Latanoprost

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Latanoprost
Latanoprost.svg
Latanoprost-3D-balls.png
Clinical data
Pronunciationla-TAN-oh-prost
Trade namesXalatan, Xelpros, Monoprost, others
AHFS/Drugs.comMonograph
MedlinePlusa697003
License data
Pregnancy
category
  • AU: B3
Routes of
administration		Topical eye drop
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismActivation by ester hydrolysis, deactivation by beta oxidation
Onset of action3–4 hours
Elimination half-life17 minutes (plasma)
Duration of action≥ 24 hours
ExcretionMainly 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 InfoCard100.162.178 Edit this at Wikidata
Chemical and physical data
FormulaC26H40O5
Molar mass432.601 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 checkY
  • Key:GGXICVAJURFBLW-CEYXHVGTSA-N checkY
  (verify)

Latanoprost, sold under the brand name Xalatan among others, is a medication used to treat increased pressure inside the eye.[2] This includes ocular hypertension and open angle glaucoma.[2] It is applied as eye drops to the eyes.[2] Onset of effects is usually within four hours, and they last for up to a day.[2]

Common side effects include blurry vision, redness of the eye, itchiness, and darkening of the iris.[2] Latanoprost is in the prostaglandin analogue family of medications.[2] It works by increasing the outflow of aqueous fluid from the eyes through the uveoscleral tract.[3]

Latanoprost was approved for medical use in the United States in 1996.[2] It is on the World Health Organization's List of Essential Medicines.[4] Latanoprost is available as a generic medication.[5] In 2020, it was the 77th most commonly prescribed medication in the United States with more than 9 million prescriptions.[6][7] It is available as a combination with netarsudil and with timolol.

Medical uses[edit]

In the United States, latanoprost is indicated for patients with open-angle glaucoma or ocular hypertension to reduce intraocular pressure (IOP).[8]

Open-angle glaucoma[edit]

Latanoprost eye drops, marketed by Pfizer
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.[9]

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.[10]

Closed-angle glaucoma[edit]

Patients who had elevated IOP despite iridotomy and/or iridectomy (including patients 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).[11]

Adverse effects[edit]

Listed from most to least common:[12][13]

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.[15]

Pregnancy[edit]

Use in pregnant women is limited due to high incidence of abortion shown in animal experiments. Because of this, latanoprost is classified as risk factor C (adverse events were observed in animal reproduction studies at maternally toxic doses) according to United States Food and Drug Administration's use-in-pregnancy ratings.[16] Drug excretion in breast milk is unknown.[3]

Interactions[edit]

Interactions are similar to other prostaglandin analogs. Paradoxically, the concomitant use of latanoprost and bimatoprost or other prostaglandins may result in increased intraocular pressure.[8] Non-steroidal anti-inflammatory drugs (NSAIDs) can reduce or increase the effect of latanoprost.[12][13]

Pharmacology[edit]

Mechanism of action[edit]

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.[12][13] 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.[8]

Pharmacokinetics[edit]

Latanoprost is absorbed well through the cornea. As a ester prodrug, it completely hydrolyses to the active latanoprost acid upon absorption to become biologically active.[8] 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 respecitvely.[12][13]

The activation and deactivation pathway is analogous to the one of tafluprost (at least up to the tetranor-metabolite);[13] compare Tafluprost#Pharmacokinetics.

Metabolism. From left to right: latanoprost, latanoprost acid (the active metabolite), 1,2-dinorlatanoprost acid, 1,2,3,4-tetranorlatanoprost acid[13]

Chemistry[edit]

Stability[edit]

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.[17]

Society and culture[edit]

The brand Xalatan is manufactured by Pfizer.[18]

Cosmetic use[edit]

  • Lengthening and thickening of the eyelashes (used, like bimatoprost, in the cosmetic industry as eyelash growth enhancers).[19]
  • There is one small study that found benefit in androgenic alopecia.[20]

References[edit]

  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. ^ a b c d e f g "Latanoprost". The American Society of Health-System Pharmacists. Archived from the original on 28 December 2016. Retrieved 8 December 2016.
  3. ^ a b 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.
  4. ^ 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.
  5. ^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 413. ISBN 9781284057560.
  6. ^ "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  7. ^ "Latanoprost - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
  8. ^ a b c d "XALATAN- latanoprost solution". DailyMed. 27 December 2022. Retrieved 30 March 2023.
  9. ^ 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.
  10. ^ 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.
  11. ^ Aung T; Wong HT; Yip CC; et al. (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): 1178–83. doi:10.1016/s0161-6420(00)00073-7. PMID 10857840.
  12. ^ a b c d Latanoprost Professional Drug Facts.
  13. ^ a b c d e f Haberfeld, H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag.
  14. ^ 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.
  15. ^ 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.
  16. ^ De Santis, M; Lucchese, A; Carducci, B; Cavaliere, A. F.; De Santis, L; Merola, A; Straface, G; Caruso, A (2004). "Latanoprost exposure in pregnancy". American Journal of Ophthalmology. 138 (2): 305–6. doi:10.1016/j.ajo.2004.03.002. PMID 15289149.
  17. ^ 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.
  18. ^ Latanoprost Monograph. Accessed 16 December 2021.
  19. ^ Johnstone, Murray A.; Albert, Daniel M. (1 August 2002). "Prostaglandin-Induced Hair Growth". Survey of Ophthalmology. 47: S185–S202. doi:10.1016/S0039-6257(02)00307-7. ISSN 0039-6257. PMID 12204716. Archived from the original on 28 August 2021. Retrieved 1 October 2019.
  20. ^ Gupta, AK; Mays, RR; Versteeg, SG; Shear, NH; Piguet, V; Piraccini, BM (March 2019). "Efficacy of Off-Label Topical Treatments for the Management of Androgenetic Alopecia: A Review" (PDF). Clinical Drug Investigation. 39 (3): 233–239. doi:10.1007/s40261-018-00743-8. hdl:11585/715894. PMID 30652260. S2CID 58659303. Archived (PDF) from the original on 5 June 2020. Retrieved 3 September 2020.

External links[edit]

  • "Latanoprost". Drug Information Portal. U.S. National Library of Medicine.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Latanoprost&oldid=1152369170"