Identification

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Name
Homatropine
Accession Number
DB11181
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
  • Homatropina
Product Ingredients
IngredientUNIICASInChI Key
Homatropine hydrobromideBEW7469QZ051-56-9DWSGTFTVBLXELC-RDYJJYPNSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
HomatropineSolution / drops50 mg/5mLOphthalmicPhysicians Total Care, Inc.2012-06-102012-06-30Us
HomatropineSolution / drops50 mg/5mLOphthalmicHub Pharmaceuticals2012-06-102012-10-01Us
Homatropine HydrobromideSolution50 mg/1mLOphthalmicOCuSOFT, INC.2014-02-10Not applicableUs
Homatropine HydrobromideSolution50 mg/1mLOphthalmicO Cu Soft, Inc.2014-02-102015-01-29Us
Homatropine Hydrobromide OphthalmicSolution50 mg/1mLOphthalmicAltaire Pharmaceuticals Inc.2013-05-16Not applicableUs
Isopto HomatropineSolution20 mg/1mLOphthalmicPhysicians Total Care, Inc.1981-06-192001-06-30Us
Isopto HomatropineSolution50 mg/1mLOphthalmicAlcon, Inc.1981-06-192013-04-30Us
Isopto HomatropineSolution20 mg/1mLOphthalmicAlcon, Inc.1981-06-192013-04-30Us
Isopto Homatropine 2%Liquid2 %OphthalmicAlcon, Inc.1951-12-312016-04-14Canada
Isopto Homatropine 5%Liquid5 %OphthalmicAlcon, Inc.1951-12-312016-03-03Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Minims Homatropine Hydrobromide 2%Liquid2 %OphthalmicChauvin Pharmaceuticals Limited1995-12-312003-07-08Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
HomatropineHomatropine hydrobromide (50 mg/5mL)Solution / dropsOphthalmicPhysicians Total Care, Inc.2012-06-102012-06-30Us
HomatropineHomatropine hydrobromide (50 mg/5mL)Solution / dropsOphthalmicHub Pharmaceuticals2012-06-102012-10-01Us
Homatropine HydrobromideHomatropine hydrobromide (50 mg/1mL)SolutionOphthalmicOCuSOFT, INC.2014-02-10Not applicableUs
Homatropine HydrobromideHomatropine hydrobromide (50 mg/1mL)SolutionOphthalmicO Cu Soft, Inc.2014-02-102015-01-29Us
Homatropine Hydrobromide OphthalmicHomatropine hydrobromide (50 mg/1mL)SolutionOphthalmicAltaire Pharmaceuticals Inc.2013-05-16Not applicableUs
Isopto HomatropineHomatropine hydrobromide (20 mg/1mL)SolutionOphthalmicAlcon, Inc.1981-06-192013-04-30Us
Isopto HomatropineHomatropine hydrobromide (20 mg/1mL)SolutionOphthalmicPhysicians Total Care, Inc.1981-06-192001-06-30Us
Isopto HomatropineHomatropine hydrobromide (50 mg/1mL)SolutionOphthalmicAlcon, Inc.1981-06-192013-04-30Us
Categories
UNII
8QS6WCL55Z
CAS number
87-00-3
Weight
Average: 275.348
Monoisotopic: 275.15214354
Chemical Formula
C16H21NO3
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

Pharmacology

Indication

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

Indicated for the induction of mydriasis in ophthalmic solutions.

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
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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.

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.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AclidiniumThe risk or severity of adverse effects can be increased when Aclidinium is combined with Homatropine.
AgmatineThe risk or severity of adverse effects can be increased when Agmatine is combined with Homatropine.
AlcuroniumThe risk or severity of adverse effects can be increased when Homatropine is combined with Alcuronium.
Aluminum sulfateThe therapeutic efficacy of Aluminum sulfate 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.
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Homatropine.
Anisotropine methylbromideThe risk or severity of adverse effects can be increased when Anisotropine methylbromide is combined with Homatropine.
AprobarbitalThe risk or severity of adverse effects can be increased when Aprobarbital is combined with Homatropine.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

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Food Interactions
Not Available

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]
External Links
KEGG Compound
C07814
PubChem Substance
347911146
ChemSpider
16498795
ChEBI
5747
ChEMBL
CHEMBL1618018
Wikipedia
Homatropine
ATC Codes
S01FA05 — Homatropine
FDA label
Download (88 KB)
MSDS
Download (47.3 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Solution / dropsOphthalmic50 mg/5mL
SolutionOphthalmic50 mg/1mL
SolutionOphthalmic20 mg/1mL
LiquidOphthalmic5 %
LiquidOphthalmic2 %
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
Not Available

Taxonomy

Classification
Not classified

Targets

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. [PubMed:8467326]
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. [PubMed:8467326]
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. [PubMed:8467326]
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. [PubMed:8467326]
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. [PubMed:8467326]

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. [PubMed:12679808]

Drug created on December 03, 2015 09:51 / Updated on July 13, 2019 00:55