Identification

Name
Oxyphencyclimine
Accession Number
DB00383  (APRD00399)
Type
Small Molecule
Groups
Approved
Description

Oxyphencyclimine is an anticholinergic drug (trade name Daricon) used in treating peptic ulcers.

Structure
Thumb
Synonyms
  • Oxifencicliminum
  • Oxyphencyclimine
  • Oxyphencycliminum
Product Ingredients
IngredientUNIICASInChI Key
Oxyphencyclimine HydrochlorideGWO1432WOU125-52-0WXAYTPABEADAAB-UHFFFAOYSA-N
International/Other Brands
Proclimine
Categories
UNII
4V44H1O8XI
CAS number
125-53-1
Weight
Average: 344.4479
Monoisotopic: 344.209992772
Chemical Formula
C20H28N2O3
InChI Key
DUDKAZCAISNGQN-UHFFFAOYSA-N
InChI
InChI=1S/C20H28N2O3/c1-22-14-8-13-21-18(22)15-25-19(23)20(24,16-9-4-2-5-10-16)17-11-6-3-7-12-17/h2,4-5,9-10,17,24H,3,6-8,11-15H2,1H3
IUPAC Name
(1-methyl-1,4,5,6-tetrahydropyrimidin-2-yl)methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate
SMILES
CN1CCCN=C1COC(=O)C(O)(C1CCCCC1)C1=CC=CC=C1

Pharmacology

Indication

For the treatment of peptic ulcer disease and the relief of smooth muscle spasms in gastrointestinal disorders.

Structured Indications
Not Available
Pharmacodynamics

Oxyphencyclimine is a synthetic anticholinergic agent which has been shown in experimental and clinical studies to have a pronounced antispasmodic and antisecretory effect on the gastrointestinal tract. Oxyphencyclimine is an antimuscarinic, anticholinergic drug.

Mechanism of action

Oxyphencyclimine binds the muscarinic acetylcholine receptor. It may block all three types of muscarinic receptors including M-1 receptors in the CNS and ganglia, M-2 receptors in the heart (vagus) and M-3 receptors at the parasympathetic NEJ system. The muscarinic acetylcholine receptors mediate various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Oxphencyclimine inhibits vagally mediated reflexes by antagonizing the action of acetylcholine. This in turn reduces the secretion of gastric acids in the stomach.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M3
antagonist
Human
AMuscarinic acetylcholine receptor M1
antagonist
Human
AMuscarinic acetylcholine receptor M2
antagonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0014527
KEGG Compound
C07851
PubChem Compound
4642
PubChem Substance
46507487
ChemSpider
4481
ChEBI
7868
ChEMBL
CHEMBL1495
Therapeutic Targets Database
DAP000835
PharmGKB
PA164776910
ATC Codes
A03CA03 — Oxyphencyclimine and psycholepticsA03AA01 — Oxyphencyclimine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Pfizer laboratories div pfizer inc
Packagers
  • Professional Co.
Dosage forms
Not Available
Prices
Unit descriptionCostUnit
Oxyphencyclimine hcl powder30.0USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility6.61 mg/L at 25 °CNot Available
logP3.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0567 mg/mLALOGPS
logP2.89ALOGPS
logP2.62ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)11.53ChemAxon
pKa (Strongest Basic)8.37ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area62.13 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity97.13 m3·mol-1ChemAxon
Polarizability38.34 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8659
Blood Brain Barrier+0.7384
Caco-2 permeable-0.536
P-glycoprotein substrateSubstrate0.8721
P-glycoprotein inhibitor IInhibitor0.7379
P-glycoprotein inhibitor IIInhibitor0.7327
Renal organic cation transporterInhibitor0.7347
CYP450 2C9 substrateNon-substrate0.7099
CYP450 2D6 substrateNon-substrate0.749
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.85
CYP450 2C9 inhibitorNon-inhibitor0.8079
CYP450 2D6 inhibitorNon-inhibitor0.5738
CYP450 2C19 inhibitorNon-inhibitor0.8212
CYP450 3A4 inhibitorNon-inhibitor0.8807
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9238
Ames testNon AMES toxic0.7718
CarcinogenicityNon-carcinogens0.9463
BiodegradationNot ready biodegradable0.9709
Rat acute toxicity2.7846 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9668
hERG inhibition (predictor II)Non-inhibitor0.5266
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
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as hydropyrimidines. These are compounds containing a hydrogenated pyrimidine ring (i.e. containing less than the maximum number of double bonds.).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Hydropyrimidines
Alternative Parents
Imidolactams / Benzene and substituted derivatives / Tertiary alcohols / Carboxylic acid esters / Propargyl-type 1,3-dipolar organic compounds / Monocarboxylic acids and derivatives / Carboximidamides / Carboxamidines / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
Monocyclic benzene moiety / Hydropyrimidine / 1,4,5,6-tetrahydropyrimidine / Benzenoid / Imidolactam / Tertiary alcohol / Carboxylic acid ester / Azacycle / Amidine / Carboxylic acid amidine
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
monocarboxylic acid (CHEBI:7868)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
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...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 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. 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. [PubMed:1426023]
  4. Schjelderup L, Kozlowski MR, Weissman A, Aasen AJ: Antimuscarinic effects of (R)- and (S)- oxyphencyclimine hydrochloride. Pharm Res. 1988 Apr;5(4):236-7. [PubMed:3247303]
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...
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. [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. 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. [PubMed:1426023]
  4. Schjelderup L, Kozlowski MR, Weissman A, Aasen AJ: Antimuscarinic effects of (R)- and (S)- oxyphencyclimine hydrochloride. Pharm Res. 1988 Apr;5(4):236-7. [PubMed:3247303]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
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...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 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. 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. [PubMed:1426023]
  4. Schjelderup L, Kozlowski MR, Weissman A, Aasen AJ: Antimuscarinic effects of (R)- and (S)- oxyphencyclimine hydrochloride. Pharm Res. 1988 Apr;5(4):236-7. [PubMed:3247303]

Drug created on June 13, 2005 07:24 / Updated on January 19, 2018 10:47