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{{Short description|Chemical compound}}
{{Use dmy dates|date=January 2020}}
{{Use dmy dates|date=January 2020}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
| verifiedrevid = 459978941
| verifiedrevid = 459978941
| drug_name =
| INN =
| type = <!-- empty -->
| image = Bimatoprost.svg
| image = Bimatoprost.svg
| width =
| width =
| alt =
| alt =
| caption =
| caption =


<!-- Clinical data -->
<!-- Clinical data -->
| pronounce =
| pronounce =
| tradename = Lumigan, Latisse, others
| tradename = Lumigan, Latisse, Durysta, others
| Drugs.com = {{drugs.com|monograph|bimatoprost}}
| Drugs.com = {{drugs.com|monograph|bimatoprost}}
| MedlinePlus = a602030
| MedlinePlus = a602030
| licence_CA = <!-- Health Canada may use generic or brand name (generic name preferred) -->
| licence_EU = yes
| DailyMedID = Bimatoprost
| DailyMedID = Bimatoprost
| licence_US = <!-- FDA may use generic or brand name (generic name preferred) -->
| pregnancy_AU = B3
| pregnancy_AU = B3
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy" />
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy" />
| pregnancy_US = N
| pregnancy_US_comment = <ref name="Drugs.com pregnancy" />
| pregnancy_category =
| pregnancy_category =
⚫
| routes_of_administration = [[Ophthalmic drug administration|eye drops]]
| dependency_liability =
| addiction_liability =
⚫
| routes_of_administration = Topical ([[eye drop]]s)
| class =
| class =
| ATCvet =
| ATC_prefix = S01
| ATC_prefix = S01
| ATC_suffix = EE03
| ATC_suffix = EE03
| ATC_supplemental =
| ATC_supplemental =


<!-- Legal status -->
<!-- Legal status -->
| legal_AU = S4
| 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>
| legal_AU_comment =
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F-->
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F-->
| legal_BR_comment =
| legal_BR_comment =
Line 48: Line 38:
| legal_UK_comment =
| legal_UK_comment =
| legal_US = Rx-only
| legal_US = Rx-only
| legal_US_comment =
| legal_US_comment = <ref name="Bimatoprost label" /><ref name="Lumigan label" />
| legal_EU = Rx-only
| legal_EU_comment =
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->
| legal_UN_comment =
| legal_UN_comment =
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| metabolites =
| metabolites =
| onset = 4 hrs
| onset = 4 hrs
| elimination_half-life = 45 min after [[intravenous|IV]] application
| elimination_half-life = 45 min after [[intravenous]] application
| duration_of_action= ≥ 24 hrs
| duration_of_action= ≥ 24 hrs
| excretion = 67% [[kidney]], 25% [[fecal]]
| excretion = 67% [[Kidney]], 25% [[fecal]]


<!-- Identifiers -->
<!-- Identifiers -->
Line 84: Line 76:
| NIAID_ChemDB =
| NIAID_ChemDB =
| PDB_ligand =
| PDB_ligand =
| synonyms =
| synonyms =


<!-- Chemical and physical data -->
<!-- Chemical and physical data -->
| IUPAC_name = 7-[3,5-dihydroxy-2- (3-hydroxy-5-phenyl-pent-1-enyl)- cyclopentyl]-''N''-ethyl-hept-5-enamide
| IUPAC_name = 7-[3,5-dihydroxy-2- (3-hydroxy-5-phenyl-pent-1-enyl)- cyclopentyl]-''N''-ethyl-hept-5-enamide
| chemical_formula =
| C=25 | H=37 | N=1 | O=4
| C=25 | H=37 | N=1 | O=4
| SMILES = CCNC(=O)CCCC=CCC1C(CC(C1C=CC(CCC2=CC=CC=C2)O)O)O
| 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
| Jmol =
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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 = 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
Line 110: Line 100:


<!-- Definition and medical uses -->
<!-- Definition and medical uses -->
'''Bimatoprost''', sold under the trade 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|accessdate=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" />
'''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" />


<!-- Side effects and mechanism -->
<!-- Side effects and mechanism -->
Common side effects include red eyes, dry eyes, change in color of the eyes, blurry vision, and [[cataracts]].<ref name=AHFS2019/><ref name="Lumigan label" /><ref name=BNF76/> 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="Lumigan label" /><ref name=BNF76/> It is a [[prostaglandin]] analog and works by increasing the outflow of [[aqueous humor|aqueous fluid]] from the eyes.<ref name=AHFS2019/>
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 humor|aqueous fluid]] from the eyes.<ref name=AHFS2019/>


<!-- History and culture -->
<!-- History and culture -->
Bimatoprost was approved for medical use in the United States in 2001.<ref name=AHFS2019/> It is available as a [[generic medication]].<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><ref name="Bimatoprost label" /><ref name=BNF76/> A 3{{nbsp}}milliliter bottle in the United Kingdom costs the [[NHS]] about {{GBP|9.30}} as of 2019.<ref name=BNF76>{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=1149|edition=76}}</ref> In the United States the wholesale cost of this amount is about US$80.<ref name=NADAC2019>{{cite web |title=NADAC as of 2019-02-27 |url=https://data.medicaid.gov/Drug-Pricing-and-Payment/NADAC-as-of-2019-02-27/s7c9-pfa6 |website=[[Centers for Medicare & Medicaid Services]] (CMS) |accessdate=3 March 2019 }}</ref> In 2017, it was the 231st most commonly prescribed medication in the United States, with more than two million prescriptions.<ref>{{cite web | title = The Top 300 of 2020 | url = https://clincalc.com/DrugStats/Top300Drugs.aspx | website = ClinCalc | access-date = 11 April 2020}}</ref><ref>{{cite web | title = Bimatoprost - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Bimatoprost | access-date = 11 April 2020}}</ref>
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=9780857113382|pages=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 2021, it was the 204th most commonly prescribed medication in the United States, with more than 2{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Bimatoprost - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Bimatoprost | access-date = 14 January 2024}}</ref>


==Uses==
==Uses==
===Medical===
===Medical===
Bimatoprost is used for the treatment of [[open-angle glaucoma]] and ocular hypertension in adult patients, either alone or in combination with a [[beta blocker]]<ref name="Lumigan label" /><ref name="AC">{{cite book|title=Austria-Codex|editor=Haberfeld, H|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2015|language=German}}</ref><ref name=AHFS2019/> (typically [[timolol]]).
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| author=Curran MP| title=Bimatoprost: a review of its use in open-angle glaucoma and ocular hypertension | journal=Drugs Aging | year= 2009 | volume= 26 | issue= 12 | pages= 1049–71 | pmid=19929032 | doi=10.2165/11203210-000000000-00000 }}</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===
===Cosmetic===
[[File:Bimatoprost eyelash growth.jpg|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 = 712–6 | year = 2015 | pmid = 25601618 | doi = 10.1016/j.jaad.2014.10.012 | url = }}</ref>{{verify source|date=December 2011}}
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==
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 (anatomy)|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" />
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 (anatomy)|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 | last=Louis | first=Catherine Saint | 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 | name-list-format=vanc }}</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=Cochrane Database Syst Rev|volume=2|pages= CD010520 |date=2017 |pmid= 28218404|doi= 10.1002/14651858.CD010520.pub2 |pmc=5419432}}</ref>
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 | name-list-style=vanc }}</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 | pages = CD010520 | date = February 2017 | pmid = 28218404 | pmc = 5419432 | doi = 10.1002/14651858.CD010520.pub2 }}</ref>

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. https://www.jlr.org/article/S0022-2275(23)00117-7/fulltext

⚫
== Interactions ==


⚫
==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" />
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==
==Pharmacology==
===Mechanism of action===
===Mechanism of action===
Bimatoprost is a [[structural analog]] of [[prostaglandin F2α|prostaglandin F<sub>2α</sub>]] (PGF<sub>2α</sub>). Like other PGF<sub>2α</sub> 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 [[prostamide]]s (which are chemically similar), a class of substances related to prostaglandins, but with an unknown mechanism of action.<ref name="AC" /><ref name=AHFS2019 /> No prostamide [[receptor (biochemistry)|receptor]] has been identified {{as of|2015|lc=on}}; the search is ongoing.<ref>{{cite journal|pmid=25960577|pmc=4422110|year=2015|last1=Shelnut|first1=E. L.|title=Design and synthesis of novel prostaglandin E<sub>2</sub> ethanolamide and glycerol ester probes for the putative prostamide receptor(s)|journal=Tetrahedron Letters|volume=56|issue=11|pages=1411–1415|last2=Nikas|first2=S. P.|last3=Finnegan|first3=D. F.|last4=Chiang|first4=N|last5=Serhan|first5=C. N.|last6=Makriyannis|authorlink6=Alexandros Makriyannis|first6=A|doi=10.1016/j.tetlet.2015.01.164}}</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 |accessdate=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|accessdate=7 July 2019}}</ref>
Bimatoprost is a [[structural analog]] of [[prostaglandin F2α|prostaglandin F<sub>2α</sub>]] (PGF<sub>2α</sub>). Like other PGF<sub>2α</sub> 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 [[prostamide]]s (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 (biochemistry)|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 E<sub>2</sub> 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===
===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 [[picogram|pg]]/ml after 1.5 hours. The substance does not [[Bioaccumulation|accumulate]] in the body.<ref name="AC" /><ref name=AHFS2019 />
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 [[picogram|pg]]/ml after 1.5 hours. The substance does not [[Bioaccumulation|accumulate]] in the body.<ref name=AHFS2019 /><ref name="AC" />


[[Plasma protein binding]] is 88%. Bimatoprost is metabolized by oxidation, ''N''-[[ethyl group|deethylation]] and [[glucuronidation]], forming a variety of [[metabolite]]s. 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="AC" /><ref name=AHFS2019 />
[[Plasma protein binding]] is 88%. Bimatoprost is metabolized by oxidation, ''N''-[[ethyl group|deethylation]] and [[glucuronidation]], forming a variety of [[metabolite]]s. 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" />


==References==
== References ==
{{Reflist}}
{{Reflist}}


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

==External links==
* {{cite web| url = https://druginfo.nlm.nih.gov/drugportal/name/bimatoprost | publisher = U.S. National Library of Medicine| work = Drug Information Portal| title = Bimatoprost }}


{{Prostaglandins}}
{{Prostaglandins}}
{{Antiglaucoma preparations and miotics}}
{{Antiglaucoma preparations and miotics}}
{{Prostanoid signaling modulators}}
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[[Category:Hair loss medications]]
[[Category:Ophthalmology drugs]]
[[Category:Prostaglandins]]
[[Category:Prostaglandins]]
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Latest revision as of 18:38, 24 April 2024

Bimatoprost
Clinical data
Trade namesLumigan, Latisse, Durysta, others
AHFS/Drugs.comMonograph
MedlinePlusa602030
License data
Pregnancy
category
Routes of
administration		eye drops
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityLow
Protein binding88%
Onset of action4 hrs
Elimination half-life45 min after intravenous application
Duration of action≥ 24 hrs
Excretion67% 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 InfoCard100.170.712 Edit this at Wikidata
Chemical and physical data
FormulaC25H37NO4
Molar mass415.574 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 checkY
  • Key:AQOKCDNYWBIDND-FTOWTWDKSA-N checkY
 ☒NcheckY (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 2021, it was the 204th 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 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]

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]

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. https://www.jlr.org/article/S0022-2275(23)00117-7/fulltext

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; 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]

References[edit]

  1. ^ a b "Bimatoprost ophthalmic (Lumigan) Use During Pregnancy". Drugs.com. 14 October 2019. Retrieved 4 January 2020.
  2. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  3. ^ a b c d e f "Bimatoprost solution/ drops". DailyMed. 18 September 2019. Retrieved 4 January 2020.
  4. ^ a b c d e f g "Lumigan- bimatoprost solution/ drops". DailyMed. 31 July 2017. Retrieved 4 January 2020.
  5. ^ 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.
  6. ^ a b c d 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. ^ a b c d e f g 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. ^ Saint Louis C (1 May 2010). "Long Lashes Without Prescription, but With Risks". The New York Times. Retrieved 18 July 2019.
  14. ^ 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.
  15. ^ 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.
  16. ^ "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.
  17. ^ "Bimatoprost". DrugBank. Retrieved 7 July 2019.

Further reading[edit]

  • "Prostaglandin Analogues for Ophthalmic Use: A Review of the Comparative Clinical Effectiveness and Cost-Effectiveness". CADTH Rapid Response Reports. July 2015. PMID 26985536.
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