Bimatoprost

Last updated

Bimatoprost
Bimatoprost.svg
Clinical data
Trade names Lumigan, Latisse, Durysta, others
AHFS/Drugs.com Monograph
MedlinePlus a602030
License data
Pregnancy
category
Routes of
administration
eye drops
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability Low
Protein binding 88%
Onset of action 4 hrs
Elimination half-life 45 min after intravenous application
Duration of action ≥ 24 hrs
Excretion 67% Kidney, 25% fecal
Identifiers
  • 7-[3,5-dihydroxy-2- (3-hydroxy-5-phenyl-pent-1-enyl)- cyclopentyl]-N-ethyl-hept-5-enamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.170.712 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C25H37NO4
Molar mass 415.574 g·mol−1
3D model (JSmol)
  • CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCc1ccccc1
  • InChI=1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3-,17-16+/t20-,21+,22+,23-,24+/m0/s1 Yes check.svgY
  • Key:AQOKCDNYWBIDND-FTOWTWDKSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Bimatoprost, sold under the brand name Lumigan among others, is a medication used to treat high pressure inside the eye including glaucoma. [5] Specifically it is used for open angle glaucoma when other agents are not sufficient. [5] [6] It may also be used to increase the size of the eyelashes. [3] [4] It is used as an eye drop and effects generally occur within four hours. [5] [4]

Contents

Common side effects include red eyes, dry eyes, change in color of the eyes, blurry vision, and cataracts. [5] [6] [4] Use during pregnancy or breastfeeding is generally not recommended. [1] [6] [4] It is a prostaglandin analog and works by increasing the outflow of aqueous fluid from the eyes. [5]

Bimatoprost was approved for medical use in the United States in 2001. [5] It is available as a generic medication. [6] [3] [7] In 2021, it was the 204th most commonly prescribed medication in the United States, with more than 2 million prescriptions. [8] [9]

Uses

Medical

Bimatoprost is used for the treatment of open-angle glaucoma and ocular hypertension in adults, either alone or in combination with a beta blocker, typically timolol. [5] [4] [10]

Studies have shown bimatoprost to be more effective than timolol in reduction of intraocular pressure (IOP) and at least as effective as the prostaglandin analogs latanoprost and travoprost in reducing IOP. [11]

Cosmetic

Bimatoprost is used cosmetically to increase eyelash prominence Bimatoprost eyelash growth.jpg
Bimatoprost is used cosmetically to increase eyelash prominence

Bimatoprost may be used to treat small or underdeveloped eyelashes. [3] [4] The medical term for this is treatment of hypotrichosis; however, the U.S. Food and Drug Administration (FDA) approval is for purely cosmetic purposes (see Prostaglandin F receptor#Clinical significance). [12] [ verification needed ]

Bimatoprost has been used to treat eyebrow hypotrichosis successfully in a 60-year old female patient. [13] The 0.03% solution was applied topically once a day for eight months and showed "increased hair growth and thickening of the eyebrow hairs".

Side effects

Side effects are similar to other prostaglandin analogs applied to the eye. The most common one is conjunctival hyperemia, which occurs in more than 10% of patients. Other effects include blurred vision, eye and eyelid redness, eye burning or other discomfort, and permanent darkening of the iris to brown. [10] [5] [3] Occasional adverse effects (in less than 1% of patients) are headache and nausea. [10]

Some side effects are specific to the cosmetic formulation, which is applied to the skin at the base of the eyelash rather than instilled into the eye. These include infection if the one-time applicators are reused, and darkening of the eyelid or of the area beneath the eye. [3] [14] 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]

Importantly, Bimatoprost and its endogenous analog prostaglandin F2α ethanolamide present the side-effect of being anti-adipogenic, and recently have been shown to be inducers of preadipocyte proliferation, as well. Through inhibiting preadipocyte differentiation and increasing their proliferation, these molecules have been suggested to maintain a reserve of adipocyte progenitor cells. This might allow for healthier development of fat tissue, which is through hyperplasia that outbalances hypertrophy and ectopic fat deposition. These findings have been behind the foundation of the Fat Four Ps Hypothesis, namely, Preadipocyte Pool Preservation by prostaglandin F2α ethanolamide, and the suggestion of Bimatoprost as a promising therapy for obesity. [16]

Interactions

No interaction studies with this substance have been performed. Interactions with systemic (for example, oral) drugs are considered unlikely because bimatoprost does not reach relevant concentrations in the bloodstream. Bimatoprost does not negatively interact with timolol eye drops. [10]

Pharmacology

Mechanism of action

Bimatoprost is a structural analog of prostaglandin F (PGF). Like other PGF analogs such as travoprost, latanoprost and tafluprost, it increases the outflow of aqueous fluid from the eye and lowers intraocular pressure. However, in contrast to these it does not act on the prostaglandin F receptor, nor on any other known prostaglandin receptor. It is thought that bimatoprost mimics the human body's own prostamides (which are chemically similar), a class of substances related to prostaglandins, but with an unknown mechanism of action. [5] [10] No prostamide receptor has been identified as of 2015; the search is ongoing. [17] As of 2019 it was thought that bimatoprost worked via the trabecular meshwork and uveoscleral pathways. [18] [19]

Pharmacokinetics

Bimatoprost is well absorbed through the cornea. It starts lowering intraocular pressure after four hours, lasting for at least 24 hours. A low percentage enters the bloodstream. In the blood plasma, peak concentrations are reached after 10 minutes, then drop below the detection limit of 25 pg/ml after 1.5 hours. The substance does not accumulate in the body. [5] [10]

Plasma protein binding is 88%. Bimatoprost is metabolized by oxidation, N-deethylation and glucuronidation, forming a variety of metabolites. Biological half-life was measured to be 45 minutes after intravenous infusion. 67% are eliminated via the kidney, and 25% via the feces. [5] [10]

Related Research Articles

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

Glaucoma is a group of eye diseases that lead to damage of the optic nerve, which 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 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">Pilocarpine</span> Medication used to treat glaucoma and dry mouth

Pilocarpine is a lactone alkaloid originally extracted from plants of the Pilocarpus genus. It is used as a medication 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 constrict the pupil after 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">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">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">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. Latanaprost 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">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.

Dorzolamide/timolol, sold under the brand name Cosopt among others, is a medication used to treat high pressure inside the eye including glaucoma. It is a combination of dorzolamide hydrochloride and timolol maleate. It may be used when a beta blocker, like timolol, is not sufficient alone. It is used as an eye drop.

<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">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">Levobunolol</span> Chemical compound

Levobunolol is a non-selective beta blocker. It is used topically in the form of eye drops to manage ocular hypertension and open-angle glaucoma.

<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.

<span class="mw-page-title-main">Prostaglandin F receptor</span> Protein-coding gene in the species Homo sapiens

Prostaglandin F receptor (FP) is a receptor belonging to the prostaglandin (PG) group of receptors. FP binds to and mediates the biological actions of Prostaglandin F (PGF). It is encoded in humans by the PTGFR gene.

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.

<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.

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

Prostamides are a class of physiologically active, lipid-like substances chemically related to prostaglandins. They occur naturally in humans and other animals. The first prostamide, called prostamide E2, was discovered in 1997.

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

Netarsudil, sold under the brand name Rhopressa among others, is a medication for the treatment of glaucoma. In the United States, in December 2017, the Food and Drug Administration (FDA) approved a 0.02% ophthalmic solution for the lowering of elevated intraocular pressure in people with open-angle glaucoma or ocular hypertension. The European Medicines Agency approved it in 2019 for the same uses under the brand name Rhokiinsa.

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.

References

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  2. "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  3. 1 2 3 4 5 6 "Bimatoprost solution/ drops". DailyMed. 18 September 2019. Retrieved 4 January 2020.
  4. 1 2 3 4 5 6 7 "Lumigan- bimatoprost solution/ drops". DailyMed. 31 July 2017. Retrieved 4 January 2020.
  5. 1 2 3 4 5 6 7 8 9 10 11 "Bimatoprost Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 26 March 2019.
  6. 1 2 3 4 British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 1149. ISBN   9780857113382.
  7. "Bimatoprost". Drugs.com. 2 December 2019. Retrieved 4 January 2020.
  8. "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  9. "Bimatoprost - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  10. 1 2 3 4 5 6 7 Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag.
  11. Curran MP (2009). "Bimatoprost: a review of its use in open-angle glaucoma and ocular hypertension". Drugs & Aging. 26 (12): 1049–1071. doi:10.2165/11203210-000000000-00000. PMID   19929032.
  12. Choi YM, Diehl J, Levins PC (April 2015). "Promising alternative clinical uses of prostaglandin F2α analogs: beyond the eyelashes". Journal of the American Academy of Dermatology. 72 (4): 712–716. doi:10.1016/j.jaad.2014.10.012. PMID   25601618.
  13. Riahi RR, Cohen PR (May 2018). "Topical Treatment of Eyebrow Hypotrichosis with Bimatoprost 0.03% Solution: Case Report and Literature Review". Cureus. 10 (5): e2666. doi: 10.7759/cureus.2666 . PMC   6054329 . PMID   30042917.
  14. Saint Louis C (1 May 2010). "Long Lashes Without Prescription, but With Risks". The New York Times . Retrieved 18 July 2019.
  15. Xu L, Wang X, Wu M (February 2017). "Topical medication instillation techniques for glaucoma". The Cochrane Database of Systematic Reviews. 2017 (2): CD010520. doi:10.1002/14651858.CD010520.pub2. PMC   5419432 . PMID   28218404.
  16. Boubertakh B, Courtemanche O, Marsolais D, Di Marzo V, Silvestri C (November 2023). "New role for the anandamide metabolite prostaglandin F ethanolamide: Rolling preadipocyte proliferation". Journal of Lipid Research. 64 (11): 100444. doi:10.1016/j.jlr.2023.100444. PMID   37730163.
  17. Shelnut EL, Nikas SP, Finnegan DF, Chiang N, Serhan CN, Makriyannis A (March 2015). "Design and synthesis of novel prostaglandin E2 ethanolamide and glycerol ester probes for the putative prostamide receptor(s)". Tetrahedron Letters. 56 (11): 1411–1415. doi:10.1016/j.tetlet.2015.01.164. PMC   4422110 . PMID   25960577.
  18. "Australian Product Information Lumigan (Bimatoprost) Eye Drops" (PDF). Retrieved 15 July 2019. Bimatoprost reduces intraocular pressure in man by increasing aqueous humour outflow through the trabecular meshwork and enhancing uveoscleral outflow.
  19. "Bimatoprost". DrugBank. Retrieved 7 July 2019.

Further reading