Bimatoprost

Bimatoprost
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
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
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 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 /ləˈtiːs/.[2]

Cosmetic use

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 at the Bascom Palmer Eye Institute, 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 Lumigan as a cosmetic drug.[3] 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.[4] The medical term for this is treatment of hypotrichosis, however, the FDA approval is for purely cosmetic purposes.[5]

For cosmetic purposes, it is administered once daily by applying the solution to the skin at the base of the eyelash.

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."[6]

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

These companies have been sued by Allergan for patent infringement.[3] 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[7] and because it is "adulterated" with bimatoprost.[8]

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 five minutes before or after bimatoprost.[1]

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.[9]

Side effects

Possible side effects of this medication are:

On November 16, 2007, the FDA issued a warning during the seizure of a bimatoprost-containing cosmetic. The warning stated that unknowingly using the medication in excess "may increase the risk of optic nerve damage [...] decreased vision and possibly blindness." [11]

References

  1. 1 2 3 "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. 1 2 Rundle, Rhonda L. (2007-11-19). "Drug That Lengthens Eyelashes Sets Off Flutter". The Wall Street Journal. Retrieved 2007-11-19.
  4. ↑ Grady, Scott. "Latisse (Bimatoprost) is Approved by the FDA in 2008". ChicLatisse.com. Retrieved 22 August 2014.
  5. ↑ The Pink Sheet: Lauren Smith December 15, 2008; Volume 70, Number 050,Page
  6. ↑ Latisse prescribing information: "Important Safety Information"
  7. ↑ MSNBC: FDA Seizes $2 Million Of Potentially Harmful SJ Eye Product KNTV-TV November 17, 2007 Archived November 19, 2007, at the Wayback Machine.
  8. ↑ Reuters: "U.S. seizes discontinued eyelash product". Jim Wolf. November 16, 2007.
  9. ↑ 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.
  10. ↑ "Long Lashes Without Prescription, but With Risks". Catherine Saint Louis. The New York Times. May 1, 2010
  11. ↑ "Approximately $2 Million of Potentially Harmful "Cosmetic" Eye Product Seized" (Press release). U.S. Food and Drug Administration (FDA). November 16, 2007. Retrieved 2016-02-12.

12. Sethi HS, Dhawan M, Naik MP, Gupta VS. Prostaglandin analogs in glaucoma. Astrocyte 2015;2:126-32.

Citations

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