Bimatoprost
 | |
| Clinical data | |
|---|---|
| Trade names | Lumigan, 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 | |
| |
| CAS Number | |
| PubChem CID | |
| IUPHAR/BPS | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.170.712 |
| Chemical and physical data | |
| Formula | C25H37NO4 |
| Molar mass | 415.574 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
  (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]
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 2022, it was the 195th most commonly prescribed medication in the United States, with more than 2 million prescriptions.[8][9]
Uses
[edit]Medical
[edit]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
[edit]
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]
Side effects
[edit]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][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.[14]
Interactions
[edit]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
[edit]Mechanism of action
[edit]Bimatoprost is a structural analog of prostaglandin F2α (PGF2α). Like other PGF2α 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[update]; the search is ongoing.[15] As of 2019 it was thought that bimatoprost worked via the trabecular meshwork and uveoscleral pathways.[16][17]
Pharmacokinetics
[edit]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]
Research
[edit]Bimatoprost has been used to treat eyebrow hypotrichosis in a 60-year old female.[18] The 0.03% solution was applied topically once a day for eight months and showed "increased hair growth and thickening of the eyebrow hairs".
Bimatoprost and its endogenous analog prostaglandin F2α ethanolamide present the side-effect of being anti-adipogenic, and have been shown to be inducers of preadipocyte proliferation. These findings suggest bimatoprost is a possible therapy for obesity.[19]
References
[edit]- ^ a b "Bimatoprost ophthalmic (Lumigan) Use During Pregnancy". Drugs.com. 14 October 2019. Retrieved 4 January 2020.
- ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
- ^ a b c d e f "Bimatoprost solution/ drops". DailyMed. 18 September 2019. Retrieved 4 January 2020.
- ^ a b c d e f g "Lumigan- bimatoprost solution/ drops". DailyMed. 31 July 2017. Retrieved 4 January 2020.
- ^ a b c d e f g h i j k "Bimatoprost Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 26 March 2019.
- ^ a b c d British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 1149. ISBN 9780857113382.
- ^ "Bimatoprost". Drugs.com. 2 December 2019. Retrieved 4 January 2020.
- ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
- ^ "Bimatoprost Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
- ^ a b c d e f g Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag.
- ^ 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.
- ^ 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.
- ^ Saint Louis C (1 May 2010). "Long Lashes Without Prescription, but With Risks". The New York Times. Retrieved 18 July 2019.
- ^ 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.
- ^ 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.
- ^ "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.
- ^ "Bimatoprost". DrugBank. Retrieved 7 July 2019.
- ^ 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.
- ^ Boubertakh B, Courtemanche O, Marsolais D, Di Marzo V, Silvestri C (November 2023). "New role for the anandamide metabolite prostaglandin F2α ethanolamide: Rolling preadipocyte proliferation". Journal of Lipid Research. 64 (11): 100444. doi:10.1016/j.jlr.2023.100444. PMC 10622703. PMID 37730163.
