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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 ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
Central role of solar information flow in pregenetic evolution.
1971 Jun
Parenteral long-acting phenothiazines.
1972 Mar 25
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
Neuroleptic malignant syndrome.
1983 Jun 18
Lessons to be learned: a case study approach. 'Spontaneous' intraperitoneal bladder rupture in a psychiatric patient--with diagnostic difficulties.
2001 Jun
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
Physostigmine as treatment for severe CNS anticholinergic toxicity.
2001 Sep
Acute dystonic reaction in an elderly patient with mood disorder after titration of paroxetine: possible mechanisms and implications for clinical care.
2002 Dec
NMDA receptors might be involved in the impairing effects of procyclidine on cognition.
2003 Dec
Effects of procyclidine on eye movements in schizophrenia.
2003 Dec
Pharmacological agents, hippocampal EEG, and anticonvulsant effects on soman-induced seizures in rats.
2003 Jun
Variable effects of previously untested muscarinic receptor antagonists on experimental myopia.
2003 Mar
Anti-parkinsonian agents procyclidine and ethopropazine alleviate thermal hyperalgesia in neuropathic rats.
2003 May
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
Drug-human serum albumin binding studied by capillary electrophoresis with electrochemiluminescence detection.
2004 Oct
Development of a screening method for the most commonly abused anticholinergic drugs in Jordan; trihexyphenidyl, procyclidine and biperiden.
2004 Oct
Lack of association between prepulse inhibition and antisaccadic deficits in chronic schizophrenia: implications for identification of schizophrenia endophenotypes.
2005 May
Primary care use of antipsychotic drugs: an audit and intervention study.
2005 Nov 29
Pharmacological therapies against soman-induced seizures in rats 30 min following onset and anticonvulsant impact.
2006 Oct 24
Anticonvulsant efficacy of drugs with cholinergic and/or glutamatergic antagonism microinfused into area tempestas of rats exposed to soman.
2008 Feb
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
Role of the central cholinergic system in the therapeutics of schizophrenia.
2008 Sep
Trends in the molecular pathogenesis and clinical therapeutics of common neurodegenerative disorders.
2009 Jun 3
Identification of neuronal target areas for nerve agents and specification of receptors for pharmacological treatment.
2010 Dec
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 Mon Mar 31 18:42:44 GMT 2025
Edited
by admin
on Mon Mar 31 18:42:44 GMT 2025
Record UNII
CQC932Z7YW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
KEMADRIN
Preferred Name English
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
PROCYCLIDINE HYDROCHLORIDE [VANDF]
Common Name English
?-Cyclohexyl-?-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 Mon Mar 31 18:42:44 GMT 2025 , Edited by admin on Mon Mar 31 18:42:44 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL86715
Created by admin on Mon Mar 31 18:42:44 GMT 2025 , Edited by admin on Mon Mar 31 18:42:44 GMT 2025
PRIMARY
MERCK INDEX
m9151
Created by admin on Mon Mar 31 18:42:44 GMT 2025 , Edited by admin on Mon Mar 31 18:42:44 GMT 2025
PRIMARY Merck Index
FDA UNII
CQC932Z7YW
Created by admin on Mon Mar 31 18:42:44 GMT 2025 , Edited by admin on Mon Mar 31 18:42:44 GMT 2025
PRIMARY
ECHA (EC/EINECS)
216-141-8
Created by admin on Mon Mar 31 18:42:44 GMT 2025 , Edited by admin on Mon Mar 31 18:42:44 GMT 2025
PRIMARY
EVMPD
SUB04054MIG
Created by admin on Mon Mar 31 18:42:44 GMT 2025 , Edited by admin on Mon Mar 31 18:42:44 GMT 2025
PRIMARY
WIKIPEDIA
Procyclidine hydrochloride
Created by admin on Mon Mar 31 18:42:44 GMT 2025 , Edited by admin on Mon Mar 31 18:42:44 GMT 2025
PRIMARY
SMS_ID
100000085102
Created by admin on Mon Mar 31 18:42:44 GMT 2025 , Edited by admin on Mon Mar 31 18:42:44 GMT 2025
PRIMARY
DRUG BANK
DBSALT001008
Created by admin on Mon Mar 31 18:42:44 GMT 2025 , Edited by admin on Mon Mar 31 18:42:44 GMT 2025
PRIMARY
RXCUI
142443
Created by admin on Mon Mar 31 18:42:44 GMT 2025 , Edited by admin on Mon Mar 31 18:42:44 GMT 2025
PRIMARY RxNorm
PUBCHEM
207841
Created by admin on Mon Mar 31 18:42:44 GMT 2025 , Edited by admin on Mon Mar 31 18:42:44 GMT 2025
PRIMARY
NCI_THESAURUS
C47689
Created by admin on Mon Mar 31 18:42:44 GMT 2025 , Edited by admin on Mon Mar 31 18:42:44 GMT 2025
PRIMARY
NSC
757293
Created by admin on Mon Mar 31 18:42:44 GMT 2025 , Edited by admin on Mon Mar 31 18:42:44 GMT 2025
PRIMARY
EPA CompTox
DTXSID8045357
Created by admin on Mon Mar 31 18:42:44 GMT 2025 , Edited by admin on Mon Mar 31 18:42:44 GMT 2025
PRIMARY
RS_ITEM_NUM
1567004
Created by admin on Mon Mar 31 18:42:44 GMT 2025 , Edited by admin on Mon Mar 31 18:42:44 GMT 2025
PRIMARY
CAS
1508-76-5
Created by admin on Mon Mar 31 18:42:44 GMT 2025 , Edited by admin on Mon Mar 31 18:42:44 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY