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Salicylamide
Salicylamide
Salicylamide
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Salicylamide
Clinical data
MedlinePlusa681004
ATC code
Pharmacokinetic data
ExcretionRenal
Identifiers
  • 2-Hydroxybenzamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.000.554 Edit this at Wikidata
Chemical and physical data
FormulaC7H7NO2
Molar mass137.138 g·mol−1
3D model (JSmol)
Density1.33 g/cm3
Solubility in waterSoluble in hot water, ether, alcohol, and chloroform. mg/mL (20 °C)
  • O=C(c1ccccc1O)N
  • InChI=1S/C7H7NO2/c8-7(10)5-3-1-2-4-6(5)9/h1-4,9H,(H2,8,10) checkY
  • Key:SKZKKFZAGNVIMN-UHFFFAOYSA-N checkY
  (verify)

Salicylamide (o-hydroxybenzamide or amide of salicyl) is a non-prescription drug with analgesic and antipyretic properties.[1] Its medicinal uses are similar to those of aspirin.[2] Salicylamide is used in combination with both aspirin and caffeine in the over-the-counter pain remedy PainAid. It was also an ingredient in the over-the-counter pain remedy BC Powder but was removed from the formulation in 2009, and Excedrin used the ingredient from 1960 to 1980 in conjunction with aspirin, acetaminophen, and caffeine. It was used in later formulations of Vincent's powders in Australia as a substitute for phenacetin.

Pure salicylamide is a white or slightly pink crystalline powder

Derivatives

[edit]

Derivatives of salicylamide include ethenzamide, labetalol, medroxalol, otilonium, oxyclozanide, salicylanilide, niclosamide, and raclopride.

See also

[edit]

References

[edit]
[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Salicylamide

View on Grokipedia
from Grokipedia
Salicylamide is a synthetic organic compound with the molecular formula C₇H₇NO₂ and a molecular weight of 137.14 g/mol, systematically named 2-hydroxybenzamide. It exists as a white to pale yellow crystalline powder, with a melting point of 139–142 °C, a density of approximately 1.3 g/cm³, and solubility in hot water, ethanol, ether, and chloroform. Historically recognized as a non-prescription analgesic and antipyretic agent, it provides pain-relieving and fever-reducing effects similar to those of aspirin but is not metabolized to salicylic acid in vivo. As a derivative of , salicylamide was introduced in the early for symptomatic relief of mild to moderate , including headaches, muscle aches, and minor arthritic discomfort, often in combination with other agents like or antihistamines for enhanced in and flu symptoms. It exerts and effects through inhibition of synthesis and central mechanisms, without to salicylic acid. Absorption is rapid but variable, leading to inconsistent therapeutic outcomes compared to established alternatives like acetaminophen or ibuprofen. Typical adult dosing ranged from 325–650 mg orally up to four times daily, but prolonged use was discouraged due to limited data on long-term safety. Despite its past availability in over-the-counter formulations, salicylamide's regulatory status has evolved; it is no longer an officially approved standalone drug by the FDA, classified among pre-1938 substances with unreliable effects, and as of 2025, it remains available in some combination OTC products internationally. Synthesis typically involves the reaction of salicylic acid with ammonia or aniline derivatives under dehydrating conditions, such as with phosphorus oxychloride, yielding the amide functional group. While derivatives continue to be explored for anti-inflammatory and antiviral applications, salicylamide itself has largely been supplanted in clinical practice.

Chemical Properties

Molecular Structure

Salicylamide has the molecular formula C₇H₇NO₂ and the IUPAC name 2-hydroxybenzamide. The molecule consists of a benzene ring substituted at the ortho position with a hydroxy group (-OH) and an amide functional group (-CONH₂). This arrangement positions the phenolic hydroxyl ortho to the carbonyl of the amide, enabling intramolecular hydrogen bonding between the OH proton and the amide oxygen. In comparison to salicylic acid, which bears a carboxylic acid (-COOH) group in the same ortho position, salicylamide replaces the acidic carboxyl with a neutral amide, altering the electronic properties while retaining the core benzamide scaffold. Computational studies reveal key bond lengths and angles that highlight the structural features. In the monomeric cis conformation, the phenolic C-O bond measures approximately 1.334 , the amide C=O bond is about 1.232 , and the amide C-N bond is around 1.357 , with ring C-C bonds averaging 1.411–1.484 . Bond angles, such as the O-C-O in the amide linkage, are near 123°, reflecting partial double-bond character in the C-N bond due to . These dimensions indicate conjugation across the ring and group, contributing to planarity. Resonance effects are prominent, particularly in the amide moiety where electron delocalization between the nitrogen lone pair and the carbonyl π* orbital shortens the C-N bond and lengthens the C=O bond relative to aliphatic . The intramolecular O-H···O=C , with an H···O distance of about 1.70 , is resonance-assisted (RAHB), stabilizing the closed conformation and enhancing the acidity of the phenolic proton through π-delocalization involving the ortho-hydroxy and groups. Salicylamide is an achiral molecule with no stereocenters or , resulting in no optical isomers.

Physical and Chemical Properties

Salicylamide is a to off-white crystalline powder. It exhibits a in the range of 140–144 °C, with literature values varying slightly between 139–141 °C and 142 °C. The compound sublimes at its melting point and has a reported of approximately 181.5 °C at reduced pressure.
PropertyValueSource
AppearanceWhite to off-white crystalline powder
Melting point140–144 °C
Solubility in water (25 °C)0.2 g/100 mL (poorly soluble)
Solubility in organic solventsSoluble in , acetone, , , and hot water
The phenolic hydroxyl group of salicylamide has a pKa of approximately 8.2, indicating moderate acidity, while the NH group is weakly acidic with a much higher pKa. This acidity influences its , allowing stable solutions to form at 9 through of the phenolic group. Salicylamide is chemically stable in the solid state under normal conditions when stored at in a dry, dark container. It decomposes at high temperatures, potentially yielding carbon oxides and oxides. The compound undergoes under acidic or basic conditions, primarily cleaving the bond to form . It is incompatible with strong oxidizing agents and strong bases. Infrared (IR) of salicylamide reveals characteristic absorption bands, including a broad O-H stretch around 3200–3400 cm⁻¹ due to hydrogen bonding of the phenolic hydroxyl, asymmetric and symmetric N-H stretches near 3390 and 3200 cm⁻¹, and an carbonyl (C=O) stretch at approximately 1650–1662 cm⁻¹. The ¹H NMR shows aromatic protons with chemical shifts typically between 6.8 and 7.9 ppm, along with signals for the NH and OH protons that can vary with and concentration due to hydrogen bonding.

Synthesis

Laboratory Synthesis

Salicylamide can be synthesized in the laboratory through the amidation of with or ammonium salts, such as , under heating conditions. The reaction involves the conversion of the group to an , represented by the equation: \ceC6H4(OH)COOH+NH3−>C6H4(OH)CONH2+H2O\ce{C6H4(OH)COOH + NH3 -> C6H4(OH)CONH2 + H2O} A standard procedure entails mixing with liquid and deionized , followed by heating to 85–110 °C in the presence of a catalyst like molybdenum phosphorus (HMoO₂P). The mixture is dehydrated for several hours to facilitate the amidation, after which the product is isolated by adding and centrifuging to separate the salicylamide from the supernatant. Another common laboratory method involves the reaction of , the methyl ester of , with . This process, developed in the early , proceeds under moderate heating and to form the while releasing . Other routes include the partial of salicylonitrile (2-hydroxybenzonitrile) using acidic or basic conditions to form the bond. Additionally, partial rearrangements from derivatives have been explored, though less commonly for direct laboratory preparation. Purification of the crude salicylamide is generally performed by recrystallization from a water-ethanol mixture, dissolving the product in hot solvent and cooling to promote crystal formation, resulting in high-purity material suitable for research applications.

Industrial Production

The primary industrial route for producing salicylamide involves the high-temperature reaction of phenol with urea in the presence of a solid base catalyst, such as metal oxides like CaO, ZnO, or MgO. This method leverages the decomposition of urea to generate ammonia in situ, facilitating amidation while minimizing the need for gaseous ammonia handling. The process is conducted in stainless steel autoclaves or cauldrons under controlled (0.1–3.5 MPa) and temperatures of 140–220 °C for 1–24 hours, with a molar ratio of phenol to ranging from 1:1 to 100:1 and catalyst loading at 0.001–10 mol% relative to . Byproducts such as and CO₂ (from decomposition) are removed in real-time via and venting to maintain reaction efficiency and prevent side reactions. Recent advancements focus on optimizing metal oxide catalysts with balanced acidic-basic sites to enhance selectivity and suppress unwanted byproducts like xanthone or 4-hydroxybenzamide. Yields typically range from 80–95%, depending on catalyst choice and conditions, with the ZnO-based system achieving up to 86% in scaled examples. The heterogeneous catalyst allows for easy separation, followed by pharmaceutical-grade purification through to remove solids and to obtain high-purity product (>98%). Currently, salicylamide is primarily synthesized as an intermediate for pharmaceutical derivatives rather than standalone bulk production, with major suppliers concentrated in , particularly , where annual capacity exceeds 9,200 tons across key manufacturers as of 2025.

Pharmacology

Mechanism of Action

Salicylamide exerts analgesic and antipyretic effects similar to those of salicylates, though not consistently produced and without established anti-inflammatory activity. It does not inhibit cyclooxygenase (COX) enzymes or hydrolyze to salicylic acid in vivo. The compound demonstrates central nervous system (CNS) depression and potential hypotensive effects, possibly through peripheral vessel dilation, contributing to its pain-relieving profile with limited peripheral anti-inflammatory actions.

Pharmacokinetics

Salicylamide is rapidly absorbed from the gastrointestinal tract following oral administration, with nearly complete absorption but low systemic bioavailability of the unchanged drug (approximately 20–80%, dose-dependent) due to extensive first-pass metabolism. Peak plasma concentrations of unchanged salicylamide occur within 30–60 minutes, while total plasma levels (including metabolites) peak at 1.5–2 hours post-dose. Diet does not significantly affect the extent of absorption. The drug is widely distributed throughout body tissues, including muscle, liver, and , with moderate protein binding of 40–55% to serum proteins at therapeutic concentrations. Human data on are limited. Metabolism occurs primarily in the liver via conjugation, forming inactive (40–70% of dose) and (25–50%) conjugates; a minor pathway involves to gentisamide . Unlike salicylates, salicylamide is not converted to . These pathways can saturate at higher doses (>600 mg), leading to nonlinear kinetics. Excretion is predominantly renal, with 90–100% of the dose recovered in within 24 hours, primarily as metabolites (<5% unchanged). The elimination is approximately 1.2 hours in humans. Due to its short , no accumulation occurs with chronic use. Factors such as liver impairment can prolong and reduce clearance by impairing first-pass . Pharmacokinetic data are limited and primarily from older studies conducted in the and .

Medical Uses

Indications

Salicylamide is primarily indicated for the symptomatic of mild to moderate , including headaches, muscle aches, and toothaches, as well as for reducing fever in conditions such as minor infections or inflammatory responses. As a non-opioid and , it provides targeted symptom management without the need for prescription in most jurisdictions. As of , it is primarily available in over-the-counter combination products, as standalone formulations are not FDA-approved. Historically, salicylamide has been incorporated into combination analgesics to potentiate pain relief, such as formulations with , acetaminophen, or aspirin, exemplified by products like PainAid for enhanced efficacy against everyday discomforts. Off-label applications occasionally include its use for dysmenorrhea-related pain and symptoms, where it aids in alleviating associated aches and fever. Clinical evidence from double-blind studies supports salicylamide's efficacy as comparable to aspirin in providing pain relief, though its effects may vary in consistency. Notably, it demonstrates reduced gastrointestinal irritation compared to aspirin, as animal models show minimal mucosal damage even after prolonged administration. However, due to its weaker anti-inflammatory potency—stemming from reversible rather than irreversible COX inhibition—salicylamide is not suitable for managing chronic inflammatory conditions like .

Dosage and Administration

Salicylamide is administered orally, typically in tablet or form, either as a single agent or in combination with other analgesics such as aspirin, acetaminophen, and . Common combination products include historical formulations like , which contains 195 mg of salicylamide per powder packet along with aspirin and . For adults, the standard dosage for relieving minor aches and pains is 325–650 mg taken 3–4 times daily, not exceeding beyond 10 days without medical supervision. In combination products, such as those with 152 mg salicylamide per tablet, the recommended intake is 1–2 tablets every 4–6 hours, with a maximum of 8 tablets per day to avoid exceeding safe limits for all components. Pediatric dosing is not well-established for self-medication, and salicylamide is generally not recommended for children under 12 years without physician advice due to limited safety data. Some clinicians suggest 65 mg/kg daily or 1.5 g/m² daily, divided into 6 doses every 4 hours (approximately 10–11 mg/kg per dose), for minor aches, pains, or fever in children, but this is requiring medical oversight. To minimize gastrointestinal irritation, salicylamide should be taken with food, milk, or at least 240 mL of . Adequate hydration is advised during use, particularly with powder forms, which may be dissolved in or placed on the followed by liquid. For short-term use in treating minor conditions, no routine monitoring is required, though prolonged or high-dose administration warrants to prevent potential .

Adverse Effects and Safety

Side Effects

Salicylamide is generally well-tolerated at therapeutic doses, but dose-related gastrointestinal () and (CNS) disturbances represent the most common adverse effects. effects, which include , , , anorexia, and , occur infrequently at doses of 325–650 mg but become more prevalent with higher intake. Similarly, CNS effects such as , drowsiness, , faintness, and are uncommon at standard doses yet increase in frequency at elevated levels. Unlike other salicylates, salicylamide produces milder irritation and has not been associated with bleeding in clinical reports. Less frequent side effects encompass flushing, , sweating, dry mouth, and , which may indicate allergic reactions in susceptible individuals. has been reported, though it appears rarer with salicylamide than with aspirin. At high doses, additional rare effects include ecchymosis, hemorrhagic lesions, and thrombocytopenic . Mild blood dyscrasias, such as , , , and , have also been documented in rare cases, particularly with excessive exposure. Overall, salicylamide exhibits a lower risk profile compared to aspirin, with animal studies confirming reduced gastric mucosal damage. In overdose, salicylamide is generally considered less toxic than other salicylates.

Contraindications and Interactions

Salicylamide is contraindicated in patients with known to salicylamide or related salicylates, as this may lead to severe allergic reactions. It should not be used in individuals with active due to the increased risk of and ulceration. Absolute contraindications also include severe renal or hepatic impairment, where the drug's elimination may be compromised, potentially leading to toxicity. Relative contraindications apply to patients with , where salicylamide may precipitate in sensitive individuals, although the risk appears lower than with traditional salicylates like aspirin. Drug interactions with salicylamide include additive when combined with sedatives or other CNS depressants, which may enhance drowsiness and respiratory risks. It can potentiate the anticoagulant effects of by affecting platelet function and increasing bleeding risk. Concomitant use with probenecid may reduce the latter's uricosuric efficacy, similar to interactions observed with other salicylates. Serum levels of salicylamide may be lowered by corticosteroids and heightened by other nonsteroidal anti-inflammatory drugs (NSAIDs), potentially altering therapeutic effects or toxicity. Salicylamide's safety in has not been established; it should be used only if the benefit outweighs the risk, and avoided in the third trimester due to potential fetal harm similar to other salicylates. During , salicylamide excretion into is minimal, but caution is recommended as safety has not been fully established.

History

Discovery

Salicylamide, known chemically as o-hydroxybenzamide, was first synthesized in 1843 by French chemist Auguste Cahours through the of . This preparation occurred amid broader 19th-century investigations into derivatives, which originated from natural sources like willow bark extracts containing . Italian chemist Raffaele Piria had isolated from in 1838, sparking interest in related compounds for their potential physiological effects, though salicylamide itself received limited attention at the time. Early explorations of salicylamide's properties in the late included animal studies that highlighted its effects. For instance, in 1899, Meyer observed that salicylamide exhibited strong activity in amphibians, surpassing that of ethyl alcohol, , or acetone, suggesting potential qualities beyond typical salicylates. These findings built on the growing recognition of salicylic derivatives' potential, though specific tests for pain relief in animals during the remain undocumented in available records. The first explicit medicinal application of salicylamide was proposed by Ernst Baas in 1890, who suggested its use for fever reduction based on preliminary observations of activity. Despite this, salicylamide remained an obscure compound throughout the pre-20th century, largely overshadowed by the more potent and widely studied and its salts, which dominated early therapeutic explorations of analgesics and antipyretics.

Commercial Development

Salicylamide was reintroduced commercially in the United States in the early by the Chemo Puro Chemical Company, establishing its role as a non-prescription and agent similar to aspirin. This development prompted other manufacturers, including Dow Chemical, , and Rhodia, to enter the market, leading to widespread incorporation into over-the-counter pain relief formulations during the mid-20th century. By the late , clinical evaluations confirmed its use for minor aches, pains, and fever reduction, with dosages typically ranging from 300 to 600 mg every four hours. The compound reached peak commercial prominence in the and through combination products, where it enhanced the efficacy of aspirin and other analgesics. In Excedrin tablets, salicylamide was included at 2 grains (approximately 130 mg) per dose alongside aspirin, acetaminophen, and , contributing to claims of faster pain relief until at least the early . Similarly, the original BC Powder formula from the 1950s featured 195 mg of salicylamide per packet with 650 mg aspirin and 33 mg for and muscle pain relief, a composition that persisted until its reformulation in 2009 to exclude salicylamide amid evolving safety standards. Regulatory scrutiny by the FDA in the and classified salicylamide as a Category III ingredient for internal use, indicating inadequate evidence of safety and effectiveness in over-the-counter applications, which contributed to its gradual decline. By the 1990s, it was largely phased out from major U.S. consumer products in favor of acetaminophen and ibuprofen, though it remains available in select generic formulations and for purposes. Outside the U.S. and , commercial adoption has been limited, with occasional veterinary applications in dogs for at doses studied in pharmacokinetic trials.

Derivatives

Pharmaceutical Derivatives

Salicylamide serves as a core in several established pharmaceutical agents, where structural modifications enhance potency and target specific therapeutic areas such as and applications. One prominent example is , a halogenated salicylamide derivative featuring chlorine substitutions at the 5-position of the ring and the anilide moiety, which confers broad-spectrum activity against tapeworms and intestinal flukes. Originally approved by the FDA in 1982 for treating infections caused by parasites like and Diphyllobothrium latum, niclosamide inhibits mitochondrial in helminths, leading to their immobilization and expulsion. These halogenation modifications not only improve the compound's and binding affinity to parasitic targets but also contribute to its repurposing in antiviral and anticancer therapies, though its primary marketed use remains . In the realm of , salicylamide itself and its analogs have been incorporated into combination formulations for enhanced and antipyretic effects. Historical preparations, such as powders (aspirin, , ), evolved in the mid-20th century to include salicylamide as a substitute for due to safety concerns, as seen in products like Vincent's powders and B.C. powders containing aspirin (325–650 mg), salicylamide (195 mg), and (32–36 mg) per dose. These combinations were widely used for and rheumatic pain relief until the 1970s, when regulatory scrutiny led to phenacetin's withdrawal, leaving salicylamide--acetaminophen blends as alternatives for mild to moderate . Salicylamide's linkage distinguishes it from ester-based analogs like salsalate, a dimer of used as a nonacetylated NSAID for and , providing similar anti-inflammatory benefits without gastrointestinal irritation from . Further structural refinements, such as esterification of the salicylamide hydroxyl or carboxylic groups, have yielded derivatives with improved and reduced ulcerogenic potential compared to unmodified salicylamide. For instance, esters formed by reacting salicylamide with acid chlorides of nonsteroidal anti-inflammatory agents, like 2-(4-isobutylphenyl), result in prodrugs that exhibit prolonged plasma levels and enhanced , achieving peak concentrations within 1 hour and sustained activity for over 7 hours in oral formulations. These modifications, dosed at 250–500 mg, are formulated into tablets or suppositories for treating inflammatory and painful conditions, offering a balance of potency and tolerability. , as in , exemplifies another key alteration that bolsters and efficacy, underscoring salicylamide's versatility as a pharmaceutical building block.

Research Applications

Salicylamide have garnered significant interest in due to their ability to inhibit key pathways. For instance, the IMD-0354, a selective inhibitor of IκB kinase β (IKKβ), suppresses activation, thereby exhibiting broad-spectrum antiviral effects against pathogens such as and . studies demonstrate that IMD-0354 reduces replication in Vero E6/ cells with an value of approximately 1.5 μM, primarily by modulating host inflammatory responses that facilitate viral entry and propagation. Similarly, , another salicylanilide , inhibits HIV-1 replication in TZM-bl and SupT1 cells with values of 0.119 μM and 0.102 μM, respectively, through post-integration suppression of proviral transcription and interference with -mediated immune evasion. These mechanisms highlight the potential of salicylamide scaffolds in developing host-targeted antivirals that circumvent viral mutation challenges. As of 2025, new like JMX0312 have shown protection against adenovirus lethal challenge in immunosuppressed models. In anticancer research, and its analogs have emerged as promising agents by targeting dysregulated Wnt/β-catenin signaling in various tumors. promotes the internalization and degradation of the Wnt co-receptor LRP6, thereby disrupting β-catenin stabilization and downstream oncogenic transcription in colorectal and ovarian cancers. Analogs such as niclosamide-based isatin hybrids exhibit enhanced potency, with studies showing values in the low micromolar range against Wnt-driven cell lines, while reducing tumor migration and invasion without significant off-target effects on healthy cells. These findings underscore the role of modified salicylamides in precision oncology, particularly for APC-mutated tumors where Wnt hyperactivation drives progression. Recent 2025 studies highlight superior anticancer and activities of sulfanyl-substituted niclosamide derivatives. Beyond antivirals and anticancer applications, salicylamide derivatives show utility in diagnostic imaging and cardioprotection. Lanthanide complexes incorporating salicylamide ligands, such as those with Tb(III) and Dy(III), display strong properties due to efficient energy transfer from the ligand's antennae effect, enabling their use as probes in and bioimaging. In ischemia-reperfusion injury models, derivatives like IMD-0354 and 3-nitro-N-methyl-salicylamide protect cardiac tissue by inhibiting phosphorylation, which modulates pro-inflammatory release (e.g., TNF-α and IL-6), reducing infiltration and in isolated rat hearts subjected to 4 hours of cold ischemia followed by reperfusion. Recent reviews, such as a 2023 analysis of salicylamide scaffolds, emphasize their versatility in for emerging infectious diseases, highlighting optimized derivatives with improved that achieve sub-micromolar against in Vero cells (e.g., at 0.28 μM). A 2025 study reports salicylamide derivatives as potent HBV inhibitors. Despite these advances, challenges persist, including poor oral and aqueous of parent compounds like , which limit their standalone clinical translation and necessitate strategies or analog development to enhance systemic exposure.

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