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

Details

Stereochemistry UNKNOWN
Molecular Formula C21H29NO
Molecular Weight 311.4611
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BIPERIDEN

SMILES

OC(CCN1CCCCC1)(C2CC3CC2C=C3)C4=CC=CC=C4

InChI

InChIKey=YSXKPIUOCJLQIE-UHFFFAOYSA-N
InChI=1S/C21H29NO/c23-21(19-7-3-1-4-8-19,11-14-22-12-5-2-6-13-22)20-16-17-9-10-18(20)15-17/h1,3-4,7-10,17-18,20,23H,2,5-6,11-16H2

HIDE SMILES / InChI

Molecular Formula C21H29NO
Molecular Weight 311.4611
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.tga.gov.au/alert/akineton-biperiden-hydrochloride-2-mg-tablets https://www.drugs.com/pro/akineton.html

Biperiden, sold under the brandname Akineton was used as an adjunct in the therapy of all forms of parkinsonism (postencephalitic, arteriosclerotic and idiopathic). Was also useful in the control of extrapyramidal disorders due to central nervous system drugs such as phenothiazines and other groups of psychotropics. Biperiden is a weak peripheral anticholinergic agent. It has, therefore, some antisecretory, antispasmodic and mydriatic effects. In addition, biperiden possesses nicotinolytic activity. Parkinsonism is thought to result from an imbalance between the excitatory (cholinergic) and inhibitory (dopaminergic) systems in the corpus striatum. The mechanism of action of centrally active anticholinergic drugs such as biperiden is considered to relate to competitive antagonism of acetylcholine at cholinergic receptors in the corpus striatum, which then restores the balance. Atropine-like side effects such as dry mouth; blurred vision; drowsiness; euphoria or disorientation; urinary retention; postural hypotension; constipation; agitation; disturbed behavior may been seen. Only limited pharmacokinetic studies of biperiden in humans are available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
AKINETON

Approved Use

For use as an adjunct in the therapy of all forms of parkinsonism (postencephalitic, arteriosclerotic and idiopathic). Useful in the control of extrapyramidal disorders due to central nervous system drugs such as phenothiazines and other groups of psychotropics.

Launch Date

1959
Palliative
AKINETON

Approved Use

For use as an adjunct in the therapy of all forms of parkinsonism (postencephalitic, arteriosclerotic and idiopathic). Useful in the control of extrapyramidal disorders due to central nervous system drugs such as phenothiazines and other groups of psychotropics.

Launch Date

1959
Palliative
AKINETON

Approved Use

For use as an adjunct in the therapy of all forms of parkinsonism (postencephalitic, arteriosclerotic and idiopathic). Useful in the control of extrapyramidal disorders due to central nervous system drugs such as phenothiazines and other groups of psychotropics.

Launch Date

1959
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
13.5 ng/mL
4 mg single, intravenous
dose: 4 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
BIPERIDEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
62.8 ng × h/mL
4 mg single, intravenous
dose: 4 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
BIPERIDEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
24.3 h
4 mg single, intravenous
dose: 4 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
BIPERIDEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
600 mg 1 times / day single, oral
Overdose
Dose: 600 mg, 1 times / day
Route: oral
Route: single
Dose: 600 mg, 1 times / day
Co-administed with::
valpromide(15g, PO, single)
alprazolam(20mg, PO, single)
Sources:
unhealthy, 35
n = 1
Health Status: unhealthy
Condition: bipolar disorder
Age Group: 35
Sex: F
Population Size: 1
Sources:
Other AEs: Hallucinations, Coma...
4 mg 3 times / day multiple, oral
Highest studied dose
Dose: 4 mg, 3 times / day
Route: oral
Route: multiple
Dose: 4 mg, 3 times / day
Sources:
unhealthy, 44 (29-55)
n = 9
Health Status: unhealthy
Condition: depression
Age Group: 44 (29-55)
Sex: M+F
Population Size: 9
Sources:
AEs

AEs

AESignificanceDosePopulation
Coma
600 mg 1 times / day single, oral
Overdose
Dose: 600 mg, 1 times / day
Route: oral
Route: single
Dose: 600 mg, 1 times / day
Co-administed with::
valpromide(15g, PO, single)
alprazolam(20mg, PO, single)
Sources:
unhealthy, 35
n = 1
Health Status: unhealthy
Condition: bipolar disorder
Age Group: 35
Sex: F
Population Size: 1
Sources:
Hallucinations
600 mg 1 times / day single, oral
Overdose
Dose: 600 mg, 1 times / day
Route: oral
Route: single
Dose: 600 mg, 1 times / day
Co-administed with::
valpromide(15g, PO, single)
alprazolam(20mg, PO, single)
Sources:
unhealthy, 35
n = 1
Health Status: unhealthy
Condition: bipolar disorder
Age Group: 35
Sex: F
Population Size: 1
Sources:
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Use of pimozide in the Pisa syndrome.
1992 Aug
Antagonism by antimuscarinic and neuroleptic compounds at the five cloned human muscarinic cholinergic receptors expressed in Chinese hamster ovary cells.
1992 Feb
A comparison of the neuroprotective efficacy of pharmacological pretreatment and antidotal treatment in soman-poisoned rats.
2003
Motor disturbances in mice with deficiency of the sodium channel gene Scn8a show features of human dystonia.
2003 Dec
[Acute dystonic reaction due to quinine].
2003 Dec
In vitro drug-drug interactions with perospirone and concomitantly administered drugs in human liver microsomes.
2003 Jan-Mar
[Utility of quetiapine in tardive dyskinesia].
2003 Nov-Dec
Influences of an anticholinergic antiparkinsonian drug, parkinsonism, and psychotic symptoms on cardiac autonomic function in schizophrenia.
2003 Oct
A CYP2D6 phenotype-genotype mismatch in Japanese psychiatric patients.
2003 Sep
Adjunctive estrogen treatment in women with chronic schizophrenia: a double-blind, randomized, and placebo-controlled trial.
2003 Sep
Anticholinergic drugs--functional antidotes for the treatment of tabun intoxication.
2004
Antiparkinsonian-like effects of Plumbago scandens on tremorine-induced tremors methodology.
2004 Dec
Effects of discontinuation of long-term anticholinergic treatment in elderly schizophrenia patients.
2004 Jan
Reversible orofacial dyskinesia after ofloxacin treatment.
2004 Jun
Comparisons of psychotropic drug prescribing patterns in acute psychiatric wards across Europe.
2004 Mar
Use of polypharmacotherapy in pregnancy: a prospective outcome in a case.
2004 May
Ecstasy and acute dystonia.
2004 Nov
Development of a screening method for the most commonly abused anticholinergic drugs in Jordan; trihexyphenidyl, procyclidine and biperiden.
2004 Oct
Tardive nocturnal akathisia due to clozapine treatment.
2005
Anaphylactic reaction and unrelated, subsequent, known side effects during therapy with thiethylperazine.
2005 Aug
Neuropsychological measures of attention and memory function in schizophrenia: relationships with symptom dimensions and serum monoamine activity.
2005 Aug 9
Pharmacological modulation of cholinergic brain activity and its reflection in special EEG frequency ranges from various brain areas in the freely moving rat (Tele-Stereo-EEG).
2005 Dec
Clozapine improves working memory updating in schizophrenia.
2005 Dec
Beneficial antipsychotic effects of allopurinol as add-on therapy for schizophrenia: a double blind, randomized and placebo controlled trial.
2005 Feb
Major depressive disorder with psychotic features induced by interferon-alpha treatment for hepatitis C in a polydrug abuser.
2005 Jan
Possible malignant neuroleptic syndrome that associated with hypothyroidism.
2005 Jun
Alterations in behavioral responses to a cholinergic agonist in post-pubertal rats with neonatal ventral hippocampal lesions: relationship to changes in muscarinic receptor levels.
2005 Jun
Administration of haloperidol with biperiden reduces mRNAs related to the ubiquitin-proteasome system in mice.
2005 Jun 15
Role of nitric oxide on motor behavior.
2005 Mar
The effects of amisulpride on five dimensions of psychopathology in patients with schizophrenia: a prospective open-label study.
2005 May 3
Evaluation of the clinical efficacy of risperidone for untreated and treated cases of schizophrenia from various aspects.
2005 Oct
Measurement of anticholinergic effects of psychotropic drugs in humans.
2005 Sep
Modulation of memory and visuospatial processes by biperiden and rivastigmine in elderly healthy subjects.
2005 Sep
Scopolamine-induced convulsions in fasted mice after food intake: effects of glucose intake, antimuscarinic activity and anticonvulsant drugs.
2005 Sep
Acute dystonia with low-dosage aripiprazole in Tourette's disorder.
2006 Apr
Modification of practice-dependent plasticity in human motor cortex by neuromodulators.
2006 Aug
[The prevalence and pharmacological cost of Parkinson's disease in Spain].
2006 Dec 1-15
Application of a generic physiologically based pharmacokinetic model to the estimation of xenobiotic levels in human plasma.
2006 Jan
Antipsychotics-induced hypersensitivity of visual perception.
2006 Jul
Sudden akathisia after a ziprasidone dose reduction.
2006 Mar
Acute dystonic reaction to metoclopramide in patients carrying homozygous cytochrome P450 2D6 genetic polymorphisms.
2006 May
Association between two distinct executive tasks in schizophrenia: a functional transcranial Doppler sonography study.
2006 May 24
Kinetic and molecular evidences that human cardiac muscle express non-M2 muscarinic receptor subtypes that are able to interact themselves.
2006 Nov
[Therapy of postoperative nausea and vomiting in ENT--tardive dyskinesia as an adverse effect of metoclopramid--a case report].
2006 Nov
Biperiden-induced delirium model in rats: a behavioral and electroencephalographic study.
2006 Oct 18
Neuroleptic malignant syndrome induced by ziprasidone on the second day of treatment.
2007
Acute dystonia resulting from abrupt bupropion discontinuation.
2007 Apr 13
Acute dystonia after injection of pegylated interferon alpha-2b.
2007 Apr 15
Early onset of treatment effects with oral risperidone.
2007 Jan 19
Simultaneous prescribing of atypical antipsychotics, conventional antipsychotics and anticholinergics-a European study.
2007 Jun
Patents

Sample Use Guides

Parkinsonism: Dosage should be individualized. Begin with 1/2 a tablet twice daily, and gradually increase to 1 tablet, 3-4 times daily.
Route of Administration: Oral
In Vitro Use Guide
(+)-Biperiden had its highest affinity to M1-receptors (pA2 = 9.07), had low affinity to cardiac M2 alpha-receptors (pA2 = 7.25) and intermediate affinity to ileal M2 beta-receptors (pA2 = 8.27). The ability of (+)-biperiden to discriminate between ileal M2 beta- and cardiac M2 alpha-receptors (factor = 10) was similar to that of 4-diphenylacetoxy-N-methylpiperidine methiodide (4-DAMP, factor = 9). In contrast, (-)-biperiden displayed low but nearly undistinguishable affinity for all muscarinic receptor subtypes studied (pA2 = 5.59 +/- 6.38). (+)-Biperiden discriminated strongly between M1- and cardiac M2 alpha-receptors (factor 66), thus being even more selective than pirenzepine (factor 28) which makes it one of the most M1-/cardiac M2 alpha-selective antimuscarinic drugs now available.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:22:52 GMT 2023
Edited
by admin
on Sat Dec 16 16:22:52 GMT 2023
Record UNII
0FRP6G56LD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BIPERIDEN
HSDB   INN   JAN   MART.   MI   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
NSC-759145
Code English
BIPERIDEN [MART.]
Common Name English
α-5-Norbornen-2-yl-α-phenyl-1-piperidinepropanol
Systematic Name English
KL 373
Code English
BIPERIDEN [JAN]
Common Name English
BIPERIDEN [USP IMPURITY]
Common Name English
BIPERIDEN [HSDB]
Common Name English
BIPERIDEN [WHO-IP]
Common Name English
BIPERIDENUM [WHO-IP LATIN]
Common Name English
BIPERIDEN [MI]
Common Name English
BIPERIDEN [VANDF]
Common Name English
biperiden [INN]
Common Name English
AKINETON-
Common Name English
1-PIPERIDINEPROPANOL, .ALPHA.-BICYCLO(2.2.1)HEPT-5-EN-2-YL-.ALPHA.-PHENYL-
Systematic Name English
Biperiden [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC N04AA02
Created by admin on Sat Dec 16 16:22:52 GMT 2023 , Edited by admin on Sat Dec 16 16:22:52 GMT 2023
LIVERTOX NBK548257
Created by admin on Sat Dec 16 16:22:52 GMT 2023 , Edited by admin on Sat Dec 16 16:22:52 GMT 2023
NCI_THESAURUS C29704
Created by admin on Sat Dec 16 16:22:52 GMT 2023 , Edited by admin on Sat Dec 16 16:22:52 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 09
Created by admin on Sat Dec 16 16:22:52 GMT 2023 , Edited by admin on Sat Dec 16 16:22:52 GMT 2023
NDF-RT N0000175574
Created by admin on Sat Dec 16 16:22:52 GMT 2023 , Edited by admin on Sat Dec 16 16:22:52 GMT 2023
NDF-RT N0000175370
Created by admin on Sat Dec 16 16:22:52 GMT 2023 , Edited by admin on Sat Dec 16 16:22:52 GMT 2023
WHO-VATC QN04AA02
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NCI_THESAURUS C38149
Created by admin on Sat Dec 16 16:22:52 GMT 2023 , Edited by admin on Sat Dec 16 16:22:52 GMT 2023
Code System Code Type Description
DRUG BANK
DB00810
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PRIMARY
EVMPD
SUB05843MIG
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PRIMARY
NCI_THESAURUS
C65263
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PRIMARY
IUPHAR
7128
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PRIMARY
FDA UNII
0FRP6G56LD
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PRIMARY
EPA CompTox
DTXSID6022680
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PRIMARY
CHEBI
3112
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PRIMARY
HSDB
7639
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PRIMARY
SMS_ID
100000090107
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PRIMARY
MERCK INDEX
m2508
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PRIMARY Merck Index
ChEMBL
CHEMBL1101
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PRIMARY
DRUG CENTRAL
374
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PRIMARY
NSC
759145
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PRIMARY
INN
915
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PRIMARY
WIKIPEDIA
BIPERIDEN
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PRIMARY
RXCUI
1589
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PRIMARY RxNorm
WHO INTERNATIONAL PHARMACOPEIA
BIPERIDEN
Created by admin on Sat Dec 16 16:22:52 GMT 2023 , Edited by admin on Sat Dec 16 16:22:52 GMT 2023
PRIMARY Description: A white or almost white, crystalline powder; odourless. Solubility: Practically insoluble in water; soluble in ether R; sparingly soluble in ethanol (~750 g/l) TS. Category: Antiparkinsonism drug. Storage: Biperiden should be kept in a well-closed container, protected from light. Definition: Biperiden contains not less than 98.0% and not more than 101.0% of C21H29NO, calculated with reference to the dried substance.
PUBCHEM
2381
Created by admin on Sat Dec 16 16:22:52 GMT 2023 , Edited by admin on Sat Dec 16 16:22:52 GMT 2023
PRIMARY
MESH
D001712
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PRIMARY
CAS
514-65-8
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PRIMARY
ECHA (EC/EINECS)
208-184-6
Created by admin on Sat Dec 16 16:22:52 GMT 2023 , Edited by admin on Sat Dec 16 16:22:52 GMT 2023
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
Related Record Type Details
ACTIVE MOIETY
http://apps.who.int/phint/pdf/b/Jb.6.1.58.pdf