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Bimatoprost
Systematic (IUPAC) name
7-[3,5-dihydroxy-2- (3-hydroxy-5-phenyl-pent-1-enyl)- cyclopentyl]-N-ethyl-hept-5-enamide
Identifiers
CAS number 155206-00-1
ATC code S01EE03
PubChem 5311027
DrugBank APRD00826
ChemSpider 4470565
Chemical data
Formula C 25H37NO4  
Mol. mass 415.566 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes Topical (eye drops)
 Yes check.svgY(what is this?)  (verify)

Bimatoprost (sold in the U.S., 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] It has also been used and prescribed off-label to lengthen eyelashes.[2] In December 2008, this use was approved by the U.S. Food and Drug Administration; the cosmetic formulation of bimatoprost is sold as Latisse (pronounced /ləˈtiːs/).[3] Recently, at least three case series have suggested that bimatoprost has the ability to reduce adipose (fat) tissue.

Contents

Cosmetic use

In patients using ophthalmic prostaglandins such as travoprost and latanoprost, as well as prostamides like bimatoprost, it has been anecdotally noted that they have grown long and lush eyelashes. Allergan has initiated clinical trials investigating the usage of Lumigan as a cosmetic drug.[4] On December 5, 2008, the FDA Dermatologic and Ophthalmic Drugs Advisory Committee voted to approve bimatoprost for the cosmetic use of darkening and lengthening eyelashes. The medical term for this is treatment of hypotrichosis, however, the FDA approval is for purely cosmetic purposes.[5]

Several cosmetics companies have released products based on prostaglandin analogs, as non-drug cosmetics.

  • Age Intervention Eyelash by Jan Marini Skin Research
  • RevitaLash by Athena Cosmetics Corp.
  • MD Lash Factor by PhotoMedex Inc.

These companies have been sued by Allergan for patent infringement.[4] The FDA has seized Age Intervention Eyelash as an "unapproved and misbranded drug" because Jan Marini Skin Research promoted it as something that increases eyelash growth[6] and because it is "adulterated" with bimatoprost.[7]

Fat-reducing properties

Reductions in orbital fat (i.e., fat around the eye) have been observed in patients using bimatoprost as glaucoma therapy.[8] Of particular interest, the loss of orbital fat was unilateral in patients who used bimatoprost on only one eye.[9] The effect appears reversible upon cessation of bimatoprost use. The effect is likely to explain deepening of the lid sulcus described in a series of three patients on bimatoprost.[10] The mechanism for the apparent fat reduction remains unclear. However, bimatoprost is chemically analogous to prostaglandin F2 alpha (PGF2alpha), a compound which is known to reduce fat by inhibition of adipocyte differentiation and survival.[11]

Formulations

Lumigan is a 0.03% solution of bimatoprost, and contains benzalkonium chloride as a preservative. Contact lenses should therefore be removed before use, and replaced no less than 15 minutes later;[1] other eye drops or ointments should be given no less than 5 minutes before or after bimatoprost.[1] It is administered once daily.

Efficacy

Studies have shown once-daily bimatoprost 0.03% ophthalmic solution to be more effective than timolol twice daily in reduction of intraocular pressure (IOP) and as effective as or more effective than the prostaglandin analogues latanoprost and travoprost in reducing IOP.[12]

Side effects

Possible side effects of this medication are:

  • May cause blurred vision.
  • May cause eyelid redness.
  • May permanently darken eyelashes.
  • May cause eye discomfort.
  • May eventually cause permanent darkening of the iris to brown.
  • May cause a temporary burning sensation during use.
  • May cause thickening of the eyelashes.

On November 19, 2007 the FDA issued a warning during the seizure of a bimatoprost-containing cosmetic.[13] The warning stated that "the extra dose of bimatoprost may decrease the prescription drug's effectiveness. Damage to the optic nerve may lead to decreased vision and possibly blindness."

References

  1. ^ a b c "Bimatoprost Ophthalmic". MedlinePlus. January 1, 2003. http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a602030.html. Retrieved 2007-11-19.  
  2. ^ "Drug That Lengthens Eyelashes Sets Off Flutter". The Wall Street Journal. 2007-11-19. http://online.wsj.com/article/SB119543055372597359.html. Retrieved 2007-11-19.  
  3. ^ Associated Press (December 26, 2008). "Allergan gets FDA approval for eyelash treatment". BusinessWeek. http://www.businessweek.com/ap/financialnews/D95AF4N81.htm.   Retrieved on December 26, 2008.
  4. ^ a b Wall Street Journal: Drug That Lengthens Eyelashes Sets Off Flutter RHONDA L. RUNDLE November 19, 2007; Page B1
  5. ^ The Pink Sheet: [1] LAUREN SMITH December 15th 2008; Volume 70, Number 050,Page
  6. ^ MSNBC: FDA Seizes $2 Million Of Potentially Harmful SJ Eye Product KNTV-TV 2:44 p.m. ET, Sat., Nov. 17, 2007
  7. ^ Reuters: U.S. seizes discontinued eyelash product Jim Wolf Fri Nov 16, 2007 11:48pm EST
  8. ^ Tappeiner C, Perren B, Iliev ME, Frueh BE, Goldblum D (May 2008). "Orbitale Fettgewebsatrophie bei lokaler Bimatoprost-Therapie - Kann Bimatoprost einen Enophthalmus verursachen? [Orbital fat atrophy in glaucoma patients treated with topical bimatoprost--can bimatoprost cause enophthalmos?]" (in German). Klinische Monatsblätter Für Augenheilkunde 225 (5): 443–5. doi:10.1055/s-2008-1027362. PMID 18454393.  
  9. ^ Filippopoulos T, Paula JS, Torun N, Hatton MP, Pasquale LR, Grosskreutz CL (2008). "Periorbital changes associated with topical bimatoprost". Ophthalmic Plastic and Reconstructive Surgery 24 (4): 302–7. doi:10.1097/IOP.0b013e31817d81df. PMID 18645437.  
  10. ^ Peplinski LS, Albiani Smith K (August 2004). "Deepening of lid sulcus from topical bimatoprost therapy". Optometry and Vision Science 81 (8): 574–7. doi:10.1097/01.opx.0000141791.16683.4a. PMID 15300114.  
  11. ^ Serrero G, Lepak NM (April 1997). "Prostaglandin F2alpha receptor (FP receptor) agonists are potent adipose differentiation inhibitors for primary culture of adipocyte precursors in defined medium". Biochemical and Biophysical Research Communications 233 (1): 200–2. doi:10.1006/bbrc.1997.6433. PMID 9144422.  
  12. ^ Curran M.Bimatoprost: A Review of its Use in Open-Angle Glaucoma and Ocular Hypertension. Drugs & Aging 2009; 26(12): 1049-1071. doi:10.2165/11203210-000000000-00000.
  13. ^ U.S. Food and Drug Administration (November 19, 2007). "Potentially Harmful "Cosmetic" Eye Product Seized". Press release. http://www.fda.gov/consumer/updates/cosmeticeye111907.html. Retrieved 2007-12-05.  

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?". Klin Monatsbl Augenheilkd 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.  
  • Tappeiner C, Perren B, Iliev ME, Frueh BE, Goldblum D (2008). "[Orbital fat atrophy in glaucoma patients treated with topical bimatoprost--can bimatoprost cause enophthalmos?]". Klin Monatsbl Augenheilkd 225 (5): 443–5. doi:10.1055/s-2008-1027362. PMID 18454393.  
  • Filippopoulos T, Paula JS, Torun N, Hatton MP, Pasquale LR, Grosskreutz CL (2008). "Periorbital changes associated with topical bimatoprost.". Ophthal Plast Reconstr Surg 24 (4): 302–7. doi:10.1097/IOP.0b013e31817d81df. PMID 18645437.  
  • Peplinski LS, Albiani Smith K (2004). "Deepening of lid sulcus from topical bimatoprost therapy.". Optom Vis Sci 81 (8): 574–7. doi:10.1097/01.opx.0000141791.16683.4a. PMID 15300114.  

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