Details
Stereochemistry | RACEMIC |
Molecular Formula | C20H31NO.ClH |
Molecular Weight | 337.927 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.OC(CCN1CCCCC1)(C2CCCCC2)C3=CC=CC=C3
InChI
InChIKey=QDWJJTJNXAKQKD-UHFFFAOYSA-N
InChI=1S/C20H31NO.ClH/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;1H
Molecular Formula | C20H31NO |
Molecular Weight | 301.4662 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
|
Toxic psychosis induced by benzhexol hydrochloride. | 1970 Oct 10 |
|
Benzhexol-induced blindness in Parkinson's disease. | 1972 Mar 4 |
|
Abnormal involuntary movements induced by anticholinergic therapy. | 1974 |
|
[Effects of diazepam on six drug-induced locomotor hyperactivities in mice (author's transl)]. | 1975 Dec 31 |
|
Amodiaquine-induced involuntary movements. | 1976 Jul 24 |
|
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 |
|
Withdrawal of trihexyphenidyl. | 1985 Mar |
|
Successful treatment of levodopa-induced myoclonus and levodopa withdrawal-induced neuroleptic malignant syndrome. A case report. | 1988 Jun |
|
[A 75-year-old man with parkinsonism and delirium]. | 1994 Jan |
|
Trihexyphenidyl withdrawal encephalopathy. | 1997 Jan |
|
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 |
|
Effects of selected anticholinergics on acoustic startle response in rats. | 2001 Dec |
|
Discriminative stimulus properties of 1.25 and 5.0 mg/kg doses of clozapine in rats: examination of the role of dopamine, serotonin, and muscarinic receptor mechanisms. | 2004 Feb |
|
Increased anticholinergic challenge-induced memory impairment associated with the APOE-epsilon4 allele in the elderly: a controlled pilot study. | 2004 Feb |
|
Acute dystonic reaction to metoclopramide in patients carrying homozygous cytochrome P450 2D6 genetic polymorphisms. | 2006 May |
|
Sclerosing mesenteritis: an ergot-related complication of pergolide therapy in Parkinson's disease? | 2008 Apr 30 |
|
Flow injection determination of benzhexol based on its sensitizing effect on the chemiluminescent reaction of Ce(IV)-sulfite. | 2010 Jul-Aug |
|
A randomised, double-blind, placebo-controlled trial of tropisetron in patients with schizophrenia. | 2010 Jun 24 |
|
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
Fri Dec 15 16:13:31 UTC 2023
by
admin
on
Fri Dec 15 16:13:31 UTC 2023
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Record UNII |
AO61G82577
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C38149
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NCI_THESAURUS |
C29704
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200-142-5
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SUB04961MIG
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AO61G82577
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100000092344
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DTXSID8045802
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66007
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CHEMBL1490
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AO61G82577
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52-49-3
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C47771
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TRIHEXYPHENIDYL HYDROCHLORIDE
Created by
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PRIMARY | Description: A white or off-white, crystalline powder; odourless or almost odourless. Solubility: Slightly soluble in water; soluble in ethanol (~750 g/l) TS and methanol R. Category: Anticholinergic; antiparkinsonism drug. Storage: Trihexyphenidyl hydrochloride should be kept in a tightly closed container. Definition: Trihexyphenidyl hydrochloride contains not less than 98.0% and not more than 101.0% of C20H31NO,HCl, calculated with reference to the dried substance. | ||
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DBSALT000448
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1115
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757357
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m11134
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1687006
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PARENT -> SALT/SOLVATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
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ACTIVE MOIETY |