U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry RACEMIC
Molecular Formula C19H29NO
Molecular Weight 287.4397
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROCYCLIDINE

SMILES

OC(CCN1CCCC1)(C2CCCCC2)C3=CC=CC=C3

InChI

InChIKey=WYDUSKDSKCASEF-UHFFFAOYSA-N
InChI=1S/C19H29NO/c21-19(17-9-3-1-4-10-17,18-11-5-2-6-12-18)13-16-20-14-7-8-15-20/h1,3-4,9-10,18,21H,2,5-8,11-16H2

HIDE SMILES / InChI
Procyclidine is a muscarinic antagonist that crosses the blood-brain. Procyclidine hydrochloride (brand name Kemadrin) is a synthetic antispasmodic compound of relatively low toxicity. It has been shown to be useful for the symptomatic treatment of parkinsonism (paralysis agitans) and extrapyramidal dysfunction caused by tranquilizer therapy. Procyclidine hydrochloride was developed at The Wellcome Research Laboratories as the most promising of a series of antiparkinsonism compounds produced by chemical modification of antihistamines. Kemadrin is indicated in the treatment of parkinsonism including the postencephalitic, arteriosclerotic, and idiopathic types. Partial control of the parkinsonism symptoms is the usual therapeutic accomplishment. Procyclidine hydrochloride is usually more efficacious in the relief of rigidity than tremor; but tremor, fatigue, weakness, and sluggishness are frequently beneficially influenced. It can be substituted for all the previous medications in mild and moderate cases. For the control of more severe cases, other drugs may be added to procyclidine therapy as indications warrant. The mechanism of action is unknown. It is thought that procyclidine acts by blocking central cholinergic receptors, and thus balancing cholinergic and dopaminergic activity in the basal ganglia. Pharmacologic tests have shown that procyclidine hydrochloride has an atropine-like action and exerts an antispasmodic effect on smooth muscle. It is a potent mydriatic and inhibits salivation. It has no sympathetic ganglionblocking activity in doses as high as 4 mg/kg, as measured by the lack of inhibition of the response of the nictitating membrane to preganglionic electrical stimulation.

CNS Activity

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
KEMADRIN

Approved Use

KEMADRIN (procyclidine hydrochloride) is indicated in the treatment of parkinsonism including the postencephalitic, arteriosclerotic, and idiopathic types. Partial control of the parkinsonism symptoms is the usual therapeutic accomplishment. Procyclidine hydrochloride is usually more efficacious in the relief of rigidity than tremor; but tremor, fatigue, weakness, and sluggishness are frequently beneficially influenced. It can be substituted for all the previous medications in mild and moderate cases. For the control of more severe cases, other drugs may be added to procyclidine therapy as indications warrant.

Launch Date

1955
Primary
KEMADRIN

Approved Use

KEMADRIN (procyclidine hydrochloride) is indicated in the treatment of parkinsonism including the postencephalitic, arteriosclerotic, and idiopathic types. Partial control of the parkinsonism symptoms is the usual therapeutic accomplishment. Procyclidine hydrochloride is usually more efficacious in the relief of rigidity than tremor; but tremor, fatigue, weakness, and sluggishness are frequently beneficially influenced. It can be substituted for all the previous medications in mild and moderate cases. For the control of more severe cases, other drugs may be added to procyclidine therapy as indications warrant.

Launch Date

1955
Primary
KEMADRIN

Approved Use

KEMADRIN (procyclidine hydrochloride) is indicated in the treatment of parkinsonism including the postencephalitic, arteriosclerotic, and idiopathic types. Partial control of the parkinsonism symptoms is the usual therapeutic accomplishment. Procyclidine hydrochloride is usually more efficacious in the relief of rigidity than tremor; but tremor, fatigue, weakness, and sluggishness are frequently beneficially influenced. It can be substituted for all the previous medications in mild and moderate cases. For the control of more severe cases, other drugs may be added to procyclidine therapy as indications warrant.

Launch Date

1955
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
116 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROCYCLIDINE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2705 ng × h/mL
10 mg single, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PROCYCLIDINE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
2007 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROCYCLIDINE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
11.5 h
10 mg single, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PROCYCLIDINE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
12.6 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROCYCLIDINE HYDROCHLORIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
Drug-induced extrapyramidal symptoms: their incidence and treatment.
1967 Jan
Sleep disturbance associated with fluphenazine HCl: a case report.
1979 Jul
Anti-nicotinic properties of anticholinergic antiparkinson drugs.
1998 Nov
An extrapyramidal reaction to ondansetron.
1998 Oct
Effects of procyclidine on prepulse inhibition of the acoustic startle response in healthy human volunteers.
2001 Mar
Acute dystonic reaction in an elderly patient with mood disorder after titration of paroxetine: possible mechanisms and implications for clinical care.
2002 Dec
Effects of 10 mg and 15 mg oral procyclidine on critical flicker fusion threshold and cardiac functioning in healthy human subjects.
2002 Jun
[Neutropenia in a patient treated with clozapine in combination with other psychotropic drugs].
2002 Nov-Dec
Probable dystonic reaction after a single dose of cyclizine in a patient with a history of encephalitis.
2003 Mar
Variable effects of previously untested muscarinic receptor antagonists on experimental myopia.
2003 Mar
Screening and semi-quantitative analysis of post mortem blood for basic drugs using gas chromatography/ion trap mass spectrometry.
2004 Dec 25
Self-reported parkinsonian symptoms in the EPIC-Norfolk cohort.
2005 Aug 24
Protection by a transdermal patch containing physostigmine and procyclidine of soman poisoning in dogs.
2005 Nov 21
Primary care use of antipsychotic drugs: an audit and intervention study.
2005 Nov 29
Efficacy of immediate and subsequent therapies against soman-induced seizures and lethality in rats.
2006 Feb
Abdominal pain with rigidity secondary to the anti-emetic drug metoclopramide.
2006 May
Pharmacological therapies against soman-induced seizures in rats 30 min following onset and anticonvulsant impact.
2006 Oct 24
The combination of donepezil and procyclidine protects against soman-induced seizures in rats.
2007 Apr 15
Stuttering priapism--a review of the therapeutic options.
2008 Aug
Enhanced cholinergic-mediated increase in the pro-inflammatory cytokine IL-6 in irritable bowel syndrome: role of muscarinic receptors.
2008 Oct
Mechanisms of action of antipsychotic drugs of different classes, refractoriness to therapeutic effects of classical neuroleptics, and individual variation in sensitivity to their actions: Part II.
2009 Dec
Fatalities associated with clozapine-related constipation and bowel obstruction: a literature review and two case reports.
2009 Jul-Aug
Physiological and pathological role of alpha-synuclein in Parkinson's disease through iron mediated oxidative stress; the role of a putative iron-responsive element.
2009 Mar
Acute dystonic reactions in a lady presenting with repetitive involuntary muscle twitching: a case report.
2009 Nov 9
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.
2010 Dec
Roles of perirhinal and posterior piriform cortices in control and generation of seizures: a microinfusion study in rats exposed to soman.
2010 Jan
Ethanol extract of Angelica gigas inhibits croton oil-induced inflammation by suppressing the cyclooxygenase - prostaglandin pathway.
2010 Mar
Behavioral side effects in rats treated with acetylcholinesterase inhibitors suggested used as prophylactics against nerve agents.
2010 May
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Patents

Sample Use Guides

For initial treatment is 2.5 mg administered three times daily after meals. If well tolerated, this dose may be gradually increased to 5 mg three times a day and occasionally 5 mg given before retiring. In some cases smaller doses may be employed with good therapeutic results.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
ELORINE
Preferred Name English
PROCYCLIDINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
VAGOSIN
Brand Name English
LERGINE
Brand Name English
(±)-PROCYCLIDINE
Common Name English
PROCYCLIDINE [VANDF]
Common Name English
NSC-169103
Code English
Procyclidine [WHO-DD]
Common Name English
PROCYCLIDINE [MI]
Common Name English
1-CYCLOHEXYL-1-PHENYL-3-(1-PYRROLIDINYL)-1-PROPANOL
Systematic Name English
TRICOLOID
Brand Name English
KEMADRINE
Brand Name English
PROCYCLIDINE [HSDB]
Common Name English
procyclidine [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QN04AA04
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
NDF-RT N0000175370
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
NCI_THESAURUS C29704
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
WHO-ATC N04AA04
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
NDF-RT N0000175574
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
Code System Code Type Description
WIKIPEDIA
PROCYCLIDINE
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
DRUG CENTRAL
2276
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
NCI_THESAURUS
C73270
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-023-0
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
NSC
169103
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
MERCK INDEX
m9151
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY Merck Index
PUBCHEM
4919
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
MESH
D011352
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
INN
224
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
RXCUI
8718
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY RxNorm
SMS_ID
100000081116
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
ChEMBL
CHEMBL86715
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
CAS
56172-67-9
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
SUPERSEDED
CAS
107661-03-0
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
SUPERSEDED
CAS
77-37-2
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
FDA UNII
C6QE1Q1TKR
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
EPA CompTox
DTXSID2023515
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
CHEBI
8448
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
HSDB
7678
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
EVMPD
SUB10064MIG
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
IUPHAR
7280
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY
DRUG BANK
DB00387
Created by admin on Mon Mar 31 17:45:34 GMT 2025 , Edited by admin on Mon Mar 31 17:45:34 GMT 2025
PRIMARY