Homatropine Methylbromide

Identification

Name
Homatropine Methylbromide
Accession Number
DB00725  (APRD01017)
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
  • 3-alpha-Hydroxy-8-methyl-1-alpha-H,5-alpha-H-tropanium bromide mandelate
  • 8-Methylhomatropinium bromide
  • Homatropine methylbromide
  • Homatropini methylbromidum
  • Methylbromure d'homatropine
  • Methylhomatropine
  • Methylhomatropine bromide
  • Methylhomatropinum bromatum
  • Metilbromuro de homatropina
  • Omatropina metilbromuro
  • Tropinium methobromide mandelate
Product Images
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Debiline HHomatropine Methylbromide (2.5 mg) + Deoxycholic Acid (100 mg) + Pepsin (50 mg)TabletOralLab Nadeau LtÉe, Division Of Technilab Inc.1951-12-311999-09-28Canada
Hydrocodone Bitartrate and Homatropine MethylbromideHomatropine Methylbromide (1.5 mg/1) + Hydrocodone bitartrate (5 mg/1)TabletOralNovel Laboratories, Inc.2014-09-23Not applicableUs
Hydrocodone Bitartrate and Homatropine MethylbromideHomatropine Methylbromide (1.5 mg/5mL) + Hydrocodone bitartrate (5 mg/5mL)SolutionOralBio Pharm, Inc.2017-03-07Not applicableUs
Hydrocodone Bitartrate and Homatropine MethylbromideHomatropine Methylbromide (1.5 mg/5mL) + Hydrocodone bitartrate (5 mg/5mL)SyrupOralRebel Distributors2008-02-08Not applicableUs
Hydrocodone Bitartrate and Homatropine MethylbromideHomatropine Methylbromide (1.5 mg/5mL) + Hydrocodone bitartrate (5 mg/5mL)LiquidOralKvk Tech,Inc2017-02-21Not applicableUs
Hydrocodone Bitartrate and Homatropine MethylbromideHomatropine Methylbromide (1.5 mg/5mL) + Hydrocodone bitartrate (5 mg/5mL)SyrupOralPhysicians Total Care, Inc.2007-11-07Not applicableUs
Hydrocodone Bitartrate and Homatropine MethylbromideHomatropine Methylbromide (1.5 mg/1) + Hydrocodone bitartrate (5 mg/1)TabletOralLupin Pharmaceuticals2014-09-23Not applicableUs
Hydrocodone Bitartrate and Homatropine MethylbromideHomatropine Methylbromide (1.5 mg/5mL) + Hydrocodone bitartrate (5 mg/5mL)SyrupOralNovel Laboratories, Inc.2017-02-13Not applicableUs
Hydrocodone Bitartrate and Homatropine MethylbromideHomatropine Methylbromide (1.5 mg/1) + Hydrocodone bitartrate (5 mg/1)TabletOralKvk Tech,Inc2017-08-07Not applicableUs
Hydrocodone Bitartrate and Homatropine MethylbromideHomatropine Methylbromide (1.5 mg/1) + Hydrocodone bitartrate (5 mg/1)TabletOralDispensing Solutions, Inc.2011-02-16Not applicableUs
Categories
UNII
68JRS2HC1C
CAS number
80-49-9
Weight
Average: 370.281
Monoisotopic: 369.093956286
Chemical Formula
C17H24BrNO3
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

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.

Structured Indications
Pharmacodynamics

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.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M2
antagonist
Human
AMuscarinic acetylcholine receptor M1
antagonist
Human
AMuscarinic acetylcholine receptor M4
antagonist
Human
AMuscarinic acetylcholine receptor M5
antagonist
Human
AMuscarinic acetylcholine receptor M3
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
HMDB14863
KEGG Drug
D02070
PubChem Compound
6646
PubChem Substance
46509020
ChemSpider
6394
ChEBI
50373
ChEMBL
CHEMBL1200851
Therapeutic Targets Database
DAP000823
PharmGKB
PA164749405
Drugs.com
Drugs.com Drug Page
Wikipedia
Homatropine_Methylbromide
ATC Codes
A03CB04 — Methylhomatropine and psycholeptics
MSDS
Download (72.8 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
LiquidOral
SolutionOral
SyrupOral
TabletOral
Prices
Unit descriptionCostUnit
Isopto homatropine 5% drops6.41USD ml
Homatropine hbr 5% eye drop6.06USD ml
Isopto homatropine 2% drops5.57USD ml
Homatropaire 5% eye drops3.82USD ml
Homatropine hbr crystals2.69USD g
Hycodan tablet1.4USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)191-192 °CPhysProp
logP3.421Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0052 mg/mLALOGPS
logP-1.9ALOGPS
logP-2.6ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)11.99ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity91.72 m3·mol-1ChemAxon
Polarizability31.18 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9235
Blood Brain Barrier+0.8747
Caco-2 permeable+0.6235
P-glycoprotein substrateSubstrate0.6323
P-glycoprotein inhibitor INon-inhibitor0.7202
P-glycoprotein inhibitor IINon-inhibitor0.9349
Renal organic cation transporterInhibitor0.5945
CYP450 2C9 substrateNon-substrate0.7299
CYP450 2D6 substrateNon-substrate0.7589
CYP450 3A4 substrateSubstrate0.7127
CYP450 1A2 substrateNon-inhibitor0.8254
CYP450 2C9 inhibitorNon-inhibitor0.9144
CYP450 2D6 inhibitorNon-inhibitor0.7952
CYP450 2C19 inhibitorNon-inhibitor0.9009
CYP450 3A4 inhibitorNon-inhibitor0.8921
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9782
Ames testNon AMES toxic0.7076
CarcinogenicityNon-carcinogens0.9333
BiodegradationReady biodegradable0.5
Rat acute toxicity2.7493 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9793
hERG inhibition (predictor II)Non-inhibitor0.5737
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 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
Tropane alkaloid / Monocyclic benzene moiety / Piperidine / N-alkylpyrrolidine / Benzenoid / Pyrrolidine / Tetraalkylammonium salt / Quaternary ammonium salt / Carboxylic acid ester / Secondary alcohol
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic bromide salt, azabicycloalkane (CHEBI:50373)

Targets

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. 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. [PubMed:2612581]
  4. 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. [PubMed:20085574]
  5. 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. [PubMed:11124384]
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. 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. [PubMed:20085574]
  4. 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. [PubMed:11124384]
Kind
Protein
Organism
Human
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
  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. Li CK, Mitchelson F: The selective antimuscarinic action of stercuronium. Br J Pharmacol. 1980 Oct;70(2):313-21. [PubMed:6893558]
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
CHRM5
Uniprot ID
P08912
Uniprot Name
Muscarinic acetylcholine receptor M5
Molecular Weight
60073.205 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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
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. Li CK, Mitchelson F: The selective antimuscarinic action of stercuronium. Br J Pharmacol. 1980 Oct;70(2):313-21. [PubMed:6893558]
  4. 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. [PubMed:11124384]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:42