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Trimethobenzamide

Trimethobenzamide is a benzamide derivative and centrally acting antiemetic agent indicated for the treatment of postoperative nausea and vomiting and nausea associated with gastroenteritis in adults.^[1] It primarily exerts its therapeutic effect by directly depressing the chemoreceptor trigger zone (CTZ) in the medulla oblongata, thereby inhibiting emetic impulses at the central level without significant peripheral anticholinergic or antihistaminic activity.^[2] The drug is administered orally as 300 mg capsules of trimethobenzamide hydrochloride, typically three to four times daily as needed, and was first approved by the U.S. Food and Drug Administration in 1974.^[1] Pharmacokinetically, trimethobenzamide is rapidly absorbed following oral dosing, achieving peak plasma concentrations in about 45 minutes, with an elimination half-life of 7 to 9 hours; approximately 30% to 50% of the dose is excreted unchanged in the urine, primarily via glomerular filtration.^[3] Dosage adjustments are recommended for patients with renal impairment (creatinine clearance ≤70 mL/min/1.73 m²) to mitigate the risk of adverse reactions, and the drug is contraindicated in individuals with known hypersensitivity to trimethobenzamide and not recommended in pediatric patients due to the potential for serious extrapyramidal symptoms and central nervous system effects.^[1] Common adverse effects include drowsiness, dizziness, headache, and diarrhea, while rare but severe reactions encompass convulsions, coma, hypotension, and jaundice.^[4] Although an injectable formulation exists for intramuscular use, the rectal suppository form was withdrawn from the U.S. market in 2007 due to insufficient evidence of efficacy.^[4] Trimethobenzamide is metabolized hepatically to an N-oxide derivative with minimal drug-drug interactions reported, though caution is advised in patients with hepatic impairment or those taking other central nervous system depressants.^[2] Hepatotoxicity is uncommon but possible, with isolated case reports of acute liver injury linked to its use.^[2]

Medical uses

Indications

Trimethobenzamide is indicated in adults for the treatment of postoperative nausea and vomiting as well as nausea associated with gastroenteritis.^[1] These approvals stem from clinical evaluations demonstrating its efficacy in controlling emesis in these settings, with the U.S. Food and Drug Administration (FDA) confirming substantial evidence of effectiveness for these uses following a drug efficacy study implementation in 2002.^[5] The drug is commonly employed for the prevention and treatment of postoperative nausea and vomiting as well as nausea associated with gastroenteritis.^[6] For instance, it helps manage nausea in surgical patients during recovery and in individuals with acute gastroenteritis, where symptoms arise from inflammatory or infectious processes in the digestive tract.^[6] Its use in these contexts is supported by early clinical trials, though with efficacy generally lower than that of phenothiazine antiemetics.^[2] Trimethobenzamide is not indicated for motion sickness, which involves vestibular mechanisms outside its primary site of action in the chemoreceptor trigger zone, nor for chemotherapy-induced nausea and vomiting, where more targeted agents like 5-HT3 antagonists are preferred due to limited comparative efficacy data from older studies.^[7] While some historical investigations explored its role in chemotherapy-related emesis, current guidelines do not recommend it for this purpose, emphasizing its restricted evidence base beyond FDA-approved indications.^[2]

Dosage and administration

Trimethobenzamide is available in oral capsule form at a strength of 300 mg and as an intramuscular (IM) injection at a concentration of 100 mg/mL.^[8]^[9] For oral administration in adults, the recommended dosage is 300 mg three to four times daily as needed for the control of nausea and vomiting, with a maximum daily dose of 1,200 mg.^[8]^[10] The lowest effective dose should be used, and adjustments can be made based on therapeutic response and tolerability.^[8] In patients with renal impairment (creatinine clearance ≤70 mL/min/1.73 m²), including some geriatric patients, the daily dosage should be reduced by increasing the dosing interval, with monitoring of renal function and further adjustments as needed.^[8] Use is not recommended in patients with signs or symptoms of hepatic impairment due to the risk of hepatotoxicity; therapy should be discontinued if liver dysfunction develops during treatment.^[1] For IM administration in adults, the recommended dosage is 200 mg (2 mL) three to four times daily, injected deeply into the upper outer quadrant of the gluteus maximus to minimize discomfort such as pain, stinging, or swelling.^[9]^[6] The onset of action following IM injection occurs within 15 to 35 minutes, with a duration of effect lasting 2 to 3 hours.^[6] IM use requires similar dosage adjustments for renal impairment as with the oral route, while hepatic impairment contraindicates use.^[9]^[1] Intravenous administration is strictly prohibited due to the risk of severe hypotension and collapse.^[9] Trimethobenzamide is intended for short-term use, typically until symptoms of nausea resolve, and is not recommended for use in pediatric patients (contraindicated for IM administration) due to risks of extrapyramidal symptoms and other serious central nervous system effects.^[8]^[9] Oral capsules may be taken with or without food.^[11]

Contraindications and precautions

Contraindications

Trimethobenzamide is contraindicated in patients with known hypersensitivity to the drug or any of its components, including those with a history of anaphylaxis or other severe allergic reactions.^[1] The intramuscular (IM) formulation of trimethobenzamide is strictly contraindicated in pediatric patients due to the high risk of toxicity, including serious central nervous system (CNS) effects and potential exacerbation of conditions resembling Reye's syndrome.^[9]

Precautions

Trimethobenzamide requires caution in elderly patients due to increased susceptibility to adverse effects, including sedation and drowsiness that may impair balance and elevate the risk of falls; dose reduction by extending the dosing interval is recommended, along with close monitoring of renal function as age-related declines can heighten toxicity risks.^[1] In patients with renal impairment (creatinine clearance ≤70 mL/min/1.73 m²), dosage adjustment is necessary because the drug is primarily excreted by the kidneys, leading to prolonged half-life and accumulation; regular renal function monitoring is advised.^[1] For hepatic impairment, trimethobenzamide should be avoided if signs of liver dysfunction are present, and discontinued if liver function deteriorates during therapy, given the potential for exacerbated effects in compromised liver metabolism.^[1] Drug interactions with trimethobenzamide include additive central nervous system (CNS) depression when combined with alcohol, opioids, or other sedatives, which can intensify drowsiness and impair psychomotor skills; concurrent use should be avoided or closely monitored.^[1] Trimethobenzamide should not be used in patients with comatose states or severe CNS depression, as administration of antiemetics in these situations can mask symptoms of underlying pathology, such as toxicity or disease progression. Reports of other CNS reactions include coma, depression of mood, disorientation, and seizures; consider dosage reduction or discontinuation if these occur.^[1] Monitoring is essential with trimethobenzamide, as its CNS effects may mask symptoms of serious underlying conditions, such as appendicitis, intestinal obstruction, or encephalopathy, potentially delaying diagnosis; thorough evaluation of the nausea cause is required before and during use.^[1] The drug is intended for short-term management of acute nausea and vomiting and should not be used long-term to avoid unnecessary exposure to risks.^[1] Regarding pregnancy, the limited available data with trimethobenzamide in pregnant women are not sufficient to inform a drug-associated risk for major birth defects and miscarriage; animal reproduction studies showed no adverse developmental effects at doses up to 1.6 times the recommended human dose. It should be used during pregnancy only if the potential benefit justifies the potential risk to the fetus.^[1] In lactation, data on trimethobenzamide excretion in human milk are lacking, and its use is not recommended due to potential risks to the nursing infant; a decision should be made to discontinue nursing or the drug, weighing benefits against hazards.^[1]

Adverse effects

Common adverse effects

The common adverse effects of trimethobenzamide primarily involve the central nervous system (CNS) and are typically mild and transient. The most frequently reported CNS effects include drowsiness, which is the predominant side effect, as well as dizziness, headache, and blurred vision; these are attributed to the drug's CNS depressant properties.^[1]^[12] Gastrointestinal (GI) effects are less common but may manifest as mild abdominal pain, cramps, or diarrhea. Other occasional effects during short-term use include muscle cramps, weakness, or tremors.^[1]^[12] Trimethobenzamide is generally well-tolerated, with these effects often resolving as the body adjusts or upon discontinuation of therapy.^[1]

Serious adverse effects

Trimethobenzamide can cause extrapyramidal symptoms, including acute dystonic reactions such as muscular spasms and opisthotonos, as well as parkinsonian-like symptoms like tremors, rigidity, akathisia, and akinesia. These effects are rare, particularly noted in children, and may be exacerbated by high doses or concurrent use of other medications that induce extrapyramidal symptoms, such as antipsychotics. These effects are a primary reason for contraindication in pediatric patients. Caution is advised in elderly patients due to general increased sensitivity to side effects. Management typically involves dosage reduction or discontinuation of the drug, with acute dystonia treated using anticholinergic agents.^[1]^[12] Hepatic effects from trimethobenzamide are uncommon but serious, manifesting as jaundice, elevated liver enzymes, or rare cases of cholestatic hepatitis.^[2] Symptoms of liver injury may include upper abdominal pain, dark urine, pale stools, nausea, vomiting, and yellowing of the skin or eyes, necessitating immediate medical evaluation and potential discontinuation.^[12] The drug should be avoided in patients with pre-existing hepatic impairment.^[1] Allergic reactions to trimethobenzamide include skin rash and urticaria, with very rare instances of severe hypersensitivity such as angioedema or anaphylaxis.^[1] These reactions require prompt intervention, and the drug is contraindicated in individuals with known hypersensitivity to it.^[1] Other serious adverse effects encompass convulsions, which have been reported in cases of overdose or in sensitive patients, often alongside coma, disorientation, or mood depression.^[1] The risk increases with concomitant use of central nervous system depressants like alcohol or sedatives, and such events are rare.^[12]

Pharmacology

Pharmacodynamics

The mechanism of action of trimethobenzamide is not fully understood but is believed to involve direct depression of the chemoreceptor trigger zone (CTZ) in the medulla oblongata, thereby inhibiting emetic impulses to the vomiting center.^[1]^[2] This central action blocks the emetic response triggered by dopamine agonists, such as apomorphine, as demonstrated in animal models where pretreatment with trimethobenzamide prevented apomorphine-induced vomiting in dogs.^[8] The drug does not directly suppress impulses at the vomiting center itself but modulates upstream signaling in the CTZ to reduce nausea and vomiting centrally mediated by chemotherapeutic agents, postoperative stimuli, or other CTZ activators.^[2] This central action provides selectivity, as trimethobenzamide does not significantly affect peripheral emetic pathways, such as those induced by intragastric irritants like copper sulfate in animal studies.^[8] Trimethobenzamide exhibits weak antihistaminic properties that may provide minor supportive inhibition of nausea signals, particularly in scenarios involving histaminergic influences on the CTZ, but lacks significant anticholinergic activity.^[2]^[13] Therapeutically, this profile makes trimethobenzamide particularly effective for nausea and vomiting arising from central CTZ activation, such as postoperative or drug-induced emesis, but it is less efficacious against vestibular or peripheral causes of nausea that do not primarily involve the CTZ.^[14]^[15]

Pharmacokinetics

Trimethobenzamide exhibits good absorption following oral or intramuscular administration. The oral bioavailability is comparable to intramuscular dosing, with plasma concentration-time profiles being similar between routes.^[9]^[6] The time to maximum plasma concentration (T_max) is about 45 minutes after a 300 mg oral capsule and 30 minutes after a 200 mg intramuscular injection.^[9] Onset of action occurs within 10-40 minutes orally and 15-35 minutes intramuscularly.^[15] The drug is widely distributed throughout the body and crosses the blood-brain barrier to reach the chemoreceptor trigger zone in the central nervous system.^[16] The volume of distribution has not been well-characterized in available studies. Trimethobenzamide undergoes hepatic metabolism primarily through oxidation to form the trimethobenzamide N-oxide metabolite, with limited data on involvement of cytochrome P450 enzymes; the pharmacologic activity of this metabolite has not been evaluated.^[17] No active metabolites have been identified. Elimination of trimethobenzamide occurs with a half-life of 7-9 hours. Approximately 30-50% of a single dose is excreted unchanged in the urine within 48-72 hours, with the remainder eliminated via feces through biliary excretion.^[9]^[15] The half-life is prolonged in patients with renal or hepatic impairment due to substantial renal elimination and hepatic metabolism, respectively.^[9]

Chemistry

Physical and chemical properties

Trimethobenzamide is a benzamide derivative with the molecular formula C_{21}H_{28}N_{2}O_{5} for the free base and C_{21}H_{29}ClN_{2}O_{5} for the hydrochloride salt, the latter having a molecular weight of 424.92 g/mol.^[14]^[16] The IUPAC name is N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4,5-trimethoxybenzamide.^[14] The compound appears as a white to off-white crystalline powder.^[18] It has a melting point of 187–191 °C for the hydrochloride salt.^[19] Trimethobenzamide hydrochloride is soluble in water (≥51 mg/mL), as well as in ethanol and dimethyl sulfoxide, though solubility in methanol is slightly lower.^[20]^[21] The hydrochloride salt exhibits a pKa of approximately 8.8 for the tertiary amine group (conjugate acid), indicating its basic ionization behavior.^[22] It is stable under normal storage conditions, such as inert atmosphere at 2–8 °C, with no significant degradation reported under standard handling.^[18] The logP value is 2.29, indicating moderate lipophilicity.^[14]

Synthesis

The primary synthesis of trimethobenzamide, as first described in a 1959 patent assigned to Hoffmann-La Roche, involves a three-step process starting from p-hydroxybenzaldehyde. In the initial step, the sodium salt of p-hydroxybenzaldehyde is alkylated with 2-(dimethylamino)ethyl chloride in a solvent such as chlorobenzene under reflux conditions for approximately 15 hours to yield 4-(2-(dimethylamino)ethoxy)benzaldehyde. This intermediate then undergoes reductive amination with ammonia gas in the presence of a Raney nickel catalyst, hydrogen gas at 80°C and 1000 psi pressure, producing 4-(2-(dimethylamino)ethoxy)benzylamine. Finally, this benzylamine is acylated by reaction with 3,4,5-trimethoxybenzoyl chloride in a solvent like acetonitrile or benzene under reflux for 8 hours, followed by treatment with hydrochloric acid to form the hydrochloride salt of trimethobenzamide in high purity.^[23] This classical route, developed by inventors Moses Wolf Goldberg and Sidney Teitel at Hoffmann-La Roche, provides the compound as its hydrochloride salt with a reported melting point of 185–186°C and is suitable for large-scale production without involvement of stereocenters, as trimethobenzamide is achiral.^[23] Modern variations focus on improving efficiency and safety by avoiding the use of hazardous acid chlorides. One such improved process employs direct amidation of 3,4,5-trimethoxybenzoic acid with 4-(2-(dimethylamino)ethoxy)benzylamine, catalyzed by boric acid in the presence of polyethylene glycol (PEG 600) as a co-solvent in xylene under reflux for 24 hours, with water removal via a Dean-Stark apparatus. The reaction mixture is then basified with aqueous sodium hydroxide, cooled, and extracted to isolate the free base, which is subsequently converted to the hydrochloride salt using ethanolic HCl, yielding trimethobenzamide hydrochloride with 99.5% HPLC purity and an overall yield of approximately 80% from the benzoic acid starting material (melting point 188–190°C). This method enhances scalability, reduces environmental impact, and minimizes impurities compared to the original acid chloride approach.^[24]

History and development

Discovery and approval

Trimethobenzamide was developed by Hoffmann-La Roche Inc. in the late 1950s as a novel antiemetic agent designed to suppress nausea and vomiting associated with gastrointestinal disorders, motion sickness, pregnancy, and therapeutic interventions.^[23] The compound, specifically 4-[2-(diethylamino)ethoxy]-N-(3,4,5-trimethoxybenzoyl)benzylamine hydrochloride, was patented under U.S. Patent 2,879,293, filed on February 19, 1957, and granted on March 24, 1959, to inventors Moses Wolf Goldberg and Sidney Teitel.^[23] This patent detailed its synthesis through the reaction of a substituted benzylamine with 3,4,5-trimethoxybenzoyl halide, highlighting its potential as an effective antiemetic based on initial pharmacological evaluations.^[23] Preclinical studies conducted during its early development demonstrated trimethobenzamide's activity on the chemoreceptor trigger zone (CTZ) in the medulla oblongata, an area responsible for detecting emetic stimuli, supporting its antiemetic efficacy in animal models.^[16] These findings paved the way for clinical evaluation, with initial marketing occurring in the early 1960s under trade names such as Tigan, prior to the 1962 Kefauver-Harris Amendments requiring proof of efficacy for new drugs.^[25] As a pre-1962 drug, trimethobenzamide underwent review under the Drug Efficacy Study Implementation (DESI) program, leading to FDA approval of its oral capsule and intramuscular injection forms in 1974 for the treatment of postoperative nausea and vomiting, as well as nausea associated with gastroenteritis.^[1] This approval marked its first widespread clinical use in these indications, confirming its safety and effectiveness based on submitted data.^[5] Key milestones in its commercialization included licensing for distribution to GlaxoSmithKline under the brand Tebamide and to King Pharmaceuticals, which acquired the new drug applications in 1999 and marketed it as Tigan.^[26]^[5]

Regulatory actions

In 2002, the U.S. Food and Drug Administration (FDA) issued a notice under the Drug Efficacy Study Implementation (DESI) program resolving outstanding issues for trimethobenzamide hydrochloride injection and capsules, confirming their efficacy for treating postoperative nausea and vomiting based on substantial evidence from adequate and well-controlled studies.^[5] This action also declared that marketing of any unapproved trimethobenzamide hydrochloride capsule formulations was unlawful and subject to regulatory enforcement, requiring manufacturers to provide proof of efficacy or cease distribution.^[27] No changes were made to the approvals for oral capsules or intramuscular injections, which remained available. A significant regulatory decision occurred in 2007 when the FDA withdrew approval for trimethobenzamide hydrochloride suppositories, effective May 9, following a long-standing DESI review initiated in 1979 that found a lack of substantial evidence demonstrating their efficacy for nausea and vomiting.^[28] The agency ordered manufacturers to immediately cease production and distribution of these suppository products, deeming their continued marketing illegal without an approved new drug application. This action stemmed from the 1979 DESI evaluation, which had provided an opportunity for hearings but ultimately concluded the suppositories did not meet modern efficacy standards.^[29] These U.S. regulatory changes shifted clinical use of trimethobenzamide to oral and intramuscular formulations only, enhancing focus on routes with established efficacy while eliminating the suppository option due to insufficient supporting data. As of 2025, there have been no reported FDA recalls or additional safety-related actions for approved trimethobenzamide products.^[30] Internationally, trimethobenzamide remains approved in select countries, including Canada and some Latin American nations, though formulations vary and often exclude suppositories; in the European Union, it has limited status with no centralized approval through the European Medicines Agency post-2000s.^[16]

Society and culture

Legal status

In the United States, trimethobenzamide is classified as a prescription-only medication and is not subject to control under any DEA schedule, as it has no recognized potential for abuse.^[31] The FDA has approved it in oral capsule form (300 mg) and intramuscular injection (100 mg/mL) for the treatment of nausea and vomiting.^[1]^[9] Internationally, trimethobenzamide requires a prescription for availability in Canada and select regions, with limited use in Europe and other markets; it is not approved or marketed as an over-the-counter product anywhere.^[16] As of 2025, its regulatory status remains unchanged, and suppository formulations continue to be withdrawn in the United States.^[28]^[32]

Brand names and availability

Trimethobenzamide is primarily marketed under the brand name Tigan, originally developed and manufactured by King Pharmaceuticals, which was acquired by Pfizer in 2010.^[33]^[34] Historical brand names include Tebamide, associated with earlier formulations of the drug.^[35] Generic versions of trimethobenzamide hydrochloride have been widely available in the United States since the expiration of the original patents. Pfizer discontinued the branded Tigan capsules in 2021, leading to a temporary shortage that was resolved with the launch of generic capsules by Chartwell in late 2023; other manufacturers include Lupin and Par Pharmaceuticals (for injection).^[34]^[36]^[37] Current formulations include 300 mg oral capsules and 200 mg/2 mL intramuscular injection vials for single-dose use.^[17]^[38] Rectal suppositories were discontinued in the U.S. in 2007 due to FDA withdrawal of approval for lack of proven efficacy.^[28] The drug is most commonly available in the United States, with limited presence in other regions such as Turkey (marketed as Emedur), and is not widely marketed in Europe or Asia.^[16]^[39] Trimethobenzamide is available only by prescription and is not sold over-the-counter in any country.^[40]

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