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Identification
NameHomatropine Methylbromide
Accession NumberDB00725  (APRD01017)
TypeSmall Molecule
GroupsApproved
DescriptionHomatropine 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
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 BrandsNot Available
Brand mixtures
NameLabellerIngredients
Hydrocodone Bitartrate and Homatropine MethylbromidePharmaceutical Associates, Inc.
HydrometActavis Mid Atlantic LLC
TussigonPfizer Laboratories Div Pfizer Inc
SaltsNot Available
Categories
UNII68JRS2HC1C
CAS number80-49-9
WeightAverage: 370.281
Monoisotopic: 369.093956286
Chemical FormulaC17H24BrNO3
InChI KeyFUFVKLQESJNNAN-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
IndicationUsed 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
PharmacodynamicsHomatropine 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 actionHomatropine 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Muscarinic acetylcholine receptor M2Proteinyes
antagonist
HumanP08172 details
Muscarinic acetylcholine receptor M1Proteinyes
antagonist
HumanP11229 details
Muscarinic acetylcholine receptor M4Proteinyes
antagonist
HumanP08173 details
Muscarinic acetylcholine receptor M5Proteinyes
antagonist
HumanP08912 details
Muscarinic acetylcholine receptor M3Proteinyes
antagonist
HumanP20309 details
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
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesA03CB04
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (72.8 KB)
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point191-192 °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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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
  • Tropane alkaloid
  • N-alkylpyrrolidine
  • Piperidine
  • Quaternary ammonium salt
  • Pyrrolidine
  • Secondary alcohol
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic bromide salt
  • Organic salt
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Organic zwitterion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

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 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. 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 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. 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 action of G proteins. Primary transducing effect is inhibition of adenylate cyclase.
Gene Name:
CHRM4
Uniprot ID:
P08173
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 action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM5
Uniprot ID:
P08912
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 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. 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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23