NAV

Cycrimine

Identification

Generic Name
Cycrimine
DrugBank Accession Number
DB00942
Background

Cycrimine is a drug used to reduce levels of acetylcholine to return a balance with dopamine in the treatment and management of Parkinson's disease.

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
Weight
Average: 287.4397
Monoisotopic: 287.224914555
Chemical Formula
C19H29NO
Synonyms
  • (±)-cycrimine
  • alpha-cyclopentyl-alpha-phenyl-1-piperidinepropanol
  • Cicrimina
  • Cycrimine
  • Cycriminum

Pharmacology

Indication

For treatment and management of Parkinson's disease.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Cycrimine 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 action

Cycrimine 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.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

14-21%

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AclidiniumThe risk or severity of adverse effects can be increased when Cycrimine is combined with Aclidinium.
AdenosineThe risk or severity of Tachycardia can be increased when Adenosine is combined with Cycrimine.
AlfentanilThe risk or severity of adverse effects can be increased when Cycrimine is combined with Alfentanil.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Cycrimine.
AmantadineThe risk or severity of adverse effects can be increased when Amantadine is combined with Cycrimine.
AmbenoniumThe therapeutic efficacy of Cycrimine can be decreased when used in combination with Ambenonium.
AmitriptylineThe risk or severity of adverse effects can be increased when Cycrimine is combined with Amitriptyline.
AmitriptylinoxideThe risk or severity of adverse effects can be increased when Cycrimine is combined with Amitriptylinoxide.
AmobarbitalThe risk or severity of adverse effects can be increased when Cycrimine is combined with Amobarbital.
AmoxapineThe risk or severity of adverse effects can be increased when Cycrimine is combined with Amoxapine.
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Cycrimine hydrochloride9RB4L4K895126-02-3WBCWFMFZMRFRLT-UHFFFAOYSA-N
International/Other Brands
Pagitane (Lilly)

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
Aralkylamines
Alternative Parents
Piperidines / Benzene and substituted derivatives / Tertiary alcohols / 1,3-aminoalcohols / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
Substituents
1,3-aminoalcohol / Alcohol / Aralkylamine / Aromatic alcohol / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Hydrocarbon derivative / Monocyclic benzene moiety / Organic oxygen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
piperidines, tertiary alcohol, tertiary amino compound (CHEBI:59692)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
543567RFQQ
CAS number
77-39-4
InChI Key
SWRUZBWLEWHWRI-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

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. [Article]
Human Metabolome Database
HMDB0015077
PubChem Compound
2911
PubChem Substance
46506736
ChemSpider
2808
RxNav
22037
ChEBI
59692
ChEMBL
CHEMBL1201227
Therapeutic Targets Database
DAP001120
PharmGKB
PA164749387
Wikipedia
Cycrimine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Eli lilly and co
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)112-113Ruddy, 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
Polarizability34.79 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0002-9000000000-43de7e4a24aa5556ad34
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Details1. Muscarinic acetylcholine receptor M1
Kind
Protein
Organism
Humans
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...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
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. [Article]
  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. [Article]
  3. Vedasiromoni JR, Ganguly DK: Cycrimine on rat diaphragm. Arch Int Pharmacodyn Ther. 1976 Jan;219(1):64-9. [Article]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created at June 13, 2005 13:24 / Updated at November 03, 2023 23:50