Bimatoprost

Bimatoprost, sold under the brand name Lumigan among others, is a medication used to treat high pressure inside the eye including glaucoma. Specifically it is used for open angle glaucoma when other agents are not sufficient. It may also be used to increase the size of the eyelashes. It is used as an eye drop and effects generally occur within four hours.

Bimatoprost
Clinical data
Trade namesLumigan, Latisse, Durysta, others
AHFS/Drugs.comMonograph
MedlinePlusa602030
License data
Pregnancy
category
  • AU: B3
Routes of
administration		eye drops
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: ℞-only
  • EU: Rx-only
Pharmacokinetic data
BioavailabilityLow
Protein binding88%
Onset of action4 hrs
Elimination half-life45 min after intravenous application
Duration of action≥ 24 hrs
Excretion67% Kidney, 25% fecal
Identifiers
  • 7-[3,5-dihydroxy-2- (3-hydroxy-5-phenyl-pent-1-enyl)- cyclopentyl]-N-ethyl-hept-5-enamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.170.712
Chemical and physical data
FormulaC25H37NO4
Molar mass415.574 g·mol−1
3D model (JSmol)
SMILES
  • CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)CCc1ccccc1
  • 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)

Common side effects include red eyes, dry eyes, change in color of the eyes, blurry vision, and cataracts. Use during pregnancy or breastfeeding is generally not recommended. It is a prostaglandin analog and works by increasing the outflow of aqueous fluid from the eyes.

Bimatoprost was approved for medical use in the United States in 2001. It is available as a generic medication. In 2021, it was the 204th most commonly prescribed medication in the United States, with more than 2 million prescriptions.

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