Fact-checked by Grok 2 weeks ago

Chlorprothixene

Chlorprothixene is a low-potency, first-generation medication belonging to the thioxanthene class, primarily used for the treatment of and other psychotic disorders. It was first marketed in under trade names such as Taractan and Truxal, and remains available in 16 countries despite the advent of newer antipsychotics. As a thioxanthene , chlorprothixene exhibits effects through its blockade of D1, D2, and D3 receptors, alongside antagonism of serotonin 5-HT2, H1, muscarinic , and alpha-1 adrenergic receptors. This multifaceted receptor binding profile also contributes to its and properties, making it useful beyond management. The drug depresses activity in the hypothalamic-hypophyseal hormone system and the reticular activating system, which underlies its calming effects on the . Compared to , a , chlorprothixene demonstrates approximately half to two-thirds the potency, requiring higher doses for equivalent therapeutic effects. Clinically, chlorprothixene is indicated for acute and chronic psychoses, including , and for managing manic episodes in . It is also employed off-label at low doses for its sedative-hypnotic properties, particularly in treating , anxiety, and neuroses due to its favorable tolerability profile at these levels. Administration is typically oral, with dosages ranging from 25-400 mg daily for effects, though it is contraindicated in patients with circulatory collapse, , or to the drug. Common side effects of chlorprothixene mirror those of other typical antipsychotics, including drowsiness, , muscle tremors, and such as and . It carries a of cardiometabolic adverse events, with studies showing an increased hazard of (adjusted HR 1.34) and major cardiovascular events (adjusted HR 1.12) compared to low-dose , particularly at cumulative doses exceeding 6000 mg for and 1500 mg for cardiovascular risks. Allergic reactions and liver damage occur less frequently than with , but monitoring for hematologic effects like is recommended. Despite its long history, chlorprothixene's use has declined in favor of atypical antipsychotics with lower side effect burdens, though it retains a niche role in certain clinical settings.

Medical Uses

Approved Indications

Chlorprothixene is approved as a for the treatment of psychotic disorders, including and other related psychoses, where it helps alleviate symptoms such as hallucinations, delusions, and thought disorders. Clinical trials have demonstrated its efficacy in reducing these core psychotic symptoms, with early double-blind studies showing significant improvements in patients with prominent delusions and hallucinations compared to . It is also indicated for the management of acute in , where it stabilizes mood and reduces agitation during manic episodes. Regulatory approvals in European countries, such as and the , support its use in these conditions based on established activity. For severe anxiety and , chlorprothixene is approved in certain jurisdictions, leveraging its properties to promote calming effects. Dosing guidelines typically start with 15-30 orally per day, divided into 2-3 doses, and may be titrated up to a maximum of 400 per day based on response and tolerability. For acute , intramuscular of 50-100 may be used, with subsequent transition to oral therapy. These regimens are derived from national product monographs and clinical recommendations in approving regions.

Off-Label Uses

Chlorprothixene has been employed off-label in low doses as a sedative-hypnotic agent for the treatment of , particularly in cases where standard therapies like benzodiazepines prove ineffective. This application leverages its calming properties to promote without the dependency risks associated with traditional hypnotics, though long-term use raises concerns about cardiometabolic side effects. In palliative care settings, chlorprothixene serves as an adjunctive therapy for managing and , drawing on its potent properties akin to other typical antipsychotics. This off-label role is particularly relevant for refractory symptoms in advanced illness, where antagonism helps control emetic pathways, though evidence remains largely observational rather than from large-scale trials. Chlorprothixene has shown utility in the management of withdrawal symptoms, including and associated psychoses, due to its sedative and effects that mitigate and hallucinations. Pediatric applications of chlorprothixene are limited and approached with caution owing to insufficient efficacy and safety data in children; nonetheless, it has been investigated for and behavioral disturbances in children with disorders. Early studies indicate modest benefits in disturbed children with disorders, but risks such as and necessitate careful monitoring and low dosing. As a co-medication in management, chlorprothixene exhibits potential despite unproven direct or mechanisms, with reports of relief in about one-third of patients with intractable conditions like post-herpetic neuralgia. This effect may stem from its modulation of central pathways, as evidenced in small uncontrolled trials where rapid alleviation occurred in most cases within days. Historically, chlorprothixene found use in treating neuroses, valued for its effects and low profile compared to earlier antipsychotics. This application, prominent in the mid-20th century, highlighted its role in calming anxious or reactive states without severe adverse reactions, influencing its off-label adoption in milder psychiatric conditions.

Safety and Tolerability

Side Effects

Chlorprothixene, a , is associated with a range of adverse effects that are generally dose-dependent and more pronounced during the initial phases of treatment. These side effects share similarities with those of other low-potency antipsychotics, such as , but allergic reactions and occur less frequently. Common side effects include strong manifesting as and , which affect more than 10% of patients, as well as anticholinergic symptoms such as dry mouth, , blurred vision (accommodation disorder), and . Cardiovascular effects like and are also frequent, occurring in 1-10% of users, alongside and increased appetite due to metabolic changes. Extrapyramidal symptoms (EPS), including , , and , are reported but at a lower incidence compared to high-potency phenothiazines, with being common (1-10%) and akathisia or uncommon (0.1-1%). Other notable effects encompass such as and decreased libido (uncommon), as well as rare instances of (NMS), a potentially life-threatening condition involving , muscle rigidity, and autonomic instability. In special populations, elderly patients exhibit heightened sensitivity to chlorprothixene, with increased risks of falls due to and , as well as confusion from effects. Compared to , chlorprothixene carries a reduced likelihood of allergic reactions or liver damage, making it somewhat better tolerated in this regard. Monitoring recommendations include regular assessment for through clinical evaluation and for metabolic changes such as and glucose intolerance, particularly in long-term use, to mitigate cardiometabolic risks.

Contraindications

Chlorprothixene is absolutely contraindicated in patients with to the drug, other thioxanthenes, or any excipients, as well as in those with cross-sensitivity to phenothiazines or thiothixene. It is also contraindicated in cases of circulatory , depressed level of (such as from , barbiturates, or opiates), , or blood dyscrasias including diseases of the hematopoietic system. The drug is contraindicated in patients with clinically significant cardiovascular disorders, including congestive heart failure, cardiac decompensation, , cerebral vascular disorders, recent , uncompensated , cardiac hypertrophy, or arrhythmias treated with class 1A or III antiarrhythmics, due to the risk of and QT prolongation. Additionally, it is contraindicated in individuals with a history of ventricular arrhythmias or Torsade de Pointes, congenital , acquired QT prolongation (QTc >450 ms in males or >470 ms in females), or uncorrected hypokalaemia or hypomagnesaemia. Other absolute contraindications include acute narrow-angle , particularly in patients with a shallow anterior chamber, where effects may precipitate acute attacks. Chlorprothixene should not be used concurrently with large amounts of or other central nervous system depressants, as this can lead to severe CNS depression or . Relative contraindications include , as chlorprothixene can lower the , and , where it may worsen . Use with caution in patients with severe hepatic or renal impairment. Use during is not recommended unless the potential benefit justifies the risk to the ( C). In breastfeeding, chlorprothixene is excreted into in small amounts, and its use should be avoided if possible, with close monitoring of the for adverse effects if administration is necessary.

Overdose

Chlorprothixene overdose can manifest as extreme progressing to , along with confusion, , , respiratory depression, seizures, and cardiac arrhythmias such as ventricular extrasystoles or fibrillation. Other features include muscle trembling or jerking, , or , and in severe cases, renal impairment or QT prolongation potentially leading to . Therapeutic blood concentrations of chlorprothixene typically range from 0.02 to 0.3 mg/L, with toxicity emerging above 0.4 mg/L and fatalities reported at postmortem levels from 0.1 to 7.0 mg/L, including one case at 0.90 mg/L where chlorprothixene was the primary cause. Oral doses up to approximately 0.4 mg/kg are generally tolerated in therapeutic contexts for adults, but intakes exceeding 1 g often result in severe , with fatal doses estimated at 2.5–4 g in adults and around 4 mg/kg in infants. Higher doses precipitate cardiovascular collapse, including cardiodepression and . Management is entirely supportive, as no specific antidote exists, and focuses on immediate decontamination via gastric lavage and administration of activated charcoal if ingestion occurred recently. Vital signs require close monitoring, with mechanical ventilation for respiratory depression, intravenous fluids and vasopressors (avoiding epinephrine due to risk of further hypotension) for cardiovascular instability, and continuous ECG surveillance for arrhythmias. Seizures should be treated with benzodiazepines such as diazepam, while extrapyramidal reactions may respond to anticholinergics like biperiden; in refractory cases, extracorporeal methods like hemoperfusion have facilitated drug elimination and recovery. Prognosis is favorable with early intervention, as evidenced by survivals following ingestions of up to 10 g in adults and 1 g in children, though the drug's elimination of 8–12 hours (potentially longer in the elderly) can prolong toxic effects and complicate recovery. Delays in treatment increase risks of cardiorespiratory arrest or secondary complications like from prolonged respiratory depression.

Drug Interactions

Chlorprothixene, as a , exhibits significant pharmacokinetic and pharmacodynamic interactions with various medications, primarily due to its effects on the (CNS) and hepatic . Concomitant use with CNS depressants such as opioids, benzodiazepines, and can lead to additive and respiratory , necessitating careful monitoring and potential dose reductions of the CNS depressant to mitigate risks. Interactions with anticholinergic agents, including antidepressants and antiparkinsonian drugs, can enhance effects, potentially resulting in severe dry mouth, , or paralytic . These amplified side effects underscore the need for caution in scenarios involving such agents. Co-administration with increases the risk of lithium , requiring close monitoring of lithium plasma levels to prevent toxicity. Similarly, combining chlorprothixene with heightens the risk of CNS depression and may lower the seizure threshold, potentially precipitating or seizures. Chlorprothixene undergoes hepatic metabolism primarily via the (CYP) 2D6 enzyme; inhibitors such as can elevate chlorprothixene plasma levels, increasing the risk of adverse effects, while inducers like may decrease its efficacy by accelerating metabolism. Clinical recommendations include dose adjustments for interacting agents, particularly opioids and CYP modulators, along with routine ECG monitoring for prolongation when used with other antipsychotics or QT-prolonging drugs to avoid cardiac arrhythmias.

Pharmacology

Pharmacodynamics

Chlorprothixene, a of the thioxanthene class, primarily mediates its therapeutic effects through antagonism of D1 and D2 receptors in the of the , which reduces excessive activity associated with psychotic symptoms such as hallucinations and delusions. This blockade inhibits postsynaptic signaling, thereby alleviating positive symptoms of . Additionally, chlorprothixene depresses the release of hypothalamic and hypophyseal hormones, contributing to its broader effects on neuroendocrine function. The drug exhibits strong antagonism at multiple other receptor types, including serotonin 5-HT<sub>2A</sub> receptors (which mitigates extrapyramidal side effects by balancing D<sub>2</sub> blockade), H<sub>1</sub> receptors (responsible for properties), muscarinic receptors (leading to effects like dry mouth and ), and α<sub>1</sub>-adrenergic receptors (associated with ). These interactions underlie both its therapeutic benefits and adverse effects profile. Binding affinities reflect this potency, with approximate K<sub>i</sub> values of 18 nM at D<sub>1</sub>, 2.96 nM at D<sub>2</sub>, 4.56 nM at D<sub>3</sub>, 9 nM at D<sub>5</sub>, and 3.75 nM at H<sub>1</sub> receptors, as determined from standardized screening assays. For 5-HT<sub>2A</sub>, affinities are in the range of 0.3–0.4 nM, indicating high potency. Chlorprothixene's receptor profile provides a relatively balanced , where concomitant 5-HT<sub>2A</sub> and muscarinic blockade counteracts the propensity for (EPS) that might otherwise arise from selective D<sub>2</sub> , resulting in milder motor side effects compared to some other typical antipsychotics. Furthermore, D<sub>2</sub> receptor blockade in the pituitary lactotroph cells competes with endogenous dopamine's inhibitory action on adenylate cyclase, leading to elevated secretion and potential endocrine effects such as or menstrual irregularities.

Pharmacokinetics

Chlorprothixene exhibits incomplete oral , with of approximately 17% for the oral solution due to significant presystemic . Relative to the oral solution, is about 56% for coated tablets and 68% for suspensions. Peak plasma concentrations are typically reached within 2 to 5 hours following . Intramuscular administration results in faster onset of effects, occurring within 10 to 30 minutes. The drug is highly bound to plasma proteins, with binding rates exceeding 95%. Chlorprothixene has a large apparent at , approximately 1035 L, indicating extensive tissue distribution. As a lipophilic , it readily crosses the blood-brain barrier to exert central effects. Chlorprothixene undergoes hepatic primarily via enzymes, including and CYP3A4. Key metabolic pathways include N-demethylation to the N-desmethylchlorprothixene, as well as sulfoxidation to chlorprothixene and epoxidation. The elimination of chlorprothixene is 8 to 12 hours. Excretion occurs mainly through and , with free chlorprothixene and its detectable in both. Genetic polymorphisms in can influence clearance rates, potentially leading to prolonged in poor metabolizers. Steady-state concentrations are generally achieved after 3 to 5 days of regular dosing.

Chemistry

Structure and Properties

Chlorprothixene is a thioxanthene derivative characterized by the molecular formula C₁₈H₁₈ClNS and a molecular weight of 315.86 g/mol. Its molecular structure consists of a tricyclic thioxanthene core, formed by two benzene rings fused to a central dibenzo-1,4-thiazepine ring containing a sulfur atom, with a chlorine substituent at the 2-position and a (Z)-3-(dimethylamino)propylidene side chain attached at the 9-position. This configuration contributes to its classification as a typical antipsychotic within the thioxanthene class. In its pure form, chlorprothixene appears as a white to pale yellow crystalline powder. Key physical properties include a of 97–98 °C for the , a of 160 °C at 0.04 , an estimated of 1.1048 g/cm³, and an estimated of 1.6000. These attributes reflect its solid-state behavior under standard laboratory conditions. Chlorprothixene exhibits limited in , with a reported value of approximately 0.386 mg/L at 22.5 °C, rendering it slightly soluble, while it demonstrates good in organic solvents such as methylene chloride and . It possesses a pKₐ of 9.3, indicating character due to the tertiary amine group in the side chain. Regarding , chlorprothixene is light-sensitive and prone to degradation in air, necessitating storage in airtight, light-protected containers to maintain integrity.

Synthesis

Chlorprothixene is synthesized primarily through the construction of the thioxanthene core followed by attachment and modification of the at the 9-position. The core begins with the reaction of 2-mercapto and 1-bromo-4-chlorobenzene to form 2-(4-chlorophenylthio), which is then converted to the acid using and undergoes intramolecular cyclization in the presence of aluminum chloride to yield 2-chlorothioxanthone. The side chain is introduced via a of 2-chlorothioxanthone with 3-(dimethylamino)propylmagnesium bromide, producing a tertiary intermediate. of this is achieved through with to form the , followed by , resulting in the exocyclic characteristic of chlorprothixene. An alternative route involves reaction of the thioxanthone with allylmagnesium bromide to form an allylic , which is chlorinated using to generate a intermediate; subsequent addition of at elevated temperatures completes the side chain. The substituent at the 2-position (beta to the in the central ring) of the thioxanthene core enhances activity compared to unsubstituted analogs, as determined from structure-activity studies of thioxanthene derivatives. Structural variations, such as modifications to the or ring substitutions, have led to related compounds like clopenthixol, which retains the core but alters the functionality for improved potency. The exocyclic at C9 exhibits E/Z isomerism, with the Z-isomer generally showing higher neuroleptic activity. This synthesis was developed by , the Danish pharmaceutical company that first introduced chlorprothixene in 1959.

History

Development

Chlorprothixene was developed in the 1950s by the Danish pharmaceutical company H. & Co. as a of antipsychotics, particularly , which had revolutionized psychiatric earlier that decade. The project was spearheaded by Poul Viggo Petersen, who aimed to create a new class of neuroleptics with enhanced tolerability by modifying the central ring of the scaffold—replacing the atom with a carbon-carbon to form the thioxanthene structure while retaining the atom. This structural innovation was intended to preserve potent effects while mitigating the and burden associated with phenothiazines, such as pronounced and autonomic disturbances. Synthesis of chlorprothixene occurred in the late , marking it as the prototype for the thioxanthene class of s. filed a for the compound in 1958, securing ahead of competitors like Merck and , who pursued similar structures through alternative synthetic routes. Initial preclinical screening focused on potential using established animal models prevalent in at the time, including of amphetamine-induced stereotypies and hyperactivity in , which served as proxies for dopamine-mediated psychotic behaviors. These tests confirmed chlorprothixene's potential by antagonizing amphetamine-induced stereotypies and hyperactivity in , behaviors associated with hyperactivity in psychotic models. Preclinical evaluations further highlighted chlorprothixene's favorable profile, demonstrating effective blockade alongside reduced induction of —a model of extrapyramidal side effects—in comparison to phenothiazines. This suggested a lower of motor disturbances and overall , with studies in animals indicating a superior to . Such findings positioned chlorprothixene as a promising advancement, paving the way for its recognition as the inaugural thioxanthene and influencing subsequent developments in the class.

Clinical Introduction

Chlorprothixene underwent initial human clinical trials in the late 1950s and early 1960s, primarily evaluating its efficacy in treating and other psychotic disorders. Phase I and II studies demonstrated its effects, with early reports indicating symptom reduction in patients with , including alleviation of hallucinations and agitation. Notably, these trials highlighted chlorprothixene's favorable side effect profile compared to contemporaries like , showing efficacy in while producing fewer (EPS), such as and . The drug received regulatory approval and was introduced in in 1959 by under the brand name Truxal, marking it as one of the early thioxanthene-class antipsychotics available for clinical use. In the United States, it was approved by the FDA and marketed as Taractan by Laboratories starting in 1962, initially for the management of psychotic disorders including . Early adoption of chlorprothixene was rapid in psychiatric practice during the , particularly for acute psychoses, , and manic episodes, where its strong properties provided rapid calming effects without excessive motor side effects. Key studies from this period, including comparative trials against , confirmed these benefits, supporting its use in agitated patients and contributing to its widespread application in settings. As an established first-generation , chlorprothixene has seen no major updates in research or indications since the , reflecting its role as a mature therapeutic option. In the US, Taractan was discontinued in 1997 amid the rise of newer antipsychotics with improved tolerability profiles.

Society and Culture

Brand Names

Chlorprothixene is primarily marketed under the brand name Truxal by H. Lundbeck A/S, available in multiple European countries including , , , , , , , the Netherlands, Norway, and . This brand is formulated as film-coated tablets in strengths such as 15 mg, 25 mg, and 50 mg. Other historical and regional brand names include Taractan (by ), which was used in the United States until its discontinuation due to lack of market success, Cloxan (by ), and Clothixen (by Yoshitomi). Generic forms of chlorprothixene are widely available as chlorprothixene , most commonly in oral tablet formulations with strengths ranging from 15 mg to 50 mg. , no active brand names exist following the withdrawal of Taractan, and the drug is not approved for use.

Availability

Chlorprothixene is widely available across , where it is authorised in multiple countries including , , , , , , , , the , , and , as well as and the , available in 16 countries as of 2025 including . It is commonly prescribed in and for psychiatric conditions, and in the UK it is accessible via imported formulations such as Truxal tablets from . In other regions, chlorprothixene is available in parts of , such as , and in various countries in , though access is more limited compared to . Availability in and remains restricted, with no widespread marketing of finished pharmaceutical products. In the United States, chlorprothixene was previously marketed under the brand name Taractan by but was discontinued in the due to lack of commercial success, and it is no longer available for prescription. Common formulations include oral tablets in strengths of 15 mg, 25 mg, 50 mg, and 90 mg in some formulations; oral solutions, such as 4% preparations suitable for pediatric use; and intramuscular injections at 25 mg/mL. Brand names like facilitate access in authorised markets. As an established older medication, chlorprothixene maintains stable supply chains globally, with no reported shortages as of 2025. Chlorprothixene is classified as a prescription-only medication (Rx-only) worldwide in jurisdictions where it remains available. In the , chlorprothixene is authorized as a nationally authorized medicinal product and requires a prescription for dispensing. In , it falls under of the Drugs and Cosmetics Rules, 1945, mandating sale only upon presentation of a valid prescription from a registered medical practitioner. In the , it is designated as a Prescription Only (POM), restricting its supply to prescriptions issued by authorized healthcare professionals. In , chlorprothixene is categorized as Class C1 among other controlled substances, subjecting it to specific regulatory oversight for possession and distribution. In the United States, chlorprothixene is not scheduled under the administered by the , though it has been withdrawn from the market and is no longer commercially available. While used historically in for , it is prohibited in equine sports and competitions in certain jurisdictions due to anti-doping regulations. Import and are subject to controls in various nations, often requiring licenses due to its as a regulated pharmaceutical. As of November 2025, no regulatory changes to chlorprothixene's status have been reported globally. It continues to be monitored for potential, particularly owing to its pronounced properties that may contribute to misuse in vulnerable populations. This contrasts with its ongoing availability in compared to its discontinuation in the .