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Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2016-02-11 01:30:43 UTC
HMDB IDHMDB14948
Secondary Accession NumbersNone
Metabolite Identification
Common NameBiperiden
DescriptionA 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]
Structure
Thumb
Synonyms
ValueSource
1-bicyclo[2.2.1]Hept-5-en-2-yl-1-phenyl-3-piperidin-1-yl-propan-1-olChEBI
alpha-5-Norbornen-2-yl-alpha-phenyl-1-piperidinepropanolChEBI
alpha-bicyclo[2.2.1]Hept-5-en-2-yl-alpha-phenyl-1-piperidinepropanolChEBI
BiperideneChEBI
BiperidenoChEBI
BiperidenumChEBI
a-5-Norbornen-2-yl-a-phenyl-1-piperidinepropanolGenerator
α-5-norbornen-2-yl-α-phenyl-1-piperidinepropanolGenerator
a-bicyclo[2.2.1]Hept-5-en-2-yl-a-phenyl-1-piperidinepropanolGenerator
α-bicyclo[2.2.1]hept-5-en-2-yl-α-phenyl-1-piperidinepropanolGenerator
BeperidenHMDB
BiperidineHMDB
Chemical FormulaC21H29NO
Average Molecular Weight311.4611
Monoisotopic Molecular Weight311.224914555
IUPAC Name1-{bicyclo[2.2.1]hept-5-en-2-yl}-1-phenyl-3-(piperidin-1-yl)propan-1-ol
Traditional Namebiperiden
CAS Registry Number514-65-8
SMILES
OC(CCN1CCCCC1)(C1CC2CC1C=C2)C1=CC=CC=C1
InChI Identifier
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
InChI KeyInChIKey=YSXKPIUOCJLQIE-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropylamines. These are compounds containing a phenylpropylamine moiety, which consists of a phenyl group substituted at the third carbon by an propan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropylamines
Direct ParentPhenylpropylamines
Alternative Parents
Substituents
  • Phenylpropylamine
  • Aralkylamine
  • Piperidine
  • Tertiary alcohol
  • 1,3-aminoalcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antidyskinetics
  • Antiparkinson Agents
  • Muscarinic Antagonists
  • Parasympatholytics
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point114 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.26e-03 g/LNot Available
LogP4.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0043 mg/mLALOGPS
logP4.28ALOGPS
logP3.54ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)13.82ChemAxon
pKa (Strongest Basic)9.3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.02 m3·mol-1ChemAxon
Polarizability36.74 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-92eb93b999cf7f5ec519View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00810
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00810
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00810
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2289
KEGG Compound IDC07941
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBiperiden
NuGOwiki LinkHMDB14948
Metagene LinkHMDB14948
METLIN IDNot Available
PubChem Compound2381
PDB IDNot Available
ChEBI ID3112
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [8420174 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. [19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular weight:
51420.4
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Hosoi R, Kobayashi K, Watanabe Y, Inoue O: Evaluation of in vivo binding properties of 3H-NMPB and 3H-QNB in mouse brain. J Neural Transm. 1999;106(7-8):583-92. [10907719 ]
  4. Pehl C, Wendl B, Kaess H, Pfeiffer A: Effects of two anticholinergic drugs, trospium chloride and biperiden, on motility and evoked potentials of the oesophagus. Aliment Pharmacol Ther. 1998 Oct;12(10):979-84. [9798802 ]
  5. Eltze M: Multiple mechanisms of action: the pharmacological profile of budipine. J Neural Transm Suppl. 1999;56:83-105. [10370904 ]
  6. Eltze M, Galvan M: Involvement of muscarinic M2 and M3, but not of M1 and M4 receptors in vagally stimulated contractions of rabbit bronchus/trachea. Pulm Pharmacol. 1994 Apr;7(2):109-20. [8081071 ]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
General function:
Involved in extracellular ligand-gated ion channel activity
Specific function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane
Gene Name:
CHRNA2
Uniprot ID:
Q15822
Molecular weight:
59764.8
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [12438524 ]