| Identification | Back Directory | [Name]
(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]-N-ethylhept-5-enamide | [CAS]
511229-72-4 | [Synonyms]
(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxodecyl)cyclopentyl]-N-ethylhept-5-enamide | [Molecular Formula]
C24H43NO4 | [MOL File]
511229-72-4.mol | [Molecular Weight]
409.603 |
| Hazard Information | Back Directory | [Description]
Lumula is a hybrid eicosanoid analog that incorporates the docosanoid and prostamide features of unoprostone and bimatoprost (17-phenyl trinor Prostaglandin F2α ethyl amide; ), respectively, prostaglandin analogs that lack potency at the prostanoid FP receptor.1,2,3 Based on classical structure-activity relationships that have been established for prostanoid receptors, lumula is predicted to have low activity at these receptors.4 The N-ethyl amide prodrug moiety it inherits from bimatoprost is slow to hydrolyze and the lower side chain modifications inherited from unoprostone interfere with FP receptor binding.5,6 Lumula is intended for use as a negative control for testing mechanisms of unoprostone and bimatoprost activity. | [Uses]
Lumula (Maxeyprost) is an ethyl amide derivative of Unoprostone (HY-106916). | [References]
1. Ota, T., Aihara, M., Narumiya, S., et al. The effects of prostaglandin analogues on IOP in prostanoid FP-receptor-deficient mice Invest. Ophthalmol. Vis. Sci. 46(11),4159-4163(2005).
2. Sharif, N.A., Kelly, C.R., and Williams, G.W. Bimatoprost (Lumiganr) is an agonist at the cloned human ocular FP prostaglandin receptor: Real-time FLIPR-based intracellular Ca2+ mobilization studies Prostaglandis Leukot. Essent. Fatty Acids 68(1),27-33(2003).
3. Yu, D.Y., Su, E.N., Cringle, S.J., et al. Comparison of the vasoactive effects of the docosanoid unoprostone and selected prostanoids on isolated perfused retinal aterioles Invest. Ophthalmol. Vis. Sci. 42(7),1499-1504(2001).
4. Abramovitz, M., Adam, M., Boie, Y., et al. The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs Biochim. Biophys. Acta 1483(2),285-293(2000).
5. Maxey, K.M., Johnson, J., and LaBrecque, J. The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist Surv. Ophthalmol. 47(Suppl 1),S34-S40(2002).
6. Balapure, A.K., Rexroad, C.E., Jr., Kawada, K., et al. Structural requirements for prostaglandin analog interaction with the ovine corpus luteum prostaglandin F2α receptor Biochem. Pharmacol. 38(14),2375-2381(1989). |
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