BIPERIDEN

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 Search

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
Sources: https://mri.cts-mrp.eu/Human/Downloads/AT_H_0521_002_FinalSPC.pdf
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor M1 168 Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9798802	Antagonist 2760

Conditions

Condition	Modality	Highest Phase	Product
Postencephalitic parkinsonism 7 Sources: https://mri.cts-mrp.eu/Human/Downloads/AT_H_0521_002_FinalSPC.pdf https://www.ncbi.nlm.nih.gov/pubmed/14393477 http://www.clinicaladvisor.com/akineton/drug/3903/	Palliative	Approved 8360	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 -3.25555192E11
Idiopathic Parkinson's disease 19 Sources: https://mri.cts-mrp.eu/Human/Downloads/AT_H_0521_002_FinalSPC.pdf http://www.clinicaladvisor.com/akineton/drug/3903/	Palliative	Approved 8360	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 -3.25555192E11
Arteriosclerotic parkinsonism 5 Sources: https://mri.cts-mrp.eu/Human/Downloads/AT_H_0521_002_FinalSPC.pdf http://www.clinicaladvisor.com/akineton/drug/3903/	Palliative	Approved 8360	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 -3.25555192E11

C_max

Value	Dose	Co-administered	Analyte	Population
13.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709619/	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

Value	Dose	Co-administered	Analyte	Population
62.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709619/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
24.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709619/	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

Dose	Population	Adverse 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: https://link.springer.com/article/10.2165/00128415-201013120-00042	unhealthy, 35 n = 1 Health Status: unhealthy Condition: bipolar disorder Age Group: 35 Sex: F Population Size: 1 Sources: https://link.springer.com/article/10.2165/00128415-201013120-00042	Other AEs: Hallucinations, Coma... Other AEs: Hallucinations Coma Sources: https://link.springer.com/article/10.2165/00128415-201013120-00042
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: https://pubmed.ncbi.nlm.nih.gov/8570773/	unhealthy, 44 (29-55) n = 9 Health Status: unhealthy Condition: depression Age Group: 44 (29-55) Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/8570773/	Sources: https://pubmed.ncbi.nlm.nih.gov/8570773/

AEs

AE	Significance	Dose	Population
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: https://link.springer.com/article/10.2165/00128415-201013120-00042	unhealthy, 35 n = 1 Health Status: unhealthy Condition: bipolar disorder Age Group: 35 Sex: F Population Size: 1 Sources: https://link.springer.com/article/10.2165/00128415-201013120-00042
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: https://link.springer.com/article/10.2165/00128415-201013120-00042	unhealthy, 35 n = 1 Health Status: unhealthy Condition: bipolar disorder Age Group: 35 Sex: F Population Size: 1 Sources: https://link.springer.com/article/10.2165/00128415-201013120-00042

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1579 activator 77 substrate 1709		inhibitor 1837 substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1437	P-gp 1527 CYP1A2 1032

Drug as perpetrator

Target	Modality	Activity
P-gp 1626	inhibitor 3240 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0MzAyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExMDEifX0%3D	no
CYP3A4 1909	activator 210 Sources: https://link.springer.com/article/10.1007%2Fs002280050455	weak [Activation 0.1 uM]
CYP3A4 1909	inhibitor 3240 Sources: https://link.springer.com/article/10.1007%2Fs002280050455	yes [Inhibition 100 uM]
CYP2D6 1875	inhibitor 3240 Sources: https://go.drugbank.com/drugs/DB00810, https://link.springer.com/article/10.1007%2Fs002280050322, https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000514658	yes [Ki 0.45 uM]

Drug as victim

Target	Modality	Activity
P-gp 1527	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/22554863/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0MzAyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExMDEifX0%3D	no
CYP2D6 1193	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/, https://www.tandfonline.com/doi/abs/10.1080/03602530903118729	yes [Km 37 uM]
CYP1A2 1032	substrate 3326 Sources: https://www.tandfonline.com/doi/abs/10.1080/03602530903118729	yes
CYP3A4 1709	substrate 3326 Sources: https://www.tandfonline.com/doi/abs/10.1080/03602530903118729	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY445564	https://www.001chemical.com/chem/514-65-8
Ambinter	Amb10843814	http://www.ambinter.com/reference/10843814
BLD Pharm	BD116739	http://www.bldpharm.com/products/514-65-8.html
BioCrick	BCC4274	http://www.biocrick.com/Biperiden-BCC4274.html
CSNpharm	CSN10453	https://www.csnpharm.com/products/biperiden.html
Chem Scene	CS-1797	http://www.chemscene.com/514-65-8.html
ChemMol	49427588	http://www.chemmol.com/chemmol/49427588.html
Chemspace	CSSB00020627468	https://chem-space.com/CSSB00020627468
DC Chemicals	DC23078	http://www.dcchemicals.com/product_show-DC23078.html
Lab Network	LN01267554	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01267554
MedChem Express	HY-13204A	https://www.medchemexpress.com/Biperiden.html
Molcore	MC445564	https://www.molcore.com/product/514-65-8
MuseChem	I003854	https://www.musechem.com/product/I003854.html
Parchem	28356	http://www.parchem.com/chemical-supplier-distributor/Biperiden-018356.aspx
Smolecule	S521354	http://www.smolecule.com/products/s521354
THE BioTek	bt-262503	https://www.thebiotek.com/product/inhibitors/bt-262503
Vesino Industrial Co Ltd	VA10409	http://www.vsnchem.com/goto/product/23881/
Vitas-M Laboratory	STL582281	http://www.request.vitasmlab.biz/index.php?option=com_search_stk&Itemid=22&stk=STL582281&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
Yuhao Chemical	HL1932	http://www.chemyuhao.com/514-65-8.html
eNovation Chemicals	D383306	http://www.enovationchem.com/productDetails.asp?productID=D383306

PubMed

Title	Date	PubMed
Tardive dystonia induced by risperidone.	1999 Jun	10389620
[A case of amoxapine-induced tardive dystonia successfully treated with a low dose anti-cholinergic agent].	2000 Apr	10967655
Quantitative prediction of catalepsy induced by amoxapine, cinnarizine and cyclophosphamide in mice.	2000 May	11180191
Insomnia related to biperiden withdrawal in two schizophrenic patients.	2000 Nov	11110012
The influence of anticholinergic drug selection on the effectiveness of oximes against soman-induced supralethal poisoning in mice.	2001	11488139
[Swollen tongue].	2001 Apr	11383358
[Effect of diazepam on the effectiveness of antidote therapy in eliminating the acute lethal effects of soman in mice].	2001 Aug	11678028
Biperiden for excessive sweating from clozapine.	2001 Aug	11481174
Effects of advanced candidate anticonvulsants under two rodent models of 'counting'.	2001 Dec	11920930
Effects of selected anticholinergics on acoustic startle response in rats.	2001 Dec	11920928
A case of child abuse: haloperidol poisoning of a child caused by his mother.	2001 Dec	11785601
Restlessness in suboccipital muscles as a manifestation of akathisia.	2001 Feb	11235864
Modulation by muscarinic antagonists of the response to carbon dioxide challenge in panic disorder.	2001 Feb	11177112
Effects of olanzapine and other antipsychotics on cognitive function in chronic schizophrenia: a longitudinal study.	2001 Mar 1	11278151
The influence of anticholinergic drug and oxime selection on the effectiveness of antidotal treatment against tabun-induced poisoning in mice.	2002	12325456
The determination of biperiden in plasma using gas chromatography mass spectrometry: pharmacokinetics after intramuscular administration to guinea pigs.	2002 Feb	11816011
[Severe parkinsonism due to metoclopramide in a patient with polypharmacy].	2002 Jan 26	11845569
A case of Meige dystonia induced by short-term quetiapine treatment.	2002 Jun	12404689
Effects of anticholinergics on serial-probe recognition accuracy of rhesus macaques (Macaca mulatta).	2002 Nov	12213528
Effect of sabcomeline on muscarinic and dopamine receptor binding in intact mouse brain.	2003 Apr	12790361
[Acute dystonic reaction due to quinine].	2003 Dec	14697088
Pharmacokinetics of intramuscularly administered biperiden in guinea pigs challenged with soman.	2003 Feb	12643036
Biperiden for excessive sweating from methadone.	2003 Feb	12562595
[Utility of quetiapine in tardive dyskinesia].	2003 Nov-Dec	14639511
A CYP2D6 phenotype-genotype mismatch in Japanese psychiatric patients.	2003 Sep	14571354
Adjunctive estrogen treatment in women with chronic schizophrenia: a double-blind, randomized, and placebo-controlled trial.	2003 Sep	14499318
Anticholinergic drugs--functional antidotes for the treatment of tabun intoxication.	2004	15168875
Antiparkinsonian-like effects of Plumbago scandens on tremorine-induced tremors methodology.	2004 Dec	15582683
Effects of discontinuation of long-term anticholinergic treatment in elderly schizophrenia patients.	2004 Jan	15101567
Reversible orofacial dyskinesia after ofloxacin treatment.	2004 Jun	15197723
Comparisons of psychotropic drug prescribing patterns in acute psychiatric wards across Europe.	2004 Mar	14747883
Ecstasy and acute dystonia.	2004 Nov	15390124
Anaphylactic reaction and unrelated, subsequent, known side effects during therapy with thiethylperazine.	2005 Aug	16101941
Major depressive disorder with psychotic features induced by interferon-alpha treatment for hepatitis C in a polydrug abuser.	2005 Jan	15671136
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	15637638
Administration of haloperidol with biperiden reduces mRNAs related to the ubiquitin-proteasome system in mice.	2005 Jun 15	15803500
Role of nitric oxide on motor behavior.	2005 Mar	16047547
The effects of amisulpride on five dimensions of psychopathology in patients with schizophrenia: a prospective open-label study.	2005 May 3	15869707
Sudden akathisia after a ziprasidone dose reduction.	2006 Mar	16513883
Acute dystonic reaction to metoclopramide in patients carrying homozygous cytochrome P450 2D6 genetic polymorphisms.	2006 May	16702617
Kinetic and molecular evidences that human cardiac muscle express non-M2 muscarinic receptor subtypes that are able to interact themselves.	2006 Nov	16965921
[Therapy of postoperative nausea and vomiting in ENT--tardive dyskinesia as an adverse effect of metoclopramid--a case report].	2006 Nov	16586284
Neuroleptic malignant syndrome induced by ziprasidone on the second day of treatment.	2007	17366349
Acute dystonia resulting from abrupt bupropion discontinuation.	2007 Apr 13	17218049
Acute dystonia after injection of pegylated interferon alpha-2b.	2007 Apr 15	17279542

Patents

Sample Use Guides

In Vivo Use Guide

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 `Thu Jul 06 21:52:35 UTC 2023` Edited by `admin` on `Thu Jul 06 21:52:35 UTC 2023`
Record UNII	0FRP6G56LD
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BIPERIDEN

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