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
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
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 |
DescriptionCurator'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
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 |
---|---|---|---|
Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9798802 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | AKINETON Approved UseFor 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 |
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Palliative | AKINETON Approved UseFor 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 |
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Palliative | AKINETON Approved UseFor 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 |
Cmax
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 |
T1/2
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) Sources: alprazolam(20mg, PO, single) |
unhealthy, 35 n = 1 Health Status: unhealthy Condition: bipolar disorder Age Group: 35 Sex: F Population Size: 1 Sources: |
Other AEs: Hallucinations, Coma... Other AEs: Hallucinations Sources: 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
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) Sources: alprazolam(20mg, PO, single) |
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) Sources: alprazolam(20mg, PO, single) |
unhealthy, 35 n = 1 Health Status: unhealthy Condition: bipolar disorder Age Group: 35 Sex: F Population Size: 1 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
weak [Activation 0.1 uM] | ||||
yes [Inhibition 100 uM] | ||||
yes [Ki 0.45 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
yes [Km 37 uM] | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
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[Treatment of the neuroleptic syndrome by biperiden hydrochloride under its delayed-action form. A 9-month study on 55 hospitalized patients]. | 1976 |
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Tardive dystonia induced by risperidone. | 1999 Jun |
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Acute dystonia associated with fluvoxamine-metoclopramide. | 1999 Mar |
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[Swollen tongue]. | 2001 Apr |
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[Acute dystonia caused by metoclopramide (Afipran) therapy]. | 2001 Aug 10 |
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Restlessness in suboccipital muscles as a manifestation of akathisia. | 2001 Feb |
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Effects of olanzapine and other antipsychotics on cognitive function in chronic schizophrenia: a longitudinal study. | 2001 Mar 1 |
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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 |
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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 |
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Population pharmacokinetics of haloperidol using routine clinical pharmacokinetic data in Japanese patients. | 2002 |
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[A case of fluvoxamine overdose]. | 2002 Jan |
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Cytochrome P450 2D6 deficiency and its clinical relevance in a patient treated with risperidone. | 2002 May |
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A comparison of the neuroprotective efficacy of pharmacological pretreatment and antidotal treatment in soman-poisoned rats. | 2003 |
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Biperiden for excessive sweating from methadone. | 2003 Feb |
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[Utility of quetiapine in tardive dyskinesia]. | 2003 Nov-Dec |
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Acute dystonia caused by low dosage of olanzapine. | 2003 Spring |
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Anticholinergic drugs--functional antidotes for the treatment of tabun intoxication. | 2004 |
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Effects of discontinuation of long-term anticholinergic treatment in elderly schizophrenia patients. | 2004 Jan |
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Development of a screening method for the most commonly abused anticholinergic drugs in Jordan; trihexyphenidyl, procyclidine and biperiden. | 2004 Oct |
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Neuropsychological measures of attention and memory function in schizophrenia: relationships with symptom dimensions and serum monoamine activity. | 2005 Aug 9 |
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Clozapine improves working memory updating in schizophrenia. | 2005 Dec |
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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 |
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Administration of haloperidol with biperiden reduces mRNAs related to the ubiquitin-proteasome system in mice. | 2005 Jun 15 |
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The effects of amisulpride on five dimensions of psychopathology in patients with schizophrenia: a prospective open-label study. | 2005 May 3 |
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Measurement of anticholinergic effects of psychotropic drugs in humans. | 2005 Sep |
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Acute dystonia with low-dosage aripiprazole in Tourette's disorder. | 2006 Apr |
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Sudden akathisia after a ziprasidone dose reduction. | 2006 Mar |
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[Therapy of postoperative nausea and vomiting in ENT--tardive dyskinesia as an adverse effect of metoclopramid--a case report]. | 2006 Nov |
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Biperiden-induced delirium model in rats: a behavioral and electroencephalographic study. | 2006 Oct 18 |
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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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3220113
(+)-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
Edited
Sat Dec 16 16:22:52 UTC 2023
by
admin
on
Sat Dec 16 16:22:52 UTC 2023
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Record UNII |
0FRP6G56LD
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-ATC |
N04AA02
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LIVERTOX |
NBK548257
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NCI_THESAURUS |
C29704
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WHO-ESSENTIAL MEDICINES LIST |
09
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NDF-RT |
N0000175574
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NDF-RT |
N0000175370
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WHO-VATC |
QN04AA02
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NCI_THESAURUS |
C38149
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DB00810
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SUB05843MIG
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C65263
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7128
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0FRP6G56LD
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DTXSID6022680
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3112
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7639
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100000090107
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m2508
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CHEMBL1101
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374
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759145
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915
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BIPERIDEN
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1589
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BIPERIDEN
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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. | ||
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2381
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D001712
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514-65-8
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208-184-6
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BINDER->LIGAND |
BINDING
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ACTIVE MOIETY |
http://apps.who.int/phint/pdf/b/Jb.6.1.58.pdf
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