Details
Stereochemistry | RACEMIC |
Molecular Formula | C20H31NO |
Molecular Weight | 301.467 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
c1ccc(cc1)C(CCN2CCCCC2)(C3CCCCC3)O
InChI
InChIKey=HWHLPVGTWGOCJO-UHFFFAOYSA-N
InChI=1S/C20H31NO/c22-20(18-10-4-1-5-11-18,19-12-6-2-7-13-19)14-17-21-15-8-3-9-16-21/h1,4-5,10-11,19,22H,2-3,6-9,12-17H2
Molecular Formula | C20H31NO |
Molecular Weight | 301.467 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: http://www.drugbank.ca/drugs/DB00376Curator's Comment:: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/006773_s036_artane.pdf
Sources: http://www.drugbank.ca/drugs/DB00376
Curator's Comment:: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/006773_s036_artane.pdf
Trihexyphenidyl (Artane, Apo-Trihex, Parkin, Pacitane), also known as benzhexol and trihex has been in clinical usage for decades.It is an anticholinergic used in the symptomatic treatment of all etiologic groups of parkinsonism and drug induced extrapyramidal reactions (except tardive dyskinesia). Trihexyphenidyl possesses both anticholinergic and antihistaminic effects, although only the former has been established as therapeutically significant in the management of parkinsonism. Trihexyphenidyl is a selective M1 muscarinic acetylcholine receptor antagonist. It is able to discriminate between the M1 (cortical or neuronal) and the peripheral muscarinic subtypes (cardiac and glandular). Trihexyphenidyl partially blocks cholinergic activity in the CNS, which is responsible for the symptoms of Parkinson's disease. It is also thought to increase the availability of dopamine, a brain chemical that is critical in the initiation and smooth control of voluntary muscle movement. Trihexyphenidyl is indicated for the treatment of parkinson's disease and extrapyramidal reactions caused by drugs.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL216 Sources: http://www.drugbank.ca/drugs/DB00376 |
1.3 nM [IC50] | ||
Target ID: CHEMBL1821 |
6.7 nM [IC50] | ||
Target ID: CHEMBL2035 |
10.3 nM [IC50] | ||
Target ID: CHEMBL245 |
26.3 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Trihexyphenidyl hydrochloride Approved UseTrihexyphenidyl HCl tablets are indicated as an adjunct in the treatment of all forms of parkinsonism (postencephalitic, arteriosclerotic, and idiopathic). It is often useful as adjuvant therapy when treating these forms of parkinsonism with levodopa. Additionally, it is indicated for the control of extrapyramidal disorders caused by central nervous system drugs such as the dibenzoxazepines, phenothiazines, thioxanthenes, and butyrophenones. Launch Date-6.5136958E11 |
|||
Secondary | Trihexyphenidyl hydrochloride Approved UseTrihexyphenidyl HCl tablets are indicated as an adjunct in the treatment of all forms of parkinsonism (postencephalitic, arteriosclerotic, and idiopathic). It is often useful as adjuvant therapy when treating these forms of parkinsonism with levodopa. Additionally, it is indicated for the control of extrapyramidal disorders caused by central nervous system drugs such as the dibenzoxazepines, phenothiazines, thioxanthenes, and butyrophenones. Launch Date-6.5136958E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3225767/ |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIHEXYPHENIDYL serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
24.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3225767/ |
5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TRIHEXYPHENIDYL serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
294 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3225767/ |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIHEXYPHENIDYL serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
334 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3225767/ |
5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TRIHEXYPHENIDYL serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3225767/ |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TRIHEXYPHENIDYL serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
8.67 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3225767/ |
5 mg 2 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TRIHEXYPHENIDYL serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
0.55 mg/kg 1 times / day multiple, oral (mean) Highest studied dose Dose: 0.55 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.55 mg/kg, 1 times / day Sources: |
unhealthy, 1-18 years n = 101 Health Status: unhealthy Condition: cerebral palsy with dystonia or/and sialorrhea Age Group: 1-18 years Sex: M+F Population Size: 101 Sources: |
Disc. AE: Constipation, Gastrointestinal disorders... AEs leading to discontinuation/dose reduction: Constipation (2 patients) Sources: Gastrointestinal disorders (4 patients) Behaviour disorder (2 patients) Movements involuntary (1 patient) Drowsiness (1 patient) Skin rash (1 patient) |
40 mg multiple, oral Higher than recommended |
unhealthy, 25 years n = 1 Health Status: unhealthy Condition: drug and alcohol dependence Age Group: 25 years Sex: M Population Size: 1 Sources: |
Other AEs: Dependence... |
5 mg 28 times / day multiple, oral Higher than recommended Dose: 5 mg, 28 times / day Route: oral Route: multiple Dose: 5 mg, 28 times / day Sources: |
unhealthy, 35 years n = 1 Health Status: unhealthy Condition: schizophrenic Age Group: 35 years Sex: F Population Size: 1 Sources: |
Other AEs: Dependence... |
0.75 mg/kg 1 times / day multiple, oral (mean) Highest studied dose Dose: 0.75 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.75 mg/kg, 1 times / day Sources: |
unhealthy, 4-15 years n = 26 Health Status: unhealthy Condition: cerebral palsy Age Group: 4-15 years Sex: M+F Population Size: 26 Sources: |
Disc. AE: Chorea, Rash... AEs leading to discontinuation/dose reduction: Chorea (1 patient) Sources: Rash (1 patient) Hyperactivity (1 patient) |
24 mg 1 times / day multiple, oral (mean) Highest studied dose Dose: 24 mg, 1 times / day Route: oral Route: multiple Dose: 24 mg, 1 times / day Co-administed with:: ethopropazine(350 mg) Sources: |
unhealthy, adult n = 52 Health Status: unhealthy Condition: torsion dystonia Age Group: adult Sex: unknown Population Size: 52 Sources: |
|
41 mg 1 times / day multiple, oral (mean) Highest studied dose Dose: 41 mg, 1 times / day Route: oral Route: multiple Dose: 41 mg, 1 times / day Sources: |
unhealthy, children n = 23 Health Status: unhealthy Condition: torsion dystonia Age Group: children Sex: unknown Population Size: 23 Sources: |
|
8 mg 1 times / day multiple, oral (mean) Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Co-administed with:: neuroleptic Sources: |
unhealthy, mean 49.7 years n = 22 Health Status: unhealthy Condition: schizophrenia or mental retardation Age Group: mean 49.7 years Sex: M+F Population Size: 22 Sources: |
Other AEs: Extrapyramidal symptoms... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Drowsiness | 1 patient Disc. AE |
0.55 mg/kg 1 times / day multiple, oral (mean) Highest studied dose Dose: 0.55 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.55 mg/kg, 1 times / day Sources: |
unhealthy, 1-18 years n = 101 Health Status: unhealthy Condition: cerebral palsy with dystonia or/and sialorrhea Age Group: 1-18 years Sex: M+F Population Size: 101 Sources: |
Movements involuntary | 1 patient Disc. AE |
0.55 mg/kg 1 times / day multiple, oral (mean) Highest studied dose Dose: 0.55 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.55 mg/kg, 1 times / day Sources: |
unhealthy, 1-18 years n = 101 Health Status: unhealthy Condition: cerebral palsy with dystonia or/and sialorrhea Age Group: 1-18 years Sex: M+F Population Size: 101 Sources: |
Skin rash | 1 patient Disc. AE |
0.55 mg/kg 1 times / day multiple, oral (mean) Highest studied dose Dose: 0.55 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.55 mg/kg, 1 times / day Sources: |
unhealthy, 1-18 years n = 101 Health Status: unhealthy Condition: cerebral palsy with dystonia or/and sialorrhea Age Group: 1-18 years Sex: M+F Population Size: 101 Sources: |
Behaviour disorder | 2 patients Disc. AE |
0.55 mg/kg 1 times / day multiple, oral (mean) Highest studied dose Dose: 0.55 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.55 mg/kg, 1 times / day Sources: |
unhealthy, 1-18 years n = 101 Health Status: unhealthy Condition: cerebral palsy with dystonia or/and sialorrhea Age Group: 1-18 years Sex: M+F Population Size: 101 Sources: |
Constipation | 2 patients Disc. AE |
0.55 mg/kg 1 times / day multiple, oral (mean) Highest studied dose Dose: 0.55 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.55 mg/kg, 1 times / day Sources: |
unhealthy, 1-18 years n = 101 Health Status: unhealthy Condition: cerebral palsy with dystonia or/and sialorrhea Age Group: 1-18 years Sex: M+F Population Size: 101 Sources: |
Gastrointestinal disorders | 4 patients Disc. AE |
0.55 mg/kg 1 times / day multiple, oral (mean) Highest studied dose Dose: 0.55 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.55 mg/kg, 1 times / day Sources: |
unhealthy, 1-18 years n = 101 Health Status: unhealthy Condition: cerebral palsy with dystonia or/and sialorrhea Age Group: 1-18 years Sex: M+F Population Size: 101 Sources: |
Dependence | 1 patient | 40 mg multiple, oral Higher than recommended |
unhealthy, 25 years n = 1 Health Status: unhealthy Condition: drug and alcohol dependence Age Group: 25 years Sex: M Population Size: 1 Sources: |
Dependence | 1 patient | 5 mg 28 times / day multiple, oral Higher than recommended Dose: 5 mg, 28 times / day Route: oral Route: multiple Dose: 5 mg, 28 times / day Sources: |
unhealthy, 35 years n = 1 Health Status: unhealthy Condition: schizophrenic Age Group: 35 years Sex: F Population Size: 1 Sources: |
Chorea | 1 patient Disc. AE |
0.75 mg/kg 1 times / day multiple, oral (mean) Highest studied dose Dose: 0.75 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.75 mg/kg, 1 times / day Sources: |
unhealthy, 4-15 years n = 26 Health Status: unhealthy Condition: cerebral palsy Age Group: 4-15 years Sex: M+F Population Size: 26 Sources: |
Hyperactivity | 1 patient Disc. AE |
0.75 mg/kg 1 times / day multiple, oral (mean) Highest studied dose Dose: 0.75 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.75 mg/kg, 1 times / day Sources: |
unhealthy, 4-15 years n = 26 Health Status: unhealthy Condition: cerebral palsy Age Group: 4-15 years Sex: M+F Population Size: 26 Sources: |
Rash | 1 patient Disc. AE |
0.75 mg/kg 1 times / day multiple, oral (mean) Highest studied dose Dose: 0.75 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.75 mg/kg, 1 times / day Sources: |
unhealthy, 4-15 years n = 26 Health Status: unhealthy Condition: cerebral palsy Age Group: 4-15 years Sex: M+F Population Size: 26 Sources: |
Extrapyramidal symptoms | 77% | 8 mg 1 times / day multiple, oral (mean) Recommended Dose: 8 mg, 1 times / day Route: oral Route: multiple Dose: 8 mg, 1 times / day Co-administed with:: neuroleptic Sources: |
unhealthy, mean 49.7 years n = 22 Health Status: unhealthy Condition: schizophrenia or mental retardation Age Group: mean 49.7 years Sex: M+F Population Size: 22 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Phenothiazines in early labour. | 1967 Feb 11 |
|
Drug-induced extrapyramidal symptoms: their incidence and treatment. | 1967 Jan |
|
Reversal of central anticholinergic syndrome in man by physostigmine. | 1968 Nov 25 |
|
Toxic psychosis induced by benzhexol hydrochloride. | 1970 Oct 10 |
|
Benzhexol-induced hallucinosis. | 1971 Mar 6 |
|
Benzhexol and side effects with long-acting fluphenazine therapy. | 1972 Jan 29 |
|
Benzhexol-induced blindness in Parkinson's disease. | 1972 Mar 4 |
|
An unusual response to chlorpromazine therapy. | 1972 Oct |
|
Toxic liver injuries. | 1973 Aug |
|
Abnormal involuntary movements induced by anticholinergic therapy. | 1974 |
|
Comparative trial of benzhexol, amantadine, and levodopa in the treatment of Parkinson's disease. | 1974 Apr |
|
[Outcome of Parkinsonism after two years of levodopa plus R04-4602 (author's transl)]. | 1975 Jul-Aug |
|
Amodiaquine-induced involuntary movements. | 1976 Jul 24 |
|
Skeletal muscle necrosis following membrane-active drugs plus serotonin. | 1976 May |
|
Anticholinergic exacerbation of phenothiazine-induced extrapyramidal syndrome. | 1976 Sep |
|
Death attributed to ventricular arrhythmia induced by thioridazine in combination with a single Contac C capsule. | 1978 Oct 7 |
|
Choreiform movements induced by anticholinergic therapy. | 1979 May 19 |
|
Neuroleptic malignant syndrome. | 1980 Jul |
|
Reversibility of long-term tardive dyskinesia associated with antiparkinsonian medication: a case report. | 1981 Aug |
|
Akathisia: an overlooked, distressing, but treatable condition. | 1981 Sep |
|
Catalepsy produced by long-acting neuroleptics, fluphenazine enanthate and fluphenazine decanoate, in mice. | 1982 |
|
Sexual dysfunction in women using major tranquilizers. | 1982 Sep |
|
Intravenous lorazepam in neuroleptic-induced catatonia. | 1983 Dec |
|
Malignant neuroleptic syndrome due to haloperidol. (A case report). | 1983 Jan |
|
Trihexyphenidyl dependence. | 1984 Jun |
|
Withdrawal of trihexyphenidyl. | 1985 Mar |
|
Pharmacological modification of DDT-induced tremor and hyperthermia in rats: distributional factors. | 1986 |
|
[Trihexyphenidyl (THP)-induced respiratory dyskinesia]. | 1986 Feb |
|
Bradycardia due to trihexyphenidyl hydrochloride. | 1986 Oct |
|
Binding and functional profiles of the selective M1 muscarinic receptor antagonists trihexyphenidyl and dicyclomine. | 1986 Sep |
|
Anticholinergic-induced chorea in the treatment of focal dystonia. | 1987 |
|
Lithium-induced akathisia. | 1987 Feb |
|
Dystonic reactions with metoclopramide: is there a risk population? | 1987 Jun |
|
Parkinson's disease and myasthenia gravis: adverse effect of trihexyphenidyl on neuromuscular transmission. | 1987 May |
|
[Parkinson's disease associated with trihexyphenidyl (THP) induced dysphonia plicae ventricularis]. | 1988 Apr |
|
Successful treatment of levodopa-induced myoclonus and levodopa withdrawal-induced neuroleptic malignant syndrome. A case report. | 1988 Jun |
|
Life-threatening cranial dystonia following trihexyphenidyl withdrawal. | 1989 |
|
Schizophrenic psychosis associated with benzhexol (artane) therapy. | 1989 Sep |
|
Memory and cognitive impairments in a case of long-term trihexyphenidyl abuse. | 1993 Mar |
|
[A 75-year-old man with parkinsonism and delirium]. | 1994 Jan |
|
Trihexyphenidyl as a possible therapeutic option in clozapine-induced nocturnal enuresis. | 1996 Mar |
|
Anticholinergic overdose induced torsade de pointes successfully treated with verapamil. | 1996 Nov |
|
Trihexyphenidyl withdrawal encephalopathy. | 1997 Jan |
|
Antiparkinsonian drugs causing inappropriate antidiuretic hormone secretion. | 1998 Jan |
|
Chronic haloperidol produces a time- and dose-related slowing of lick rhythm in rats: implications for rodent models of tardive dyskinesia and neuroleptic-induced parkinsonism. | 1998 May |
|
Anti-nicotinic properties of anticholinergic antiparkinson drugs. | 1998 Nov |
|
Risperidone-induced rabbit syndrome. | 1998 Sep |
|
Electromyography in cervical dystonia: changes after botulinum and trihexyphenidyl. | 1998 Sep |
|
Therapeutic and cosmeceutical potential of ethosomes: An overview. | 2010 Jul |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/trihexyphenidyl.html
Usual Adult Dose for Extrapyramidal Reaction
4 to 10 mg orally each day. The total daily dose is best tolerated when administered in 2 or three equally separated doses.
Usual Adult Dose for Parkinson's Disease
Initial: 1 mg/day; increase by 2 mg increments at intervals of 3 to 5 days
Usual dose: 6 to 10 mg/day in 3 to 4 divided doses; doses of 12 to 15 mg/day may be required
Drug-induced extrapyramidal symptoms: Initial: 1 mg/day; increase as necessary to usual range of 5 to 15 mg/day in 3 to 4 divided doses
Use in combination with levodopa: Usual range: 3 to 6 mg/day in divided doses
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1376014
Trihexyphenidyl 10, 50, and 100 umol/L depressed the maximal upstroke velocity (Vmax) and the action potential amplitude (APA) of SAP in guinea pig papillary muscles.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 11:31:38 UTC 2021
by
admin
on
Sat Jun 26 11:31:38 UTC 2021
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Record UNII |
6RC5V8B7PO
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C38149
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WHO-ATC |
N04AA01
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LIVERTOX |
999
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NCI_THESAURUS |
C29704
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WHO-VATC |
QN04AA01
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Code System | Code | Type | Description | ||
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7315
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SUB11295MIG
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Trihexyphenidyl
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3196
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2745
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6RC5V8B7PO
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5572
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10811
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144-11-6
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D014282
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205-614-4
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144-11-6
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1318
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CHEMBL1490
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C61988
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DB00376
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TRIHEXYPHENIDYL
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ACTIVE MOIETY |