Identification
- Generic Name
- Hexocyclium
- DrugBank Accession Number
- DB06787
- Background
Hexocyclium is a muscarinic acetylcholine receptor antagonist which was presumably used in the treatment of gastric ulcer or diarrhea. It was once available under the tradename Tral marketed by Abbvie Inc. but has been discontinued. Proton pump inhibitors like Omeprazole and opiate anti-diarrheal agents like Loperamide have largely replaced the use of anti-muscarinics in the treatment of gastric ulcers and diarrhea due to their more favorable side effect profiles.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Hexocyclium (DB06787)
- Weight
- Average: 317.496
Monoisotopic: 317.258740111 - Chemical Formula
- C20H33N2O
- Synonyms
- Not Available
Pharmacology
- Indication
The World Health Organization classifies hexocyclium as a drug for functional gastrointestinal disorders 5. Like other anti-muscarinic agents, hexocyclium was likely used to treat peptic ulcers or diarrhea.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Hexocyclium reduces gastrointesitinal motility and gastric acid secretion 2,3.
- Mechanism of action
Hexocyclium binds to and inhibits muscarinic acetylcholine receptors 1. This decreases gastric acid secretion by preventing the activation of M3 receptors on pareital cells and subsequent stimulation of gastric acid secretion 4. The antagonism of M3 receptors in the intestine inhibits smooth muscle contraction resulting in a decrease in motility. The binding of hexocyclium to other muscarinic receptor types produces typical anti-muscarinic side effects.
Target Actions Organism AMuscarinic acetylcholine receptor M3 antagonistHumans UMuscarinic acetylcholine receptor M1 antagonistHumans UMuscarinic acetylcholine receptor M2 antagonistHumans UMuscarinic acetylcholine receptor M4 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAclidinium The risk or severity of adverse effects can be increased when Hexocyclium is combined with Aclidinium. Adenosine The risk or severity of Tachycardia can be increased when Adenosine is combined with Hexocyclium. Albuterol The risk or severity of Tachycardia can be increased when Salbutamol is combined with Hexocyclium. Alfentanil The risk or severity of adverse effects can be increased when Hexocyclium is combined with Alfentanil. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Hexocyclium. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Hexocyclium methylsulfate 84OPZ2Q0VB 115-63-9 NSILVESQCSUIAJ-UHFFFAOYSA-M - International/Other Brands
- Tral (Abbott) / Traline (Abbott)
Categories
- ATC Codes
- A03AB10 — Hexocyclium
- 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
- N-methylpiperazines / Benzene and substituted derivatives / Tetraalkylammonium salts / Tertiary alcohols / Trialkylamines / 1,2-aminoalcohols / Azacyclic compounds / Organopnictogen compounds / Organic salts / Hydrocarbon derivatives show 2 more
- Substituents
- 1,2-aminoalcohol / 1,4-diazinane / Alcohol / Aralkylamine / Aromatic alcohol / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Hydrocarbon derivative / Monocyclic benzene moiety show 14 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- amine (CHEBI:5707)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- LL3147PI1T
- CAS number
- 6004-98-4
- InChI Key
- ZRYHPQCHHOKSMD-UHFFFAOYSA-N
- InChI
- InChI=1S/C20H33N2O/c1-22(2)15-13-21(14-16-22)17-20(23,18-9-5-3-6-10-18)19-11-7-4-8-12-19/h3,5-6,9-10,19,23H,4,7-8,11-17H2,1-2H3/q+1
- IUPAC Name
- 4-(2-cyclohexyl-2-hydroxy-2-phenylethyl)-1,1-dimethylpiperazin-1-ium
- SMILES
- C[N+]1(C)CCN(CC(O)(C2CCCCC2)C2=CC=CC=C2)CC1
References
- Synthesis Reference
U.S. Patent 2,907,765.
- General References
- Waelbroeck M, Camus J, Tastenoy M, Feifel R, Mutschler E, Tacke R, Strohmann C, Rafeiner K, Rodrigues de Miranda JF, Lambrecht G: Binding and functional properties of hexocyclium and sila-hexocyclium derivatives to muscarinic receptor subtypes. Br J Pharmacol. 1994 Jun;112(2):505-14. [Article]
- KASICH AM, FEIN HD: Hexocyclium methosulfate in active duodenal ulcer; evaluation of a new anticholinergic drug in conventional and long-acting forms, especially its effect on gastric pH as studied in 48-hour analysis. Am J Dig Dis. 1958 Jan;3(1):12-23. [Article]
- Grundhofer B, Gibaldi M: Biopharmaceutic factors that influence effects of anticholinergic drugs: comparison of propantheline, hexocyclium, and isopropamide. J Pharm Sci. 1977 Oct;66(10):1433-5. [Article]
- Rang, H. P. and Dale, M. M. (2012). Rang and Dale's Pharmacology (7th ed.). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
- WHOCC-ATC: Hexocyclium [Link]
- External Links
- KEGG Compound
- C07811
- PubChem Compound
- 24199
- PubChem Substance
- 310264885
- ChemSpider
- 22621
- BindingDB
- 81959
- 26867
- ChEBI
- 5707
- ChEMBL
- CHEMBL1201325
- Wikipedia
- Hexocyclium
- MSDS
- Download (671 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 203-204 U.S. Patent 2,907,765. - Predicted Properties
Property Value Source Water Solubility 0.000576 mg/mL ALOGPS logP -1.1 ALOGPS logP -0.99 Chemaxon logS -5.8 ALOGPS pKa (Strongest Acidic) 13.51 Chemaxon pKa (Strongest Basic) 4.95 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 23.47 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 108.16 m3·mol-1 Chemaxon Polarizability 38.29 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-057l-7940000000-f8b6f6e51eb3a973396b Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 174.30992 predictedDeepCCS 1.0 (2019) [M+H]+ 176.66792 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.1247 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- Waelbroeck M, Camus J, Tastenoy M, Feifel R, Mutschler E, Tacke R, Strohmann C, Rafeiner K, Rodrigues de Miranda JF, Lambrecht G: Binding and functional properties of hexocyclium and sila-hexocyclium derivatives to muscarinic receptor subtypes. Br J Pharmacol. 1994 Jun;112(2):505-14. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Waelbroeck M, Camus J, Tastenoy M, Feifel R, Mutschler E, Tacke R, Strohmann C, Rafeiner K, Rodrigues de Miranda JF, Lambrecht G: Binding and functional properties of hexocyclium and sila-hexocyclium derivatives to muscarinic receptor subtypes. Br J Pharmacol. 1994 Jun;112(2):505-14. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Waelbroeck M, Camus J, Tastenoy M, Feifel R, Mutschler E, Tacke R, Strohmann C, Rafeiner K, Rodrigues de Miranda JF, Lambrecht G: Binding and functional properties of hexocyclium and sila-hexocyclium derivatives to muscarinic receptor subtypes. Br J Pharmacol. 1994 Jun;112(2):505-14. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Guanyl-nucleotide exchange factor 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
- CHRM4
- Uniprot ID
- P08173
- Uniprot Name
- Muscarinic acetylcholine receptor M4
- Molecular Weight
- 53048.65 Da
References
- Waelbroeck M, Camus J, Tastenoy M, Feifel R, Mutschler E, Tacke R, Strohmann C, Rafeiner K, Rodrigues de Miranda JF, Lambrecht G: Binding and functional properties of hexocyclium and sila-hexocyclium derivatives to muscarinic receptor subtypes. Br J Pharmacol. 1994 Jun;112(2):505-14. [Article]
Drug created at September 14, 2010 16:21 / Updated at February 02, 2024 22:54