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 169 Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9798802	Antagonist 2778

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 8429	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
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 8429	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
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 8429	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

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 1587 activator 80 substrate 1737		inhibitor 1852 substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461	P-gp 1537 CYP1A2 1054

Drug as perpetrator

Target	Modality	Activity
P-gp 1650	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0MzAyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExMDEifX0%3D	no
CYP3A4 1925	activator 214 Sources: https://link.springer.com/article/10.1007%2Fs002280050455	weak [Activation 0.1 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://link.springer.com/article/10.1007%2Fs002280050455	yes [Inhibition 100 uM]
CYP2D6 1891	inhibitor 3277 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 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22554863/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0MzAyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExMDEifX0%3D	no
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/, https://www.tandfonline.com/doi/abs/10.1080/03602530903118729	yes [Km 37 uM]
CYP1A2 1054	substrate 3367 Sources: https://www.tandfonline.com/doi/abs/10.1080/03602530903118729	yes
CYP3A4 1737	substrate 3367 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
Fluphenazine enanthate induced decompensations.	1975	1178807
Use of pimozide in the Pisa syndrome.	1992 Aug	1322069
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
The influence of pilocarpine and biperiden on pH value and calcium, phosphate, and bicarbonate concentrations in saliva during and after radiotherapy for head and neck cancer.	2001 Nov	11709686
The influence of anticholinergic drug and oxime selection on the effectiveness of antidotal treatment against tabun-induced poisoning in mice.	2002	12325456
Influence of lipophilicity and lysosomal accumulation on tissue distribution kinetics of basic drugs: a physiologically based pharmacokinetic model.	2002 Mar	12040887
Cytochrome P450 2D6 deficiency and its clinical relevance in a patient treated with risperidone.	2002 May	12107857
A case of Parkinsonism due to lithium intoxication: treatment with Pramipexole.	2002 May	12093142
Effects of anticholinergics on serial-probe recognition accuracy of rhesus macaques (Macaca mulatta).	2002 Nov	12213528
Sexual disinhibition induced by risperidone in a child.	2002 Winter	12626000
Transient and reversible parkinsonism after acute organophosphate poisoning.	2003	12645970
Control of nerve agent-induced seizures is critical for neuroprotection and survival.	2003 Apr 15	12691725
Motor disturbances in mice with deficiency of the sodium channel gene Scn8a show features of human dystonia.	2003 Dec	14769375
Pharmacokinetics of intramuscularly administered biperiden in guinea pigs challenged with soman.	2003 Feb	12643036
Anticholinergic drugs--functional antidotes for the treatment of tabun intoxication.	2004	15168875
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
Use of polypharmacotherapy in pregnancy: a prospective outcome in a case.	2004 May	15093969
Ecstasy and acute dystonia.	2004 Nov	15390124
Development of a screening method for the most commonly abused anticholinergic drugs in Jordan; trihexyphenidyl, procyclidine and biperiden.	2004 Oct	15363448
Tardive nocturnal akathisia due to clozapine treatment.	2005	16240977
Anaphylactic reaction and unrelated, subsequent, known side effects during therapy with thiethylperazine.	2005 Aug	16101941
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	16009538
Clozapine improves working memory updating in schizophrenia.	2005 Dec	15905072
Beneficial antipsychotic effects of allopurinol as add-on therapy for schizophrenia: a double blind, randomized and placebo controlled trial.	2005 Feb	15694232
Major depressive disorder with psychotic features induced by interferon-alpha treatment for hepatitis C in a polydrug abuser.	2005 Jan	15671136
Possible malignant neuroleptic syndrome that associated with hypothyroidism.	2005 Jun	15927337
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
The effects of amisulpride on five dimensions of psychopathology in patients with schizophrenia: a prospective open-label study.	2005 May 3	15869707
Evaluation of the clinical efficacy of risperidone for untreated and treated cases of schizophrenia from various aspects.	2005 Oct	16194258
Measurement of anticholinergic effects of psychotropic drugs in humans.	2005 Sep	16189744
Scopolamine-induced convulsions in fasted mice after food intake: effects of glucose intake, antimuscarinic activity and anticonvulsant drugs.	2005 Sep	15919102
Acute dystonia with low-dosage aripiprazole in Tourette's disorder.	2006 Apr	16569800
Modification of practice-dependent plasticity in human motor cortex by neuromodulators.	2006 Aug	16221926
[The prevalence and pharmacological cost of Parkinson's disease in Spain].	2006 Dec 1-15	17133323
Antipsychotics-induced hypersensitivity of visual perception.	2006 Jul	16860706
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
Association between two distinct executive tasks in schizophrenia: a functional transcranial Doppler sonography study.	2006 May 24	16723019
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
Biperiden-induced delirium model in rats: a behavioral and electroencephalographic study.	2006 Oct 18	16938281
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
Early onset of treatment effects with oral risperidone.	2007 Jan 19	17239237
Simultaneous prescribing of atypical antipsychotics, conventional antipsychotics and anticholinergics-a European study.	2007 Jun	17333501

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 `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

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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