Bimatoprost

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Bimatoprost
Bimatoprost.svg
Systematic (IUPAC) name
7-[3,5-dihydroxy-2- (3-hydroxy-5-phenyl-pent-1-enyl)- cyclopentyl]-N-ethyl-hept-5-enamide
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)
Legal status
Legal status
Pharmacokinetic data
Bioavailability Low
Protein binding 88%
Onset of action 4 hrs
Biological half-life 45 min after IV application
Duration of action ≥ 24 hrs
Excretion 67% renal, 25% fecal
Identifiers
CAS Number 155206-00-1 YesY
ATC code S01EE03 (WHO)
PubChem CID 5311027
IUPHAR/BPS 1958
DrugBank DB00905 YesY
ChemSpider 4470565 YesY
UNII QXS94885MZ YesY
KEGG D02724
ChEBI CHEBI:51230 YesY
ChEMBL CHEMBL1200963 N
Chemical data
Formula C25H37NO4
Molar mass 415.566 g/mol
 NYesY (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[edit]

Medical[edit]

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[edit]

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.[citation needed] 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.[8][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.[3][4][9] 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.[9][10]

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.[3]

Pharmacology[edit]

Mechanism of action[edit]

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.[11]

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.[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[edit]

  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. Retrieved December 26, 2008. 
  3. ^ a b c d e f g Haberfeld, H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. 
  4. ^ a b c d e 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. Retrieved 22 August 2014. 
  8. ^ The Pink Sheet: [1] Lauren Smith, December 15, 2008; Volume 70, Number 050.
  9. ^ a b Latisse prescribing information
  10. ^ "Long Lashes Without Prescription, but With Risks". Catherine Saint Louis. The New York Times. May 1, 2010
  11. ^ 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[edit]

  • 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.