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Oxyphencyclimine
Identification
- Name
- Oxyphencyclimine
- Accession Number
- DB00383
- Description
Oxyphencyclimine is an anticholinergic drug (trade name Daricon) used in treating peptic ulcers.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Oxyphencyclimine (DB00383)
- Weight
- Average: 344.4479
Monoisotopic: 344.209992772 - Chemical Formula
- C20H28N2O3
- Synonyms
- Oxifencicliminum
- Oxyphencyclimine
- Oxyphencycliminum
Pharmacology
- Indication
For the treatment of peptic ulcer disease and the relief of smooth muscle spasms in gastrointestinal disorders.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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.
Target Actions Organism AMuscarinic acetylcholine receptor M3 antagonistHumans AMuscarinic acetylcholine receptor M1 antagonistHumans AMuscarinic acetylcholine receptor M2 antagonistHumans - 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
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- 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.
Drug Interaction Unlock Additional DataAcetazolamide Acetazolamide may increase the central nervous system depressant (CNS depressant) activities of Oxyphencyclimine. Acetophenazine Acetophenazine may increase the central nervous system depressant (CNS depressant) activities of Oxyphencyclimine. Aclidinium The risk or severity of adverse effects can be increased when Oxyphencyclimine is combined with Aclidinium. Adenosine The risk or severity of Tachycardia can be increased when Oxyphencyclimine is combined with Adenosine. Agomelatine Agomelatine may increase the central nervous system depressant (CNS depressant) activities of Oxyphencyclimine. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Oxyphencyclimine. Alimemazine Alimemazine may increase the central nervous system depressant (CNS depressant) activities of Oxyphencyclimine. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Oxyphencyclimine. Almotriptan Almotriptan may increase the central nervous system depressant (CNS depressant) activities of Oxyphencyclimine. Alosetron Alosetron may increase the central nervous system depressant (CNS depressant) activities of Oxyphencyclimine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Oxyphencyclimine hydrochloride GWO1432WOU 125-52-0 WXAYTPABEADAAB-UHFFFAOYSA-N - International/Other Brands
- Proclimine
Categories
- ATC Codes
- A03AA01 — Oxyphencyclimine
- A03AA — Synthetic anticholinergics, esters with tertiary amino group
- A03A — DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS
- A03 — DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,4,5,6-tetrahydropyrimidine / Alcohol / Amidine / Aromatic alcohol / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboximidamide / Carboxylic acid amidine show 16 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- monocarboxylic acid (CHEBI:7868)
Chemical Identifiers
- UNII
- 4V44H1O8XI
- CAS number
- 125-53-1
- 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
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014527
- KEGG Drug
- D08325
- KEGG Compound
- C07851
- PubChem Compound
- 4642
- PubChem Substance
- 46507487
- ChemSpider
- 4481
- 32698
- ChEBI
- 7868
- ChEMBL
- CHEMBL1495
- Therapeutic Targets Database
- DAP000835
- PharmGKB
- PA164776910
- Wikipedia
- Oxyphencyclimine
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Pfizer laboratories div pfizer inc
- Packagers
- Professional Co.
- Dosage Forms
Form Route Strength Tablet 5 mg - Prices
Unit description Cost Unit Oxyphencyclimine hcl powder 30.0USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility 6.61 mg/L at 25 °C Not Available logP 3.7 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0567 mg/mL ALOGPS logP 2.89 ALOGPS logP 2.62 ChemAxon logS -3.8 ALOGPS pKa (Strongest Acidic) 11.53 ChemAxon pKa (Strongest Basic) 8.37 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 62.13 Å2 ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 97.13 m3·mol-1 ChemAxon Polarizability 38.34 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8659 Blood Brain Barrier + 0.7384 Caco-2 permeable - 0.536 P-glycoprotein substrate Substrate 0.8721 P-glycoprotein inhibitor I Inhibitor 0.7379 P-glycoprotein inhibitor II Inhibitor 0.7327 Renal organic cation transporter Inhibitor 0.7347 CYP450 2C9 substrate Non-substrate 0.7099 CYP450 2D6 substrate Non-substrate 0.749 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Non-inhibitor 0.85 CYP450 2C9 inhibitor Non-inhibitor 0.8079 CYP450 2D6 inhibitor Non-inhibitor 0.5738 CYP450 2C19 inhibitor Non-inhibitor 0.8212 CYP450 3A4 inhibitor Non-inhibitor 0.8807 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9238 Ames test Non AMES toxic 0.7718 Carcinogenicity Non-carcinogens 0.9463 Biodegradation Not ready biodegradable 0.9709 Rat acute toxicity 2.7846 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9668 hERG inhibition (predictor II) Non-inhibitor 0.5266
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- 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
- 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]
- 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]
- 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]
- 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
- 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
- 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]
- 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]
- 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]
- 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
- Humans
- 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
- 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]
- 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]
- 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]
- 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 July 02, 2020 07:26
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