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Homatropine
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AHFS/Drugs.comMonograph
MedlinePlusa601006
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  • In general: ℞ (Prescription only)
Identifiers
  • (N-Methyl-8-azabicyclo[3.2.1]oct-3-yl) 2-hydroxy-2-phenylacetate
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PubChem CID
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ECHA InfoCard100.001.561 Edit this at Wikidata
Chemical and physical data
FormulaC16H21NO3
Molar mass275.348 g·mol−1
3D model (JSmol)
  • CN3[C@H]1CC[C@@H]3C[C@@H](C1)OC(=O)C(O)c2ccccc2
  • 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? checkY
  • Key:ZTVIKZXZYLEVOL-MCOXGKPRSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Homatropine (Equipin, Isopto Homatropine) is an anticholinergic medication that is an antagonist at muscarinic acetylcholine receptors and thus the parasympathetic nervous system. It is used in eye drops as a cycloplegic (to temporarily paralyze accommodation), and as a mydriatic (to dilate the pupil).

The related chemical compound homatropine methylbromide (methylhomatropine) is a different medication. Homatropine is less potent than atropine and has a shorter duration of action. It is available as the hydrobromide salt. Homatropine is also given as an atropine substitute,[1] given to reverse the muscarinic and CNS effects associated with indirect cholinomimetic (anti-AChase) administration.

Homatropine hydrobromide is on the World Health Organization's List of Essential Medicines.[2]

It is an antagonist of all five muscarinic acetylcholine receptors.[3]

Side effects

[edit]

Contraindications

[edit]

References

[edit]
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Homatropine

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Homatropine is a synthetic anticholinergic agent that functions as a competitive antagonist at muscarinic acetylcholine receptors, blocking parasympathetic nerve impulses to produce effects such as pupil dilation and reduced glandular secretions.[1] Chemically, it is the mandelic acid ester of tropine, a tropane alkaloid derivative structurally similar to atropine but with milder and shorter-acting properties.[2] First introduced as a mydriatic drug in 1883 by Merck Darmstadt, homatropine is available in forms such as hydrobromide for ophthalmic use and methylbromide for oral administration.[3] In ophthalmology, homatropine hydrobromide is applied topically as eye drops to induce mydriasis (pupil dilation) and cycloplegia (paralysis of the ciliary muscle for accommodation), facilitating cycloplegic refraction and treating inflammatory conditions like uveitis.[4] Its effects onset within 15-20 minutes, peak in 30-90 minutes, and last 1-3 days for mydriasis, offering a balance between efficacy and reduced risk of prolonged paralysis compared to atropine.[5] Contraindications include glaucoma or narrow-angle predisposition due to potential intraocular pressure elevation, and caution is advised in children, the elderly, and those with conditions like Down syndrome owing to heightened systemic absorption risks.[4] Orally, homatropine methylbromide is combined with hydrocodone bitartrate in antitussive formulations to suppress cough while its anticholinergic action discourages abuse by causing unpleasant effects like dry mouth and blurred vision upon overdose.[6] Historically, it has also been used for gastrointestinal disorders such as ulcers and spasms due to its antispasmodic properties, though such applications are less common today.[7] Common side effects across uses include blurred vision, photophobia, dry mouth, and tachycardia, with systemic anticholinergic toxicity possible from excessive ophthalmic dosing.[4]

Overview

Definition and classification

Homatropine is a synthetic anticholinergic drug that functions as a competitive antagonist at muscarinic acetylcholine receptors, thereby inhibiting parasympathetic nervous system activity.[8] It belongs to the class of muscarinic antagonists and is primarily recognized for its role in modulating cholinergic transmission without the broader systemic effects associated with more potent analogs.[8] Chemically, homatropine is classified as a tropane alkaloid derivative, featuring a bicyclic tropane core esterified with mandelic acid, which distinguishes it from naturally occurring tropane alkaloids like atropine and scopolamine.[5] Unlike atropine, which is derived from tropic acid, homatropine exhibits reduced potency and a shorter duration of action, making it suitable for targeted applications requiring transient effects.[5] Homatropine is available in two principal salt forms that influence its pharmacokinetic profile and administration routes. Homatropine hydrobromide, a tertiary amine, is the form commonly employed in topical ophthalmic solutions due to its ability to penetrate ocular tissues effectively.[8] In contrast, homatropine methylbromide is a quaternary ammonium compound with limited gastrointestinal absorption, rendering it appropriate for oral use in formulations aimed at local gastrointestinal or respiratory effects.[9]

Forms and administration

Homatropine is primarily formulated as homatropine hydrobromide for ophthalmic use and homatropine methylbromide for oral administration in combination products. Ophthalmic preparations are sterile topical solutions available in concentrations of 2% or 5% (50 mg/mL), supplied in 5 mL plastic dropper bottles.[1][10] These solutions contain preservatives such as benzalkonium chloride (0.005%) and inactive ingredients including boric acid, edetate disodium, and potassium chloride, with pH adjusted using boric acid or sodium carbonate. Administration involves topical ocular instillation, typically 1-2 drops directly into the affected eye(s), with gentle compression of the lacrimal sac for 2-3 minutes afterward to minimize systemic absorption; the solution is not intended for injection.[10] Oral formulations of homatropine methylbromide are available exclusively in combination with hydrocodone bitartrate as antitussive agents. These include syrups at a concentration of 1.5 mg homatropine methylbromide per 5 mL (alongside 5 mg hydrocodone bitartrate), supplied as cherry-flavored red liquid in 473 mL bottles, and tablets containing 1.5 mg homatropine methylbromide per tablet (with 5 mg hydrocodone bitartrate), provided in bottles of 30, 100, or 500 units as white, round, scored, biconvex tablets.[6][11] Oral administration is by mouth, with the syrup measured using a teaspoon or dosing device and tablets swallowed whole.[6][11] All homatropine formulations require storage at controlled room temperature (15°-30°C or 59°-86°F), protected from light and excessive heat, in tight, light-resistant containers to maintain stability; ophthalmic solutions should be discarded if the color changes or if contamination is suspected.[10][6][11]

Medical uses

Ophthalmic indications

Homatropine is primarily employed in ophthalmology as a mydriatic agent to induce pupil dilation, facilitating eye examinations and diagnostic procedures such as funduscopy, where visualization of the retina and optic disc is essential.[12] It also serves as a cycloplegic to temporarily paralyze the ciliary muscle, enabling accurate refraction testing, particularly in children or patients with high accommodative ability who may otherwise yield unreliable non-cycloplegic measurements.[13] This application is supported by its role as a muscarinic antagonist, which briefly referenced from its pharmacological profile, blocks parasympathetic stimulation to the iris and ciliary body.[1] In the management of inflammatory ocular conditions, homatropine is indicated for anterior uveitis and iritis, where it alleviates ciliary spasm, reduces associated pain, and minimizes photophobia.[12] By paralyzing the iris sphincter, it plays an adjunctive role in preventing posterior synechiae—adhesions between the iris and lens that can lead to complications like iris bombe and elevated intraocular pressure.[14] This is particularly valuable in acute presentations, where timely mydriasis helps stabilize the blood-aqueous barrier and supports concurrent anti-inflammatory therapy.[15] Typical administration involves instilling 1-2 drops of a 2-5% homatropine hydrobromide solution into the affected eye, with dosing intervals varying by indication: every 5-10 minutes for initial refraction (up to three doses) or every 3-4 hours for uveitis until resolution.[16] The effects, including mydriasis and cycloplegia, onset within 15-30 minutes and persist for 1-3 days, offering a shorter duration compared to atropine (7-14 days), which allows for more rapid recovery of accommodation and reduces prolonged visual impairment.[17] Higher concentrations or repeated applications may be necessary in patients with darkly pigmented irides to achieve adequate dilation.[12]

Respiratory indications

Homatropine methylbromide is primarily utilized as an antitussive agent in combination with opioids such as hydrocodone for the symptomatic relief of dry, non-productive coughs associated with conditions like colds, allergies, or upper respiratory irritants.[18] In formulations like Hycodan, the combination targets the cough reflex by leveraging hydrocodone's central suppression of the cough center in the brain alongside homatropine's anticholinergic properties.[19] These properties include a drying effect on respiratory tract mucosa and secretions, which reduces irritation and helps diminish the cough reflex without promoting expectoration.[20] This therapy is administered orally, typically in tablet or syrup form, with standard dosing for adults consisting of 1.5 mg homatropine methylbromide combined with 5 mg hydrocodone bitartrate every 4 to 6 hours as needed, not exceeding six doses per day.[21] However, it is contraindicated for productive coughs, where clearing secretions is beneficial, and should not be used long-term due to the risk of physical dependence, tolerance, and abuse potential inherent to the opioid component.[18] The use of homatropine-hydrocodone combinations has significantly declined since the mid-2010s, driven by stricter opioid regulations, including the 2014 rescheduling of hydrocodone products to Schedule II and 2018 FDA labeling restrictions limiting prescriptions to adults aged 18 and older.[22][23] Prescriptions for such hydrocodone cough medications dropped by approximately 76% from 2014 to 2019.[24] Non-opioid alternatives like dextromethorphan have largely supplanted these combinations for safer, over-the-counter management of non-productive coughs.

Pharmacology

Mechanism of action

Homatropine acts as a competitive antagonist at muscarinic acetylcholine receptors (mAChRs), specifically targeting the M1 through M5 subtypes, with predominant activity at the M3 subtype in ocular and respiratory tissues. By competitively binding to these receptors, it prevents the action of acetylcholine, thereby inhibiting parasympathetic nervous system signaling without intrinsic agonistic activity.[8][25][26] In the eye, homatropine blocks muscarinic receptors on the iris sphincter muscle, inhibiting its contraction and leading to pupil dilation (mydriasis); it also relaxes the ciliary muscle, resulting in paralysis of accommodation (cycloplegia). In respiratory tissues, it antagonizes M3 receptors on bronchial smooth muscle to promote relaxation and bronchodilation, while reducing glandular secretions in the bronchi and suppressing the cough reflex through diminished parasympathetic tone. These effects collectively counteract parasympathetic stimulation in targeted peripheral sites.[8][26][25] Compared to atropine, homatropine exhibits lower binding affinity to muscarinic receptors and undergoes faster enzymatic hydrolysis, rendering it a weaker and shorter-acting agent. The tertiary amine form, homatropine hydrobromide, demonstrates minimal penetration of the blood-brain barrier, limiting central nervous system effects, whereas the quaternary ammonium form, homatropine methylbromide, does not cross the barrier at all. Homatropine shows no significant activity at nicotinic acetylcholine receptors.[26][27][9]

Pharmacokinetics

Homatropine hydrobromide exhibits rapid absorption following topical ocular administration, primarily through the conjunctiva and nasal mucosa, with mydriasis onset occurring within 10–30 minutes and maximum effect achieved in 30–90 minutes.[28] Systemic absorption from eye drops is limited, resulting in low overall bioavailability comparable to other ophthalmic anticholinergics, where less than 5% of the dose typically reaches systemic circulation due to rapid nasolacrimal drainage and precorneal loss.[29] For the oral quaternary form, homatropine methylbromide, absorption from the gastrointestinal tract is poor owing to its charged structure, limiting systemic exposure despite use in antitussive combinations.[30] Distribution of homatropine hydrobromide is not fully characterized, but it demonstrates low systemic penetration from ocular routes, with minimal central nervous system involvement in therapeutic use.[28] The drug has been detected in human breast milk following topical application, indicating some distribution into maternal compartments, and it is believed to cross the placenta.[31] Volume of distribution data are unavailable, though quaternary derivatives like homatropine methylbromide show restricted tissue penetration due to poor membrane crossing. Metabolism of homatropine hydrobromide likely involves hepatic esterase-mediated hydrolysis, similar to related tropane alkaloids, yielding tropine and mandelic acid as primary products, though specific pathways remain poorly documented.[32] In contrast, the quaternary ammonium salt, homatropine methylbromide, undergoes minimal metabolism and is largely excreted unchanged, consistent with its ionic nature.[30] Elimination of homatropine primarily occurs via renal excretion, with recovery from ocular effects (mydriasis and cycloplegia) typically within 1–3 days, reflecting prolonged local action despite unknown plasma half-life.[28] Pharmacokinetic parameters such as half-life are not well-established, but systemic clearance is inferred to be rapid based on the drug's design as a shorter-acting atropine analog.[32] In the oral combination form, peak plasma concentrations align with those of co-administered agents around 1–2 hours, though specific data for homatropine are lacking.[18] Pharmacokinetics may be altered in the elderly due to reduced organ function and heightened sensitivity to anticholinergic effects, necessitating dose adjustments.[28] Hepatic impairment could prolong elimination if metabolism contributes significantly, though no dedicated studies confirm this; caution is advised in such patients.[30]

Chemistry

Chemical structure

Homatropine, also known as tropine mandelate, is a semisynthetic anticholinergic compound consisting of an ester linkage between the alcohol group of tropine and the carboxylic acid of mandelic acid. The molecular formula of the free base is C16_{16}H21_{21}NO3_{3}, while the commonly used hydrobromide salt has the formula C16_{16}H22_{22}BrNO3_{3}.[33][34] The systematic IUPAC name for homatropine is (1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-hydroxy-2-phenylacetate. This nomenclature reflects its core tropane scaffold, a bridged bicyclic system with a nitrogen atom at position 8 bearing a methyl substituent, and an ester at the 3-position connected to the 2-hydroxy-2-phenylacetic acid moiety. The tropane core is an 8-azabicyclo[3.2.1]octane, a bridged bicyclic system incorporating a pyrrolidine ring and a piperidine ring that share the bridgehead carbons and nitrogen atom, providing the rigidity essential for its pharmacological properties.[1][8] Stereochemically, homatropine adopts the endo configuration at the C3 ester linkage, with bridgehead stereocenters at C1 (R) and C5 (S), mirroring the natural configuration found in tropane alkaloids like atropine. The mandelic acid portion introduces a chiral center at the alpha carbon, though commercial preparations are typically racemic at this position. In contrast to atropine, which features tropic acid (3-hydroxy-2-phenylpropanoic acid) with an additional hydroxymethyl group on the alpha carbon, homatropine's simpler mandelic acid structure contributes to its reduced potency and shorter duration of action as an anticholinergic agent.[8][5]

Physical properties

Homatropine hydrobromide is typically obtained as colorless crystals or a white, crystalline powder that is odorless.[35] It exhibits good solubility in water at a ratio of 1:5, is sparingly soluble in alcohol, and is insoluble in ether, which influences its formulation for aqueous-based preparations.[36][37] The hydrobromide salt has a melting point of 214–217 °C.[36] As a tertiary amine, homatropine possesses a pKa of approximately 9.8, contributing to its ionization behavior in physiological environments.[8] Its logP value is around 1.8, reflecting moderate lipophilicity that facilitates penetration across ocular tissues.[37] Homatropine hydrobromide maintains stability in aqueous solutions at pH 4–6, as evidenced by pharmacopeial specifications for ophthalmic formulations where pH is controlled in this range to prevent degradation.[35][38]

Adverse effects

Common side effects

Homatropine, when used as an ophthalmic solution, commonly causes ocular side effects due to its cycloplegic and mydriatic actions. These include blurred vision from paralysis of accommodation and photophobia from pupillary dilation, which typically last several hours to days depending on the dose. Transient stinging or burning upon instillation is also frequently reported. Increased intraocular pressure may occur, particularly in patients with narrow anterior chamber angles, potentially precipitating angle-closure glaucoma in susceptible individuals; this risk is dose-dependent and requires prior assessment of the anterior chamber depth.[10][39] Prolonged topical use can lead to local ocular irritation, manifesting as follicular conjunctivitis, vascular congestion, edema, exudates, or eczematoid dermatitis. Ocular effects such as blurred vision and photophobia are direct consequences of the drug's pharmacological action.[10] Systemic absorption from ophthalmic administration is minimal but can result in anticholinergic effects, including dry mouth and thirst; tachycardia is rare. These systemic effects from eye drops are uncommon with standard topical use.[10][39] In oral combinations with opioids like hydrocodone for antitussive use, homatropine contributes anticholinergic side effects such as dry mouth, constipation, and urinary retention, which may be enhanced by the opioid component leading to increased drowsiness. These effects are commonly reported in users of such formulations.[18][40]

Contraindications and precautions

Homatropine is contraindicated in patients with primary glaucoma or a predisposition to angle-closure glaucoma, such as those with a narrow anterior chamber angle, as it may precipitate an acute attack by inducing pupillary dilation.[4] It is also absolutely contraindicated in individuals with known hypersensitivity to homatropine, other anticholinergics, or any components of the formulation, due to the risk of severe allergic reactions.[4] Relative contraindications include conditions where anticholinergic effects could exacerbate underlying issues, such as prostatic hypertrophy, myasthenia gravis, or gastrointestinal obstruction, owing to the potential for urinary retention, worsened muscle weakness, or delayed gastric emptying.[41] Homatropine should be avoided in patients with pyloric stenosis, particularly infants, as it may intensify obstructive symptoms through reduced gastrointestinal motility.[4] Precautions are advised in specific populations due to heightened risks of systemic absorption and adverse effects. In elderly patients, homatropine warrants caution because of increased susceptibility to central nervous system disturbances like delirium and agitation from even minimal systemic exposure.[4] For children, especially infants under 3 months, use is not recommended due to enhanced systemic toxicity risks; in older children, compress the lacrimal sac post-instillation to minimize absorption.[4] During pregnancy, homatropine is classified as Category C, with no adequate human or animal data on fetal risk, and should only be used if the potential benefit justifies possible harm to the fetus.[4] Drug interactions primarily involve additive anticholinergic effects when combined with other agents in the class, such as tricyclic antidepressants (e.g., amitriptyline), necessitating close monitoring for enhanced toxicity like dry mouth or constipation.[41] In formulations combining homatropine with opioids for respiratory use, additive central nervous system depression may occur, increasing risks of sedation and respiratory issues.[42] Monitoring is essential in at-risk patients; intraocular pressure should be assessed prior to and during therapy in those with glaucoma risk factors to prevent angle-closure events, and systemic symptoms should be watched in vulnerable groups like the elderly and children.[4]

History and availability

Development

Homatropine was synthesized in 1883 by German chemist Albert Ladenburg through the esterification of tropine with mandelic acid, creating an analog of the natural alkaloid atropine derived from tropic acid.[43] This modification aimed to produce a compound with milder mydriatic effects and reduced systemic toxicity compared to atropine, addressing limitations in ophthalmic applications where prolonged pupil dilation was needed without excessive side effects.[43] Ladenburg's work built on earlier efforts in tropane chemistry during the 1870s and 1880s, which focused on elucidating and synthesizing alkaloids from plants like belladonna (Atropa belladonna) to expand the repertoire of anticholinergic agents.[5] Following its initial description in Ladenburg's publication in the Annalen der Chemie, homatropine was commercialized by E. Merck & Co. in 1883 as a mydriatic agent, marking one of the early semi-synthetic pharmaceuticals in ophthalmology. By the 1910s, it had become established in ophthalmic practice for pupil dilation and cycloplegia, offering a safer alternative to atropine for routine eye examinations and treatment of uveal inflammation.[44] In the mid-20th century, homatropine's anticholinergic properties led to its incorporation into combination therapies, particularly as an adjunct in antitussive formulations during the 1940s and 1950s to mitigate opioid-related side effects while suppressing cough reflexes.[45] This expansion reflected the broader evolution of anticholinergic drugs from plant-derived origins toward targeted synthetic applications in respiratory medicine.[5]

Regulatory status

Homatropine hydrobromide ophthalmic solution has been available in the United States since the early 20th century and is considered grandfathered under the Federal Food, Drug, and Cosmetic Act of 1938, allowing continued marketing without a modern New Drug Application (NDA) as long as it maintains the same formulation and labeling as pre-1938 products.[46] In contrast, combination products like Hycodan (hydrocodone bitartrate and homatropine methylbromide) received initial FDA approval on March 23, 1943, under NDA 005213 for symptomatic cough relief.[45] These opioid-anticholinergic combinations were originally classified as Schedule III controlled substances but were rescheduled to Schedule II by the Drug Enforcement Administration effective October 6, 2014, due to concerns over abuse potential comparable to other Schedule II opioids.[22] In the United States and European Union, homatropine is available only by prescription; ophthalmic drops for cycloplegia and uveitis are widely accessible through pharmacies, while oral forms in opioid combinations face stricter controls, including no automatic refills and enhanced monitoring under the opioid Risk Evaluation and Mitigation Strategy (REMS).[47][48] Post-2014 rescheduling and amid the ongoing opioid crisis, prescriptions for antitussive combinations like hydrocodone/homatropine have been restricted, with FDA labeling changes in 2018 limiting use to adults 18 years and older to mitigate risks of misuse and respiratory depression.[23] Internationally, homatropine eye drops are included on the World Health Organization's Model List of Essential Medicines (23rd list, 2023) as an alternative to atropine or cyclopentolate for treating anterior uveitis and inducing mydriasis/cycloplegia.[49] While the pure ophthalmic form faces few restrictions, opioid-homatropine antitussive combinations are subject to international narcotic controls under the UN Single Convention on Narcotic Drugs due to hydrocodone's abuse potential in cough syrups. Common brand names for homatropine ophthalmic solutions include Isopto Homatropine and Homatropaire, with generic versions widely produced and available.[50] As of 2025, regulatory scrutiny on opioid combinations has intensified, including updated REMS requirements effective October 2024 mandating patient education on risks, contributing to some manufacturer discontinuations of low-volume antitussive products amid declining prescriptions. For example, in September 2025, hydrocodone bitartrate and homatropine methylbromide syrup (NDC 0472-1030-16) was discontinued.[48][51]

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  14. Ophthalmic Manifestations of Rheumatologic Disease - PMC - NIH
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  32. Bioorganic Chemistry, Toxinology, and Pharmaceutical Uses of ...
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  47. Drug Products Containing Hydrocodone; Enforcement Action Dates
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  49. Opioid Analgesic Risk Evaluation and Mitigation Strategy (REMS)
  50. [PDF] WHO EML 23rd List (2023) - IRIS
  51. Nigeria bans cough syrup with codeine after addiction outcry - BBC
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