Bimatoprost

• CAT Number: A000688
• CAS Number: 155206-00-1
• Molecular Formula: C25H37NO4
• Molecular Weight: 415.6
• Purity: ≥95%
• Synonyms: Lumigan; Latisse; 155206-00-1; AGN 192024; Bimatoprostum
• Target: Prostaglandin Receptor
• Solubility: >21.3mg/mL in DMSO
• Storage: -20°C
• 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
• 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
• InChIKey: AQOKCDNYWBIDND-FTOWTWDKSA-N
• SMILES: CCNC(=O)CCCC=CCC1C(CC(C1C=CC(CCC2=CC=CC=C2)O)O)O

Bimatoprost(CAS 155206-00-1), also known as AGN 192024, is a potent FP receptor agonist. Bimatoprost ophthalmic solution is a topical medication used for controlling the progression of glaucoma or ocular hypertension, by reducing intraocular pressure. It is a prostaglandin analogue that works by increasing the outflow of aqueous fluid from the eyes. It binds to the prostanoid FP receptor.

Overview of Clinical Research

Bimatoprost, a prostaglandin F2alpha receptor agonist, was initially approved by the FDA in 2001 for ocular hypertension and later approved for hypothrichosis in 2008, as eyelash growth became a desirable adverse effect for patients using this drug.

 

Reference

1. Drugs Aging. 2009;26(12):1049-71. doi: 10.2165/11203210-000000000-00000.
Bimatoprost: a review of its use in open-angle glaucoma and ocular hypertension.
Curran MP(1).
Author information:
(1)Adis, a Wolters Kluwer Business, Auckland, New Zealand.
Bimatoprost (Lumigan) is a synthetic prostamide that reduces intraocular pressure (IOP) by increasing the outflow of aqueous humour. In patients with open-angle glaucoma or ocular hypertension, long-term treatment (for up to 48 months) with once-daily bimatoprost 0.03% ophthalmic solution was more effective than timolol twice daily in providing a sustained and stable reduction in IOP. Bimatoprost 0.03% ophthalmic solution demonstrated efficacy similar to, or greater than, the prostaglandin analogues latanoprost and travoprost in reducing IOP and achieving target IOP levels. Switching to bimatoprost was as effective in maintaining diurnal IOP control as switching to a fixed combination of latanoprost/timolol (in patients with IOP levels controlled with a nonfixed combination of latanoprost plus timolol), and similarly, or more, effective in lowering IOP and providing overall diurnal IOP control than switching to a combination of dorzolamide/timolol (in patients with IOP inadequately controlled with other antiglaucoma agents including timolol). Treatment with bimatoprost was generally well tolerated, with conjunctival hyperaemia (mostly mild), growth of eyelashes and ocular pruritus being commonly reported. Other adverse events included increases in the pigmentation of the iris, perorbital areas and eyelashes.
2. Cardiovasc Drug Rev. 2004 Summer;22(2):103-20.
Bimatoprost: a novel antiglaucoma agent.
Woodward DF(1), Phelps RL, Krauss AH, Weber A, Short B, Chen J, Liang Y, Wheeler LA.
Author information:
(1)Department of Biological Sciences, Allergan, Inc., 2525 Dupont Drive (RD-2C), Irvine, CA 92612, USA. .
The aim of glaucoma therapy is to preserve vision by reducing intraocular pressure (IOP). Following recent National Eye Institute sponsored studies, it is becoming increasingly apparent that every mmHg of extra IOP lowering counts. Bimatoprost is the newest and most effective addition to the physician/'s armamentarium of ocular hypotensive drugs. Direct clinical comparisons have demonstrated that it is more efficacious than the prostaglandin (PG) FP receptor agonist prodrugs, latanoprost and travoprost, as well as a beta-adrenoceptor antagonist, timolol, alone or in fixed combination with the carbonic anhydrase inhibitor, dorzolamide. Moreover, patients that are refractory to latanoprost therapy may be successfully treated with bimatoprost. Such evidence provides support, at the clinical level, for the contention that bimatoprost is pharmacologically distinct from PG FP receptor agonist prodrugs. Bimatoprost is a structural analog of PGF2alpha-ethanolamide (prostamide F2alpha), which is formed from the endocannabinoid anandamide by a biosynthetic pathway involving cyclooxygenase-2 (COX-2). Their pharmacology is remarkably similar, such that bimatoprost may be regarded as a prostamide mimetic. The target receptor for bimatoprost and the prostamides appears unique and unrelated to PG- and endocannabinoid-sensitive receptors. Extensive ocular distribution/metabolism studies in non-human primates demonstrate that bimatoprost is not a prodrug, it remains essentially intact. Its profound ocular hypotensive effects may, therefore, be attributed to its prostamide-mimetic properties.
3. Surv Ophthalmol. 2004 Mar;49 Suppl 1:S5-11.
Update on the mechanism of action of bimatoprost: a review and discussion of new evidence.
Krauss AH(1), Woodward DF.
Author information:
(1)Allergan, Inc, Irvine, California 92612-1531, USA.
Bimatoprost is a pharmacologically unique and highly efficacious anti-glaucoma agent. It appears to mimic the activity of the prostamides, which are biosynthesized from the natural endocannabinoid anandamide by the enzyme cyclo-oxygenase 2 (COX-2). Bimatoprost has also been suggested to lower intraocular pressure by behaving as a prodrug or, alternatively, by stimulating FP receptors directly. These three distinctly different hypotheses for the mechanism of bimatoprost activity are discussed in the light of current evidence.