What are sulfonamides. How do sulfonamides work. What are the common uses of sulfonamides. What are the side effects of sulfonamides. Who should avoid taking sulfonamides. How are sulfonamides administered. What is the mechanism of action for sulfonamides.

Understanding Sulfonamides: A Synthetic Antibiotic Class

Sulfonamides are a class of synthetic bacteriostatic antibiotics that play a crucial role in treating various bacterial infections. These drugs work by competitively inhibiting the conversion of p-aminobenzoic acid to dihydropteroate, a process essential for bacterial folate synthesis. This mechanism ultimately disrupts purine and DNA synthesis in bacteria, effectively halting their growth and reproduction.

What makes sulfonamides particularly effective against bacteria while being relatively safe for humans? The answer lies in the fundamental difference between bacterial and human folate metabolism. Bacteria synthesize their own folate, making them vulnerable to sulfonamide action. In contrast, humans obtain folate from their diet, which means our DNA synthesis is less affected by these antibiotics.

Common Sulfonamide Drugs

• Mafenide
• Sulfacetamide
• Sulfadiazine
• Sulfadoxine
• Sulfamethizole
• Sulfamethoxazole
• Sulfanilamide
• Sulfasalazine
• Sulfisoxazole

Formulations and Administration Routes of Sulfonamides

Sulfonamides are available in various formulations to suit different medical needs. How are these drugs typically administered? Let’s explore the common routes of administration and available formulations:

Oral Formulations

Three sulfonamides are available as single drugs for oral use:

1. Sulfisoxazole
2. Sulfamethizole
3. Sulfasalazine

Additionally, sulfamethoxazole is often coformulated with trimethoprim, known as TMP/SMX, which enhances its antibacterial effects. Another combination drug, sulfadoxine with pyrimethamine, is also available for oral administration.

Topical Formulations

Several sulfonamides are formulated for topical use, including:

• Silver sulfadiazine (burn cream)
• Mafenide (burn cream)
• Sulfanilamide (vaginal cream and suppositories)
• Sulfacetamide (ophthalmic solution)

Pharmacokinetics and Distribution of Sulfonamides

Understanding how sulfonamides behave in the body is crucial for their effective use. What are the key pharmacokinetic properties of these drugs?

Sulfonamides are generally well-absorbed when taken orally. They can also be absorbed through the skin when applied topically, particularly in burn treatments. Once in the bloodstream, these drugs are distributed throughout the body, reaching various tissues and organs.

The metabolism of sulfonamides primarily occurs in the liver, where they undergo various chemical transformations. The kidneys are responsible for excreting the metabolized drug from the body. It’s worth noting that sulfonamides compete with bilirubin for binding sites on albumin, which can have implications for patients with certain liver conditions or newborns.

Antimicrobial Spectrum and Clinical Applications

Sulfonamides exhibit a broad spectrum of antimicrobial activity, making them valuable in treating various infections. What types of microorganisms are susceptible to sulfonamides?

• A wide range of gram-positive bacteria
• Many gram-negative bacteria
• Plasmodium species (malaria parasites)
• Toxoplasma species

Given their broad antimicrobial activity, sulfonamides find use in treating numerous clinical conditions. What are some common applications of these drugs?

1. Urinary tract infections
2. Nocardiosis
3. Chloroquine-resistant falciparum malaria
4. Inflammatory bowel disease (specifically sulfasalazine)
5. Burn treatments (topical formulations)
6. Vaginitis (topical formulations)
7. Superficial ocular infections (ophthalmic formulations)

Resistance Patterns and Combination Therapies

As with many antibiotics, bacterial resistance to sulfonamides is a growing concern. How widespread is sulfonamide resistance, and what implications does this have for treatment?

Sulfonamide resistance is unfortunately widespread among many bacterial species. An important characteristic of this resistance is that it typically applies to all sulfonamides. In other words, if a bacterium is resistant to one sulfonamide, it is likely to be resistant to all drugs in this class.

To combat resistance and enhance efficacy, sulfonamides are often used in combination with other antimicrobial agents. A prime example is the combination of sulfamethoxazole with trimethoprim (TMP/SMX), which targets two different steps in the bacterial folate synthesis pathway, making it more effective than either drug alone.

Contraindications and Precautions

While sulfonamides are effective antimicrobial agents, they are not suitable for all patients. Who should avoid taking sulfonamides?

• Patients with a history of allergic reactions to sulfonamides
• Individuals with porphyria
• Patients with group A streptococcal pharyngitis (sulfonamides do not eradicate the bacteria in this case)

It’s important to note that sulfonamides should be used with caution in certain populations. Pregnant women, for instance, require careful consideration before being prescribed these drugs. The evidence regarding an association between sulfonamides and birth defects is mixed, necessitating a careful risk-benefit analysis for use during pregnancy.

Side Effects and Adverse Reactions

Like all medications, sulfonamides can cause side effects. What are some common adverse reactions associated with sulfonamide use?

• Gastrointestinal disturbances (nausea, vomiting, diarrhea)
• Skin rashes and photosensitivity reactions
• Hematological effects (rare but serious, including agranulocytosis and aplastic anemia)
• Hepatotoxicity (liver damage)
• Renal complications (crystalluria, particularly with older sulfonamides)
• Allergic reactions (ranging from mild to severe, including Stevens-Johnson syndrome)

It’s crucial for healthcare providers to monitor patients closely for these potential side effects, especially during the initial stages of treatment. Patients should be educated about possible adverse reactions and instructed to report any unusual symptoms promptly.

Special Considerations for Newborns

Sulfonamides require special consideration when used in newborns. Why is this the case? The competition between sulfonamides and bilirubin for albumin binding sites can be particularly problematic in newborns. This interaction can potentially lead to kernicterus, a serious condition caused by bilirubin toxicity in the brain. As a result, sulfonamides are generally avoided in neonates, especially those with jaundice or at risk for hyperbilirubinemia.

Future Perspectives and Research Directions

Despite the challenges of bacterial resistance, sulfonamides continue to be an important class of antibiotics. What are some current areas of research and future perspectives for sulfonamide use?

1. Development of new sulfonamide derivatives with enhanced activity against resistant strains
2. Investigation of novel combination therapies to overcome resistance mechanisms
3. Exploration of non-antimicrobial applications, such as the use of certain sulfonamides as carbonic anhydrase inhibitors in glaucoma treatment
4. Research into the potential anti-inflammatory and immunomodulatory effects of some sulfonamides
5. Studies on the long-term ecological impact of sulfonamide use in human and veterinary medicine

As our understanding of bacterial resistance mechanisms grows and new technologies emerge, the role of sulfonamides in medical treatment may evolve. Ongoing research aims to maximize the benefits of these drugs while minimizing their drawbacks, ensuring their continued relevance in the fight against infectious diseases.

Sulfonamides in Veterinary Medicine

While our focus has been on human medicine, it’s worth noting that sulfonamides also play a significant role in veterinary practice. How are these drugs used in animal health, and what are the implications for human medicine?

In veterinary medicine, sulfonamides are widely used to treat various bacterial infections in livestock, companion animals, and aquaculture. Common applications include:

• Treatment of respiratory infections in cattle and swine
• Management of coccidiosis in poultry
• Control of urinary tract infections in dogs and cats
• Treatment of certain fish diseases in aquaculture

The extensive use of sulfonamides in veterinary medicine raises concerns about the development and spread of antibiotic-resistant bacteria. This issue highlights the importance of the One Health approach, which recognizes the interconnectedness of human, animal, and environmental health. Responsible use of sulfonamides in both human and veterinary medicine is crucial to preserve their efficacy and minimize the risk of resistance.

Regulatory Considerations

Given the potential for residues in food-producing animals, what measures are in place to ensure food safety? Regulatory agencies worldwide have established maximum residue limits (MRLs) for sulfonamides in animal products intended for human consumption. These regulations aim to protect consumers from potential health risks associated with antibiotic residues while allowing for the necessary use of these drugs in animal husbandry.

Compliance with withdrawal periods – the time required between the last dose of the drug and slaughter or milk production – is crucial to ensure that residue levels are below the established MRLs. Ongoing monitoring and surveillance programs help enforce these regulations and maintain public confidence in food safety.

Environmental Impact of Sulfonamides

As we consider the broader implications of sulfonamide use, it’s important to address their environmental impact. How do these drugs affect ecosystems, and what measures can be taken to mitigate any negative effects?

Sulfonamides, like many pharmaceuticals, can enter the environment through various routes, including:

• Excretion by humans and animals
• Improper disposal of unused medications
• Wastewater from pharmaceutical manufacturing facilities
• Runoff from agricultural areas where they are used in livestock

Once in the environment, sulfonamides can persist for varying periods, potentially affecting soil and aquatic ecosystems. What are some potential ecological consequences of environmental sulfonamide contamination?

1. Development of antibiotic-resistant bacteria in the environment
2. Disruption of microbial communities in soil and water, which play crucial roles in nutrient cycling
3. Potential toxic effects on non-target organisms, including plants and aquatic life
4. Bioaccumulation in the food chain, potentially affecting higher-level organisms

To address these concerns, various strategies are being explored and implemented:

• Advanced wastewater treatment technologies to remove pharmaceutical residues
• Proper disposal programs for unused medications
• Development of more readily biodegradable sulfonamide derivatives
• Implementation of best practices in agriculture to minimize environmental contamination
• Continued research into the long-term ecological effects of sulfonamides and other pharmaceuticals

By considering the environmental impact of sulfonamides, we can work towards more sustainable use of these important antibiotics, balancing their critical role in human and animal health with the need to protect our ecosystems.

Sulfonamides – Infectious Diseases – Merck Manuals Professional Edition

By

Brian J. Werth

, PharmD, University of Washington School of Pharmacy

Reviewed/Revised May 2022 | Modified Sep 2022

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Topic Resources

Sulfonamides are synthetic bacteriostatic antibiotics Overview of Antibacterial Drugs Antibacterial drugs are derived from bacteria or molds or are synthesized de novo. Technically, “antibiotic” refers only to antimicrobials derived from bacteria or molds but is often (including… read more that competitively inhibit conversion of p-aminobenzoic acid to dihydropteroate, which bacteria need for folate synthesis and ultimately purine and DNA synthesis. Humans do not synthesize folate but acquire it in their diet, so their DNA synthesis is less affected.

Sulfonamides include the following:

• Mafenide

• Sulfacetamide

• Sulfadiazine

• Sulfadoxine

• Sulfamethizole

• Sulfamethoxazole

• Sulfanilamide

• Sulfasalazine

• Sulfisoxazole

Three sulfonamides, sulfisoxazole, sulfamethizole, and sulfasalazine, are available as single drugs for oral use. Sulfamethoxazole is coformulated with trimethoprim (as TMP/SMX Trimethoprim and Sulfamethoxazole Trimethoprim is available as a single drug or in combination with sulfamethoxazole (a sulfonamide antibiotic). The drugs act synergistically to block sequential steps in bacterial folate metabolism… read more ). Sulfadoxine combined with pyrimethamine is available for oral use.

Sulfonamides available for topical use include silver sulfadiazine and mafenide burn cream, sulfanilamide vaginal cream and suppositories, and sulfacetamide ophthalmic.

Sulfonamide resistance is widespread, and resistance to one sulfonamide indicates resistance to all.

Most sulfonamides are readily absorbed orally and, when applied to burns, topically. Sulfonamides are distributed throughout the body. They are metabolized mainly by the liver and excreted by the kidneys. Sulfonamides compete for bilirubin-binding sites on albumin.

Sulfonamides are active against

• A broad spectrum of gram-positive and many gram-negative bacteria

• Plasmodium Malaria Malaria is infection with Plasmodium species. Symptoms and signs include fever (which may be periodic), chills, rigors, sweating, diarrhea, abdominal pain, respiratory distress, confusion… read more and Toxoplasma Toxoplasmosis Toxoplasmosis is infection with Toxoplasma gondii. Symptoms range from none to benign lymphadenopathy, a mononucleosis-like illness, to life-threatening central nervous system (CNS) disease. .. read more species

Sulfasalazine can be used orally for inflammatory bowel disease Irritable Bowel Syndrome (IBS) Irritable bowel syndrome is characterized by recurrent abdominal discomfort or pain with at least two of the following characteristics: relation to defecation, association with a change in frequency… read more .

Sulfonamides are most commonly used with other drugs (eg, for nocardiosis Nocardiosis Nocardiosis is an acute or chronic, often disseminated, suppurative or granulomatous infection caused by various aerobic soil saprophytes of the gram-positive bacilli genus Nocardia…. read more , urinary tract infection Bacterial Urinary Tract Infections Bacterial urinary tract infections (UTIs) can involve the urethra, prostate, bladder, or kidneys. Symptoms may be absent or include urinary frequency, urgency, dysuria, lower abdominal pain… read more , and chloroquine-resistant falciparum malaria Treatment of Malaria in the United States ).

Topical sulfonamides can be used to treat the following:

• Burns Burns Burns are injuries of skin or other tissue caused by thermal, radiation, chemical, or electrical contact. Burns are classified by depth (superficial and deep partial-thickness, and full-thickness)… read more : Silver sulfadiazine and mafenide acetate

• Vaginitis Overview of Vaginitis Vaginitis is infectious or noninfectious inflammation of the vaginal mucosa, sometimes with inflammation of the vulva. Symptoms include vaginal discharge, irritation, pruritus, and erythema… read more : Vaginal cream and suppositories with sulfanilamide

• Superficial ocular infections: Ophthalmic sulfacetamide

Sulfonamides are contraindicated in patients who have had an allergic reaction to them or who have porphyria.

Sulfonamides do not eradicate group A streptococci in patients with pharyngitis and should not be used to treat group A streptococcal pharyngitis.

Evidence regarding an association between sulfonamides and birth defects is mixed. Animal studies with sulfonamides show some risk, and adequate studies have not been done in pregnant women.

Use near term and in breastfeeding mothers is contraindicated, as is use in patients kernicterus Kernicterus Kernicterus is brain damage caused by unconjugated bilirubin deposition in basal ganglia and brain stem nuclei. Normally, bilirubin bound to serum albumin stays in the intravascular space. However… read more in the fetus or neonate.

Sulfonamides enter breast milk.

Adverse effects of sulfonamides can result from oral and sometimes topical sulfonamides; effects include

• Hypersensitivity reactions, such as rashes, Stevens-Johnson syndrome Stevens-Johnson Syndrome (SJS) and Toxic Epidermal Necrolysis (TEN) Stevens-Johnson syndrome and toxic epidermal necrolysis are severe cutaneous hypersensitivity reactions. Drugs, especially sulfa drugs, antiseizure drugs, and antibiotics, are the most common… read more , vasculitis, serum sickness, drug fever, anaphylaxis, and angioedema

• Crystalluria, oliguria, and anuria

• Hematologic reactions, such as agranulocytosis, thrombocytopenia, and, in patients with glucose-6-phosphate dehydrogenase (G6PD) deficiency Glucose-6-Phosphate Dehydrogenase (G6PD) Deficiency Glucose-6-phosphate dehydrogenase (G6PD) deficiency is an X-linked enzymatic defect common in people with African ancestry that can result in hemolysis after acute illnesses or intake of oxidant… read more , hemolytic anemia

• Kernicterus in neonates

• Photosensitivity

• Neurologic effects, such as insomnia, and headache

Hypothyroidism, hepatitis, and activation of quiescent systemic lupus erythematosus may occur in patients taking sulfonamides. These drugs can exacerbate porphyrias.

Incidence of adverse effects is different for the various sulfonamides, but cross-sensitivity is common.

Sulfasalazine can reduce intestinal absorption of folate (folic acid). Thus, use of this drug may trigger folate deficiency in patients with inflammatory bowel disease, which also reduces absorption, especially if dietary intake is also inadequate.

Mafenide may cause metabolic acidosis by inhibiting carbonic anhydrase.

To avoid crystalluria, clinicians should hydrate patients well (eg, to produce a urinary output of 1200 to 1500 mL/day). Sulfonamides can be used in patients with renal insufficiency, but peak plasma levels should be measured and sulfamethoxazole levels should not exceed 120 mcg/mL.

Sulfonamides can potentiate sulfonylureas (with consequent hypoglycemia), phenytoin (with increased adverse effects), and coumarin anticoagulants.

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Sulfonamides: Types, Usage, Side Effects & More

Sulfonamides were the first antibiotics discovered and used, and have been used by doctors since the 1930s.

Also referred to as sulfa drugs, sulfonamides are man-made antibiotics that are used to treat bacterial infections.

If you are struggling with a UTI, bronchitis, pneumonia, or have an eye or ear infection that requires an antibiotic, your health care provider may prescribe you sulfonamides. 

In this article, I’ll explain what sulfonamides are, how they work, and what conditions they’re used to treat.

I’ll list some common sulfa drugs, and talk about their side effects and dosage.

I’ll also provide some precautions about these antibiotics, and tell you when you should talk to a doctor.

What are Sulfonamides?

Sulfonamides are a class of broad-spectrum antibiotics, meaning they work against a wide range of bacteria. 

How do Sulfonamides Work?

Sulfonamides, or sulfa drugs, are a class of broad-spectrum antibiotics that act on a wide range of gram-positive and gram-negative bacteria.

Sulfa drugs do not kill bacteria, but instead work by inhibiting the bacteria from growing and multiplying, thus stopping the infection.

They do this by stopping bacteria from making folic acid, which is necessary for their growth.

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What are Sulfonamides Used to Treat?

Sulfonamides have been around since the 1930s and were some of the first effective antibiotics to be introduced into clinical medicine.

Unfortunately, bacterial resistance to sulfonamides is now common, making them less effective against the most common bacteria.

Urinary tract infections

If you have a urinary tract infection (UTI) that is known to be susceptible to sulfonamides, you may be prescribed these antibiotics by your doctor.

UTIs occur when bacteria from the skin or rectum enter the urethra and infect the urinary tract.

A UTI can infect any part of the urinary system, including your kidneys, bladder, or urethra 

Bronchitis

Bronchitis is an infection of the lungs that causes the lining of your bronchial tubes to become inflamed.

While most cases of bronchitis are caused by a virus, it can sometimes also be caused by bacteria.

If you have persistent bronchitis, or other symptoms that lead your healthcare provider to suspect that it may be due to a bacterial infection, they may prescribe you antibacterial agents such as sulfonamides.

Eye infections

If you have a bacterial eye infection such as conjunctivitis, your doctor may prescribe you sulfonamides to treat it.

For eye infections, antibiotics are typically prescribed in the form of eye drops or ointment.

Bacterial meningitis 

Meningitis is a severe brain infection that can be viral or bacterial.

When it is caused by a bacteria called Listeria monocytogenes and the patient has an allergy to penicillin, sulfa drugs may be prescribed to treat meningitis. 

Pneumonia

If you are diagnosed with pneumonia, this means the air sacs of one or both lungs have become inflamed and may also be full of liquid or pus, making it difficult to breathe.

Pneumonia is caused by bacteria, fungi, viruses, or chemical irritants.

When pneumonia is caused by a bacterial infection, your doctor may prescribe sulfonamide antibiotics to treat it.

Ear infections

Sulfonamides are used to treat bacterial ear infections, especially in children.

The medication is usually a combination of erythromycin and sulfafurazole, and has been proven to be highly effective, with significant improvement within a few days.

Burns

If you have an extensive second or third-degree burn, you may contract a bacterial infection.

Sulfa drugs can help treat these infections and may sometimes be used prophylactically, especially when applied in the form of a cream to the affected skin.

Common Sulfonamides

Gantrisin 

Gantrisin (acetyl sulfisoxazole pediatric suspension) (sulfisoxazole) is an antibacterial sulfonamide used to treat bladder infections, ear infections, and meningitis.

It is available in liquid form, which is especially useful for pediatric patients.

It is also available as an eye drop or ophthalmic ointment.

Sulfadiazine

Sulfadiazine is usually prescribed in tablet form.

It is used to treat infections including urinary tract infections, ear infections and parasitic infections such as toxoplasmosis.

It can also help prevent rheumatic fever and meningitis.

Bactrim or Septra

Bactrim or Septra are two antibiotics (sulfamethoxazole and trimethoprim) that are usually prescribed together to treat common infections, including urinary tract infections and skin infections. 

Azulfidine

Sulfasalazine delayed-release (Azulfidine EN-tabs) is used to treat a specific type of bowel disease called ulcerative colitis.

It can also be used for rheumatoid arthritis in adults and children when other medications have not worked effectively.

Sulfasalazine is an anti-inflammatory drug that works by reducing inflammation in the body.

Zonegran

Zonegran is primarily used as an epilepsy medication.

It is used to prevent and control seizures in adults in conjunction with other medicines. 

Side Effects of Sulfonamides

Sulfonamides may cause you to have adverse reactions that require medical attention.

Common side effects you may experience from taking sulfonamides include:

• Lethargy
• Diarrhea
• Nausea 
• Vomiting
• Dizziness
• Headache
• Itchiness or skin rash
• Photosensitivity 

Less common side effects you might experience include:

• Aching muscles and joints
• Trouble swallowing
• Sore throat 
• Fever
• Unusual bleeding or bruising
• Yellow eyes or skin
• Pale skin

In rare circumstances, you may experience any of the following:

• Abdominal or stomach cramps, pain, or tenderness 
• Blood in urine
• Diarrhea that is watery or bloody
• Changes in urination: urinating a lot, or not at all
• Pain or burning when urinating
• Dehydration
• Mood changes
• Lower back pain
• Swelling of the front part of the neck

Always check with your healthcare professional if you have any of the above symptoms.

If you suspect you are having a serious allergic reaction or have overdosed, stop taking the medication immediately and call 9-1-1.

You can also report your symptoms to the FDA at 1-800-FDA-1088.

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Sulfonamides Precautions

Before taking sulfonamides, tell your doctor about all medical conditions you have, especially if you have any liver, kidney, or blood disorders.

Mention all prescription and non-prescription drugs that you are taking, including all herbal, nutritional, or dietary supplements.

Sulfa drugs should not be given to infants younger than two months old.

Tell your doctor if you are pregnant, planning on becoming pregnant, or are breastfeeding, as the drug can be passed through breast milk.

Sulfa drugs can cause a serious, even life-threatening, skin rash and make your skin extremely sensitive to the sun.

Avoid unnecessary sun exposure, and inform your healthcare provider immediately if you notice a rash or other unusual skin changes.

Always read all of the information on the prescription label and only take the medication as directed by your doctor or pharmacist.

Your dosage may change as your doctor monitors your body’s response to the medicine.

If you feel dizzy or nauseous, avoid driving or operating heavy machinery. 

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Frequently Asked Questions

What are examples of sulfonamides?

Sulfonamides include Gantrisin, Sulfadiazine, Bactrim or Septra, Azulfidine, and Zonegran.

Which drugs are sulfa drugs?

Sulfa drugs are broad-spectrum antibiotics that are used to treat a wide variety of bacterial infections. Sulfa drugs include Gantrisin, Sulfadiazine, Bactrim or Septra, Azulfidine, and Zonegran.

What are sulfonamides used for?

Sulfonamides inhibit the growth of harmful bacteria in the body. They are used to treat a variety of infections, including urinary tract infections, skin infections, lung infections, and other bacterial and parasitic infections.

What is the mechanism of action of sulfonamide?

Sulfonamides work by preventing bacteria from making folic acid, preventing their growth and reproduction.

K Health articles are all written and reviewed by MDs, PhDs, NPs, or PharmDs and are for informational purposes only. This information does not constitute and should not be relied on for professional medical advice. Always talk to your doctor about the risks and benefits of any treatment.

K Health has strict sourcing guidelines and relies on peer-reviewed studies, academic research institutions,
and medical associations. We avoid using tertiary references.

• How Sulfa Drugs Work. (2012).
  https://www.nih.gov/news-events/nih-research-matters/how-sulfa-drugs-work

• Sulfonamides. (2017).
  https://pubmed.ncbi.nlm.nih.gov/31643703/

• Sulfonamides. (2017).
  https://www.ncbi.nlm.nih.gov/books/NBK548382/

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 oral sulfonamides (including sulfanilamide) 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

Reset filters

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)

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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 oral sulfonamides (including sulfanilamide) 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

Reset filters

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.