Tropicamide

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Tropicamide
Tropicamide.svg
Clinical data
Trade names Mydriacyl, others
AHFS/Drugs.com Monograph
License data
Pregnancy
category
  • C
Routes of
administration
Topical eye drops
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding 45%
Identifiers
  • (RS)-N-Ethyl-3-hydroxy-2-phenyl-N-(pyridin-4-ylmethyl)propanamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.014.673 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H20N2O2
Molar mass 284.359 g·mol−1
3D model (JSmol)
  • CCN(Cc1ccncc1)C(=O)C(CO)c1ccccc1
  • InChI=1S/C17H20N2O2/c1-2-19(12-14-8-10-18-11-9-14)17(21)16(13-20)15-6-4-3-5-7-15/h3-11,16,20H,2,12-13H2,1H3
  • Key:BGDKAVGWHJFAGW-UHFFFAOYSA-N
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Tropicamide, sold under the brand name Mydriacyl among others, is a medication used to dilate the pupil and help with examination of the eye. [3] Specifically it is used to help examine the back of the eye. [4] It is applied as eye drops. [3] Effects occur within 40 minutes and last for up to a day. [3]

Contents

Common side effects include blurry vision, increased intraocular pressure, and sensitivity to light. [3] Another rare but severe side effect is psychosis, particularly in children. [3] It is unclear if use during pregnancy is safe for the fetus. [5] Tropicamide is in the antimuscarinic part of the anticholinergic family of medications. [3] It works by making the muscles within the eye unable to respond to nerve signals. [3]

Tropicamide was approved for medical use in the United States in 1960. [3] It is on the World Health Organization's List of Essential Medicines. [6]

Medical use

Anisocoria caused by tropicamide instilled into the subject's right eye only. Anizokoria.JPG
Anisocoria caused by tropicamide instilled into the subject's right eye only.

Tropicamide is an antimuscarinic drug that produces short acting mydriasis (dilation of the pupil) and cycloplegia [7] when applied as eye drops. It is used to allow better examination of the lens, vitreous humor, and retina. Due to its relatively short duration of effect (48 hours), it is typically used during eye examinations such as the dilated fundus examination, but it may also be used before or after eye surgery. Cycloplegic drops are often also used to treat anterior uveitis, decreasing risk of posterior synechiae and decreasing inflammation in the anterior chamber of the eye.

Tropicamide is occasionally administered in combination with p-hydroxyamphetamine (brand name Paremyd), which is a sympathomimetic. The use of the sympathomimetic drug causes the iris dilator muscle to be directly stimulated, causing increased dilation. In the United States, the sympathomimetic drop most commonly used along with tropicamide, is 2.5% phenylephrine hydrochloride (brand name AK-Dilate).

Side effects

Tropicamide induces transient stinging and a slight and transient rise in intraocular pressure in the majority of patients. It may cause redness or conjunctivitis (inflammation) and also blurs near vision for a short while after instillation (care must be taken, and the patient must only drive when vision returns to normal). Tropicamide may, in very rare cases, [8] cause an attack of acute angle-closure glaucoma. This tends to be in patients with narrow anterior chamber angles, and closure risk must be assessed by the practitioner prior to instillation.

Tropicamide is often preferred to atropine because atropine has a longer half-life, causing prolonged dilation and blurry vision for up to a week. Atropine has less sting effect, but can be toxic or fatal if ingested in large quantities by children or adults.

With eye drops, systemic effects are minimal to nonexistent due to very low absorption into the bloodstream. [9]

Recreational use

Tropicamide is sometimes abused (injected intravenously e.g. by insulin syringe) as an inexpensive recreational deliriant drug (along with naphazoline). This was initially reported in Russia, but has subsequently spread to various other countries in the former Soviet Union and around Europe, and later in the United States. [10] [11] [12] [13]

Stereochemistry

Tropicamide has a chiral center and two enantiomers. Medications are racemates. [14]

Enantiomers
(R)-Tropicamid Structural Formula V1.svg
(R)-Tropicamid
CAS: 92934-63-9
(S)-Tropicamid Structural Formula V1.svg
(S)-Tropicamid
CAS: 92934-64-0

Related Research Articles

<span class="mw-page-title-main">Glaucoma</span> Group of eye diseases

Glaucoma is a group of eye diseases that result in damage to the optic nerve and cause vision loss. The most common type is open-angle glaucoma, in which the drainage angle for fluid within the eye remains open, with less common types including closed-angle glaucoma and normal-tension glaucoma. Open-angle glaucoma develops slowly over time without pain. Peripheral vision may begin to decrease, followed by central vision, resulting in blindness if not treated. Closed-angle glaucoma can present gradually or suddenly. The sudden presentation may involve severe eye pain, blurred vision, mid-dilated pupil, redness of the eye, and nausea. Vision loss from glaucoma, once it has occurred, is permanent. Eyes affected by glaucoma are referred to as being glaucomatous.

<span class="mw-page-title-main">Atropine</span> Tropane alkaloid anticholinergic medication & used as antidote for nerve agent poisoning

Atropine is a tropane alkaloid and anticholinergic medication used to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate, and to decrease saliva production during surgery. It is typically given intravenously or by injection into a muscle. Eye drops are also available which are used to treat uveitis and early amblyopia. The intravenous solution usually begins working within a minute and lasts half an hour to an hour. Large doses may be required to treat some poisonings.

Mydriasis is the dilation of the pupil, usually having a non-physiological cause, or sometimes a physiological pupillary response. Non-physiological causes of mydriasis include disease, trauma, or the use of certain types of drug. It may also be of unknown cause.

<span class="mw-page-title-main">Xylometazoline</span> Medication used to reduce symptoms of nasal congestion, allergic rhinitis, and sinusitis

Xylometazoline, also spelled xylomethazoline, is a medication used to reduce symptoms of nasal congestion, allergic rhinitis, and sinusitis. Use is not recommended for more than seven days. Use is also not recommended in those less than three months of age and some say not less than 6 years of age. It is used directly in the nose as a spray or drops.

Cycloplegia is paralysis of the ciliary muscle of the eye, resulting in a loss of accommodation. Because of the paralysis of the ciliary muscle, the curvature of the lens can no longer be adjusted to focus on nearby objects. This results in similar problems as those caused by presbyopia, in which the lens has lost elasticity and can also no longer focus on close-by objects. Cycloplegia with accompanying mydriasis is usually due to topical application of muscarinic antagonists such as atropine and cyclopentolate.

<span class="mw-page-title-main">Cyclopentolate</span> Pair of enantiomers

Cyclopentolate is a muscarinic antagonist. It is commonly used as an eye drop during pediatric eye examinations to dilate the eye (mydriatic) and prevent the eye from focusing/accommodating (cycloplegic). Cyclopentolate or atropine can also be administered to reverse muscarinic and central nervous system effects of indirect cholinomimetic (anti-AChase) administration.

Anticholinergics are substances that block the action of the neurotransmitter called acetylcholine (ACh) at synapses in the central and peripheral nervous system.

<span class="mw-page-title-main">Pilocarpine</span> Medication used to treat glaucoma and dry mouth

Pilocarpine is a medication used to reduce pressure inside the eye and treat dry mouth. As an eye drop it is used to manage angle closure glaucoma until surgery can be performed, ocular hypertension, primary open angle glaucoma, and to bring about constriction of the pupil following its dilation. However, due to its side effects it is no longer typically used for long-term management. Onset of effects with the drops is typically within an hour and lasts for up to a day. By mouth it is used for dry mouth as a result of Sjögren syndrome or radiation therapy.

<span class="mw-page-title-main">Synechia (eye)</span> Condition in which the iris adheres to the cornea or lens

Ocular synechia is an eye condition where the iris adheres to either the cornea or lens. Synechiae can be caused by ocular trauma, iritis or iridocyclitis and may lead to certain types of glaucoma. It is sometimes visible on careful examination but usually more easily through an ophthalmoscope or slit-lamp.

<span class="mw-page-title-main">Ipratropium bromide</span> Type of anticholinergic

Ipratropium bromide, sold under the trade name Atrovent among others, is a type of anticholinergic medication which opens up the medium and large airways in the lungs. It is used to treat the symptoms of chronic obstructive pulmonary disease and asthma. It is used by inhaler or nebulizer. Onset of action is typically within 15 to 30 minutes and lasts for three to five hours.

<span class="mw-page-title-main">Uveitis</span> Inflammation of the uvea of the eye

Uveitis is inflammation of the uvea, the pigmented layer of the eye between the inner retina and the outer fibrous layer composed of the sclera and cornea. The uvea consists of the middle layer of pigmented vascular structures of the eye and includes the iris, ciliary body, and choroid. Uveitis is described anatomically, by the part of the eye affected, as anterior, intermediate or posterior, or panuveitic if all parts are involved. Anterior uveitis (iridocyclitis) is the most common, with the incidence of uveitis overall affecting approximately 1:4500, most commonly those between the ages of 20-60. Symptoms include eye pain, eye redness, floaters and blurred vision, and ophthalmic examination may show dilated ciliary blood vessels and the presence of cells in the anterior chamber. Uveitis may arise spontaneously, have a genetic component, or be associated with an autoimmune disease or infection. While the eye is a relatively protected environment, its immune mechanisms may be overcome resulting in inflammation and tissue destruction associated with T-cell activation.

<span class="mw-page-title-main">Eye drop</span> Liquid applied directly to the eye

Eye drops or eyedrops are liquid drops applied directly to the surface of the eye usually in small amounts such as a single drop or a few drops. Eye drops usually contain saline to match the salinity of the eye. Drops containing only saline and sometimes a lubricant are often used as artificial tears to treat dry eyes or simple eye irritation such as itching or redness. Eye drops may also contain one or more medications to treat a wide variety of eye diseases. Depending on the condition being treated, they may contain steroids, antihistamines, sympathomimetics, beta receptor blockers, parasympathomimetics, parasympatholytics, prostaglandins, nonsteroidal anti-inflammatory drugs (NSAIDs), antibiotics, antifungals, or topical anesthetics.

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<span class="mw-page-title-main">Latanoprost</span> Chemical compound

Latanoprost, sold under the brand name Xalatan among others, is a medication used to treat increased pressure inside the eye. This includes ocular hypertension and open angle glaucoma. It is applied as eye drops to the eyes. Onset of effects is usually within four hours, and they last for up to a day.

<span class="mw-page-title-main">Cyclizine</span> Antiemetic/motion sickness

Cyclizine, sold under a number of brand names, is a medication used to treat and prevent nausea, vomiting and dizziness due to motion sickness or vertigo. It may also be used for nausea after general anaesthesia or that which developed from opioid use. It is taken by mouth, in the rectum, or injected into a vein.

<span class="mw-page-title-main">Biperiden</span> Group of stereoisomers

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<span class="mw-page-title-main">Homatropine</span> Medication

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<span class="mw-page-title-main">Muscarinic antagonist</span> Drug that binds to but does not activate muscarinic cholinergic receptors

A muscarinic receptor antagonist (MRA) is a type of anticholinergic agent that blocks the activity of the muscarinic acetylcholine receptor. The muscarinic receptor is a protein involved in the transmission of signals through certain parts of the nervous system, and muscarinic receptor antagonists work to prevent this transmission from occurring. Notably, muscarinic antagonists reduce the activation of the parasympathetic nervous system. The normal function of the parasympathetic system is often summarised as "rest-and-digest", and includes slowing of the heart, an increased rate of digestion, narrowing of the airways, promotion of urination, and sexual arousal. Muscarinic antagonists counter this parasympathetic "rest-and-digest" response, and also work elsewhere in both the central and peripheral nervous systems.

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References

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  2. "Mydriacyl 1% eye drops, solution - Summary of Product Characteristics (SmPC)". Electronic Medicines Compendium . 12 February 2020. Archived from the original on 27 June 2022. Retrieved 29 July 2020.
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  5. "Tropicamide ophthalmic Use During Pregnancy". Drugs.com . Archived from the original on 28 December 2016. Retrieved 28 December 2016.
  6. World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl: 10665/325771 . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
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  8. Liew G, Mitchell P, Wang JJ, Wong TY (January 2006). "Fundoscopy: to dilate or not to dilate?". BMJ . 332 (7532): 3. doi:10.1136/bmj.332.7532.3. PMC   1325111 . PMID   16399709.
  9. Vuori ML, Kaila T, Iisalo E, Saari KM (1994-01-01). "Systemic absorption and anticholinergic activity of topically applied tropicamide". Journal of Ocular Pharmacology. 10 (2): 431–437. doi:10.1089/jop.1994.10.431. PMID   8083562.
  10. Bersani FS, Corazza O, Simonato P, Mylokosta A, Levari E, Lovaste R, Schifano F (2013). "Drops of madness? Recreational misuse of tropicamide collyrium; early warning alerts from Russia and Italy". General Hospital Psychiatry . 35 (5): 571–3. doi:10.1016/j.genhosppsych.2013.04.013. PMID   23706777.
  11. Walker S (21 June 2011). "Krokodil: The drug that eats junkies". The Independent . Archived from the original on 2017-09-22.
  12. Bersani FS, Imperatori C, Prilutskaya M, Kuliev R, Corazza O (July 2015). "Injecting eye-drops: a mini-review on the non-clinical use of tropicamide". Hum Psychopharmacol. 30 (4): 262–4. doi:10.1002/hup.2481. PMID   26216560. S2CID   190289.
  13. Bellman V, Ukolova A, Erovichenkova E, Lam S, Srivastava HK, Bruce J, Burgess DM (November 2022). "Abuse of tropicamide eye drops: review of clinical data". Braz J Psychiatry . 44 (5): 522–531. doi:10.47626/1516-4446-2021-2446. PMC   9561840 . PMID   35739063.
  14. Rote Liste (in German). Vol. 57. Frankfurt/Main: Rote Liste Service GmbH. 2017. p. 224. ISBN   978-3-946057-10-9. Arzneimittelverzeichnis für Deutschland (einschließlich EU-Zulassungen und bestimmter Medizinprodukte)