Latanoprost

Last updated

Latanoprost
Latanoprost.svg
Latanoprost-3D-balls.png
Clinical data
Trade names Xalatan, others
AHFS/Drugs.com Monograph
MedlinePlus a697003
License data
Pregnancy
category
  • AU:B3
Routes of
administration 		Topical eye drop
ATC code
Legal status
Legal status
Pharmacokinetic data
Metabolism Activation by ester hydrolysis, deactivation by beta oxidation
Onset of action 3–4 hours
Elimination half-life 17 minutes (plasma)
Duration of action ≥ 24 hours
Excretion Mainly via kidney
Identifiers
  • Isopropyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2- [(3R)3-hydroxy-5-phenylpentyl]-cyclopentyl] hept-5-enoate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.162.178 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C26H40O5
Molar mass 432.601 g·mol−1
3D model (JSmol)
  • O=C(OC(C)C)CCC/C=C\C[C@H]2[C@@H](O)C[C@@H](O)[C@@H]2CC[C@@H](O)CCc1ccccc1
  • InChI=1S/C26H40O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,19,21-25,27-29H,4,9,12-18H2,1-2H3/b8-3-/t21-,22+,23+,24-,25+/m0/s1 Yes check.svgY
  • Key:GGXICVAJURFBLW-CEYXHVGTSA-N Yes check.svgY
   (verify)

Latanoprost, sold under the brand name Xalatan among others, is a medication used to treat increased pressure inside the eye (intraocular pressure). [5] This includes ocular hypertension and open-angle glaucoma. [5] Latanaprost is applied as eye drops to the eyes. [5] Onset of effects is usually within four hours, and they last for up to a day. [5]

Contents

Common side effects include blurry vision, redness of the eye, itchiness, and darkening of the iris. [5] Latanoprost is in the prostaglandin analogue family of medications. [5] It works by increasing the outflow of aqueous fluid from the eyes through the uveoscleral tract. [6]

Latanoprost was approved for medical use in the United States and the European Union in 1996. [5] [3] It is on the World Health Organization's List of Essential Medicines. [7] Latanoprost is available as a generic medication. [8] In 2022, it was the 67th most commonly prescribed medication in the United States, with more than 9 million prescriptions. [9] [10] It is available as a fixed-dose combination with netarsudil as netarsudil/latanoprost and with timolol as latanoprost/timolol.

Medical uses

In the United States, latanoprost is indicated for the reduction of elevated intraocular pressure in people with open-angle glaucoma or ocular hypertension. [2]

Open-angle glaucoma

Latanoprost eye drops, marketed by Pfizer Pfizer xalaTAN latanoprost eye drops.jpg
Latanoprost eye drops, marketed by Pfizer
Latanoprost in Japanese-language packaging Latanoprost.jpg
Latanoprost in Japanese-language packaging

In people with ocular hypertension (IOP ≥21  mm Hg) including open-angle glaucoma, treatment with latanoprost reduced IOP levels by 22 to 39% over 1 to 12 months’ treatment. Latanoprost is more effective than timolol 0.5% twice daily in 3 of 4 large (n = 163 to 267) randomised, double-blind trials. Latanoprost demonstrated a stable long-term IOP-lowering effect in 1- or 2-year continuations of these trials, with no sign of diminishing effect during prolonged treatment. [11]

Meta-analysis suggests that latanoprost is more effective than timolol in lowering intraocular pressure (IOP). However, it often causes iris pigmentation. While current[ when? ] evidence suggests that this pigmentation is benign, careful lifetime evaluation of patients is still justified. [12]

Closed-angle glaucoma

People who had elevated IOP despite iridotomy and/or iridectomy (including people of Asian descent), latanoprost was significantly more effective than timolol in two double-blind, monotherapy trials (8.2 and 8.8 mm Hg vs 5.2 and 5.7 mm Hg for latanoprost vs timolol at 12 and 2 weeks, respectively). [13]

Adverse effects

Listed from most to least common: [14] [15]

Research suggests that wiping the eye with an absorbent pad after the administration of eye drops can result in shorter eyelashes and a lesser chance of hyperpigmentation in the eyelid, compared to not wiping off excess fluid. [17]

Pregnancy

Interactions

Interactions are similar to other prostaglandin analogs. Paradoxically, the concomitant use of latanoprost and bimatoprost or other prostaglandins may result in increased intraocular pressure. [2] Non-steroidal anti-inflammatory drugs (NSAIDs) can reduce or increase the effect of latanoprost. [14] [15]

Pharmacology

Mechanism of action

Like other prostaglandin analogues, latanoprost acid is an analog of prostaglandin F2α that acts as a selective agonist at the prostaglandin F receptor. Prostaglandins increase the sclera's permeability to aqueous fluid. By giving latanoprorost, it increases prostaglandin's scleral activity, increasing outflow of aqueous fluid and lowering intraocular pressure. [14] [15] The outflow of aqueous fluid would reduce the intraocular pressure in the eye, reducing the likelihood of complications such as optic nerve damage and visual field loss. [2]

Pharmacokinetics

Latanoprost is absorbed well through the cornea. As an ester prodrug, it completely hydrolyses to the active latanoprost acid upon absorption to become biologically active. [2] Highest concentrations of the acid in the aqueous humour are reached two hours after application, lowering of intraocular pressure starts after 3 to 4 hours, with its highest effect found after 8 to 12 hours, and its effect still present for at least 24 hours. When latanoprost acid reaches the circulation, it is quickly metabolised in the liver by fatty acid beta oxidation to 1,2-dinor- and 1,2,3,4-tetranor-latanoprost acid; blood plasma half life is only 17 minutes. The metabolites are mainly excreted via the kidney, with 88% of the topical dose and 98% of an intravenous dose being recovered in the urine respectively. [14] [15]

The activation and deactivation pathway is analogous to the one of tafluprost (at least up to the tetranor-metabolite); [15] compare Tafluprost#Pharmacokinetics.

Metabolism. From left to right: latanoprost, latanoprost acid (the active metabolite), 1,2-dinorlatanoprost acid, 1,2,3,4-tetranorlatanoprost acid Latanoprost metabolism.svg
Metabolism. From left to right: latanoprost, latanoprost acid (the active metabolite), 1,2-dinorlatanoprost acid, 1,2,3,4-tetranorlatanoprost acid

Chemistry

Stability

Latanoprost exhibits thermal and solar instability. The concentration of latanoprost stored at 50 °C will decrease by 10% every 8.25 days. When stored at 70 °C the concentration will decrease by 10% every 1.32 days. Ultraviolet light, for example in sunlight, causes rapid degradation of latanoprost. [18]

Society and culture

Latanoprost was approved for medical use in the United States and the European Union in 1996. [5] [3]

In September 2023, the Committee for Medicinal Products for Human Use of the European Medicines Agency adopted a positive opinion, recommending the granting of a marketing authorization for the medicinal product Catiolanze, intended for the reduction of elevated intraocular pressure in adults with open angle glaucoma or ocular hypertension and in children from four years and adolescents with elevated intraocular pressure and pediatric glaucoma. [3] The applicant for this medicinal product is Santen Oy. [3] Catiolanze was approved for medical use in the European Union in November 2023. [3] [4]

Brand names

Latanoprost is sold under many brand names including Xalatan, [2] [19] Iyuzeh, [20] Xelpros, [21] and Catiolanze. [3]

In the US, Xalatan is marketed by Viatris after Upjohn was spun off from Pfizer. [22] [23] [24]

Cosmetic use

Related Research Articles

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

Glaucoma is a group of eye diseases that can lead to damage of the optic nerve. The optic nerve transmits visual information from the eye to the brain. Glaucoma may cause vision loss if left untreated. It has been called the "silent thief of sight" because the loss of vision usually occurs slowly over a long period of time. A major risk factor for glaucoma is increased pressure within the eye, known as intraocular pressure (IOP). It is associated with old age, a family history of glaucoma, and certain medical conditions or the use of some medications. The word glaucoma comes from the Ancient Greek word γλαυκός, meaning 'gleaming, blue-green, gray'.

Prostaglandin analogues are a class of drugs that bind to a prostaglandin receptor.

<span class="mw-page-title-main">Intraocular pressure</span> Fluid pressure inside the eye

Intraocular pressure (IOP) is the fluid pressure inside the eye. Tonometry is the method eye care professionals use to determine this. IOP is an important aspect in the evaluation of patients at risk of glaucoma. Most tonometers are calibrated to measure pressure in millimeters of mercury (mmHg).

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

Betaxolol is a selective beta1 receptor blocker used in the treatment of hypertension and angina. It is also a adrenergic blocker with no partial agonist action and minimal membrane stabilizing activity. Being selective for beta1 receptors, it typically has fewer systemic side effects than non-selective beta-blockers, for example, not causing bronchospasm as timolol may. Betaxolol also shows greater affinity for beta1 receptors than metoprolol. In addition to its effect on the heart, betaxolol reduces the pressure within the eye. This effect is thought to be caused by reducing the production of the liquid within the eye. The precise mechanism of this effect is not known. The reduction in intraocular pressure reduces the risk of damage to the optic nerve and loss of vision in patients with elevated intraocular pressure due to glaucoma.

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

Timolol is a beta blocker medication used either by mouth or as eye drops. As eye drops it is used to treat increased pressure inside the eye such as in ocular hypertension and glaucoma. By mouth it is used for high blood pressure, chest pain due to insufficient blood flow to the heart, to prevent further complications after a heart attack, and to prevent migraines.

Ocular hypertension is the presence of elevated fluid pressure inside the eye, usually with no optic nerve damage or visual field loss.

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

Brimonidine is an α2 agonist medication used to treat open-angle glaucoma, ocular hypertension, and rosacea. In rosacea it improves the redness. It is used as eye drops or applied to the skin.

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

Brinzolamide is a carbonic anhydrase inhibitor used to lower intraocular pressure in patients with open-angle glaucoma or ocular hypertension.

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

Dorzolamide, sold under the brand name Trusopt among others, is a medication used to treat high pressure inside the eye, including in cases of glaucoma. It is used as an eye drop. Effects begin within three hours and last for at least eight hours. It is also available as the combination dorzolamide/timolol.

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

Bimatoprost, sold under the brand name Lumigan among others, is a medication used to treat high pressure inside the eye including glaucoma. Specifically it is used for open angle glaucoma when other agents are not sufficient. It may also be used to increase the size of the eyelashes. It is used as an eye drop and effects generally occur within four hours.

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

Travoprost, sold under the brand name Travatan among others, is a medication used to treat high pressure inside the eye including glaucoma. Specifically it is used for open angle glaucoma when other agents are not sufficient. It is used as an eye drop. Effects generally occur within two hours.

Brimonidine/timolol, sold under the brand name Combigan among others, is a fixed-dose combination medication eye drop used for the treatment of glaucoma. It is a combination of brimonidine and timolol.

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

Tafluprost is a prostaglandin analogue. It is used topically to control the progression of open-angle glaucoma and in the management of ocular hypertension, alone or in combination with other medication. It reduces intraocular pressure by increasing the outflow of aqueous fluid from the eyes.

Latanoprost/timolol, sold under the brand name Xalacom, is a combination drug used for the treatment of glaucoma, consisting of latanoprost and timolol.

<span class="mw-page-title-main">Glaucoma medication</span> Eye condition medication

Glaucoma medication is divided into groups based on chemical structure and pharmacologic action. The goal of currently available glaucoma therapy is to preserve visual function by lowering intraocular pressure (IOP) in patients that have an increased intraocular pressure.

Ripasudil, a derivative of fasudil, is a rho kinase inhibitor drug used for the treatment of glaucoma and ocular hypertension.

Bimatoprost/timolol, sold under the brand name Ganfort, is a medication for the treatment of certain conditions involving high pressure in the eyes, specifically open angle glaucoma and ocular hypertension. It is available as eye drops.

Netarsudil/latanoprost, sold under the brand name Rocklatan among others, is a fixed-dose combination medication use to treat elevated intraocular pressure (IOP) in people with open-angle glaucoma or ocular hypertension. It contains netarsudil mesylate and latanoprost. It is applied as eye drops to the eyes.

Brinzolamide/brimonidine, sold under the brand name Simbrinza, is a fixed-dose combination medication used to reduce intra-ocular pressure in adults with ocular hypertension or in those with an eye condition known as open-angle glaucoma. It contains brinzolamide and brimonidine tartrate. It is used as an eye drop.

Posner–Schlossman syndrome (PSS) also known as glaucomatocyclitic crisis (GCC) is a rare acute ocular condition with unilateral attacks of mild granulomatous anterior uveitis and elevated intraocular pressure. It is sometimes considered as a secondary inflammatory glaucoma.

References

  1. ↑ "Latanoprost 50 micrograms/ml eye drops, solution - Summary of Product Characteristics (SmPC)". (emc). 1 July 2022. Archived from the original on 1 July 2022. Retrieved 1 July 2022.
  2. 1 2 3 4 5 6 "Xalatan- latanoprost solution". DailyMed. 27 December 2022. Archived from the original on 30 March 2023. Retrieved 30 March 2023.
  3. 1 2 3 4 5 6 7 "Catiolanze EPAR". European Medicines Agency (EMA). 14 September 2023. Archived from the original on 5 December 2023. Retrieved 11 December 2023.
  4. 1 2 "Catiolanze Product information". Union Register of medicinal products. 16 November 2023. Retrieved 11 December 2023.
  5. 1 2 3 4 5 6 7 8 "Latanoprost Monograph". The American Society of Health-System Pharmacists. Archived from the original on 28 December 2016. Retrieved 8 December 2016.
  6. ↑ Patel SS, Spencer CM (1996). "Latanoprost. A review of its pharmacological properties, clinical efficacy and tolerability in the management of primary open-angle glaucoma and ocular hypertension". Drugs Aging. 9 (5): 363–378. doi:10.2165/00002512-199609050-00007. PMID   8922563. S2CID   25169085.
  7. ↑ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl: 10665/371090 . WHO/MHP/HPS/EML/2023.02.
  8. ↑ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 413. ISBN   9781284057560.
  9. ↑ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  10. ↑ "Latanoprost Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  11. ↑ Perry CM, McGavin JK, Culy CR, Ibbotson T (2003). "Latanoprost. An Update of its Use in Glaucoma and Ocular Hypertension". Drugs & Aging. 20 (8): 597–630. doi:10.2165/00002512-200320080-00005. PMID   12795627. S2CID   24493058.
  12. ↑ Zhang WY, Wan Po AL, Dua HS, Azuara-Blanco A (2001). "Meta-analysis of randomised controlled trials comparing latanoprost with timolol in the treatment of patients with open angle glaucoma or ocular hypertension". British Journal of Ophthalmology. 85 (8): 983–990. doi:10.1136/bjo.85.8.983. PMC   1724079 . PMID   11466259.
  13. ↑ Aung T, Wong HT, Yip CC, Leong JY, Chan YH, Chew PT (June 2000). "Comparison of the intraocular pressure-lowering effect of latanoprost and timolol in patients with chronic angle closure glaucoma: a preliminary study". Ophthalmology. 107 (6): 1178–1183. doi:10.1016/s0161-6420(00)00073-7. PMID   10857840.
  14. 1 2 3 4 Latanoprost Professional Drug Facts .
  15. 1 2 3 4 5 6 Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag.
  16. ↑ Amano S, Nakai Y, Ko A, Inoue K, Wakakura M (2008). "A case of keratoconus progression associated with the use of topical latanoprost". Japanese Journal of Ophthalmology. 52 (4): 334–6. doi:10.1007/s10384-008-0554-6. PMID   18773275. S2CID   189795938.
  17. ↑ Xu L, Wang X, Wu M (2017). "Topical medication instillation techniques for glaucoma". Cochrane Database Syst Rev. 2017 (2): CD010520. doi:10.1002/14651858.CD010520.pub2. PMC   5419432 . PMID   28218404.
  18. ↑ Morgan PV, Proniuk S, Blanchard J, Noecker RJ (2001). "Effect of temperature and light on the stability of latanoprost and its clinical relevance". Journal of Glaucoma. 10 (5): 401–405. doi:10.1097/00061198-200110000-00007. PMID   11711838. S2CID   26568064.
  19. ↑ https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020597Orig1s000rev.pdf [ bare URL PDF ]
  20. ↑ "Drug Approval Package: Iyuzeh". accessdata.fda.gov. 20 September 2023. Retrieved 27 December 2023.
  21. ↑ "Drug Approval Package: Xelpros". accessdata.fda.gov. 28 May 2019. Retrieved 27 December 2023.
  22. ↑ "Pfizer Completes Transaction to Combine Its Upjohn Business with Mylan". Pfizer. 16 November 2020. Retrieved 17 June 2024– via Business Wire.
  23. ↑ "Xalatan". Pfizer. Retrieved 17 June 2024.
  24. ↑ "Brands". Viatris. 16 November 2020. Retrieved 17 June 2024.
  25. ↑ Johnstone MA, Albert DM (August 2002). "Prostaglandin-induced hair growth". Survey of Ophthalmology. 47 (Suppl 1): S185–S202. doi:10.1016/S0039-6257(02)00307-7. PMID   12204716.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.