Bimatoprost

Bimatoprost
Clinical data
Trade names Lumigan
AHFS/Drugs.com Monograph
MedlinePlus a602030
License data
Pregnancy
category
  • US: C (Risk not ruled out)
    Routes of
    administration
    Topical (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 IV application
    Duration of action ≥ 24 hrs
    Excretion 67% renal, 25% fecal
    Identifiers
    CAS Number
    PubChem CID
    IUPHAR/BPS
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    ECHA InfoCard 100.170.712
    Chemical and physical data
    Formula C25H37NO4
    Molar mass 415.566 g/mol
    3D model (JSmol)
     NY (what is this?)  (verify)

    Bimatoprost (marketed in the US, Canada and Europe by Allergan, under the trade name Lumigan) is a prostaglandin analog used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. It reduces intraocular pressure (IOP) by increasing the outflow of aqueous fluid from the eyes.[1] In December 2008, the indication to lengthen eyelashes was approved by the U.S. Food and Drug Administration (FDA); the cosmetic formulation of bimatoprost is sold as Latisse /ləˈts/.[2]

    Uses

    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[3][4] (typically timolol).

    Studies have shown bimatoprost to be more effective than timolol in reduction of intraocular pressure (IOP) and as least as effective as the prostaglandin analogs latanoprost and travoprost in reducing IOP.[5]

    Cosmetic

    In patients using ophthalmic prostaglandins such as travoprost and latanoprost, it has been noted that there had been an increase in diameter, density and length of eyelashes. A study published in May 2010 found that bimatoprost in a gel suspension, when applied at the base of the upper eyelid eyelashes, significantly increased eyelash length. Allergan initiated clinical trials investigating the usage of bimatoprost as a cosmetic drug.[6] In 2008, the FDA Dermatologic and Ophthalmic Drugs Advisory Committee voted to approve bimatoprost for the cosmetic use of darkening and lengthening eyelashes.[7] The medical term for this is treatment of hypotrichosis; however, the FDA approval is for purely cosmetic purposes (see Prostaglandin F receptor#Clinical Significance).[8][9]

    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.[3][4][10] Occasional adverse effects (in less than 1% of patients) are headache and nausea.[3]

    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.[10][11] 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.[12]

    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.[3]

    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.[3][4] No prostamide receptor has been identified as of 2015; the search is ongoing.[13]

    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.[3][4]

    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.[3][4]

    References

    1. "Bimatoprost Ophthalmic". MedlinePlus. January 1, 2003. Archived from the original on 2007-10-05. Retrieved 2007-11-19.
    2. "Allergan gets FDA approval for eyelash treatment". BusinessWeek. Associated Press. December 26, 2008. Archived from the original on December 29, 2008. Retrieved December 26, 2008.
    3. 1 2 3 4 5 6 7 Haberfeld, H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag.
    4. 1 2 3 4 5 Drugs.com: Bimatoprost Monograph.
    5. Curran MP (2009). "Bimatoprost: a review of its use in open-angle glaucoma and ocular hypertension". Drugs Aging. 26 (12): 1049–71. doi:10.2165/11203210-000000000-00000. PMID 19929032.
    6. Rundle, Rhonda L. (2007-11-19). "Drug That Lengthens Eyelashes Sets Off Flutter". The Wall Street Journal. Retrieved 2007-11-19.
    7. Grady, Scott. "Latisse (Bimatoprost) is Approved by the FDA in 2008". ChicLatisse.com. Archived from the original on 26 August 2014. Retrieved 22 August 2014.
    8. The Pink Sheet: Lauren Smith, December 15, 2008; Volume 70, Number 050.
    9. Choi YM, Diehl J, Levins PC (2015). "Promising alternative clinical uses of prostaglandin F2α analogs: beyond the eyelashes". Journal of the American Academy of Dermatology. 72 (4): 712–6. doi:10.1016/j.jaad.2014.10.012. PMID 25601618.
    10. 1 2 Latisse prescribing information
    11. "Long Lashes Without Prescription, but With Risks". Catherine Saint Louis. The New York Times. May 1, 2010
    12. Xu L, Wang X, Wu M (2017). "Topical medication instillation techniques for glaucoma". Cochrane Database Syst Rev. 2: CD010520. doi:10.1002/14651858.CD010520.pub2. PMC 5419432. PMID 28218404.
    13. Shelnut, E. L.; Nikas, S. P.; Finnegan, D. F.; Chiang, N; Serhan, C. N.; Makriyannis, A (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.

    Citations

    • Chen M, Cheng C, Chen Y, Chou C, Hsu W (2006). "Effects of bimatoprost 0.03% on ocular hemodynamics in normal tension glaucoma". J Ocul Pharmacol Ther. 22 (3): 188–93. doi:10.1089/jop.2006.22.188. PMID 16808680. 
    • Kruse P, Rieck P, Sherif Z, Liekfeld A (2006). "Cystoid macular edema in a pseudophakic patient after several glaucoma procedures. Is local therapy with bimatoprost the reason?". Klinische Monatsblätter für Augenheilkunde. 223 (6): 534–7. doi:10.1055/s-2005-858992. PMID 16804825. 
    • Steinhäuser S (2006). "Decreased high-density lipoprotein serum levels associated with topical bimatoprost therapy". Optometry. 77 (4): 177–9. doi:10.1016/j.optm.2006.02.001. PMID 16567279. 
    • Park J, Cho HK, Moon JI (2011). "Changes to upper eyelid orbital fat from use of topical bimatoprost, travoprost, and latanoprost". Japanese Ophthalmological Society. 55 (1): 22–27. doi:10.1007/s10384-010-0904-z. PMID 21331688. 
    • Jayaprakasam A, Ghazi-Nouri S (2010). "Periorbital fat atrophy - an unfamiliar side effect of prostaglandin analogues". Orbit. 29 (6): 357–359. doi:10.3109/01676830.2010.527028. PMID 21158579. 
    • Filippopoulos T, Paula JS, Torun N, Hatton MP, Pasquale LR, Grosskreutz CL (2008). "Periorbital changes associated with topical bimatoprost". Ophthalmology Plastic and Reconstructive Surgery. 24 (4): 302–307. doi:10.1097/IOP.0b013e31817d81df. PMID 18645437. 
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