Bimatoprost

{{Short description|Chemical compound}} {{Use dmy dates|date=January 2020}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | Verifiedfields = changed | verifiedrevid = 459978941 | image = Bimatoprost.svg | image_class = skin-invert-image | width = | alt = | caption =

| pronounce = | tradename = Lumigan, others | Drugs.com = {{drugs.com|monograph|bimatoprost}} | MedlinePlus = a602030 | DailyMedID = Bimatoprost | pregnancy_AU = B3 | pregnancy_AU_comment = <ref name="Drugs.com pregnancy" /> | pregnancy_category = | routes_of_administration = eye drops | class = | ATC_prefix = S01 | ATC_suffix = EE03 | ATC_supplemental =

| legal_AU = S4 | legal_AU_comment = <ref>{{cite web | title=Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/resources/publication/publications/prescription-medicines-registration-new-generic-medicines-and-biosimilar-medicines-2017 | access-date=30 March 2024}}</ref><ref>{{cite web | title=Therapeutic Goods (Poisons Standard— June 2025) Instrument 2025 | website=Therapeutic Goods Administration (TGA) | date=May 2025 | url=https://www.legislation.gov.au/F2025L00599/asmade/2025-05-28/text/original/pdf | format=pdf | access-date=31 August 2025}}</ref> | legal_BR =  | legal_BR_comment = | legal_CA =  | legal_CA_comment = | legal_DE =  | legal_DE_comment = | legal_NZ =  | legal_NZ_comment = | legal_UK =  | legal_UK_comment = | legal_US = Rx-only | legal_US_comment = <ref name="Bimatoprost label" /><ref name="Lumigan label" /> | legal_EU = Rx-only | legal_EU_comment = | legal_UN =  | legal_UN_comment = | legal_status =

| CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 155206-00-1 | CAS_supplemental = | PubChem = 5311027 | PubChemSubstance = | IUPHAR_ligand = 1958 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB00905 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4470565 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = QXS94885MZ | KEGG_Ref = {{keggcite|changed|kegg}} | KEGG = D02724 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 51230 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 1200963 | NIAID_ChemDB = | PDB_ligand = | synonyms =

| IUPAC_name = 7-[3,5-dihydroxy-2- (3-hydroxy-5-phenyl-pent-1-enyl)- cyclopentyl]-''N''-ethyl-hept-5-enamide | C=25 | H=37 | N=1 | O=4 | SMILES = 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 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChI_comment = | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = AQOKCDNYWBIDND-FTOWTWDKSA-N | density = | density_notes = | melting_point = | melting_high = | melting_notes = | boiling_point = | boiling_notes = | solubility = | sol_units = | specific_rotation = }}

'''Bimatoprost''', sold under the brand name '''Lumigan''' among others, is a medication used to treat high pressure inside the eye including glaucoma.<ref name=AHFS2019>{{cite web|url=https://www.drugs.com/monograph/bimatoprost.html|title=Bimatoprost Monograph for Professionals|website=Drugs.com|publisher=American Society of Health-System Pharmacists|access-date=26 March 2019}}</ref> Specifically it is used for open angle glaucoma when other agents are not sufficient.<ref name=AHFS2019/><ref name=BNF76/> It may also be used to increase the size of the eyelashes.<ref name="Bimatoprost label">{{cite web | title=Bimatoprost solution/ drops | website=DailyMed | date=18 September 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=27bef7e1-750a-4ac1-ab5f-e4c0121ffcbc | access-date=4 January 2020}}</ref><ref name="Lumigan label">{{cite web | title=Lumigan- bimatoprost solution/ drops | website=DailyMed | date=31 July 2017 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a5e67c75-db88-4372-bb07-c8dd15c97631 | access-date=4 January 2020}}</ref> It is used as an eye drop and effects generally occur within four hours.<ref name=AHFS2019/><ref name="Lumigan label" />

Common side effects include red eyes, dry eyes, change in color of the eyes, blurry vision, and cataracts.<ref name=AHFS2019/><ref name=BNF76/><ref name="Lumigan label" /> Use during pregnancy or breastfeeding is generally not recommended.<ref name="Drugs.com pregnancy">{{cite web | title=Bimatoprost ophthalmic (Lumigan) Use During Pregnancy | website=Drugs.com | date=14 October 2019 | url=https://www.drugs.com/pregnancy/bimatoprost-ophthalmic.html | access-date=4 January 2020}}</ref><ref name=BNF76/><ref name="Lumigan label" /> It is a prostaglandin analog and works by increasing the outflow of aqueous fluid from the eyes.<ref name=AHFS2019/>

Bimatoprost was approved for medical use in the United States in 2001.<ref name=AHFS2019/> It is available as a generic medication.<ref name=BNF76>{{cite book|title=British national formulary: BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=978-0-85711-338-2|page=1149|edition=76}}</ref><ref name="Bimatoprost label" /><ref>{{cite web | title=Bimatoprost | website=Drugs.com | date=2 December 2019 | url=https://www.drugs.com/international/bimatoprost.html | access-date=4 January 2020}}</ref> In 2023, it was the 238th most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2023 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=12 August 2025 | archive-date=12 August 2025 | archive-url=https://web.archive.org/web/20250812130026/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Bimatoprost Drug Usage Statistics, United States, 2014 - 2023 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Bimatoprost | access-date = 20 August 2025 }}</ref>

==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.<ref name=AHFS2019/><ref name="Lumigan label" /><ref name="AC">{{cite book|title=Austria-Codex| veditors = Haberfeld H |publisher=Österreichischer Apothekerverlag|location=Vienna|year=2015|language=de}}</ref>

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.<ref name="pmid19929032">{{cite journal | vauthors = Curran MP | title = Bimatoprost: a review of its use in open-angle glaucoma and ocular hypertension | journal = Drugs & Aging | volume = 26 | issue = 12 | pages = 1049–1071 | year = 2009 | pmid = 19929032 | doi = 10.2165/11203210-000000000-00000 }}</ref>

===Cosmetic=== thumb|260x260px|Bimatoprost is used cosmetically to increase eyelash prominence Bimatoprost may be used to treat small or underdeveloped eyelashes.<ref name="Bimatoprost label"/><ref name="Lumigan label" /> 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).<ref name="pmid25601618">{{cite journal | vauthors = Choi YM, Diehl J, Levins PC | title = Promising alternative clinical uses of prostaglandin F2α analogs: beyond the eyelashes | journal = Journal of the American Academy of Dermatology | volume = 72 | issue = 4 | pages = 712–716 | date = April 2015 | pmid = 25601618 | doi = 10.1016/j.jaad.2014.10.012 }}</ref>{{verify source|date=December 2011}}

==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.<ref name="AC" /><ref name=AHFS2019 /><ref name="Bimatoprost label"/> Occasional adverse effects (in less than 1% of patients) are headache and nausea.<ref name="AC" />

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.<ref name="Bimatoprost label"/><ref>{{cite news | vauthors = Saint Louis C | title=Long Lashes Without Prescription, but With Risks | work=The New York Times | date=1 May 2010 | url=https://www.nytimes.com/2010/05/02/health/02latisse.html | access-date=18 July 2019 }}</ref> 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.<ref name="Xu">{{cite journal | vauthors = Xu L, Wang X, Wu M | title = Topical medication instillation techniques for glaucoma | journal = The Cochrane Database of Systematic Reviews | volume = 2017 | issue = 2 | article-number = CD010520 | date = February 2017 | pmid = 28218404 | pmc = 5419432 | doi = 10.1002/14651858.CD010520.pub2 }}</ref>

== 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.<ref name="AC" />

==Pharmacology== ===Mechanism of action=== 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.<ref name=AHFS2019 /><ref name="AC" /> No prostamide receptor has been identified {{as of|2015|lc=on}}; the search is ongoing.<ref>{{cite journal | vauthors = Shelnut EL, Nikas SP, Finnegan DF, Chiang N, Serhan CN, Makriyannis A | title = Design and synthesis of novel prostaglandin E2 ethanolamide and glycerol ester probes for the putative prostamide receptor(s) | journal = Tetrahedron Letters | volume = 56 | issue = 11 | pages = 1411–1415 | date = March 2015 | pmid = 25960577 | pmc = 4422110 | doi = 10.1016/j.tetlet.2015.01.164 | author-link6 = Alexandros Makriyannis }}</ref> As of 2019 it was thought that bimatoprost worked via the trabecular meshwork and uveoscleral pathways.<ref>{{cite web |title=Australian Product Information Lumigan (Bimatoprost) Eye Drops |url=https://allergan-web-cdn-prod.azureedge.net/allerganaustralia/allerganaustralia/media/allergan-australia/products/pdfs/pi/lumigan-pi.pdf |access-date=15 July 2019|quote=Bimatoprost reduces intraocular pressure in man by increasing aqueous humour outflow through the trabecular meshwork and enhancing uveoscleral outflow.}}</ref><ref>{{cite web |title=Bimatoprost |url=https://www.drugbank.ca/drugs/DB00905#reference-L6877 |website=DrugBank|access-date=7 July 2019}}</ref>

===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.<ref name=AHFS2019 /><ref name="AC" />

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.<ref name=AHFS2019 /><ref name="AC" />

== Research == Bimatoprost has been used to treat eyebrow hypotrichosis in a 60-year old female.<ref>{{cite journal | vauthors = Riahi RR, Cohen PR | title = Topical Treatment of Eyebrow Hypotrichosis with Bimatoprost 0.03% Solution: Case Report and Literature Review | journal = Cureus | volume = 10 | issue = 5 | article-number = e2666 | date = May 2018 | pmid = 30042917 | pmc = 6054329 | doi = 10.7759/cureus.2666 | doi-access = free }}</ref> 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.<ref>{{cite journal | vauthors = Boubertakh B, Courtemanche O, Marsolais D, Di Marzo V, Silvestri C | title = New role for the anandamide metabolite prostaglandin F2α ethanolamide: Rolling preadipocyte proliferation | journal = Journal of Lipid Research | volume = 64 | issue = 11 | article-number = 100444 | date = November 2023 | pmid = 37730163 | doi = 10.1016/j.jlr.2023.100444 | pmc = 10622703 }}</ref>

== References == {{Reflist}}

== Further reading == * {{cite journal | vauthors = | title = Prostaglandin Analogues for Ophthalmic Use: A Review of the Comparative Clinical Effectiveness and Cost-Effectiveness | journal = CADTH Rapid Response Reports | date = July 2015 | pmid = 26985536 }}

{{Prostaglandins}} {{Antiglaucoma preparations and miotics}} {{Prostanoid signaling modulators}} {{Portal bar | Medicine}}

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