Tropicamide

Last updated
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
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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]

Pharmacology

Pharmacodynamics

Tropicamide is an anticholinergic. [10] It is specifically an antimuscarinic, acting as a selective muscarinic acetylchline M1 and M4 receptor antagonist. [10] However, it has also been reported to be a non-selective antagonist of all five muscarinic acetylcholine receptors. [11] As with other antimuscarinics, tropicamide can produce deliriant effects. [10]

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. [12] [13] [14]

Tropicamide severely destroys internal organs when injected. [15] [16]

Stereochemistry

Tropicamide has a chiral center and two enantiomers. Medications are racemates. [17]

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">Atropine</span> 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.

<span class="mw-page-title-main">Benzatropine</span> Medication for movement disorders

Benzatropine (INN), known as benztropine in the United States and Japan, is a medication used to treat movement disorders like parkinsonism and dystonia, as well as extrapyramidal side effects of antipsychotics, including akathisia. It is not useful for tardive dyskinesia. It is taken by mouth or by injection into a vein or muscle. Benefits are seen within two hours and last for up to ten hours.

<span class="mw-page-title-main">Mydriasis</span> Excessive dilation of the pupil

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">Hyoscyamine</span> Tropane alkaloid

Hyoscyamine is a naturally occurring tropane alkaloid and plant toxin. It is a secondary metabolite found in certain plants of the family Solanaceae, including henbane, mandrake, angel's trumpets, jimsonweed, the sorcerers' tree, and Atropa belladonna. It is the levorotary isomer of atropine and thus sometimes known as levo-atropine.

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 acetylcholine (ACh) neurotransmitter at synapses in the central and peripheral nervous system.

<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 is applied by different routes: inhaler, nebulizer, or nasal spray, for different reasons.

<span class="mw-page-title-main">Phenylephrine</span> Decongestant medication

Phenylephrine, sold under the brand names Neosynephrine and Sudafed PE among numerous others, is a medication used as a decongestant for uncomplicated nasal congestion, used to dilate the pupil, used to increase blood pressure, and used to relieve hemorrhoids. It can be taken by mouth, as a nasal spray, given by injection into a vein or muscle, applied to the skin, or as a rectal suppository.

<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.

<span class="mw-page-title-main">Deliriant</span> Class of psychoactive drugs

Deliriants are a subclass of hallucinogen. The term was coined in the early 1980s to distinguish these drugs from psychedelics such as LSD and dissociatives such as ketamine, due to their primary effect of causing delirium, as opposed to the more lucid and less disturbed states produced by other types of hallucinogens. The term generally refers to anticholinergic drugs, which are substances that inhibit the function of the neurotransmitter acetylcholine.

<span class="mw-page-title-main">Cyclizine</span> Medication for motion sickness or vertigo

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

Biperiden, sold under the brand name Akineton among others, is a medication used to treat Parkinson disease, certain drug-induced movement disorders and Tourette Syndrome. It is not recommended for tardive dyskinesias. It is taken by mouth, injection into a vein, or muscle.

<span class="mw-page-title-main">Trihexyphenidyl</span> Antispasmodic drug

Trihexyphenidyl is an antispasmodic drug used to treat stiffness, tremors, spasms, and poor muscle control. It is an agent of the antimuscarinic class and is often used in management of Parkinson's disease. It was approved by the FDA for the treatment of Parkinson's in the US in 2003.

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

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, and as a mydriatic.

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

Procyclidine is an anticholinergic drug principally used for the treatment of drug-induced parkinsonism, akathisia and acute dystonia, Parkinson's disease, and idiopathic or secondary dystonia.

<span class="mw-page-title-main">Dilated fundus examination</span> Method of viewing the interior of the eye

Dilated fundus examination (DFE) is a diagnostic procedure that uses mydriatic eye drops to dilate or enlarge the pupil in order to obtain a better view of the fundus of the eye. Once the pupil is dilated, examiners use ophthalmoscopy to view the eye's interior, which makes it easier to assess the retina, optic nerve head, blood vessels, and other important features. DFE has been found to be a more effective method for evaluating eye health when compared to non-dilated examination, and is the best method of evaluating structures behind the iris. It is frequently performed by ophthalmologists and optometrists as part of an eye examination.

A spasm of accommodation is a condition in which the ciliary muscle of the eye remains in a constant state of contraction. Normal accommodation allows the eye to "accommodate" for near-vision. However, in a state of perpetual contraction, the ciliary muscle cannot relax when viewing distant objects. This causes vision to blur when attempting to view objects from a distance. This may cause pseudomyopia or latent hyperopia.

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

A muscarinic acetylcholine receptor antagonist, also simply known as a muscarinic antagonist or as an antimuscarinic agent, is a type of anticholinergic drug that blocks the activity of the muscarinic acetylcholine receptors (mAChRs). The muscarinic receptors are proteins 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.

<span class="mw-page-title-main">Cholinergic blocking drug</span> Drug that block acetylcholine in synapses of cholinergic nervous system

Cholinergic blocking drugs are a group of drugs that block the action of acetylcholine (ACh), a neurotransmitter, in synapses of the cholinergic nervous system. They block acetylcholine from binding to cholinergic receptors, namely the nicotinic and muscarinic receptors.

References

  1. "Summary for ARTG Entry: 25356 Mydriacyl tropicamide 0.5% eye drops bottle". Therapeutic Goods Administration . Archived from the original on 5 June 2023. Retrieved 5 June 2023.
  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.
  3. 1 2 3 4 5 6 7 8 "Tropicamide". Drugs.com . American Society of Health-System Pharmacists. Archived from the original on 28 December 2016. Retrieved 8 December 2016.
  4. World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 314. hdl: 10665/44053 . ISBN   9789241547659.
  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.
  7. Manny RE, Hussein M, Scheiman M, Kurtz D, Niemann K, Zinzer K (July 2001). "Tropicamide (1%): an effective cycloplegic agent for myopic children". Investigative Ophthalmology & Visual Science . 42 (8): 1728–35. PMID   11431435. Archived from the original on 2013-01-12.
  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. 1 2 3 Lakstygal AM, Kolesnikova TO, Khatsko SL, Zabegalov KN, Volgin AD, Demin KA, Shevyrin VA, Wappler-Guzzetta EA, Kalueff AV (May 2019). "DARK Classics in Chemical Neuroscience: Atropine, Scopolamine, and Other Anticholinergic Deliriant Hallucinogens". ACS Chem Neurosci. 10 (5): 2144–2159. doi:10.1021/acschemneuro.8b00615. PMID   30566832.
  11. Lavrador M, Cabral AC, Veríssimo MT, Fernandez-Llimos F, Figueiredo IV, Castel-Branco MM (January 2023). "A Universal Pharmacological-Based List of Drugs with Anticholinergic Activity". Pharmaceutics. 15 (1): 230. doi: 10.3390/pharmaceutics15010230 . PMC   9863833 . PMID   36678858.
  12. 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.
  13. 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.
  14. 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.
  15. "Bellman, V., Ukolova, A., Erovichenkova, E., Lam, S., Srivastava, H. K., Bruce, J., & Burgess, D. M. (2022). Abuse of tropicamide eye drops: review of clinical data. Revista brasileira de psiquiatria (Sao Paulo, Brazil : 1999)". Braz J Psychiatry. 44. 2 Nov 2022.
  16. "Krokodil: Russia's Deadliest Drug (NSFW)". YouTube . 17 May 2012.
  17. 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)