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Sulfanilamide

Sulfanilamide is a synthetic sulfonamide antibiotic with the molecular formula C₆H₈N₂O₂S, recognized as the prototype of the sulfonamide class and one of the first effective chemotherapeutic agents against bacterial infections.^[1] As a bacteriostatic drug, it inhibits the growth of a wide spectrum of gram-positive and many gram-negative bacteria by competitively antagonizing p-aminobenzoic acid in the folic acid synthesis pathway essential for bacterial replication.^[1] First synthesized in 1908 by Austrian chemist Paul Gelmo during dye research, its antibacterial properties were not identified until the 1930s.^[2] The discovery of sulfanilamide's therapeutic potential stemmed from work on the related compound Prontosil. In 1932, German pathologist Gerhard Domagk tested Prontosil, a red azo dye developed by Bayer chemists, and found it cured streptococcal infections in mice that would otherwise be fatal.^[3] Prontosil was introduced commercially in 1935, marking the first sulfonamide antibiotic available for clinical use, and Domagk received the Nobel Prize in Physiology or Medicine in 1939 for this breakthrough, though the award was initially delayed due to political pressures in Nazi Germany.^[3] In 1937, researchers at the Pasteur Institute, including Jacques and Thérèse Trefouël, demonstrated that Prontosil is a prodrug metabolized in vivo to the active component sulfanilamide, which lacks the dye moiety but retains full antibacterial activity.^[4] This revelation spurred the rapid development of numerous sulfanilamide derivatives, transforming infectious disease treatment before the widespread availability of penicillin. Sulfanilamide's introduction revolutionized medicine, dramatically reducing mortality from bacterial infections such as pneumonia, meningitis, and puerperal sepsis during the pre-antibiotic era.^[2] It was widely used orally, topically, and intravenously starting in 1936 in the United States, with production scaling up due to its low cost and lack of patent protection on the core molecule.^[4] However, its legacy is also tied to a tragic event: in 1937, the S.E. Massengill Company produced Elixir Sulfanilamide, an oral liquid formulation using diethylene glycol—a sweet-tasting but highly toxic solvent analogous to antifreeze—as the vehicle, since the drug was poorly soluble in water.^[5] This untested product caused acute kidney failure and killed at least 107 people, mostly children, across the U.S., exposing critical gaps in drug safety regulations under the 1906 Pure Food and Drugs Act, which did not require proof of safety for new formulations.^[5] The Elixir Sulfanilamide disaster prompted swift public outcry and congressional action, leading to the passage of the Federal Food, Drug, and Cosmetic Act in 1938, which mandated pre-market safety testing and approval for new drugs.^[5] Although effective, sulfanilamide and early sulfonamides were later overshadowed by antibiotics like penicillin due to issues such as allergic reactions, crystalluria, and emerging bacterial resistance.^[1] Today, sulfanilamide itself is rarely used clinically and is primarily of historical significance, though sulfonamide derivatives continue in treatments for urinary tract infections, toxoplasmosis, and other conditions.^[1]

Medical Aspects

Uses and Indications

Sulfanilamide was historically employed as a systemic antibiotic in the 1930s and 1940s to treat a range of severe bacterial infections, including streptococcal diseases such as puerperal sepsis and septicemia, pneumococcal pneumonia, and meningococcal meningitis.^[6] Its introduction dramatically reduced mortality rates in these conditions; for instance, sulfonamide therapy lowered the fatality rate in meningococcal meningitis from over 70% to around 20% in pediatric cases by 1937.^[7] This marked a pivotal advancement in infectious disease management prior to the widespread availability of penicillin.^[8] In contemporary medical practice, sulfanilamide's role has significantly diminished due to the emergence of safer, more effective antibiotics and antifungals. Commercial products like AVC vaginal cream were discontinued in the US in 2016, limiting its use primarily to compounded topical formulations for treating uncomplicated vulvovaginal candidiasis caused by Candida albicans in non-pregnant women as of 2025.^[9] ^[10] It is indicated specifically for vulvovaginitis associated with this yeast infection and was available in products such as AVC vaginal cream, applied intravaginally to alleviate symptoms like itching, burning, and discharge. Evidence from pre-1980 clinical trials supports its efficacy, with cure rates ranging from 48% to 71% in active treatment groups compared to 24% to 49% in placebo controls across three controlled studies involving 30-day regimens.^[11] In veterinary medicine, sulfonamides persist in some topical ointments and compounded formulations for managing superficial wound infections in animals, particularly where bacterial contamination requires localized antimicrobial action, though sulfanilamide specifically is used topically in species like horses; its application is cautious due to potential delays in wound healing.^[12] ^[13] Relative to modern antifungals like clotrimazole, which offer mycological cure rates of 75% to 95% with shorter 1- to 7-day courses and fewer adverse effects, sulfanilamide's niche status stems from its lower potency, longer required treatment duration, and higher risk of local irritation, rendering it a second-line option in resistant or specific cases.^[14]^[15]

Administration and Dosage

Sulfanilamide is primarily administered topically for vaginal infections, available as a 15% vaginal cream or suppositories. For vaginal use, one applicatorful (approximately 6 g of cream) is applied intravaginally once or twice daily for up to 30 days, with improvements typically observed within a few days.^[16] Alternatively, vaginal suppositories containing 1.05 g of sulfanilamide may be inserted twice daily for 7 days.^[17] These formulations are applied using a provided applicator, with hands washed before and after insertion, and are not intended for ocular, oral, or external skin use.^[11] Historically, sulfanilamide was given orally for systemic bacterial infections at doses of 0.5 to 1 g every 4 to 6 hours, totaling 4 to 6 g daily, with adjustments based on body weight to maintain therapeutic blood levels.^[18] Tablets and powders were common formulations for oral administration during the mid-20th century. In pediatric patients over 2 months of age, historical dosing ranged from 50 to 100 mg/kg/day, divided into multiple doses, though use in infants under 2 months was contraindicated due to elevated blood levels and toxicity risks. During emergencies, such as in World War II wound treatment, sulfanilamide powder was applied locally to wounds or administered intraperitoneally in doses of 5 to 10 g, often as sodium salts to improve solubility.^[19] For patients with renal impairment, systemic dosing required caution and adjustment to prevent crystalluria, typically by reducing the dose or increasing fluid intake. Modern vaginal products remain available over-the-counter in some regions, such as Singapore, or as compounded formulations for candidal vulvovaginitis as of 2025.^[16]^[17]

Pharmacology

Mechanism of Action

Sulfanilamide, a prototypical sulfonamide antibiotic, exerts its antibacterial effects through competitive inhibition of the bacterial enzyme dihydropteroate synthase (DHPS), which catalyzes the essential step of incorporating para-aminobenzoic acid (PABA) into dihydropteroic acid, a key precursor in the folate biosynthesis pathway.^[20] By binding to the PABA substrate site on DHPS, sulfanilamide prevents the formation of dihydropteroic acid, thereby disrupting the de novo synthesis of folic acid required for bacterial nucleotide and amino acid production.^[21] The structural mimicry between sulfanilamide and PABA is central to this inhibition; the amino group attached to the benzene ring of sulfanilamide occupies the same binding pocket as PABA's amino group, while the sulfonamide moiety emulates the carboxyl group, allowing sulfanilamide to act as a substrate analog with high affinity.^[22] This blockade results in a bacteriostatic effect, as folic acid depletion halts thymidine and purine synthesis, essential for bacterial DNA replication and protein synthesis, without impacting human cells that rely on dietary folate rather than endogenous production.^[23] Sulfanilamide demonstrates activity against a broad spectrum of pathogens, including Gram-positive bacteria such as Streptococcus species and certain Gram-negative organisms, due to the conservation of the DHPS enzyme across these taxa.^[24] Bacterial resistance to sulfanilamide commonly arises from point mutations in the folP gene encoding DHPS, which alter the enzyme's PABA-binding site to reduce drug affinity, or from plasmid-mediated overproduction of PABA that overwhelms the inhibitor. The efficacy of sulfanilamide is enhanced when combined with trimethoprim, which targets the downstream enzyme dihydrofolate reductase in the folate pathway, creating a synergistic sequential inhibition that amplifies bacteriostatic or bactericidal effects against susceptible bacteria.^[25]

Pharmacokinetics

Sulfanilamide is rapidly and nearly completely absorbed from the gastrointestinal tract after oral administration, with bioavailability estimated at 70-100%, primarily in the small intestine. The drug appears in the urine within 30 minutes of ingestion, indicating quick onset of absorption. Peak plasma concentrations are typically reached within 1-2 hours post-dose, facilitating prompt therapeutic levels in systemic circulation.^[1]^[26] The drug exhibits wide distribution throughout the body, diffusing into various tissues, secretions such as milk and fetal products, and fluids including cerebrospinal fluid (CSF), pleural, peritoneal, synovial, and ocular fluids at concentrations comparable to those in plasma. Its apparent volume of distribution is approximately 0.6 L/kg, consistent with equilibration in total body water. Sulfanilamide demonstrates low plasma protein binding, ranging from 10-20%, which contributes to its extensive tissue penetration.^[1]^[27] Metabolism of sulfanilamide occurs primarily in the liver via N-acetylation to form the inactive metabolite N-acetylsulfanilamide, catalyzed by N-acetyltransferase enzymes. The extent of acetylation varies between 20-40%, influenced by genetic polymorphisms in acetylator status, with slow acetylators exhibiting lower rates and potentially higher parent drug exposure. This metabolic pathway is characteristic of sulfonamides and affects overall elimination.^[28]^[29] Excretion is predominantly renal, with approximately 90% of the dose eliminated in the urine as unchanged drug or acetylated metabolites within 24 hours. The elimination half-life is 5-8 hours in individuals with normal renal function, though it prolongs in renal impairment. Sulfonamides like sulfanilamide have low solubility in acidic urine, posing a risk of crystalluria and potential renal tubular obstruction if urinary pH is not maintained alkaline through adequate hydration and alkalinization. Small amounts are also excreted via bile, feces, milk, and other secretions. Dosage adjustments may be necessary in patients with compromised renal function to ensure adequate tissue levels for antibacterial activity.^[1]^[29] When applied topically, such as in vaginal creams or suppositories, sulfanilamide shows minimal systemic absorption, typically less than 5%, which limits overall exposure and reduces the risk of systemic adverse effects compared to oral routes. Absorption occurs through the vaginal mucosa, but limited data exist on the exact fraction entering systemic circulation.^[9]^[1]

Chemistry

Chemical Structure and Properties

Sulfanilamide is an organic sulfur-containing compound with the molecular formula C₆H₈N₂O₂S and a molecular weight of 172.21 g/mol.^[1] It features a benzene ring substituted at the 1-position with a sulfonamide functional group (-SO₂NH₂) and at the 4-position with an amino group (-NH₂), systematically named as 4-aminobenzenesulfonamide.^[1] Sulfanilamide exists as a white to faintly yellowish crystalline powder or leaflets.^[1] Its melting point ranges from 164.5 °C to 166.5 °C, with a density of 1.08 g/cm³ at 25 °C.^[1] The compound exhibits two pKa values: approximately 2.3 for the protonated amino group and 10.25 for the sulfonamide group, reflecting its amphoteric nature. Sulfanilamide shows limited solubility in water, dissolving at about 0.75 g per 100 mL at 25 °C, but is more soluble in organic solvents such as ethanol (around 2.7 g per 100 mL at 25 °C) and acetone (approximately 20 g per 100 mL).^[1] Under normal conditions, sulfanilamide remains stable, but it is light-sensitive in solution and can decompose upon exposure to strong acids or bases.^[1]^[30]

Synthesis

The classical synthesis of sulfanilamide involves a three-step process starting from acetanilide, which serves as a protected form of aniline to direct electrophilic substitution to the para position. In the first step, chlorosulfonation occurs by adding acetanilide to excess chlorosulfonic acid at 40-50°C to form 4-acetamidobenzenesulfonyl chloride, minimizing side reactions and controlling the exothermic process.^[31] The intermediate is then subjected to ammonolysis with aqueous ammonia at 40-45°C, yielding 4-acetamidobenzenesulfonamide through nucleophilic substitution of the chloride by ammonia.^[31] Finally, acid hydrolysis of the acetamido group is performed by refluxing the sulfonamide in 20% HCl for 2-3 hours, followed by neutralization to isolate sulfanilamide.^[32] On an industrial scale, the synthesis follows the same classical route but is optimized for efficiency, often leveraging intermediates from azo dye production such as those related to Prontosil, where the azo linkage is cleaved reductively to access the core structure.^[33] Overall yields for the process typically range from 70-80%, reflecting improvements in reaction control and recycling of byproducts like ammonium chloride.^[31] The process is conducted in large reactors with careful temperature management to handle the corrosive nature of chlorosulfonic acid. Modern variants in research include catalytic hydrogenation of nitro-substituted precursors, such as reducing 4-nitrobenzenesulfonamide to the amino analog, offering milder conditions and avoiding harsh chlorosulfonation, though these remain less common than the classical method.^[34] Enzymatic approaches, utilizing amidases for selective deacetylation, have also been explored in laboratory settings but are not yet predominant in production.^[35] Purification of sulfanilamide is achieved through recrystallization from hot water or ethanol, yielding material with greater than 99% purity suitable for pharmaceutical use.^[32]

History

Discovery and Development

Sulfanilamide was first synthesized in 1908 by Austrian chemist Paul Gelmo as part of his doctoral dissertation on sulfonamide derivatives for use in azo dye production at the Vienna University of Technology.^[36] Gelmo's work focused on the chemical properties of these compounds in industrial applications, and although he documented the structure of sulfanilamide (p-aminobenzenesulfonamide), there was no immediate recognition or pursuit of its potential biological activity.^[37] The compound remained largely overlooked for over two decades, with its synthesis detailed in Gelmo's thesis but not explored beyond dye chemistry.^[38] The antibacterial potential of sulfanilamide was rediscovered in 1932 through research led by Gerhard Domagk at the IG Farben laboratories in Germany.^[39] As part of a systematic screening of azo dyes for chemotherapeutic properties, Domagk tested Prontosil—a red azo compound containing a sulfanilamide moiety—on mice infected with deadly doses of hemolytic streptococci.^[40] Initial in vitro tests showed no activity, but in vivo experiments revealed dramatic protection against the infection, marking a breakthrough in identifying the first effective chemical treatment for bacterial diseases.^[41] Domagk's findings were published in 1935, reporting that all mice treated with Prontosil survived streptococcal infections, while all untreated controls succumbed within days.^[42] This work earned him the Nobel Prize in Physiology or Medicine in 1939 for demonstrating the therapeutic value of Prontosil against systemic bacterial infections. In 1937, a team of French researchers at the Pasteur Institute, including Jacques Tréfouël, Thérèse Tréfouël, Federico Nitti, and Daniel Bovet, elucidated that Prontosil's efficacy stemmed from its metabolic hydrolysis in the body to release free sulfanilamide as the active agent.^[43] Their experiments confirmed sulfanilamide's direct bacteriostatic action, shifting focus from the dye to the simpler metabolite and paving the way for broader sulfonamide development.^[44]

Clinical Introduction and Impact

Sulfanilamide was introduced to clinical practice in the United States in 1937 as an oral antibiotic for treating bacterial infections, marking a pivotal advancement in antimicrobial therapy. However, its initial rollout was marred by tragedy when the S.E. Massengill Company produced Elixir Sulfanilamide, a liquid formulation dissolved in the toxic solvent diethylene glycol, without adequate safety testing. This product caused the deaths of at least 107 individuals, primarily children and adults unable to swallow tablets, across 15 states, exposing critical gaps in drug regulation. The incident galvanized public and legislative support, directly leading to the enactment of the Federal Food, Drug, and Cosmetic Act in 1938, which mandated premarket safety demonstrations for new drugs and expanded the Food and Drug Administration's oversight authority.^[45] During World War II, sulfanilamide played a crucial role in military medicine, significantly lowering mortality from wound infections among both Allied and Axis forces. Soldiers carried sulfanilamide powder in first-aid kits to sprinkle directly on wounds, which helped prevent bacterial complications such as gas gangrene and sepsis; this contributed to lower overall mortality from wound infections compared to prior conflicts. Its widespread use in battlefield settings, including intraperitoneal administration for abdominal injuries, underscored its practical impact, saving countless lives before the broader availability of penicillin.^[19]^[46]^[47] The drug's adoption spread rapidly worldwide following its licensing in 1937-1938 across Europe and North America, enabling treatment of thousands of cases of severe infections like puerperal fever, a leading cause of maternal mortality. Clinical trials demonstrated sulfanilamide's efficacy in reducing puerperal sepsis deaths by up to 81%, transforming obstetric care and averting numerous fatalities in postpartum settings.^[6]^[48] By the late 1940s, sulfanilamide's prominence waned as penicillin became widely available, offering superior efficacy against a broader spectrum of bacteria with fewer side effects. Emerging bacterial resistance to sulfonamides, combined with the drug's inherent toxicity profile, further diminished its use in systemic therapy.^[4]^[49] Sulfanilamide's legacy endures as the cornerstone of the antibiotic era, inspiring the development of safer sulfonamide derivatives such as sulfadiazine, which retained its core structure while improving solubility and reducing adverse reactions. This foundational role paved the way for modern antimicrobial chemotherapy, influencing subsequent drug discoveries and emphasizing the need for rigorous safety evaluations.^[6]^[4]

Safety Profile

Adverse Effects

Sulfanilamide, like other sulfonamides, commonly causes gastrointestinal disturbances such as nausea, vomiting, and headache with oral administration.^[50] Topical application may lead to local irritation, including burning or redness.^[9] Hypersensitivity reactions represent a significant risk, manifesting as sulfa allergy with rash, fever, or more severe conditions like Stevens-Johnson syndrome, with an overall incidence of 1-3% among users and cross-reactivity potential with other sulfonamides.^[51] These reactions are typically immune-mediated, involving IgE or T-cell responses to the sulfonamide moiety.^[52] Hematologic adverse effects include hemolytic anemia, particularly in individuals with glucose-6-phosphate dehydrogenase (G6PD) deficiency, where oxidative stress from the drug triggers red blood cell destruction, with reported rates ranging from 1.3% to 12% in affected populations.^[53] Agranulocytosis, a rare bone marrow suppression leading to severe neutropenia, occurs in less than 0.1% of cases.^[24] Renal complications arise from the drug's low solubility in acidic urine, leading to crystalluria and potential hematuria due to crystal precipitation in the renal tubules.^[54] In neonates, especially those under 2 months with jaundice, sulfanilamide poses a high risk of kernicterus by displacing bilirubin from albumin binding sites, allowing free bilirubin to cross the blood-brain barrier and cause encephalopathy.^[55] Notably, the 1937 Elixir Sulfanilamide disaster involved solvent toxicity rather than the drug itself, resulting in acute renal failure and numerous deaths.^[56]

Contraindications and Precautions

Sulfanilamide is contraindicated in patients with known hypersensitivity to the drug or other sulfonamides, as severe and potentially fatal reactions, including Stevens-Johnson syndrome and toxic epidermal necrolysis, may occur.^[11]^[57] It is also absolutely contraindicated in infants under 2 months of age due to the risk of kernicterus from bilirubin displacement in the neonatal brain.^[58] Use during the third trimester of pregnancy is prohibited because sulfonamides cross the placenta and can cause neonatal jaundice, hemolytic anemia, and kernicterus.^[11]^[57] Relative contraindications include lactation, as sulfanilamide is excreted in breast milk and may cause kernicterus in nursing infants; alternative therapies are recommended.^[11] Patients with glucose-6-phosphate dehydrogenase (G6PD) deficiency should avoid sulfanilamide due to the risk of hemolytic anemia.^[59] It requires caution in individuals with severe renal or hepatic impairment, where drug accumulation may lead to toxicity, including fulminant hepatic necrosis.^[16]^[57] Precautions are necessary for dehydrated patients, in whom sulfanilamide may precipitate crystalluria; adequate hydration and urinary alkalinization are advised to mitigate this risk.^[29] The drug is contraindicated in porphyria, as it may trigger acute attacks.^[60]^[29] Concurrent use with para-aminobenzoic acid (PABA)-containing products can reduce efficacy by competitively inhibiting the drug's antibacterial action.^[61] Coadministration with methotrexate increases toxicity risk through protein binding displacement and renal transport competition.^[62] Patients should be monitored for hypersensitivity reactions, such as skin rash, and the drug discontinued if they appear.^[11] In special populations, sulfanilamide is not recommended for HIV-infected patients owing to a markedly elevated risk of hypersensitivity reactions compared to the general population.^[63] Safety and efficacy in pediatric patients beyond neonates have not been established.^[11] Veterinary applications of sulfanilamide formulations generally do not adhere to human contraindications, focusing instead on species-specific tolerances. Regulatory considerations classify topical sulfanilamide as FDA pregnancy category C, indicating potential fetal risks but possible use if benefits outweigh harms; systemic forms, if available, are category D due to documented adverse effects.^[11]^[57] Oral sulfanilamide was eventually phased out in favor of more effective antibiotics and is no longer used clinically; topical use was limited to specific indications like vulvovaginal candidiasis. However, as of 2025, all sulfanilamide formulations have been discontinued and are no longer commercially available.^[10]^[2]

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List of Sulfonamides + Uses, Types & Side Effects - Drugs.com
Apr 13, 2023 · Common side effects reported with sulfonamides include: Gastrointestinal effects (such as diarrhea, nausea, stomach upset, vomiting) ...
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Allergy to sulfonamides
Under treatment with sulfonamide antimicrobial agents, approximately 2% of the general population have adverse drug reactions suggestive of an allergic ...Missing: incidence | Show results with:incidence
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Clinical Manifestations and Genetic Influences in Sulfonamide ... - NIH
Jul 21, 2022 · It has been widely reported that sulfonamide antimicrobials cause hypersensitivity reactions mediated by IgE or T cells. This review identifies ...
[53]
Medications and glucose-6-phosphate dehydrogenase deficiency
Early reports showed rates of haemolysis following sulfanilamide administration ranging from 1.3% to 12% in various populations.
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The Mechanism of Renal Complications in Sulfonamide Therapy
temperature. Crystalluria, as determined by the observation of ordinary cooled urines, is probably without sig- nificance unless there is oliguria, hematuria or.
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Kernicterus: Background, Pathophysiology, Etiology
Feb 14, 2024 · Additionally, some drugs, such as sulfonamides and some penicillins, can displace bilirubin from its albumin-binding site, effectively ...Missing: sulfanilamide | Show results with:sulfanilamide
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[PDF] Sulfanilamide Disaster - FDA
The medicine that killed Dr. Calhoun's patients was Elixir Sulfanilamide. During September and October 1937 this drug was responsible for the deaths of more ...Missing: discovery | Show results with:discovery
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(sulfanilamide) dosing, indications, interactions, adverse effects, and ...
Dosage Forms & Strengths: vaginal cream. Candida: Vulvovaginitis. 1 applicatorful (~6 g) intravaginally qDay or q12hr for 30 days.
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Sulfadiazine Monograph for Professionals - Drugs.com
Oct 10, 2025 · Contraindicated in infants <2 months of age (except when considered necessary for adjunctive use with pyrimethamine for treatment of congenital ...
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Silver Sulfadiazine - F.A. Davis PT Collection - McGraw Hill Medical
Contraindicated in: Hypersensitivity (cross-sensitivity with sulfonamides may occur); Infants ... kernicterus in infant); G6PD deficiency; Porphyria. ++. Use ...
[60]
Sulfonamides General Statement (Monograph) - Drugs.com
Sulfonamides are contraindicated in patients with porphyria, since the drugs may precipitate an acute attack. Sulfasalazine (but not other sulfonamides) is ...
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Para-Aminobenzoic Acid (Paba) - Uses, Side Effects, and More
Moderate Interaction · Antibiotics (Sulfonamide antibiotics) interacts with Para-Aminobenzoic Acid (PABA) · Cortisone interacts with Para-Aminobenzoic Acid (PABA).Missing: sulfanilamide | Show results with:sulfanilamide
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[PDF] Reference ID: 5534786 - accessdata.fda.gov
Methotrexate Avoid concurrent use Sulfonamides can also displace methotrexate from plasma protein binding sites and can compete with the renal transport of ...
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Sulfonamide Allergies - PMC - NIH
Sep 11, 2019 · Compared to the general population, patients with HIV are at increased risk for experiencing allergic reactions to sulfonamide antimicrobials.