What are sulfonamides. How do sulfonamides work as antibiotics. What are the main types of sulfonamide drugs. What are the primary uses of sulfonamides in medicine. What are the contraindications and potential side effects of sulfonamide use.

The Fundamentals of Sulfonamide Drugs

Sulfonamides are a class of synthetic bacteriostatic antibiotics that have played a crucial role in the treatment of various bacterial infections since their discovery. These drugs work by competitively inhibiting the conversion of p-aminobenzoic acid to dihydropteroate, a vital component 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 less harmful to humans than bacteria? The key lies in our ability to obtain folate from our diet, whereas bacteria must synthesize it themselves. This difference in folate acquisition allows sulfonamides to target bacterial processes while minimally affecting human cellular functions.

Key Characteristics of Sulfonamides

• Synthetic origin
• Bacteriostatic action
• Competitive inhibition of bacterial folate synthesis
• Broad-spectrum activity against gram-positive and many gram-negative bacteria
• Efficacy against certain protozoal infections

Types and Formulations of Sulfonamide Drugs

The sulfonamide family encompasses a diverse range of drugs, each with specific applications and formulations. Understanding the various types can help healthcare professionals select the most appropriate treatment for different conditions.

Common Sulfonamide Drugs

1. Mafenide
2. Sulfacetamide
3. Sulfadiazine
4. Sulfadoxine
5. Sulfamethizole
6. Sulfamethoxazole
7. Sulfanilamide
8. Sulfasalazine
9. Sulfisoxazole

Which sulfonamides are available as single drugs for oral use? Three options stand out: sulfisoxazole, sulfamethizole, and sulfasalazine. These medications offer flexibility in treating various bacterial infections without the need for combination therapy.

It’s worth noting that some sulfonamides are commonly combined with other drugs to enhance their efficacy. For instance, sulfamethoxazole is often coformulated with trimethoprim (known as TMP/SMX), creating a powerful synergistic effect against bacterial pathogens. Similarly, sulfadoxine is combined with pyrimethamine for oral use, particularly in the treatment of certain parasitic infections.

Topical Sulfonamide Formulations

• Silver sulfadiazine (burn treatment)
• Mafenide acetate (burn cream)
• Sulfanilamide (vaginal cream and suppositories)
• Sulfacetamide (ophthalmic preparations)

How do topical sulfonamides differ from oral formulations? Topical sulfonamides are designed for localized treatment of specific conditions, such as burns, vaginal infections, or ocular infections. These formulations allow for direct application to the affected area, minimizing systemic exposure and potential side effects.

Pharmacokinetics and Distribution of Sulfonamides

Understanding the pharmacokinetics of sulfonamides is crucial for optimizing their therapeutic use and minimizing potential adverse effects. These drugs exhibit several important characteristics that influence their absorption, distribution, metabolism, and excretion within the body.

Absorption and Distribution

How are sulfonamides absorbed and distributed in the body? Most sulfonamides are readily absorbed when administered orally, allowing for efficient systemic distribution. Additionally, when applied to burns, sulfonamides can be absorbed topically, providing localized and systemic effects.

Once absorbed, sulfonamides are distributed throughout the body, reaching various tissues and organs. This widespread distribution contributes to their effectiveness against diverse types of infections in different body systems.

Metabolism and Excretion

What happens to sulfonamides after they’ve exerted their therapeutic effect? The primary site of sulfonamide metabolism is the liver, where these drugs undergo various biotransformation processes. Following metabolism, sulfonamides and their metabolites are primarily excreted by the kidneys through urine.

An important consideration in sulfonamide pharmacokinetics is their interaction with albumin. Sulfonamides compete for bilirubin-binding sites on albumin molecules. This competition can have implications for patients with certain conditions, such as neonatal jaundice, where elevated free bilirubin levels may pose a risk.

Antimicrobial Spectrum and Clinical Applications

Sulfonamides exhibit a broad spectrum of antimicrobial activity, making them valuable tools in treating various infections. Their effectiveness extends beyond bacteria to include certain protozoal pathogens, expanding their clinical utility.

Bacterial Targets

Which bacterial species are susceptible to sulfonamides? These drugs demonstrate activity against:

• A wide range of gram-positive bacteria
• Many gram-negative bacteria

This broad-spectrum activity allows sulfonamides to be used in treating diverse bacterial infections affecting different body systems.

Protozoal Targets

Beyond bacteria, sulfonamides also show efficacy against certain protozoal pathogens, including:

• Plasmodium species (causative agents of malaria)
• Toxoplasma species (responsible for toxoplasmosis)

How do sulfonamides contribute to the treatment of protozoal infections? In the case of malaria, sulfonamides like sulfadoxine are often combined with other antimalarial drugs to enhance efficacy and combat drug resistance. For toxoplasmosis, sulfonamides can be part of a multi-drug treatment regimen, particularly in immunocompromised patients.

Specific Clinical Applications

What are some common clinical scenarios where sulfonamides are employed? These drugs find use in various medical contexts, including:

1. Urinary tract infections
2. Nocardiosis
3. Chloroquine-resistant falciparum malaria
4. Inflammatory bowel disease (specifically sulfasalazine)
5. Topical treatment of burns (silver sulfadiazine and mafenide acetate)
6. Management of certain vaginal infections (sulfanilamide)
7. Treatment of superficial ocular infections (sulfacetamide)

It’s important to note that sulfonamides are often used in combination with other drugs to enhance efficacy and prevent the development of resistance. For instance, the combination of trimethoprim and sulfamethoxazole (TMP/SMX) is widely used for various infections due to its synergistic effect.

Resistance Patterns and Considerations

As with many antimicrobial agents, the development of resistance to sulfonamides poses a significant challenge in clinical practice. Understanding resistance patterns is crucial for appropriate prescribing and effective treatment outcomes.

Prevalence of Sulfonamide Resistance

How common is resistance to sulfonamides? Unfortunately, sulfonamide resistance is widespread among many bacterial pathogens. This resistance has developed over decades of use and can limit the effectiveness of these drugs in certain clinical scenarios.

Cross-Resistance Among Sulfonamides

Does resistance to one sulfonamide mean resistance to all? Generally, yes. Resistance to one sulfonamide typically indicates resistance to the entire class. This cross-resistance is due to the shared mechanism of action among sulfonamides, where bacterial adaptations that confer resistance to one drug often protect against others in the same class.

Implications for Clinical Practice

What are the practical implications of sulfonamide resistance? Healthcare providers must consider local resistance patterns when prescribing sulfonamides. In many cases, susceptibility testing may be necessary to ensure the chosen treatment will be effective. Additionally, the widespread resistance has led to increased use of sulfonamides in combination with other antibiotics, such as the TMP/SMX combination, to overcome resistance mechanisms and enhance efficacy.

Contraindications and Precautions in Sulfonamide Use

While sulfonamides are valuable antimicrobial agents, they are not suitable for all patients or conditions. Understanding the contraindications and precautions associated with sulfonamide use is essential for safe and effective prescribing.

Absolute Contraindications

In which situations should sulfonamides never be used? Sulfonamides are absolutely contraindicated in the following cases:

• Patients with a history of allergic reactions to sulfonamides
• Individuals with porphyria, a group of disorders affecting heme biosynthesis

Why are these contraindications so important? Allergic reactions to sulfonamides can be severe, potentially leading to life-threatening conditions such as Stevens-Johnson syndrome or toxic epidermal necrolysis. In patients with porphyria, sulfonamides can trigger acute attacks, exacerbating the condition.

Specific Precautions

What precautions should be taken when considering sulfonamide use? Healthcare providers should exercise caution in the following scenarios:

1. Neonates and young infants: Due to the risk of kernicterus from bilirubin displacement
2. Patients with glucose-6-phosphate dehydrogenase (G6PD) deficiency: Increased risk of hemolytic anemia
3. Individuals with renal impairment: May require dose adjustment to prevent drug accumulation
4. Patients with liver disease: Altered metabolism may affect drug clearance
5. Pregnant women: Potential risks to the fetus, especially near term

Inappropriate Use in Streptococcal Infections

Why shouldn’t sulfonamides be used to treat group A streptococcal pharyngitis? Sulfonamides do not effectively eradicate group A streptococci in patients with pharyngitis. This inadequate bacterial clearance can lead to treatment failure and potential complications. Therefore, other antibiotics, such as penicillin or erythromycin, are preferred for treating streptococcal throat infections.

Potential Adverse Effects and Monitoring

While sulfonamides are generally well-tolerated, they can cause a range of adverse effects. Awareness of these potential complications and appropriate monitoring strategies is crucial for safe and effective use of these drugs.

Common Adverse Effects

What are the most frequent side effects associated with sulfonamide use? Common adverse effects include:

• Gastrointestinal disturbances (nausea, vomiting, diarrhea)
• Skin rashes
• Photosensitivity reactions
• Headache
• Dizziness

These effects are generally mild and often resolve with continued treatment or upon discontinuation of the drug.

Serious Adverse Effects

Which adverse effects of sulfonamides require immediate medical attention? Serious adverse effects, though less common, can include:

1. Severe allergic reactions (anaphylaxis, Stevens-Johnson syndrome, toxic epidermal necrolysis)
2. Blood dyscrasias (agranulocytosis, aplastic anemia, thrombocytopenia)
3. Hepatotoxicity
4. Kidney damage (crystalluria, interstitial nephritis)
5. Hemolytic anemia (particularly in G6PD-deficient individuals)

How can healthcare providers mitigate the risk of serious adverse effects? Careful patient selection, monitoring, and prompt recognition of early warning signs are key. Patients should be educated about potential symptoms to report, such as unexplained fever, sore throat, or unusual bleeding or bruising.

Monitoring Recommendations

What monitoring strategies should be employed for patients on sulfonamide therapy? Depending on the specific drug, duration of treatment, and patient factors, monitoring may include:

• Regular complete blood counts to detect hematologic abnormalities
• Liver function tests to assess hepatotoxicity
• Renal function tests, especially in patients with pre-existing kidney disease
• Urinalysis to check for crystalluria
• Clinical assessment for signs of allergic reactions or other adverse effects

By implementing appropriate monitoring protocols, healthcare providers can optimize the safety and efficacy of sulfonamide therapy, ensuring the best possible outcomes for patients requiring these important antimicrobial agents.

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.

NOTE:


This is the Professional Version.


CONSUMERS:



View Consumer Version

Copyright © 2023 Merck & Co., Inc., Rahway, NJ, USA and its affiliates. All rights reserved.

Test your knowledge

Take a Quiz! 

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.

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

Contents

• Structural formula

• Russian name

• English title

• 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

• A46 Erysipelas

• J03. 9 Acute tonsillitis, unspecified (tonsillitis, agranulocytic)

• L01 Impetigo

• L02 Skin abscess, furuncle and carbuncle

• L08.0 Pyoderma

• L70. 0 Acne vulgaris

• L73.8.1* Folliculitis

• L98 Other diseases of skin and subcutaneous tissue, not elsewhere classified

• L98.4 Chronic skin ulcer, not elsewhere classified

• T30 Thermal and chemical burns, unspecified

• T79. 3 Post-traumatic wound infection, not elsewhere classified

CAS code

63-74-1

Pharmacological activity

Pharmacological activity –

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

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.
Are you a healthcare professional?

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

Contents

• Structural formula

• Russian name

• English title

• 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

• A46 Erysipelas

• J03. 9 Acute tonsillitis, unspecified (tonsillitis, agranulocytic)

• L01 Impetigo

• L02 Skin abscess, furuncle and carbuncle

• L08.0 Pyoderma

• L70. 0 Acne vulgaris

• L73.8.1* Folliculitis

• L98 Other diseases of skin and subcutaneous tissue, not elsewhere classified

• L98.4 Chronic skin ulcer, not elsewhere classified

• T30 Thermal and chemical burns, unspecified

• T79. 3 Post-traumatic wound infection, not elsewhere classified

CAS code

63-74-1

Pharmacological activity

Pharmacological activity –

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

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.