Homatropine

Identification

Summary

Homatropine is an anticholinergic agent used to dilate the pupil, treat inflammation of the uveal tract, and suppress a cough.

Generic Name
Homatropine
DrugBank Accession Number
DB11181
Background

Homatropine is an anticholinergic drug that acts as an antagonist at muscarinic acetylcholine receptors. It is present in antitussives, under the trade name Hycodan, in combination with hydrocodone (dihydrocodeinone) bitartrate indicated for the symptomatic relief of cough as oral tablets or solutions. Homatropine is included in subtherapeutic amounts as homatropine methylbromide to discourage deliberate overdosage. Homatropine hydrobromide has been administered as ophthalmic solutions as a cycloplegic to temporarily paralyze accomodation, and to induce mydriasis (the dilation of the pupil); however such therapeutic use has not been approved by the FDA to be safe and effective.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 275.348
Monoisotopic: 275.15214354
Chemical Formula
C16H21NO3
Synonyms
  • Homatropina
  • Omatropina

Pharmacology

Indication

Indicated as an overdose-rescuing agent in combination with hydrocodone antitussive Label.

Indicated for the induction of mydriasis in ophthalmic solutions.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Adjunct therapy in treatment ofStrabismus•••••••••••••••••••• • •••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Homatropine is an anticholinergic drug that produces typical anticholinergic effects inducing mydriasis and cycloplegia. Other effects of structurally-related atropine that could also apply to homatropine include inhibition of secretions, tachycardia, relaxation of smooth muscle and central nervous effects including excitation 1.

Mechanism of action

Homatropine is a competitive muscarinic receptor antagonist with a bulky aromatic group in place of the acetyl group of acetylcholine. It is expected to act in similar manner as atropine, producing similar parasympatholytic effects. By blocking muscarinic receptors and cholinergic signalling pathways, homatropine blocks the response of the iris sphincter muscle and cause the pupil to become unresponsive to light upon dilation or mydriasis. It also blocks the accommodative muscle of the ciliary body to cholinergic stimulation 1.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Humans
AMuscarinic acetylcholine receptor M2
antagonist
Humans
AMuscarinic acetylcholine receptor M3
antagonist
Humans
AMuscarinic acetylcholine receptor M4
antagonist
Humans
AMuscarinic acetylcholine receptor M5
antagonist
Humans
Absorption

No pharmacokinetic data available.

Volume of distribution

No pharmacokinetic data available.

Protein binding

No pharmacokinetic data available.

Metabolism

No pharmacokinetic data available.

Route of elimination

No pharmacokinetic data available.

Half-life

No pharmacokinetic data available.

Clearance

No pharmacokinetic data available.

Adverse Effects
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Toxicity

Acute oral LD50 is 1200 mg/kg in rat, 1400 mg/kg in mouse, and 1000 mg/kg in guinea pig MSDS. Systemic toxicity may occur following topical overdose of structurally-related ophthalmic atropine, particularly in children. It is characterized by flushing and dryness of the skin, blurred vision, a rapid and irregular pulse, fever, convulsions and hallucinations, and the loss of neuromuscular coordination. Abdominal distension may be observed with infants. Severe intoxication is manifested by central nervous system depression, coma, circulatory and respiratory failure, and death Label. Symptomatic and supportive treatment should be initiated. In case of accidental use or overdose in infants and small children, the body surface should be kept moist Label.

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.
DrugInteraction
AclidiniumThe risk or severity of adverse effects can be increased when Aclidinium is combined with Homatropine.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Homatropine.
AmantadineThe risk or severity of adverse effects can be increased when Amantadine is combined with Homatropine.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Homatropine.
AmobarbitalThe risk or severity of adverse effects can be increased when Amobarbital is combined with Homatropine.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Homatropine hydrobromideBEW7469QZ051-56-9DWSGTFTVBLXELC-RDYJJYPNSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
HomatropineSolution / drops50 mg/5mLOphthalmicPhysicians Total Care, Inc.2012-06-102012-06-30US flag
HomatropineSolution / drops50 mg/5mLOphthalmicHub Pharmaceuticals2012-06-102012-10-01US flag
Homatropine HydrobromideSolution50 mg/1mLOphthalmicOCuSOFT, INC.2014-02-102019-07-16US flag
Homatropine HydrobromideSolution50 mg/1mLOphthalmicO Cu Soft, Inc.2014-02-102015-01-29US flag
Homatropine Hydrobromide OphthalmicSolution50 mg/1mLOphthalmicAltaire Pharmaceuticals Inc.2018-06-01Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Minims Homatropine Hydrobromide 2%Liquid2 %OphthalmicChauvin Pharmaceuticals Limited1995-12-312003-07-08Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
HomatropineHomatropine hydrobromide (50 mg/5mL)Solution / dropsOphthalmicPhysicians Total Care, Inc.2012-06-102012-06-30US flag
HomatropineHomatropine hydrobromide (50 mg/5mL)Solution / dropsOphthalmicHub Pharmaceuticals2012-06-102012-10-01US flag
Homatropine HydrobromideHomatropine hydrobromide (50 mg/1mL)SolutionOphthalmicOCuSOFT, INC.2014-02-102019-07-16US flag
Homatropine HydrobromideHomatropine hydrobromide (50 mg/1mL)SolutionOphthalmicO Cu Soft, Inc.2014-02-102015-01-29US flag
Homatropine Hydrobromide OphthalmicHomatropine hydrobromide (50 mg/1mL)SolutionOphthalmicAltaire Pharmaceuticals Inc.2018-06-01Not applicableUS flag

Categories

ATC Codes
S01FA05 — Homatropine
Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
8QS6WCL55Z
CAS number
87-00-3
InChI Key
ZTVIKZXZYLEVOL-MCOXGKPRSA-N
InChI
InChI=1S/C16H21NO3/c1-17-12-7-8-13(17)10-14(9-12)20-16(19)15(18)11-5-3-2-4-6-11/h2-6,12-15,18H,7-10H2,1H3/t12-,13+,14+,15?
IUPAC Name
(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-2-phenylacetate
SMILES
[H][C@]12CC[C@]([H])(C[C@@H](C1)OC(=O)C(O)C1=CC=CC=C1)N2C

References

General References
  1. 13. (2012). In Rang and Dale's Pharmacology (7th ed., pp. 159-161). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
KEGG Compound
C07814
PubChem Substance
347911146
ChemSpider
16498795
BindingDB
50240066
RxNav
27084
ChEBI
5747
ChEMBL
CHEMBL1618018
Wikipedia
Homatropine
FDA label
Download (88 KB)
MSDS
Download (47.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedTreatmentCorneal Diseases1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Solution / dropsOphthalmic
Solution / dropsOphthalmic50 mg/5mL
SolutionOphthalmic50 mg/1mL
SolutionOphthalmic20 mg/1mL
LiquidOphthalmic5 %
LiquidOphthalmic2 %
SolutionOphthalmic
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)191°C as methylbromide and 212°C as hydrobromideMSDS
water solubilitySoluble as hydrobromideMSDS
Predicted Properties
PropertyValueSource
Water Solubility5.57 mg/mLALOGPS
logP1.91ALOGPS
logP1.59Chemaxon
logS-1.7ALOGPS
pKa (Strongest Acidic)11.99Chemaxon
pKa (Strongest Basic)9.38Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area49.77 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity75.81 m3·mol-1Chemaxon
Polarizability29.79 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0090000000-33d57aeac00280f5f9dc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05di-0590000000-3c323792686ae6de5e15
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0970000000-7a9ba483aacb93e47583
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-7910000000-b6ad90e0bd24e787a855
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fr-2910000000-b6548a18e97680b6b011
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-2910000000-36d582f1e6d2bc27fb78
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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insights and accelerate drug research.
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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
  1. Sim MK, Manjeet S: Muscarinic receptors in the aortae of normo- and hypertensive rats: a binding study. Clin Exp Hypertens. 1993 Mar;15(2):409-21. [Article]
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
  1. Sim MK, Manjeet S: Muscarinic receptors in the aortae of normo- and hypertensive rats: a binding study. Clin Exp Hypertens. 1993 Mar;15(2):409-21. [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
  1. Sim MK, Manjeet S: Muscarinic receptors in the aortae of normo- and hypertensive rats: a binding study. Clin Exp Hypertens. 1993 Mar;15(2):409-21. [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
  1. Sim MK, Manjeet S: Muscarinic receptors in the aortae of normo- and hypertensive rats: a binding study. Clin Exp Hypertens. 1993 Mar;15(2):409-21. [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
  1. Sim MK, Manjeet S: Muscarinic receptors in the aortae of normo- and hypertensive rats: a binding study. Clin Exp Hypertens. 1993 Mar;15(2):409-21. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Triglyceride lipase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
Molecular Weight
62520.62 Da
References
  1. Bencharit S, Morton CL, Xue Y, Potter PM, Redinbo MR: Structural basis of heroin and cocaine metabolism by a promiscuous human drug-processing enzyme. Nat Struct Biol. 2003 May;10(5):349-56. [Article]

Drug created at December 03, 2015 16:51 / Updated at February 18, 2021 21:13