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Identification
NameCycrimine
Accession NumberDB00942  (APRD00731)
TypeSmall Molecule
GroupsApproved
DescriptionCycrimine is a drug used to reduce levels of acetylcholine to return a balance with dopamine in the treatment and management of Parkinson's disease.
Structure
Thumb
Synonyms
(+-)-Cycrimine
alpha-Cyclopentyl-alpha-phenyl-1-piperidinepropanol
Cicrimina
Cycriminum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
PagitaneLilly
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Cycrimine hydrochloride
Thumb
  • InChI Key: WBCWFMFZMRFRLT-UHFFFAOYNA-N
  • Monoisotopic Mass: 323.201592294
  • Average Mass: 323.901
DBSALT000820
Categories
UNII543567RFQQ
CAS number77-39-4
WeightAverage: 287.4397
Monoisotopic: 287.224914555
Chemical FormulaC19H29NO
InChI KeySWRUZBWLEWHWRI-UHFFFAOYSA-N
InChI
InChI=1S/C19H29NO/c21-19(18-11-5-6-12-18,17-9-3-1-4-10-17)13-16-20-14-7-2-8-15-20/h1,3-4,9-10,18,21H,2,5-8,11-16H2
IUPAC Name
1-cyclopentyl-1-phenyl-3-(piperidin-1-yl)propan-1-ol
SMILES
OC(CCN1CCCCC1)(C1CCCC1)C1=CC=CC=C1
Pharmacology
IndicationFor treatment and management of Parkinson's disease.
Structured Indications Not Available
PharmacodynamicsCycrimine is a central anticholenergic used in the treatment of the symptoms of Parkinson's disease. It is a drug used to reduce levels of acetylcholine. Acetylcholine is usually in balance with dopamine neurotransmitters, however lower levels of dopamine are present in the brain of patients suffering from Parkinson's disease. By lowering levels of acetylcholine, it is thought that this balance may be restored.
Mechanism of actionCycrimine binds the muscarinic acetylcholine receptor M1, effectively inhibiting acetylcholine. This decrease in acetylcholine restores the normal dopamine-acetylcholine balance and relieves the symptoms of Parkinson's disease.
TargetKindPharmacological actionActionsOrganismUniProt ID
Muscarinic acetylcholine receptor M1Proteinyes
antagonist
HumanP11229 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein binding14-21%
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis Reference

Ruddy, A.W. and Becker, T.J.; U.S. Patent 2,680,115; June 1, 1954; assigned to Winthrop-Stearns Inc.

General References
  1. Vedasiromoni JR, Ganguly DK: Cycrimine on rat diaphragm. Arch Int Pharmacodyn Ther. 1976 Jan;219(1):64-9. [PubMed:1267542 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9465
Blood Brain Barrier+0.9686
Caco-2 permeable+0.6502
P-glycoprotein substrateSubstrate0.654
P-glycoprotein inhibitor IInhibitor0.5407
P-glycoprotein inhibitor IINon-inhibitor0.8279
Renal organic cation transporterInhibitor0.7739
CYP450 2C9 substrateNon-substrate0.8273
CYP450 2D6 substrateNon-substrate0.8337
CYP450 3A4 substrateNon-substrate0.5554
CYP450 1A2 substrateNon-inhibitor0.9193
CYP450 2C9 inhibitorNon-inhibitor0.9181
CYP450 2D6 inhibitorInhibitor0.9056
CYP450 2C19 inhibitorNon-inhibitor0.9102
CYP450 3A4 inhibitorNon-inhibitor0.8257
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9336
Ames testNon AMES toxic0.856
CarcinogenicityNon-carcinogens0.9292
BiodegradationNot ready biodegradable0.9172
Rat acute toxicity2.7260 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.6253
hERG inhibition (predictor II)Inhibitor0.5169
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point112-113Ruddy, A.W. and Becker, T.J.; U.S. Patent 2,680,115; June 1, 1954; assigned to Winthrop-Stearns Inc.
logP4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00909 mg/mLALOGPS
logP4.15ALOGPS
logP3.79ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)13.84ChemAxon
pKa (Strongest Basic)9.32ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity88.6 m3·mol-1ChemAxon
Polarizability34.78 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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 heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
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
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. [PubMed: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. [PubMed:17016423 ]
  3. Vedasiromoni JR, Ganguly DK: Cycrimine on rat diaphragm. Arch Int Pharmacodyn Ther. 1976 Jan;219(1):64-9. [PubMed:1267542 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23