Bimatoprost

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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
Licence data US Daily Med:link
Pregnancy cat. C (US)
Legal status -only (US)
Routes Topical (eye drops)
Identifiers
CAS number 155206-00-1 YesY
ATC code S01EE03
PubChem CID 5311027
IUPHAR ligand 1958
DrugBank DB00905
ChemSpider 4470565 YesY
UNII QXS94885MZ YesY
ChEBI CHEBI:51230 YesY
ChEMBL CHEMBL1200963 N
Chemical data
Formula C25H37NO4 
Mol. mass 415.566 g/mol
 N (what is this?)  (verify)

Bimatoprost (marketed in the U.S., Canada and Europe by Allergan, under the trade name Lumigan) is a prostaglandin analog/prodrug 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] In 2008-2011, at least three case series suggested that bimatoprost has the ability to reduce adipose (fat) tissue.[3][4][5]

Cosmetic use[edit]

In patients using ophthalmic prostaglandins such as travoprost and latanoprost, it has been anecdotally noted[by whom?] that there had been an increase in diameter, density and length of eyelashes. Allergan has initiated[when?] clinical trials investigating the usage of Lumigan as a cosmetic drug.[6] 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.[citation needed] The medical term for this is treatment of hypotrichosis, however, the FDA approval is for purely cosmetic purposes.[7]

For cosmetic purposes, it is administered once daily by applying the solution to the skin at the base of the eyelash using an applicator device "Application Guide", where it has its effect upon the hair follicle.

Bimatoprost activates prostamide alpha F2 receptors found in the hair follicle to stimulate its growth rate. Research led by Professor Randall and the University of Bradford found that it may also offer a treatment for scalp hair regrowth in trials conducted on samples taken from men undergoing hair transplants.[8]

According to Allergan's package labeling, users of its Latisse cosmetic product didn't develop darker irises in clinical studies; however, "patients should be advised about the potential for increased brown iris pigmentation which is likely to be permanent."[9]

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.

These companies have been sued by Allergan for patent infringement.[6] 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[10] and because it is "adulterated" with bimatoprost.[11]

Fat-reducing properties[edit]

Reductions in orbital fat (i.e., fat around the eye) have been observed in patients using bimatoprost as glaucoma therapy.[12] Of particular interest, the loss of orbital fat was unilateral in patients who used bimatoprost on only one eye.[13] The effect appears reversible upon cessation of bimatoprost use.[citation needed] The effect is likely to explain deepening of the lid sulcus described in a series of three patients on bimatoprost.[14] The mechanism for the apparent fat reduction remains unclear. However, bimatoprost is chemically analogous to prostaglandin F (PGF), a compound which is known to reduce fat by inhibition of adipocyte differentiation and survival.[15]

Formulations[edit]

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 five minutes before or after bimatoprost.[1]

Efficacy[edit]

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.[16]

Side effects[edit]

Possible side effects of this medication are:[citation needed]

  • 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.
  • It may cause unexpected growth of hair if applied inappropriately, on the cheek, for example.
  • It may cause infection if the one-time applicators which come with the genuine product are reused.
  • Lashes may grow so long that they become ingrown and scratch the cornea.
  • May cause darkening of the eyelid or of the area beneath the eye.[17]

On November 19, 2007, the FDA issued a warning during the seizure of a bimatoprost-containing cosmetic.[18] 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[edit]

  1. ^ a b c "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. ^ 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. 
  4. ^ 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. 
  5. ^ 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. 
  6. ^ a b Rundle, Rhonda L. (2007-11-19). "Drug That Lengthens Eyelashes Sets Off Flutter". The Wall Street Journal. Retrieved 2007-11-19. 
  7. ^ The Pink Sheet: [1] Lauren Smith December 15, 2008; Volume 70, Number 050,Page[verification needed]
  8. ^ Federation of American Societies for Experimental Biology Journal "The prostamide-related glaucoma therapy, bimatoprost, offers a novel approach for treating scalp alopecias" Randall et all. October 26, 2012.
  9. ^ Latisse prescribing information: "Important Safety Information"
  10. ^ MSNBC: FDA Seizes $2 Million Of Potentially Harmful SJ Eye Product KNTV-TV November 17, 2007[dead link]
  11. ^ Reuters: "U.S. seizes discontinued eyelash product". Jim Wolf. November 16, 2007.
  12. ^ 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?]. Klinische Monatsblätter für Augenheilkunde (in German) 225 (5): 443–5. doi:10.1055/s-2008-1027362. PMID 18454393. 
  13. ^ 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. 
  14. ^ 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. 
  15. ^ 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. 
  16. ^ 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. 
  17. ^ "Long Lashes Without Prescription, but With Risks". Catherine Saint Louis. The New York Times. May 1, 2010
  18. ^ "Potentially Harmful "Cosmetic" Eye Product Seized" (Press release). U.S. Food and Drug Administration (FDA). November 19, 2007. Retrieved 2007-12-05. 

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. 

External links[edit]

  • Eye Drops: [The generic name of the Latisse eye drop is Bimatoprost Ophthalmic Solution 0.03%]. Crazzy Paul. Aug 01, 2013