U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

Molecular Formula C19H29NO
Molecular Weight 287.4397
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

-4.55500792E11
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

-4.55500792E11
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

-4.55500792E11
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
Doses

Doses

DosePopulationAdverse events​
10 mg single, intravenous
Dose: 10 mg
Route: intravenous
Route: single
Dose: 10 mg
Sources:
healthy, 22-48 years
n = 6
Health Status: healthy
Age Group: 22-48 years
Sex: M+F
Population Size: 6
Sources:
250 mg single, oral
Overdose
Dose: 250 mg
Route: oral
Route: single
Dose: 250 mg
Co-administed with::
amoxapine(2500 mg)
Sources:
unhealthy, 26 years
n = 1
Health Status: unhealthy
Condition: schizo-affective disorder
Age Group: 26 years
Sex: F
Population Size: 1
Sources:
Other AEs: Pancreatitis...
Other AEs:
Pancreatitis (1 patient)
Sources:
15 mg single, oral
Highest studied dose
Dose: 15 mg
Route: oral
Route: single
Dose: 15 mg
Sources:
unhealthy
n = 13
Health Status: unhealthy
Condition: Schizophrenia
Population Size: 13
Sources:
250 mg single, oral
Highest studied dose|Studied dose
Dose: 250 mg
Route: oral
Route: single
Dose: 250 mg
Sources:
unhealthy
n = 9
Health Status: unhealthy
Condition: duodenal ulcer
Population Size: 9
Sources:
50 mg single, intramuscular
Dose: 50 mg
Route: intramuscular
Route: single
Dose: 50 mg
Sources:
unhealthy
n = 3
Health Status: unhealthy
Population Size: 3
Sources:
AEs

AEs

AESignificanceDosePopulation
Pancreatitis 1 patient
250 mg single, oral
Overdose
Dose: 250 mg
Route: oral
Route: single
Dose: 250 mg
Co-administed with::
amoxapine(2500 mg)
Sources:
unhealthy, 26 years
n = 1
Health Status: unhealthy
Condition: schizo-affective disorder
Age Group: 26 years
Sex: F
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
A controlled trial of anti-Parkinson drugs in drug-induced Parkinsonism.
1966 Jun
Drug-induced extrapyramidal symptoms: their incidence and treatment.
1967 Jan
Double-blind comparison of levodopa and procyclidine in parkinsonism, with illustrations of levodopa-induced movement disorders.
1970 Dec
Double-blind comparison of levodopa and procyclidine in parkinsonism, with illustrations of levodopa-induced movement disorders.
1970 Dec
Central role of solar information flow in pregenetic evolution.
1971 Jun
Parenteral long-acting phenothiazines.
1972 Mar 25
Letter: Delayed drug-induced dystonias.
1973 Oct 20
Abnormal involuntary movements induced by anticholinergic therapy.
1974
A comparison of piribedil, procyclidine and placebo in the control of phenothiazine-induced parkinsonism.
1977 Jun
Death attributed to ventricular arrhythmia induced by thioridazine in combination with a single Contac C capsule.
1978 Oct 7
Sleep disturbance associated with fluphenazine HCl: a case report.
1979 Jul
Ethopropazine and benztropine in neuroleptic-induced parkinsonism.
1979 Mar
Fluphenazine enanthate and fluphenazine decanoate in the treatment of schizophrenic outpatients: extrapyramidal symptoms and therapeutic effect.
1982 Mar
Toxic neurological reaction to lithium/thioridazine.
1983 Apr 2
Neuroleptic malignant syndrome.
1983 Jun 18
Effects of mianserin in neuroleptic-induced parkinsonism.
1986
Rapid cycling following antidepressant in an adolescent.
1990 May 15
Antipsychotic drug-induced dysphoria.
1996 Oct
Bilateral ulnar nerve paralysis: an unreported complication of drug-induced extrapyramidal rigidity.
1997 Jun
Anti-nicotinic properties of anticholinergic antiparkinson drugs.
1998 Nov
An extrapyramidal reaction to ondansetron.
1998 Oct
Effects of combinational prophylactics composed of physostigmine and procyclidine on soman-induced lethality, seizures and brain injuries.
2002 Jan
Low dose quetiapine induced galactorrhoea: a case report.
2007 Jul 24
An overview of the clinical use of ondansetron in preschool age children.
2007 Jun
Simultaneous prescribing of atypical antipsychotics, conventional antipsychotics and anticholinergics-a European study.
2007 Jun
Newer antipsychotics and the rabbit syndrome.
2007 Jun 11
Measurements with fluorescent probes in primary neural cultures; improved multiwell techniques.
2007 Nov-Dec
Clozapine and co-prescribed psychotropics: a short report.
2008 Apr 25
Stuttering priapism--a review of the therapeutic options.
2008 Aug
Anticonvulsant efficacy of drugs with cholinergic and/or glutamatergic antagonism microinfused into area tempestas of rats exposed to soman.
2008 Feb
The present approaches to the development of prophylactic and therapeutic antidotes against nerve agents.
2008 Jun
Amisulpride plus valproate vs haloperidol plus valproate in the treatment of acute mania of bipolar I patients: a multicenter, open-label, randomized, comparative trial.
2008 Jun
Antiparkinson drugs used as prophylactics for nerve agents: studies of cognitive side effects in rats.
2008 Jun
Enhanced cholinergic-mediated increase in the pro-inflammatory cytokine IL-6 in irritable bowel syndrome: role of muscarinic receptors.
2008 Oct
Role of the central cholinergic system in the therapeutics of schizophrenia.
2008 Sep
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
Trends in the molecular pathogenesis and clinical therapeutics of common neurodegenerative disorders.
2009 Jun 3
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
Selective T-type calcium channel blockade alleviates hyperalgesia in ob/ob mice.
2009 Nov
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
Identification of neuronal target areas for nerve agents and specification of receptors for pharmacological treatment.
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
The use of organotypic hippocampal slice cultures to evaluate protection by non-competitive NMDA receptor antagonists against excitotoxicity.
2010 Mar
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
Structured relaxation in the treatment of akathisia: case series.
2010 May 25
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Two medical therapies very effective shortly after high levels of soman poisoning in rats, but only one with universal utility.
2013 Dec 15
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:04:35 UTC 2023
Edited
by admin
on Fri Dec 15 15:04:35 UTC 2023
Record UNII
C6QE1Q1TKR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
ELORINE
Brand 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 Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
NDF-RT N0000175370
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
NCI_THESAURUS C29704
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
WHO-ATC N04AA04
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
NDF-RT N0000175574
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
Code System Code Type Description
WIKIPEDIA
PROCYCLIDINE
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY
DRUG CENTRAL
2276
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY
NCI_THESAURUS
C73270
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY
ECHA (EC/EINECS)
201-023-0
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY
NSC
169103
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY
MERCK INDEX
m9151
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY Merck Index
PUBCHEM
4919
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY
MESH
D011352
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY
INN
224
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY
RXCUI
8718
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY RxNorm
SMS_ID
100000081116
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY
ChEMBL
CHEMBL86715
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY
CAS
56172-67-9
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
SUPERSEDED
CAS
107661-03-0
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
SUPERSEDED
CAS
77-37-2
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY
FDA UNII
C6QE1Q1TKR
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY
EPA CompTox
DTXSID2023515
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY
CHEBI
8448
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY
HSDB
7678
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY
EVMPD
SUB10064MIG
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY
IUPHAR
7280
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY
DRUG BANK
DB00387
Created by admin on Fri Dec 15 15:04:35 UTC 2023 , Edited by admin on Fri Dec 15 15:04:35 UTC 2023
PRIMARY
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