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| 10mg |
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| Targets |
D2 Receptor
Haloperidol decanoate targets the central dopamine D2 receptor. The prodrug itself has no intrinsic activity; its pharmacodynamic actions are those of haloperidol—primarily that of central antidopamine activity. Haloperidol antagonises the effects of apomorphine and amphetamine and releases prolactin. After intramuscular injection, haloperidol decanoate is gradually released from muscle tissue and hydrolyzed slowly into free haloperidol which enters the systemic circulation. The D2 receptor antagonism underlies its antipsychotic effects. |
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| ln Vitro |
Haloperidol decanoate is an organic molecular entity.
Haloperidol Decanoate is the decanoate ester of haloperidol, a phenylbutylpiperadine derivative with antipsychotic, neuroleptic and antiemetic effects. Haloperidol competitively blocks postsynaptic dopamine (D2) receptors in the mesolimbic system of the brain leading to anti-delusionary and anti-hallucinogenic effects. The antagonistic activity mediated through D2 dopamine receptors in the chemoreceptive trigger zone (CTZ) account for its antiemetic activity.
In vitro, haloperidol decanoate has no intrinsic activity as it is a prodrug. Its pharmacodynamic actions are those of haloperidol following hydrolysis. Haloperidol itself acts as a potent antagonist at dopamine D2 receptors, as well as having affinity for D1 receptors, serotonin 5-HT2A receptors, histamine H1 receptors, and alpha-1 adrenergic receptors. The compound's effects on dopamine receptor signaling have been extensively studied in cell-based assays using receptor-expressing cell lines. |
| ln Vivo |
Haloperidol decanoate is a depot preparation of haloperidol, a commonly used butyrophenone derivative with antipsychotic activity. Haloperidol decanoate has no intrinsic activity: its pharmacodynamic actions are those of haloperidol--primarily that of central antidopamine activity. The monthly administered depot formulation has several clinical and practical advantages over oral haloperidol: better compliance and more predictable absorption; more controlled plasma concentrations; fewer extrapyramidal side effects; less frequent reminders of condition; and reduced medical workload. In open and controlled studies, haloperidol decanoate has produced adequate maintenance or improvement of the condition of patients with psychoses (mainly schizophrenia) when an abrupt change from orally administered haloperidol or other antipsychotic drugs has been instituted. Limited comparative studies indicate that the depot and oral forms of haloperidol are equally effective, and that haloperidol decanoate is at least as effective as depot forms of fluphenazine, pipothiazine, flupenthixol and perphenazine in controlling the symptoms of psychosis. Extrapyramidal side effects and the need for concomitant anti-Parkinsonian drugs may be a problem, but may be less frequent than with oral haloperidol or other depot antipsychotics. Thus, haloperidol decanoate offers a useful alternative in the treatment of psychoses to orally administered haloperidol or to other depot antipsychotic drugs[1].
In vivo, haloperidol decanoate provides sustained antipsychotic activity through gradual release and hydrolysis of the ester bond. The depot formulation achieves a ~3-week elimination half-life for 4-week dosing intervals. Plasma concentrations following the decanoate injection are generally lower than, but clinically equivalent to, those attained with the oral form of the drug. The recommended dose of haloperidol decanoate is 20 times that of the daily oral dose (mg/day) given monthly, reduced to a factor of 15 in geriatric patients. Steady-state plasma levels are achieved in 2-3 months. |
| Enzyme Assay |
In cell-free receptor binding assays, haloperidol demonstrates high affinity binding to dopamine D2 receptors. Radioligand displacement studies using membrane preparations from cells expressing recombinant receptors are used to determine the compound's binding affinity. Haloperidol also shows affinity for D1 receptors, serotonin 5-HT2A receptors, histamine H1 receptors, and alpha-1 adrenergic receptors. The prodrug haloperidol decanoate is not typically evaluated in cell-free assays due to its lack of intrinsic activity.
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| Cell Assay |
Cellular assays for haloperidol decanoate typically involve evaluating the activity of the released haloperidol at dopamine D2 receptors expressed in cell lines. Receptor signaling assays measure the compound's ability to antagonize dopamine-induced responses, such as cAMP accumulation or calcium mobilization. The prodrug itself is not active in these assays; hydrolysis to haloperidol is required for activity. Studies have also examined the compound's effects on prolactin release in pituitary cell cultures.
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| Animal Protocol |
Animal models for haloperidol decanoate include rodent models of psychosis and dopamine-mediated behaviors. The compound is administered via intramuscular injection to evaluate its sustained antipsychotic effects. Studies have examined the compound's ability to antagonize apomorphine-induced behaviors and amphetamine-induced hyperactivity. The compound's effects on prolactin release have also been studied in animal models. The depot formulation provides sustained drug levels and prolonged pharmacological effects compared to oral haloperidol.
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| ADME/Pharmacokinetics |
Pharmacokinetic studies show that haloperidol decanoate has an elimination half-life of approximately 3 weeks, allowing for 4-week dosing intervals. Plasma concentrations following decanoate injection are generally lower than, but clinically equivalent to, those attained with oral haloperidol. The prodrug is hydrolyzed slowly to release free haloperidol. Steady-state plasma levels are achieved in 2-3 months. The molecular weight is 530.1 g/mol with a formula of C31H41ClFNO3. The compound is soluble in DMSO and should be stored dry, dark, at 0-4°C for short term or -20°C for long term.
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| Toxicity/Toxicokinetics |
Female TDLo intravenous injection 11600 ug/kg/4D Cardiac: arrhythmia (including conduction changes); Cardiac: ECG changes, but the above diseases cannot be diagnosed; Cardiac: heart rate changes. Annals of Internal Medicine, 119(391), 1993 [PMID:8338292]
Rat LD50 oral 1717 mg/kg Sensory organs and special senses: tearing: eyes; Sensory organs and special senses: ptosis: eyes; Behavior: somnolence (reduced overall activity) Kiso to Rinsho. Clinical Reports, 19(6731), 1985 Intraperitoneal LD50 in rats: 328 mg/kg. Sensory organs and special senses: tearing: eye; sensory organs and special senses: ptosis: eye; behavior: lethargy (reduced overall activity). Kiso to Rinsho. Clinical Reports, 19(6731), 1985 Subcutaneous LD50 in rats: 780 mg/kg. Sensory organs and special senses: tearing: eye; sensory organs and special senses: ptosis: eye; behavior: lethargy (reduced overall activity). Kiso to Rinsho. Clinical Reports, 19(6731), 1985 Intramuscular LD50 in rats: >1525 mg/kg. Sensory organs and special senses: tearing: eye; sensory organs and special senses: ptosis: eye; behavior: lethargy (reduced overall activity). Kiso to Rinsho. Clinical Reports, 19(6731), 1985 Haloperidol decanoate is generally well-tolerated as a depot antipsychotic. Common side effects are those associated with haloperidol, including extrapyramidal symptoms, sedation, and hyperprolactinemia. ACLAIMS RCT data show mean 3.8 kg weight loss over 24 months vs. 6.0 kg gain with paliperidone palmitate (p<0.001). The compound is 19F MRS-compatible for non-invasive injection-site pharmacokinetic tracking. Standard safety precautions for handling pharmaceutical compounds apply. |
| References |
[1]. Haloperidol decanoate. A preliminary review of its pharmacodynamic and pharmacokinetic properties and therapeutic use in psychosis. Drugs. 1987 Jan;33(1):31-49.
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| Additional Infomation |
Haloperidol decanoate is an organic molecular entity. Haloperidol decanoate is the decanoate ester of haloperidol, a phenylbutylpiperidine derivative with antipsychotic, anti-nerve-blocking, and antiemetic effects. Haloperidol competitively blocks postsynaptic dopamine (D2) receptors in the limbic system of the brain, thereby producing anti-delusional and anti-hallucinatory effects. Its antiemetic activity originates from antagonistic action mediated by D2 dopamine receptors in the chemoreceptor trigger zone (CTZ). See also: Haloperidol (containing the active moiety).
Haloperidol decanoate is a long-acting injectable depot formulation of haloperidol, a butyrophenone typical antipsychotic. It is used for the treatment of psychoses, offering a useful alternative to orally administered haloperidol or to other depot antipsychotic drugs. The prodrug has no intrinsic activity and requires hydrolytic activation to haloperidol for D2 antagonism. The compound is for research use only and not for human administration. The CAS number is 74050-97-8. |
| Molecular Formula |
C31H41CLFNO3
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|---|---|
| Molecular Weight |
530.11
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| Exact Mass |
529.276
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| Elemental Analysis |
C, 70.24; H, 7.80; Cl, 6.69; F, 3.58; N, 2.64; O, 9.05
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| CAS # |
74050-97-8
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| PubChem CID |
52919
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| Appearance |
Typically exists as White to off-white solid at room temperature
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| Density |
1.14 g/cm3
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| Boiling Point |
615.5ºC at 760 mmHg
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| Melting Point |
326.1ºC
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| Flash Point |
326.1ºC
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| Index of Refraction |
1.554
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| LogP |
8.055
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
16
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| Heavy Atom Count |
37
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| Complexity |
665
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCCCCCCCCC(OC1(C2C=CC(Cl)=CC=2)CCN(CCCC(C2C=CC(F)=CC=2)=O)CC1)=O
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| InChi Key |
GUTXTARXLVFHDK-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C31H41ClFNO3/c1-2-3-4-5-6-7-8-11-30(36)37-31(26-14-16-27(32)17-15-26)20-23-34(24-21-31)22-9-10-29(35)25-12-18-28(33)19-13-25/h12-19H,2-11,20-24H2,1H3
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| Chemical Name |
[4-(4-chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl] decanoate
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| Synonyms |
HALOPERIDOL DECANOATE; 74050-97-8; Halomonth; Haldol decanoate; Haldol decanoas; Depot haloperidol; Haloperidol depot; KD 16;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~188.64 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.72 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.8864 mL | 9.4320 mL | 18.8640 mL | |
| 5 mM | 0.3773 mL | 1.8864 mL | 3.7728 mL | |
| 10 mM | 0.1886 mL | 0.9432 mL | 1.8864 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT00947375 | TERMINATED | Drug: Lamictal TM Drug: Haloperidol Decanoate |
Schizophrenia | Central Mental Clinic for Outpatients of Baku City | 2005-01 | Phase 4 |
| NCT05995457 | NOT YET RECRUITING | Other: Intramuscular injection of Haloperidol decanoate using the "Z-track" and "Airlock" techniques Other: Intramuscular injection of Haloperidol decanoate using standard techniques |
Schizophrenia; Psychosis | Centre Hospitalier St Anne/td> | 2023-09-01 | Not Applicable |
| NCT00018642 | COMPLETED | Drug: quetiapine Drug: haloperidol decanoate |
Schizoaffective Disorder Schizophrenia |
US Department of Veterans Affairs | 1997-04 | Not Applicable |
| NCT01174290 | COMPLETED | Drug: Haloperidol decanoate Drug: Placebo |
Subsyndromal Delirium | Northeastern University | 2010-09 | Phase 4 |
| NCT04327843 | COMPLETEDWITH RESULTS | Behavioral: Customized Adherence Enhancement Drug: Haloperidol Decanoate |
Medication Nonadherence Schizo Affective Disorder Schizophrenia |
Case Western Reserve University | 2019-11-05 | Phase 3 |
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