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
Licence data	US Daily Med:link
Pregnancy category	US: C (Risk not ruled out)
Legal status	US: ℞-only
Routes of administration	Topical (eye drops)
Identifiers
CAS Number	155206-00-1 Y
ATC code	S01EE03 (WHO)
PubChem	CID: 5311027
IUPHAR/BPS	1958
DrugBank	DB00905 Y
ChemSpider	4470565 Y
UNII	QXS94885MZ Y
ChEBI	CHEBI:51230 Y
ChEMBL	CHEMBL1200963 N
Chemical data
Formula	C25H37NO4
Molecular mass	415.566 g/mol
SMILES O=C(NCC)CCC/C=C\C[C@H]2[C@@H](O)C[C@@H](O)[C@@H]2/C=C/[C@@H](O)CCc1ccccc1
InChI InChI=1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3-,17-16+/t20-,21+,22+,23-,24+/m0/s1 Y Key:AQOKCDNYWBIDND-FTOWTWDKSA-N Y
NY (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. 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/.

Cosmetic use

In patients using ophthalmic prostaglandins such as travoprost and latanoprost, it has been anecdotally noted that there had been an increase in diameter, density and length of eyelashes. Allergan initiated clinical trials investigating the usage of Lumigan as a cosmetic drug. 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.

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."

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. 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 and because it is "adulterated" with bimatoprost.

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; other eye drops or ointments should be given no less than five minutes before or after bimatoprost.

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.

Side effects

Possible side effects of this medication are:

• May cause blurred vision.
• May cause eyelid redness.
• May darken eyelids temporarily if not applied with brush
• 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 infection if the one-time applicators which come with the genuine product are reused.
• May cause darkening of the eyelid or of the area beneath the eye.

On November 19, 2007, the FDA issued a warning during the seizure of a bimatoprost-containing cosmetic. 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."