Identification
- Summary
Homatropine methylbromide is a muscarinic receptor antagonist used to treat peptic ulcers, gastric ulcers, and duodenal ulcers.
- Brand Names
- Hycodan, Hydromet
- Generic Name
- Homatropine methylbromide
- DrugBank Accession Number
- DB00725
- Background
Homatropine methylbromide is a quaternary ammonium muscarinic acetylcholine receptor antagonist belonging to the group of medicines called anti-muscarinics. Homatropine is used to treat duodenal or stomach ulcers or intestine problems. It can be used together with antacids or other medicine in the treatment of peptic ulcer. It may also be used to prevent nausea, vomiting, and motion sickness.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Homatropine methylbromide (DB00725)
- Weight
- Average: 370.281
Monoisotopic: 369.093956286 - Chemical Formula
- C17H24BrNO3
- Synonyms
- 3-alpha-Hydroxy-8-methyl-1-alpha-H,5-alpha-H-tropanium bromide mandelate
- 8-Methylhomatropinium bromide
- Homatropine methylbromide
- Homatropini methylbromidum
- Méthylbromure d'homatropine
- Methylhomatropine
- Methylhomatropine bromide
- Methylhomatropinum bromatum
- Metilbromuro de homatropina
- Omatropina metilbromuro
- Tropinium methobromide mandelate
Pharmacology
- Indication
Used in conjunction with antacids or histamine H2-receptor antagonists in the treatment of peptic ulcers, gastric ulcers and duodenal ulcers, to reduce further gastric acid secretion and delay gastric emptying.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Cough Combination Product in combination with: Hydrocodone (DB00956) •••••••••••• Used in combination for symptomatic treatment of Cough Combination Product in combination with: Hydrocodone (DB00956) •••••••••••• - Contraindications & Blackbox Warnings
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Homatropine methylbromide belongs to the group of medicines called anti-muscarinics. Homatropine is used to treat duodenal or stomach ulcers or intestine problems. It can be used together with antacids or other medicine in the treatment of peptic ulcer. It may also be used to prevent nausea, vomiting, and motion sickness.
- Mechanism of action
Homatropine is a quaternary ammonium muscarinic acetylcholine receptor antagonist. 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. Homatropine methylbromide inhibits the muscarinic actions of acetylcholine on structures innervated by postganglionic cholinergic nerves as well as on smooth muscles that respond to acetylcholine but lack cholinergic innervation. These postganglionic receptor sites are present in the autonomic effector cells of the smooth muscle, cardiac muscle, sinoatrial and atrioventricular nodes, and exocrine glands. Depending on the dose, anticholinergics may reduce the motility and secretory activity of the gastrointestinal system, and the tone of the ureter and urinary bladder and may have a slight relaxant action on the bile ducts and gallbladder.
Target Actions Organism AMuscarinic acetylcholine receptor M2 antagonistHumans AMuscarinic acetylcholine receptor M1 antagonistHumans AMuscarinic acetylcholine receptor M4 antagonistHumans AMuscarinic acetylcholine receptor M5 antagonistHumans AMuscarinic acetylcholine receptor M3 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
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Homatropine methylbromide is combined with Aclidinium. Adenosine The risk or severity of Tachycardia can be increased when Adenosine is combined with Homatropine methylbromide. Alfentanil The risk or severity of adverse effects can be increased when Homatropine methylbromide is combined with Alfentanil. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Homatropine methylbromide. Amantadine The risk or severity of adverse effects can be increased when Homatropine methylbromide is combined with Amantadine. - Food Interactions
- No interactions found.
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.- Active Moieties
Name Kind UNII CAS InChI Key Homatropine unknown 8QS6WCL55Z 87-00-3 ZTVIKZXZYLEVOL-MCOXGKPRSA-N - Product Images
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Acidobyl Homatropine methylbromide (0.5 mg) + Dehydrocholic acid (120 mg) + Docusate sodium (60 mg) + Sodium taurocholate (120 mg) Tablet Oral Desbergers LtÉe, Division Of Technilab Inc. 1951-12-31 1999-09-17 Canada 
Antitussive hydrocodone bitartrate and homatropine methylbromide Homatropine methylbromide (1.5 mg/1) + Hydrocodone bitartrate (5 mg/1) Tablet Oral Actavis Totowa LLC 2001-01-01 2008-08-20 US 
Debiline H Homatropine methylbromide (2.5 mg / tab) + Deoxycholic acid (100 mg / tab) + Pepsin (50 mg / tab) Tablet Oral Lab Nadeau LtÉe, Division Of Technilab Inc. 1951-12-31 1999-09-28 Canada Hycodan Homatropine methylbromide (1.5 mg/1) + Hydrocodone bitartrate (5 mg/1) Tablet Oral Genus Lifesciences Inc. 2021-11-01 Not applicable US Hycodan Homatropine methylbromide (1.5 mg/5mL) + Hydrocodone bitartrate (5 mg/5mL) Syrup Oral Endo Pharmaceuticals, Inc. 1943-03-23 2008-12-31 US
Categories
- ATC Codes
- A03CB04 — Homatropine methylbromide and psycholeptics
- A03CB — Belladonna and derivatives in combination with psycholeptics
- A03C — ANTISPASMODICS IN COMBINATION WITH PSYCHOLEPTICS
- A03 — DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Agents producing tachycardia
- Alimentary Tract and Metabolism
- Alkaloids
- Anticholinergic Agents
- Aza Compounds
- Azabicyclo Compounds
- Belladonna Alkaloids, Semisynthetic, Quaternary Ammonium Compounds
- Belladonna and Derivatives, Plain
- Drugs for Functional Gastrointestinal Disorders
- Muscarinic Antagonists
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Tropane alkaloids
- Sub Class
- Not Available
- Direct Parent
- Tropane alkaloids
- Alternative Parents
- Piperidines / Benzene and substituted derivatives / N-alkylpyrrolidines / Tetraalkylammonium salts / Secondary alcohols / Carboxylic acid esters / Azacyclic compounds / Monocarboxylic acids and derivatives / Organic bromide salts / Hydrocarbon derivatives show 6 more
- Substituents
- Alcohol / Amine / Aromatic alcohol / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative show 19 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organic bromide salt, azabicycloalkane (CHEBI:50373)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 68JRS2HC1C
- CAS number
- 80-49-9
- InChI Key
- FUFVKLQESJNNAN-UHFFFAOYSA-M
- InChI
- InChI=1S/C17H24NO3.BrH/c1-18(2)13-8-9-14(18)11-15(10-13)21-17(20)16(19)12-6-4-3-5-7-12;/h3-7,13-16,19H,8-11H2,1-2H3;1H/q+1;/p-1
- IUPAC Name
- 3-[(2-hydroxy-2-phenylacetyl)oxy]-8,8-dimethyl-8-azabicyclo[3.2.1]octan-8-ium bromide
- SMILES
- [Br-].C[N+]1(C)C2CCC1CC(C2)OC(=O)C(O)C1=CC=CC=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014863
- KEGG Drug
- D02070
- PubChem Compound
- 6646
- PubChem Substance
- 46509020
- ChemSpider
- 6394
- 1546413
- ChEBI
- 50373
- ChEMBL
- CHEMBL1200851
- Therapeutic Targets Database
- DAP000823
- PharmGKB
- PA164749405
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Homatropine_methylbromide
- MSDS
- Download (72.8 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Alcon Laboratories
- Altaire Pharmaceuticals
- Amend
- Conta Care Ophthalmics and Diagnostics
- Dispensing Solutions
- DRX Pharmaceuticals
- HUB Pharmaceuticals
- Invision Pharmaceuticals
- Lake Erie Medical and Surgical Supply
- Mission Pharmacal
- Nephron Pharmaceuticals Corp.
- Novartis AG
- Ocusoft
- OMJ Pharmaceuticals
- Pharmedix
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Tablet Oral Injection Parenteral Capsule, coated Oral Liquid Oral Solution Oral Syrup Oral - Prices
Unit description Cost Unit Isopto homatropine 5% drops 6.41USD ml Homatropine hbr 5% eye drop 6.06USD ml Isopto homatropine 2% drops 5.57USD ml Homatropaire 5% eye drops 3.82USD ml Homatropine hbr crystals 2.69USD g Hycodan tablet 1.4USD each 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 melting point (°C) 191-192 °C PhysProp logP 3.421 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0052 mg/mL ALOGPS logP -1.9 ALOGPS logP -2.6 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 11.99 Chemaxon pKa (Strongest Basic) -4.1 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 46.53 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 91.72 m3·mol-1 Chemaxon Polarizability 31.18 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9235 Blood Brain Barrier + 0.8747 Caco-2 permeable + 0.6235 P-glycoprotein substrate Substrate 0.6323 P-glycoprotein inhibitor I Non-inhibitor 0.7202 P-glycoprotein inhibitor II Non-inhibitor 0.9349 Renal organic cation transporter Inhibitor 0.5945 CYP450 2C9 substrate Non-substrate 0.7299 CYP450 2D6 substrate Non-substrate 0.7589 CYP450 3A4 substrate Substrate 0.7127 CYP450 1A2 substrate Non-inhibitor 0.8254 CYP450 2C9 inhibitor Non-inhibitor 0.9144 CYP450 2D6 inhibitor Non-inhibitor 0.7952 CYP450 2C19 inhibitor Non-inhibitor 0.9009 CYP450 3A4 inhibitor Non-inhibitor 0.8921 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9782 Ames test Non AMES toxic 0.7076 Carcinogenicity Non-carcinogens 0.9333 Biodegradation Ready biodegradable 0.5 Rat acute toxicity 2.7493 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9793 hERG inhibition (predictor II) Non-inhibitor 0.5737
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0a4r-3900000000-340f2398d1807e9c012c - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 165.61835 predictedDeepCCS 1.0 (2019) [M+H]+ 167.97635 predictedDeepCCS 1.0 (2019) [M+Na]+ 174.95546 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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. [Article]
- 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]
- Manjeet S, Sim MK: Atropine- and scopolamine-resistant subtypes of muscarinic receptors in the rabbit aorta. Eur J Pharmacol. 1989 Dec 12;174(1):99-105. [Article]
- George N, Shiny PJ, Miriam J, Nancy CA, Dhanasekar KR, Peedicayil J: Inhibitory effect of anticholinergics on the contraction of isolated caprine urinary bladder detrusor muscle. Auton Autacoid Pharmacol. 2010 Jul;30(3):173-7. doi: 10.1111/j.1474-8673.2009.00447.x. Epub 2010 Jan 19. [Article]
- Gil L, Gomez LE, Duran I, Cueva-Rolon R: Muscarinic mediation of the urethro genital reflex in spinal cord-transected rats. Pharmacol Biochem Behav. 2000 Oct;67(2):215-23. [Article]
- 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. [Article]
- 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]
- George N, Shiny PJ, Miriam J, Nancy CA, Dhanasekar KR, Peedicayil J: Inhibitory effect of anticholinergics on the contraction of isolated caprine urinary bladder detrusor muscle. Auton Autacoid Pharmacol. 2010 Jul;30(3):173-7. doi: 10.1111/j.1474-8673.2009.00447.x. Epub 2010 Jan 19. [Article]
- Gil L, Gomez LE, Duran I, Cueva-Rolon R: Muscarinic mediation of the urethro genital reflex in spinal cord-transected rats. Pharmacol Biochem Behav. 2000 Oct;67(2):215-23. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- Li CK, Mitchelson F: The selective antimuscarinic action of stercuronium. Br J Pharmacol. 1980 Oct;70(2):313-21. [Article]
- 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
- CHRM5
- Uniprot ID
- P08912
- Uniprot Name
- Muscarinic acetylcholine receptor M5
- Molecular Weight
- 60073.205 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. [Article]
- 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]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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. [Article]
- 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]
- Li CK, Mitchelson F: The selective antimuscarinic action of stercuronium. Br J Pharmacol. 1980 Oct;70(2):313-21. [Article]
- Gil L, Gomez LE, Duran I, Cueva-Rolon R: Muscarinic mediation of the urethro genital reflex in spinal cord-transected rats. Pharmacol Biochem Behav. 2000 Oct;67(2):215-23. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:54