1221. Bimatoprost

Nomenclature

CAS number: 155206-00-1
(5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-5-heptenamide; (5Z,9α,11α,13E,15S)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinorprosta-5,13-dienoic acid ethylamide; 17-phenyl-18,19,20-trinorprostaglandin F2α ethylamide; AGN-192024; Latisse (Allergan); Lumigan (Allergan).
C25H37NO4; mol wt 415.57.
C 72.25%, H 8.97%, N 3.37%, O 15.40%.

Description and references

Synthetic prostamide; structurally related to prostaglandin F2α, q.v. Prepn: D. F. Woodward et al., WO 9406433; eidem, US 6403649 (1994, 2002 both to Allergan). Pharmacology: D. F. Woodward et al., J. Pharmacol. Exp. Ther. 305, 772 (2003) DOI PubMed. Clinical potential for treatment of eyelash hypotrichosis: A. Tosti et al., J. Am. Acad. Dermatol. 51, S149 (2004) DOI PubMed. Clinical trial in glaucoma and ocular hypertension: R. Quinones et al., J. Ocul. Pharmacol. Ther. 20, 115 (2004) DOI PubMed. Review of pharmacology and clinical efficacy: L. B. Cantor, Expert Opin. Invest. Drugs 10, 721-731 (2001) DOI PubMed; of mechanism of action: A. H.-P. Krauss, D. F. Woodward, Surv. Ophthalmol. 49, Suppl. 1, S5-S11 (2004) DOI PubMed. Long-term safety and efficacy in glaucoma and ocular hypertension: R. D. Williams et al., Br. J. Ophthalmol. 92, 1387 (2008) DOI PubMed.

Chemical structure

Properties

Powder. Very sol in ethanol, methanol; slightly sol in water.

Therapeutic Category

Antiglaucoma; in treatment of hypotrichosis of the eyelashes.

Therapeutic Category (Veterinary)

Antiglaucoma in dogs.

Keywords

Antiglaucoma; Prostaglandin/Prostaglandin Analog