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Record Information
Version2.0
Creation Date2009-07-21 20:26:46 UTC
Update Date2014-12-24 20:25:51 UTC
Accession NumberT3D2773
Identification
Common NameProcyclidine
ClassSmall Molecule
DescriptionProcyclidine is only found in individuals that have used or taken this drug. It is a muscarinic antagonist that crosses the blood-brain barrier and is used in the treatment of drug-induced extrapyramidal disorders and in parkinsonism. The mechanism of action is unknown. It is thought that Procyclidine acts by blocking central cholinergic receptors, and thus balancing cholinergic and dopaminergic activity in the basal ganglia. Many of its effects are due to its pharmacologic similarities with atropine. Procyclidine exerts an antispasmodic effect on smooth muscle, and may produce mydriasis and reduction in salivation.
Compound Type
  • Amine
  • Antidyskinetic
  • Antiparkinson Agent
  • Drug
  • Metabolite
  • Muscarinic Antagonist
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
1-cyclohexyl-1-phenyl-3-pyrrolidin-1-yl-propan-1-ol hydrochloride
1-Cyclohexyl-1-phenyl-3-pyrrolidino-1-propanol
Arpicolin
Extranil
Kdrine
Kemadren
Kemadrin
Osnervan
Prociclidina
Procyclidin
Procyclidinum
Prodine
Proimer
Tricyclamol
Chemical FormulaC19H29NO
Average Molecular Mass287.440 g/mol
Monoisotopic Mass287.225 g/mol
CAS Registry Number77-37-2
IUPAC Name1-cyclohexyl-1-phenyl-3-(pyrrolidin-1-yl)propan-1-ol
Traditional Nameprocyclidine
SMILESOC(CCN1CCCC1)(C1CCCCC1)C1=CC=CC=C1
InChI IdentifierInChI=1/C19H29NO/c21-19(17-9-3-1-4-10-17,18-11-5-2-6-12-18)13-16-20-14-7-8-15-20/h1,3-4,9-10,18,21H,2,5-8,11-16H2
InChI KeyInChIKey=WYDUSKDSKCASEF-UHFFFAOYNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • N-alkylpyrrolidine
  • 1,3-aminoalcohol
  • Pyrrolidine
  • Tertiary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organopnictogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point86°C
Boiling PointNot Available
SolubilityModerately soluble in water, ~ 30 mg/ml
LogP4.2
Predicted Properties
PropertyValueSource
Water Solubility0.0098 g/LALOGPS
logP4.13ALOGPS
logP3.79ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)13.84ChemAxon
pKa (Strongest Basic)9.45ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity88.6 m³·mol⁻¹ChemAxon
Polarizability34.43 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-9510000000-bb5c957fcb63641b16dfJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00c3-9371000000-a8f31f6dd1ab688edc1cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0090000000-346bcbb2ab2d7175b1bcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9240000000-b149734e30140564cb67JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9210000000-752d38a1eb305bdc9d05JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-15b4d4f82fafa22bb285JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9080000000-bcb7857676f4ed8009edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9010000000-1fd43c480f58b0322708JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-001i-9010000000-7d7f1b16f54aaca37f10JSpectraViewer | MoNA
Toxicity Profile
Route of ExposureOral
Mechanism of ToxicityThe mechanism of action is unknown. It is thought that Procyclidine acts by blocking central cholinergic receptors, and thus balancing cholinergic and dopaminergic activity in the basal ganglia. Many of its effects are due to its pharmacologic similarities with atropine. Procyclidine exerts an antispasmodic effect on smooth muscle, and may produce mydriasis and reduction in salivation.
MetabolismNot Available
Toxicity ValuesLD50=60 mg/kg (IV in mice)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of all forms of Parkinson's Disease, as well as control of extrapyramidal reactions induced by antipsychotic agents.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsLD50=60 mg/kg (IV in mice)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00387
HMDB IDHMDB14531
PubChem Compound ID4919
ChEMBL IDCHEMBL86715
ChemSpider ID4750
KEGG IDC07378
UniProt IDNot Available
OMIM ID
ChEBI ID8448
BioCyc IDNot Available
CTD IDNot Available
Stitch IDProcyclidine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkProcyclidine
References
Synthesis ReferenceNot Available
MSDST3D2773.pdf
General References
  1. Theodoridis GC, Stark L: Central role of solar information flow in pregenetic evolution. J Theor Biol. 1971 Jun;31(3):377-88. [5556140 ]
  2. Drugs.com [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Phosphatidylinositol phospholipase c activity
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:
51420.375 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.0046 uMNot AvailableBindingDB 50062598
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. Bolden C, Cusack B, Richelson E: Antagonism by antimuscarinic and neuroleptic compounds at the five cloned human muscarinic cholinergic receptors expressed in Chinese hamster ovary cells. J Pharmacol Exp Ther. 1992 Feb;260(2):576-80. [1346637 ]
General Function:
G-protein coupled acetylcholine receptor activity
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 adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then triggers calcium ion release into the cytosol.
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular Weight:
51714.605 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.025 uMNot AvailableBindingDB 50062598
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. Bolden C, Cusack B, Richelson E: Antagonism by antimuscarinic and neuroleptic compounds at the five cloned human muscarinic cholinergic receptors expressed in Chinese hamster ovary cells. J Pharmacol Exp Ther. 1992 Feb;260(2):576-80. [1346637 ]
General Function:
Receptor activity
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:
CHRM3
Uniprot ID:
P20309
Molecular Weight:
66127.445 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.0124 uMNot AvailableBindingDB 50062598
References
  1. Myhrer T: Identification of neuronal target areas for nerve agents and specification of receptors for pharmacological treatment. Neurotoxicology. 2010 Dec;31(6):629-38. doi: 10.1016/j.neuro.2010.07.002. Epub 2010 Jul 17. [20624420 ]
  2. Waelbroeck M, Camus J, Tastenoy M, Mutschler E, Strohmann C, Tacke R, Schjelderup L, Aasen A, Lambrecht G, Christophe J: Stereoselective interaction of procyclidine, hexahydro-difenidol, hexbutinol and oxyphencyclimine, and of related antagonists, with four muscarinic receptors. Eur J Pharmacol. 1992 Sep 1;227(1):33-42. [1426023 ]
  3. Bolden C, Cusack B, Richelson E: Antagonism by antimuscarinic and neuroleptic compounds at the five cloned human muscarinic cholinergic receptors expressed in Chinese hamster ovary cells. J Pharmacol Exp Ther. 1992 Feb;260(2):576-80. [1346637 ]
General Function:
Guanyl-nucleotide exchange factor activity
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 inhibition of adenylate cyclase.
Gene Name:
CHRM4
Uniprot ID:
P08173
Molecular Weight:
53048.65 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.007 uMNot AvailableBindingDB 50062598
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. Bolden C, Cusack B, Richelson E: Antagonism by antimuscarinic and neuroleptic compounds at the five cloned human muscarinic cholinergic receptors expressed in Chinese hamster ovary cells. J Pharmacol Exp Ther. 1992 Feb;260(2):576-80. [1346637 ]