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
Structure for Homatropine (DB11181)
- 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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- Contraindications & Blackbox Warnings
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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.
Target Actions Organism AMuscarinic acetylcholine receptor M1 antagonistHumans AMuscarinic acetylcholine receptor M2 antagonistHumans AMuscarinic acetylcholine receptor M3 antagonistHumans AMuscarinic acetylcholine receptor M4 antagonistHumans AMuscarinic acetylcholine receptor M5 antagonistHumans - 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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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAclidinium The risk or severity of adverse effects can be increased when Aclidinium is combined with Homatropine. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Homatropine. Amantadine The risk or severity of adverse effects can be increased when Amantadine is combined with Homatropine. Amitriptyline The risk or severity of adverse effects can be increased when Amitriptyline is combined with Homatropine. Amobarbital The risk or severity of adverse effects can be increased when Amobarbital is combined with Homatropine. Amoxapine The risk or severity of adverse effects can be increased when Amoxapine is combined with Homatropine. Anisotropine methylbromide The risk or severity of adverse effects can be increased when Anisotropine methylbromide is combined with Homatropine. Aripiprazole The risk or severity of adverse effects can be increased when Aripiprazole is combined with Homatropine. Atracurium The risk or severity of adverse effects can be increased when Homatropine is combined with Atracurium. Atracurium besylate The risk or severity of adverse effects can be increased when Atracurium besylate is combined with Homatropine. 
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- 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.- Product Ingredients
Ingredient UNII CAS InChI Key Homatropine hydrobromide BEW7469QZ0 51-56-9 DWSGTFTVBLXELC-RDYJJYPNSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Homatropine Solution / drops 50 mg/5mL Ophthalmic Hub Pharmaceuticals 2012-06-10 2012-10-01 US 
Homatropine Solution / drops 50 mg/5mL Ophthalmic Physicians Total Care, Inc. 2012-06-10 2012-06-30 US Homatropine Hydrobromide Solution 50 mg/1mL Ophthalmic O Cu Soft, Inc. 2014-02-10 2015-01-29 US Homatropine Hydrobromide Solution 50 mg/1mL Ophthalmic OCuSOFT, INC. 2014-02-10 2019-07-16 US Homatropine Hydrobromide Ophthalmic Solution 50 mg/1mL Ophthalmic Altaire Pharmaceuticals Inc. 2018-06-01 Not applicable US Isopto Homatropine Solution 20 mg/1mL Ophthalmic Physicians Total Care, Inc. 1981-06-19 2001-06-30 US Isopto Homatropine Solution 20 mg/1mL Ophthalmic Alcon, Inc. 1981-06-19 2013-04-30 US Isopto Homatropine Solution 50 mg/1mL Ophthalmic Alcon, Inc. 1981-06-19 2013-04-30 US Isopto Homatropine 2% Liquid 2 % Ophthalmic Alcon, Inc. 1951-12-31 2016-04-14 Canada 
Isopto Homatropine 5% Liquid 5 % Ophthalmic Alcon, Inc. 1951-12-31 2016-03-03 Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Minims Homatropine Hydrobromide 2% Liquid 2 % Ophthalmic Chauvin Pharmaceuticals Limited 1995-12-31 2003-07-08 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Homatropine Homatropine hydrobromide (50 mg/5mL) Solution / drops Ophthalmic Hub Pharmaceuticals 2012-06-10 2012-10-01 US Homatropine Homatropine hydrobromide (50 mg/5mL) Solution / drops Ophthalmic Physicians Total Care, Inc. 2012-06-10 2012-06-30 US Homatropine Hydrobromide Homatropine hydrobromide (50 mg/1mL) Solution Ophthalmic O Cu Soft, Inc. 2014-02-10 2015-01-29 US Homatropine Hydrobromide Homatropine hydrobromide (50 mg/1mL) Solution Ophthalmic OCuSOFT, INC. 2014-02-10 2019-07-16 US Homatropine Hydrobromide Ophthalmic Homatropine hydrobromide (50 mg/1mL) Solution Ophthalmic Altaire Pharmaceuticals Inc. 2018-06-01 Not applicable US Isopto Homatropine Homatropine hydrobromide (20 mg/1mL) Solution Ophthalmic Physicians Total Care, Inc. 1981-06-19 2001-06-30 US Isopto Homatropine Homatropine hydrobromide (20 mg/1mL) Solution Ophthalmic Alcon, Inc. 1981-06-19 2013-04-30 US Isopto Homatropine Homatropine hydrobromide (50 mg/1mL) Solution Ophthalmic Alcon, Inc. 1981-06-19 2013-04-30 US
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
- 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
- BindingDB
- 50240066
- 27084
- ChEBI
- 5747
- ChEMBL
- CHEMBL1618018
- Wikipedia
- Homatropine
- FDA label
- Download (88 KB)
- MSDS
- Download (47.3 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count Not Available Completed Treatment Corneal Diseases 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution / drops Ophthalmic Solution / drops Ophthalmic 50 mg/5mL Solution Ophthalmic 50 mg/1mL Solution Ophthalmic 20 mg/1mL Liquid Ophthalmic 5 % Liquid Ophthalmic 2 % Solution Ophthalmic - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 191°C as methylbromide and 212°C as hydrobromide MSDS water solubility Soluble as hydrobromide MSDS - Predicted Properties
Property Value Source Water Solubility 5.57 mg/mL ALOGPS logP 1.91 ALOGPS logP 1.59 Chemaxon logS -1.7 ALOGPS pKa (Strongest Acidic) 11.99 Chemaxon pKa (Strongest Basic) 9.38 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 49.77 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 75.81 m3·mol-1 Chemaxon Polarizability 29.79 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
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
- 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
- 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
- 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
- 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
- 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
- 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
- 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