What are sulfonamides. How do sulfonamides work. What are the common side effects of sulfonamides. Who should avoid taking sulfonamides. How are sulfonamides administered. What infections can sulfonamides treat. Are there any drug interactions with sulfonamides.

The Basics of 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 inhibiting the bacterial synthesis of folate, an essential component for DNA production. Unlike bacteria, humans obtain folate from their diet, which makes sulfonamides an effective and relatively safe treatment option for many infections.

Some common sulfonamides include:

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

Mechanism of Action: How Sulfonamides Combat Bacterial Growth

Sulfonamides work by competitively inhibiting the conversion of p-aminobenzoic acid to dihydropteroate, a crucial step in bacterial folate synthesis. This inhibition ultimately disrupts the bacteria’s ability to produce purines and DNA, effectively halting their growth and reproduction.

Why are sulfonamides effective against bacteria but not harmful to human cells? Human cells do not synthesize folate internally but instead acquire it through dietary sources. This fundamental difference in folate metabolism between bacteria and humans is what makes sulfonamides a valuable antibiotic class with relatively low toxicity to human cells.

Available Formulations and Routes of Administration

Sulfonamides are available in various formulations to treat different types of infections:

1. Oral medications: Sulfisoxazole, sulfamethizole, and sulfasalazine are available as single-drug oral formulations.
2. Combination drugs: Sulfamethoxazole is often combined with trimethoprim (TMP/SMX) for enhanced efficacy.
3. Topical preparations: Silver sulfadiazine and mafenide are used in burn creams, while sulfanilamide is available in vaginal creams and suppositories.
4. Ophthalmic solutions: Sulfacetamide is used for treating eye infections.

How are sulfonamides absorbed and distributed in the body? Most sulfonamides are readily absorbed when taken orally. They can also be absorbed through the skin when applied topically, especially on burn wounds. Once in the bloodstream, sulfonamides are distributed throughout the body, metabolized primarily by the liver, and excreted by the kidneys.

Spectrum of Activity: What Infections Can Sulfonamides Treat?

Sulfonamides demonstrate efficacy against a wide range of pathogens, including:

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

In addition to their antimicrobial properties, some sulfonamides have other therapeutic uses. For instance, sulfasalazine is used orally to treat inflammatory bowel disease.

Are sulfonamides typically used alone or in combination with other drugs? Sulfonamides are often used in combination with other medications to enhance their effectiveness and prevent the development of resistance. Common combinations include:

• Trimethoprim-sulfamethoxazole (TMP/SMX) for urinary tract infections and other bacterial infections
• Sulfadoxine with pyrimethamine for chloroquine-resistant falciparum malaria
• Combination therapies for nocardiosis

Topical Applications: Treating Surface Infections

Sulfonamides are not limited to systemic use. They also play a crucial role in treating various surface infections:

Burns

Silver sulfadiazine and mafenide acetate are commonly used in burn creams to prevent and treat infections in burn wounds. These topical preparations help reduce the risk of bacterial colonization and promote healing.

Vaginitis

Sulfanilamide is available in vaginal creams and suppositories to treat certain types of vaginal infections. These formulations provide localized treatment and can be effective against susceptible pathogens.

Ocular Infections

Ophthalmic sulfacetamide solutions are used to treat superficial eye infections. These preparations are specially formulated for ocular use and can help combat bacterial conjunctivitis and other eye-related infections.

Contraindications and Precautions: When to Avoid Sulfonamides

While sulfonamides are generally safe and effective, there are certain situations where their use is contraindicated:

• Allergic reactions: Patients who have had a previous allergic reaction to sulfonamides should avoid these drugs.
• Porphyria: Sulfonamides are contraindicated in patients with porphyria, a group of rare inherited blood disorders.
• Pregnancy: The evidence regarding the association between sulfonamides and birth defects is mixed. Caution is advised when considering sulfonamide use during pregnancy.
• Streptococcal pharyngitis: Sulfonamides do not effectively eradicate group A streptococci in pharyngitis cases and should not be used for this purpose.

What precautions should be taken when using sulfonamides? Healthcare providers should carefully consider the patient’s medical history, current medications, and potential risk factors before prescribing sulfonamides. Monitoring for adverse reactions and adjusting dosages in patients with impaired kidney or liver function may be necessary.

Potential Side Effects and Adverse Reactions

Like all medications, sulfonamides can cause side effects. Some common adverse reactions include:

• Gastrointestinal disturbances (nausea, vomiting, diarrhea)
• Skin rashes or photosensitivity reactions
• Headache
• Dizziness
• Fatigue

More serious, but less common, side effects may include:

• Severe allergic reactions (anaphylaxis)
• Blood disorders (e.g., agranulocytosis, aplastic anemia)
• Liver or kidney damage
• Stevens-Johnson syndrome or toxic epidermal necrolysis

How can the risk of side effects be minimized? To reduce the risk of adverse reactions, it’s crucial to follow the prescribed dosage and duration of treatment. Patients should be advised to report any unusual symptoms or side effects to their healthcare provider promptly.

Drug Interactions and Special Considerations

Sulfonamides can interact with various medications and substances, potentially altering their effectiveness or increasing the risk of side effects. Some important interactions to consider include:

• Anticoagulants: Sulfonamides may enhance the effects of warfarin and other blood thinners.
• Methotrexate: Sulfonamides can increase methotrexate levels, potentially leading to toxicity.
• Oral hypoglycemics: Sulfonamides may potentiate the effects of some diabetes medications.
• Phenytoin: Sulfonamides can increase phenytoin levels, requiring dose adjustments.

Are there any special considerations for specific patient populations? Yes, certain groups require extra caution when using sulfonamides:

• Elderly patients: May be more susceptible to side effects and require dose adjustments.
• Patients with G6PD deficiency: At higher risk of hemolytic anemia with sulfonamide use.
• Individuals with HIV: May have an increased risk of adverse reactions to sulfonamides.
• Patients with impaired kidney or liver function: May require dose adjustments to prevent drug accumulation.

Antibiotic Resistance: A Growing Concern

Sulfonamide resistance is a significant issue in modern medicine. Resistance to one sulfonamide typically indicates resistance to all drugs in this class. This cross-resistance poses challenges in treating infections and highlights the importance of appropriate antibiotic use.

How does sulfonamide resistance develop? Bacterial resistance to sulfonamides can occur through several mechanisms:

• Mutations in the target enzyme (dihydropteroate synthase)
• Increased production of p-aminobenzoic acid
• Development of alternative metabolic pathways
• Enhanced efflux of the drug from bacterial cells

What strategies can help combat sulfonamide resistance? To preserve the effectiveness of sulfonamides and other antibiotics, healthcare providers and patients should:

• Use antibiotics only when necessary and as prescribed
• Complete the full course of antibiotic treatment
• Avoid sharing antibiotics or using leftover medications
• Implement antibiotic stewardship programs in healthcare settings
• Promote research into new antibiotic classes and treatment strategies

Future Perspectives: Ongoing Research and Developments

Despite the challenges of antibiotic resistance, research into sulfonamides and related compounds continues. Some areas of ongoing investigation include:

• Development of new sulfonamide derivatives with enhanced activity and reduced side effects
• Exploration of combination therapies to overcome resistance mechanisms
• Investigation of sulfonamides’ potential in treating non-infectious diseases, such as certain cancers
• Studying the long-term effects of sulfonamide use on the human microbiome

What potential breakthroughs might we see in sulfonamide research? While it’s difficult to predict specific outcomes, some promising areas include:

• Novel drug delivery systems to improve the efficacy and reduce side effects of sulfonamides
• Development of rapid diagnostic tests to quickly identify sulfonamide-resistant infections
• Exploration of sulfonamides’ potential synergistic effects with other classes of antibiotics or natural compounds
• Investigation of sulfonamides’ role in modulating the immune response in various diseases

As research progresses, our understanding of sulfonamides and their potential applications continues to evolve. This ongoing work is crucial for addressing the challenges of antibiotic resistance and improving patient outcomes in the treatment of infectious diseases.

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

View Patient Education

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)

Information for healthcare professionals only.
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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

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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.