 100 people were poisoned with diethylene glycol. This led to the passage of the Federal Food, Drug, and Cosmetic Act in 1938. As the first and only effective antibiotic available in the years before Penicillin, sulfa drugs continued to thrive through the early years of World War II. They are credited with saving the lives of tens of thousands of patients including Franklin Delano Roosevelt, Jr. (in 1936) and Winston Churchill. Sulfa had a central role in preventing wound infections during the war. American soldiers were issued a first aid kit containing sulfa powder and were told to sprinkle it on any open wound. During the years 1942 to 1943, Nazi doctors conducted sulfanilamide experiments on prisoners in concentration camps.

The sulfanilamide compound is more active in the protonated form, which in case of the acid works better in a basic environment. The solubility of the drug is very low and sometimes can crystalize in the kidneys, due to its first pK_a of around 10. This is a very painful experience so patients are told to take the medication with copious amounts of water. Newer compounds have a pK_a of around 5-6 so the problem is avoided.

Many thousands of molecules containing the sulfanilamide structure have been created since its discovery (by one account, over 5400 permutations by 1945), yielding improved formulations with greater effectiveness and less toxicity. Sulfa drugs are still widely used for conditions such as acne and urinary tract infections, and are receiving renewed interest for the treatment of infections caused by bacteria resistant to other antibiotics.

Sulpha is an alternate (British English) spelling of the common name for sulfonamide antibiotics.

Preparation

Sulfonamides are prepared by the reaction of a sulfonyl chloride with ammonia or an amine.
Certain sulfonamides (sulfadiazine or sulfamethoxazole) are sometimes mixed with the drug trimethoprim, which acts against dihydrofolate reductase.
Also known as Sulfa Powder. Used largely in WWII to treat any wound.

List of Sulfonamides

• Benzolamide
• Bumetanide
• Celecoxib
• Chlorthalidone
• Clopamide
• Dichlophenamide
• Ethoxzolamide
• Indapamide
• Mafenide
• Mefruside
• Metolazone
• Probenecid
• Sulfacetamide
• Sulfanilamides
• Sulfamethoxazole
• Sulfasalazine
• Sultiame
• Sumatriptan
• Xipamide

Side effects

Sulfonamides have the potential to cause a variety of untoward reactions, including urinary tract disorders, haemopoietic disorders, porphyria and hypersensitivity reactions. When used in large dose, it may develop a strong allergic reaction. One of the most serious is Stevens Johnson syndrome (or toxic epidermal necrolysis). Some of the original sulfonamide drugs were derived from azo dyes and had the interesting effect of temporarily turning the patient red.

See also

• Antibiotic
• Timeline of antibiotics
• Sulfa drug
• Elixir Sulfanilamide

External links

• http://www.nlm.nih.gov/cgi/mesh/2004/MB_cgi?field=entry&term=Sulfonamides – List of sulfonamides
• http://www.thomashager.net – author of “The Demon under the Microscope,” a history of the discovery of the sulfa drugs
• http://www.lung.ca/tb/tbhistory/treatment/chemo.html – A History of the Fight Against Tuberculosis in Canada (Chemotherapy)
• http://www.nobel.se/medicine/laureates/1939/press.html – Presentation speech, Nobel Prize in Physiology and Medicine, 1939
• http://home.att.net/~steinert/wwii.htm – The History of WW II Medicine
• http://www. life.umd.edu/classroom/bsci424/Chemotherapy/AntibioticsHistory.htm – A history of antibiotics

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Sulfanilamide – description of the substance, pharmacology, use, contraindications, formula

Contents

• Structural formula

• Russian name

• English name

• Latin name

• chemical name

• Gross formula

• Pharmacological group of the substance Sulfanilamide

• Nosological classification

• CAS code

• pharmachologic effect

• Characteristic

• Pharmacology

• Application of the substance Sulfanilamide

• Contraindications

• Application restrictions

• Use during pregnancy and lactation

• Side effects of the substance Sulfanilamide

• Interaction

• Dosage and administration

• Precautionary measures

• Trade names with the active substance Sulfanilamide

Structural formula

Russian name

Sulfanilamide

English name

Sulfanilamide

Latin name

genus Sulfanilamidi)

Chemical name

4-Aminobenzenesulfonamide

General formula

C ₆ H ₈ N ₂ O ₂ S

Pharmacological group of the substance Sulfanilamide

Sulfonamides

Nosological classification

ICD-10 code list

CAS code

63-74-1

Pharmacological action

Pharmacological action 90 097-

antimicrobial .

Description

Refers to short-acting sulfa drugs. Sulfanilamide is a white, odorless, crystalline powder with a slightly bitter taste and a sweet aftertaste. Easily soluble in boiling water (1:2), difficult – in ethanol (1:37), soluble in solutions of hydrochloric acid, caustic alkalis, acetone (1:5), glycerin, propylene glycol; practically insoluble in ether, chloroform, benzene, petroleum ether. Molecular weight – 172.21.

Also used as sodium methane sulfate (Streptocide soluble) – white crystalline powder; soluble in water, practically insoluble in organic solvents.

Pharmacology

The mechanism of antimicrobial action of sulfanilamide is associated with the antagonism of PABA, with which it has a chemical similarity. Sulfanilamide is captured by the microbial cell, prevents the incorporation of PABA into dihydrofolic acid and, in addition, competitively inhibits the bacterial enzyme dihydropteroate synthetase (the enzyme responsible for the incorporation of PABA into dihydrofolic acid), as a result, the synthesis of dihydrofolic acid is disrupted, and the formation of metabolically active tetrahydrofolic acid from it, which is necessary for the formation of purines and pyrimidines, stops the growth and development of microorganisms (bacteriostatic effect).

Active against gram-positive and gram-negative cocci (including streptococci, pneumococci, meningococci, gonococci), Escherichia coli, Shigella spp. Chlamydia spp. , Actinomyces israelii, Toxoplasma gondii.

When applied topically, promotes rapid wound healing.

When taken orally, it is rapidly absorbed from the gastrointestinal tract. max”>C _max in the blood is created after 1–2 hours and decreases by 50%, usually in less than 8 hours. It passes through the histohematic, including the BBB, placental barriers. It is distributed in tissues, after 4 hours it is found in the cerebrospinal fluid. It is acetylated in the liver with loss of antibacterial properties. It is excreted mainly (90-95%) by the kidneys.

There is no information on carcinogenicity, mutagenicity and effects on fertility with long-term use in animals and humans.

Sulfanilamide used to be used orally to treat angina, erysipelas, cystitis, pyelitis, enterocolitis, prevention and treatment of wound infection. Sulfanilamide (Streptocid soluble) has been used in the past as 5% aqueous solutions for intravenous administration, which were prepared ex tempore ; currently used only in the form of liniment for external use.

Application of Sulfanilamide Sulfanilamide Sulfanilamide

local : tonsillitis, purulent-inflammatory lesions of the skin, infected wounds of various etiologies (including ulcers, cracks), furunculus, carbuncle, pyoderma, erysipelas, vulgar acne, impetigo, burns (I and II degrees).

Contraindications

Hypersensitivity (including to other sulfonamides and sulfonamides), diseases of the hematopoietic system, anemia, renal / hepatic insufficiency, congenital deficiency of glucose-6-phosphate dehydrogenase, azotemia, porphyria.

Restrictions for use

Pregnancy, lactation.

Use in pregnancy and lactation

Systemically absorbed sulfanilamide can rapidly cross the placenta and be detected in the blood of the fetus (the concentration in the blood of the fetus is 50-90% of that in the mother’s blood), as well as cause toxic effects. The safety of sulfanilamide during pregnancy has not been established. It is not known whether sulfonamide can cause fetal harm when taken by pregnant women. In experimental studies in rats and mice treated during pregnancy with certain short, intermediate and long-acting sulfonamides (including sulfanilamide) orally at high doses (7-25 times the therapeutic oral dose for humans), a significant increase in the incidence of cleft palate and other fetal bone malformations.

Passes into breast milk, may cause kernicterus in neonates.

Adverse effects of the substance Sulfanilamide

Allergic reactions; with prolonged local use in large quantities – a systemic effect: headache, dizziness, paresthesia, tachycardia, nausea, vomiting, dyspepsia, leukopenia, agranulocytosis, crystalluria, cyanosis.

Interaction

Myelotoxic drugs increase hematotoxicity.

Dosage and administration

Local . With superficial infectious diseases of the skin and mucous membranes of the nasal cavity and ear, with burns, ulcers, etc. used in the form of 10% ointment, 5% liniment or powder. Liniment or ointment is applied directly to the affected surface or smeared on a gauze; dressings are made in 1-2 days. For deep wounds, sulfanilamide is introduced into the wound cavity in the form of a carefully ground sterilized powder (5–10–15 g), while sulfanilamide or other antibacterial drugs are administered orally. In a mixture with sulfathiazole, benzylpenicillin and ephedrine, it is sometimes used topically (for acute rhinitis) in powder form (by blowing or drawing it into the nose when inhaling).

Precautions

Periodic peripheral blood testing is necessary for long-term use.

Trade names with active ingredient Sulfanilamide

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Lek. form
All lek. forms liniment ointment for local and external use ointment for external use powder for external use substance substance-powder

Dosage
All dosages 10 g 10% 15 g 2 g 25 g 5 g 5% No dosage

Manufacturer
All manufacturers Avexima Siberia LLC Aromasintez LLC BioPharmCombinat LLC Biosintez OJSC Biosintez PJSC Zelenaya Dubrava CJSC Ivanovskaya Pharmaceutical Factory Irbit Chemical and Pharmaceutical Plant OJSC Lekar Lumi LLC [St. Petersburg] Meligen FP CJSC Moscow Pharmaceutical Factory NIZHFARM OAO Ozone LLC Samaramedprom Tver Pharmaceutical Factory OJSC Technopark -Center LLC Tula Pharmaceutical Factory LLC Tyumen Chemical-Pharmaceutical Plant Usolye-Sibirsky CPP JSC Usolye-Sibirsky CPP JSC Flora of the Caucasus JSC Flora of the Caucasus JSC Hubei Maxpharm Industries Co. Zhejiang Kemsen Pharm Co., Ltd. Empils-Foch JSC YuzhFarm LLC Yaroslavl Pharmaceutical Factory (ZAO YAFF)

Diabetes mellitus and coronary heart disease: the mystery of sulfonamides | Aleksandrov

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