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

Details

Stereochemistry RACEMIC
Molecular Formula C19H29NO.ClH
Molecular Weight 323.901
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROCYCLIDINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=ZFSPFXJSEHCTTR-UHFFFAOYSA-N
InChI=1S/C19H29NO.ClH/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;1H

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 ( + / - )

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

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
Central role of solar information flow in pregenetic evolution.
1971 Jun
Parenteral long-acting phenothiazines.
1972 Mar 25
Abnormal involuntary movements induced by anticholinergic therapy.
1974
Sleep disturbance associated with fluphenazine HCl: a case report.
1979 Jul
Rapid cycling following antidepressant in an adolescent.
1990 May 15
Antipsychotic drug-induced dysphoria.
1996 Oct
Anti-nicotinic properties of anticholinergic antiparkinson drugs.
1998 Nov
Effects of procyclidine on prepulse inhibition of the acoustic startle response in healthy human volunteers.
2001 Mar
Simultaneous determination of enantiomers of structurally related anticholinergic analogs in human serum by liquid chromatography-electrospray ionization mass spectrometry with on-line sample cleanup.
2001 Oct 25
Effects of oral procyclidine administration on cognitive functions in healthy subjects: implications for schizophrenia.
2002 Apr
Effects of 10 mg and 15 mg oral procyclidine on critical flicker fusion threshold and cardiac functioning in healthy human subjects.
2002 Jun
A possible association between high normal and high dose olanzapine and prolongation of the PR interval.
2002 Jun
[Neutropenia in a patient treated with clozapine in combination with other psychotropic drugs].
2002 Nov-Dec
Anti-parkinsonian agents procyclidine and ethopropazine alleviate thermal hyperalgesia in neuropathic rats.
2003 May
Screening and semi-quantitative analysis of post mortem blood for basic drugs using gas chromatography/ion trap mass spectrometry.
2004 Dec 25
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
Drug-human serum albumin binding studied by capillary electrophoresis with electrochemiluminescence detection.
2004 Oct
Self-reported parkinsonian symptoms in the EPIC-Norfolk cohort.
2005 Aug 24
Soman-induced convulsions in rats terminated with pharmacological agents after 45 min: neuropathology and cognitive performance.
2005 Jan
The combination of donepezil and procyclidine protects against soman-induced seizures in rats.
2007 Apr 15
Low dose quetiapine induced galactorrhoea: a case report.
2007 Jul 24
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
Enhanced cholinergic-mediated increase in the pro-inflammatory cytokine IL-6 in irritable bowel syndrome: role of muscarinic receptors.
2008 Oct
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
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
Ethanol extract of Angelica gigas inhibits croton oil-induced inflammation by suppressing the cyclooxygenase - prostaglandin pathway.
2010 Mar
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 17:14:41 GMT 2023
Edited
by admin
on Fri Dec 15 17:14:41 GMT 2023
Record UNII
CQC932Z7YW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROCYCLIDINE HYDROCHLORIDE
MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
PROCYCLIDINE HYDROCHLORIDE [MART.]
Common Name English
PROCYCLIDINE HCL
Common Name English
KEMADRIN
Brand Name English
PROCYCLIDINE HYDROCHLORIDE [VANDF]
Common Name English
α-Cyclohexyl-α-phenyl-1-pyrrolidinepropanol hydrochloride
Systematic Name English
PROCYCLIDINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
1-PYRROLIDINEPROPANOL, .ALPHA.-CYCLOHEXYL-.ALPHA.-PHENYL-, HYDROCHLORIDE
Systematic Name English
PROCYCLIDINE HYDROCHLORIDE [USP-RS]
Common Name English
PROCYCLIDINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
NSC-757293
Code English
Procyclidine hydrochloride [WHO-DD]
Common Name English
PROCYCLIDINE HYDROCHLORIDE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C38149
Created by admin on Fri Dec 15 17:14:41 GMT 2023 , Edited by admin on Fri Dec 15 17:14:41 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL86715
Created by admin on Fri Dec 15 17:14:41 GMT 2023 , Edited by admin on Fri Dec 15 17:14:41 GMT 2023
PRIMARY
MERCK INDEX
m9151
Created by admin on Fri Dec 15 17:14:41 GMT 2023 , Edited by admin on Fri Dec 15 17:14:41 GMT 2023
PRIMARY Merck Index
FDA UNII
CQC932Z7YW
Created by admin on Fri Dec 15 17:14:41 GMT 2023 , Edited by admin on Fri Dec 15 17:14:41 GMT 2023
PRIMARY
ECHA (EC/EINECS)
216-141-8
Created by admin on Fri Dec 15 17:14:41 GMT 2023 , Edited by admin on Fri Dec 15 17:14:41 GMT 2023
PRIMARY
EVMPD
SUB04054MIG
Created by admin on Fri Dec 15 17:14:41 GMT 2023 , Edited by admin on Fri Dec 15 17:14:41 GMT 2023
PRIMARY
WIKIPEDIA
Procyclidine hydrochloride
Created by admin on Fri Dec 15 17:14:41 GMT 2023 , Edited by admin on Fri Dec 15 17:14:41 GMT 2023
PRIMARY
SMS_ID
100000085102
Created by admin on Fri Dec 15 17:14:41 GMT 2023 , Edited by admin on Fri Dec 15 17:14:41 GMT 2023
PRIMARY
DRUG BANK
DBSALT001008
Created by admin on Fri Dec 15 17:14:41 GMT 2023 , Edited by admin on Fri Dec 15 17:14:41 GMT 2023
PRIMARY
RXCUI
142443
Created by admin on Fri Dec 15 17:14:41 GMT 2023 , Edited by admin on Fri Dec 15 17:14:41 GMT 2023
PRIMARY RxNorm
PUBCHEM
207841
Created by admin on Fri Dec 15 17:14:41 GMT 2023 , Edited by admin on Fri Dec 15 17:14:41 GMT 2023
PRIMARY
NCI_THESAURUS
C47689
Created by admin on Fri Dec 15 17:14:41 GMT 2023 , Edited by admin on Fri Dec 15 17:14:41 GMT 2023
PRIMARY
NSC
757293
Created by admin on Fri Dec 15 17:14:41 GMT 2023 , Edited by admin on Fri Dec 15 17:14:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID8045357
Created by admin on Fri Dec 15 17:14:41 GMT 2023 , Edited by admin on Fri Dec 15 17:14:41 GMT 2023
PRIMARY
RS_ITEM_NUM
1567004
Created by admin on Fri Dec 15 17:14:41 GMT 2023 , Edited by admin on Fri Dec 15 17:14:41 GMT 2023
PRIMARY
CAS
1508-76-5
Created by admin on Fri Dec 15 17:14:41 GMT 2023 , Edited by admin on Fri Dec 15 17:14:41 GMT 2023
PRIMARY
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