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Details

Stereochemistry RACEMIC
Molecular Formula C20H31NO
Molecular Weight 301.4662
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIHEXYPHENIDYL

SMILES

OC(CCN1CCCCC1)(C2CCCCC2)C3=CC=CC=C3

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

HIDE SMILES / InChI

Molecular Formula C20H31NO
Molecular Weight 301.4662
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.3 nM [IC50]
6.7 nM [IC50]
10.3 nM [IC50]
26.3 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Trihexyphenidyl hydrochloride
Secondary
Trihexyphenidyl hydrochloride

Cmax

ValueDoseCo-administeredAnalytePopulation
14.9 ng/mL
5 mg single, oral
TRIHEXYPHENIDYL serum
Homo sapiens
24.4 ng/mL
5 mg 2 times / day multiple, oral
TRIHEXYPHENIDYL serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
294 ng × h/mL
5 mg single, oral
TRIHEXYPHENIDYL serum
Homo sapiens
334 ng × h/mL
5 mg 2 times / day multiple, oral
TRIHEXYPHENIDYL serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
10.1 h
5 mg single, oral
TRIHEXYPHENIDYL serum
Homo sapiens
8.67 h
5 mg 2 times / day multiple, oral
TRIHEXYPHENIDYL serum
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
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
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
Record UNII
6RC5V8B7PO
Record Status Validated (UNII)
Record Version