Structure via PubChem · Public domain (PubChem)
bimatoprost
Sign in to saveAlso known as AGN 192024, LS-181817, (Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl}-N-ethyl-5-heptenamide
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.
Chemical data
- Formula
- C25H37NO4
- Molecular weight
- 415.6 g/mol
- IUPAC name
- (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide
- SMILES
- CCNC(=O)CCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@H](CCC2=CC=CC=C2)O)O)O
- InChIKey
- AQOKCDNYWBIDND-FTOWTWDKSA-N
- XLogP
- 2.8
- Polar surface area
- 89.8 Ų
- H-bond donors
- 4
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2001
- Admin. routes
- topical
- Indications
- open-angle glaucoma, ocular hypertension, androgenetic alopecia, Graves ophthalmopathy
via ChEMBL · EBI
Research
1,037 papers- Bimatoprost Implant: First Approval.Drugs & aging · 2020
- Bimatoprost Intracameral Implant (Durysta®): A New Era in Glaucoma Management Through Sustained-Release Innovation.Drug design, development and therapy · 2025
- Intracameral sustained release bimatoprost implants (Durysta).Seminars in ophthalmology · 2022
- Bimatoprost: a novel antiglaucoma agent.Cardiovascular drug reviews · 2004
- Bimatoprost for the treatment of eyelash, eyebrow and scalp alopecia.Expert opinion on investigational drugs · 2017
via PubMed
Wikidata facts
- Subclass of
- prostaglandins
- Mass
- 415.272
- Has use
- medication
Show 7 more facts
- Commons category
- Bimatoprost
- chemical formula
- C₂₅H₃₇NO₄
- medical condition treated
- glaucoma
- isomeric SMILES
- CCNC(=O)CCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@H](CCC2=CC=CC=C2)O)O)O
- canonical SMILES
- CCNC(=O)CCCC=CCC1C(CC(C1C=CC(CCC2=CC=CC=C2)O)O)O
- World Health Organisation international non-proprietary name
- bimatoprost
- subject has role
- antihypertensive drug
Sources (6)
via Wikidata · CC0
~5 min read
Encyclopedic overview
11 sectionsContents
- Uses
- Medical
- Cosmetic
- Side effects
- Interactions
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Research
- References
- Further reading
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.
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.
Excerpted from Wikipedia’s “bimatoprost” article, available under the CC BY-SA 4.0 licence.