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Identification
NameOxyphencyclimine
Accession NumberDB00383  (APRD00399)
TypeSmall Molecule
GroupsApproved
Description

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

Structure
Thumb
Synonyms
Oxifencicliminum
Oxyphencyclimine
Oxyphencycliminum
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
ProclimineNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Oxyphencyclimine Hydrochloride
Thumb
  • InChI Key: WXAYTPABEADAAB-UHFFFAOYNA-N
  • Monoisotopic Mass: 380.186670511
  • Average Mass: 380.909
DBSALT000812
Categories
UNII4V44H1O8XI
CAS number125-53-1
WeightAverage: 344.4479
Monoisotopic: 344.209992772
Chemical FormulaC20H28N2O3
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • Imidolactam
  • 1,4,5,6-tetrahydropyrimidine
  • Hydropyrimidine
  • Tertiary alcohol
  • Tertiary amine
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid amidine
  • Amidine
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of peptic ulcer disease and the relief of smooth muscle spasms in gastrointestinal disorders.
PharmacodynamicsOxyphencyclimine 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 actionOxyphencyclimine 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
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
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Pfizer laboratories div pfizer inc
Packagers
  • Professional Co.
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Oxyphencyclimine hcl powder30.0USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesA03AA01A03CA03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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 action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM3
Uniprot ID:
P20309
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 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. 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 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 trigge...
Gene Name:
CHRM2
Uniprot ID:
P08172
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 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10