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

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
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
Death attributed to ventricular arrhythmia induced by thioridazine in combination with a single Contac C capsule.
1978 Oct 7
Fluphenazine enanthate and fluphenazine decanoate in the treatment of schizophrenic outpatients: extrapyramidal symptoms and therapeutic effect.
1982 Mar
Pimozide-induced depression associated with polyuria and polydipsia.
1992 Apr
Lessons to be learned: a case study approach. 'Spontaneous' intraperitoneal bladder rupture in a psychiatric patient--with diagnostic difficulties.
2001 Jun
Effects of procyclidine on prepulse inhibition of the acoustic startle response in healthy human volunteers.
2001 Mar
NMDA receptors might be involved in the impairing effects of procyclidine on cognition.
2003 Dec
Cognitive side effects in rats caused by pharmacological agents used to prevent soman-induced lethality.
2004 Jan 12
Protection against soman-induced seizures in rats: relationship among doses of prophylactics, soman, and adjuncts.
2004 May 1
Protection by sustained release of physostigmine and procyclidine of soman poisoning in rats.
2004 Nov 28
Development of a screening method for the most commonly abused anticholinergic drugs in Jordan; trihexyphenidyl, procyclidine and biperiden.
2004 Oct
Soman-induced convulsions in rats terminated with pharmacological agents after 45 min: neuropathology and cognitive performance.
2005 Jan
Simultaneous prescribing of atypical antipsychotics, conventional antipsychotics and anticholinergics-a European study.
2007 Jun
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
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:04:35 GMT 2023
Edited
by admin
on Fri Dec 15 15:04:35 GMT 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 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
NDF-RT N0000175370
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
NCI_THESAURUS C29704
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
WHO-ATC N04AA04
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
NDF-RT N0000175574
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
Code System Code Type Description
WIKIPEDIA
PROCYCLIDINE
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY
DRUG CENTRAL
2276
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY
NCI_THESAURUS
C73270
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-023-0
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY
NSC
169103
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY
MERCK INDEX
m9151
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY Merck Index
PUBCHEM
4919
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY
MESH
D011352
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY
INN
224
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY
RXCUI
8718
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY RxNorm
SMS_ID
100000081116
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY
ChEMBL
CHEMBL86715
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY
CAS
56172-67-9
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
SUPERSEDED
CAS
107661-03-0
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
SUPERSEDED
CAS
77-37-2
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY
FDA UNII
C6QE1Q1TKR
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID2023515
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY
CHEBI
8448
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY
HSDB
7678
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY
EVMPD
SUB10064MIG
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY
IUPHAR
7280
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY
DRUG BANK
DB00387
Created by admin on Fri Dec 15 15:04:35 GMT 2023 , Edited by admin on Fri Dec 15 15:04:35 GMT 2023
PRIMARY
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