Latisse

Bimatoprost

Clinical data
Trade names	Lumigan
AHFS/Drugs.com	Monograph
MedlinePlus	a602030
License data	US DailyMed: 46098
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Topical (eye drops)
ATC code	S01EE03 (WHO)
Legal status
Legal status	US: ℞-only
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
IUPAC name 7-[3,5-dihydroxy-2- (3-hydroxy-5-phenyl-pent-1-enyl)- cyclopentyl]-N-ethyl-hept-5-enamide
CAS Number	155206-00-1 Y
PubChem CID	5311027
IUPHAR/BPS	1958
DrugBank	DB00905 Y
ChemSpider	4470565 Y
UNII	QXS94885MZ
KEGG	D02724 N
ChEBI	CHEBI:51230 Y
ChEMBL	CHEMBL1200963 N
ECHA InfoCard	100.170.712
Chemical and physical data
Formula	C25H37NO4
Molar mass	415.566 g/mol
3D model (JSmol)	Interactive image
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?)

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. 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/.

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 (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.

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. Allergan initiated clinical trials investigating the usage of bimatoprost as a cosmetic drug. In 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 (see Prostaglandin F receptor#Clinical Significance).