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514-65-8 molecular structure
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1-{bicyclo[2.2.1]hept-5-en-2-yl}-1-phenyl-3-(piperidin-1-yl)propan-1-ol

ChemBase ID: 689
Molecular Formular: C21H29NO
Molecular Mass: 311.46106
Monoisotopic Mass: 311.22491455
SMILES and InChIs

SMILES:
OC(C1C2CC(C1)C=C2)(CCN1CCCCC1)c1ccccc1
Canonical SMILES:
OC(C1CC2CC1C=C2)(c1ccccc1)CCN1CCCCC1
InChI:
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
InChIKey:
YSXKPIUOCJLQIE-UHFFFAOYSA-N

Cite this record

CBID:689 http://www.chembase.cn/molecule-689.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-{bicyclo[2.2.1]hept-5-en-2-yl}-1-phenyl-3-(piperidin-1-yl)propan-1-ol
IUPAC Traditional name
biperiden
biperidene
Brand Name
Akineton
Akinophyl
Synonyms
Biperiden [Usan:Ban:Inn:Jan]
Biperiden Hydrochloride
Biperidene Hydrochloride
Biperidene [INN-French]
Biperideno [INN-Spanish]
Biperidenum [INN-Latin]
Biperidine
Biperidine Hydrochloride
Beperiden
Biperiden
CAS Number
514-65-8
PubChem SID
46508325
160964152
PubChem CID
2381
CHEBI ID
3112
ATC CODE
N04AA02
CHEMBL
1101
Chemspider ID
2289
DrugBank ID
DB00810
KEGG ID
D00779
Unique Ingredient Identifier
0FRP6G56LD
Wikipedia Title
Biperiden
Medline Plus
a699058

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.820097  H Acceptors
H Donor LogD (pH = 5.5) 0.21261095 
LogD (pH = 7.4) 1.6437268  Log P 3.5365074 
Molar Refractivity 97.0158 cm3 Polarizability 37.70881 Å3
Polar Surface Area 23.47 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 4.28  LOG S -4.86 
Solubility (Water) 4.26e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Bioassay(PubChem)
Solubility
25.1 mg/L expand Show data source
Hydrophobicity(logP)
4.1 expand Show data source
Admin Routes
Oral, IM, IV expand Show data source
Bioavailability
33 ± 5% (oral) expand Show data source
Excretion
Renal expand Show data source
Half Life
18 to 24 hours expand Show data source
Metabolism
Hepatic hydroxylation expand Show data source
Protein Bound
60% expand Show data source
Legal Status
Rx-only (US) expand Show data source
Pregnancy Category
B2 (Australia) expand Show data source
C (US) expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB00810 external link
Item Information
Drug Groups approved
Description A muscarinic antagonist that has effects in both the central and peripheral nervous systems. It has been used in the treatment of arteriosclerotic, idiopathic, and postencephalitic parkinsonism. It has also been used to alleviate extrapyramidal symptoms induced by phenothiazine derivatives and reserpine. [PubChem]
Indication For use as an adjunct in the therapy of all forms of parkinsonism and control of extrapyramidal disorders secondary to neuroleptic drug therapy.
Pharmacology Biperiden is a weak peripheral anticholinergic agent. It has, therefore, some antisecretory, antispasmodic and mydriatic effects. In addition, biperiden possesses nicotinolytic activity. The parenteral form of biperiden is an effective and reliable agent for the treatment of acute episodes of extrapyramidal disturbances sometimes seen during treatment with neuroleptic agents. Akathisia, akinesia, dyskinetic tremors, rigor, oculogyric crisis, spasmodic torticollis, and profuse sweating are markedly reduced or eliminated. With parenteral biperiden, these drug-induced disturbances are rapidly brought under control.
Toxicity LD50=760 mg/kg (Orally in rats). Signs of overdose include dilated and sluggish pupils, warm, dry skin, facial flushing, decreased secretions of the mouth, pharynx, nose, and bronchi, foul-smelling breath, elevated temperature, tachycardia, cardiac arrhythmias, decreased bowel sounds, urinary retention, delirium, disorientation, anxiety, hallucinations, illusions, confusion, incoherence, agitation, hyperactivity, ataxia, loss of memory, paranoia, combativeness, and seizures.
Affected Organisms
Humans and other mammals
Biotransformation The metabolism of biperiden is not completely understood, but does involve hydroxylation.
Absorption 87% bioavailability
Protein Binding 60%
References
Nishiyama K, Mizuno T, Sakuta M, Kurisaki H: Chronic dementia in Parkinson's disease treated by anticholinergic agents. Neuropsychological and neuroradiological examination. Adv Neurol. 1993;60:479-83. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

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  • • Nishiyama K, Mizuno T, Sakuta M, Kurisaki H: Chronic dementia in Parkinson's disease treated by anticholinergic agents. Neuropsychological and neuroradiological examination. Adv Neurol. 1993;60:479-83. Pubmed
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PATENTS

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