15-keto-17-phenyl trinor Prostaglandin F2α

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CAS:949564-89-0
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15-keto-17-phenyl trinor Prostaglandin F2α Basic information
Product Name:15-keto-17-phenyl trinor Prostaglandin F2α
Synonyms:15-keto-17-phenyl trinor Prostaglandin F2α;HHEYLKRDELKWGI-RKJYIPPQSA-N;(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E)-3-oxo-5-phenylpent-1-enyl]cyclopentyl]hept-5-enoic acid;15-keto-17-phenyl trinor Prostaglandin F2α;5-Heptenoic acid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-oxo-5-phenyl-1-penten-1-yl]cyclopentyl]-, (5Z)-;9α,11α-dihydroxy-15-oxo-17-phenyl-18,19,20-trinor-prosta-5Z,13E-dien-1-oicacid
CAS:949564-89-0
MF:C23H30O5
MW:386.48
EINECS:
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Mol File:949564-89-0.mol
15-keto-17-phenyl trinor Prostaglandin F2α Structure
15-keto-17-phenyl trinor Prostaglandin F2α Chemical Properties
Boiling point 594.2±50.0 °C(Predicted)
density 1.216±0.06 g/cm3(Predicted)
storage temp. Store at -20°C
solubility DMF: 30 mg/ml; DMSO: 25 mg/ml; Ethanol: 30 mg/ml; PBS (pH 7.2): 2.5 mg/ml
pka4.76±0.10(Predicted)
Safety Information
MSDS Information
15-keto-17-phenyl trinor Prostaglandin F2α Usage And Synthesis
DescriptionBimatoprost is an F-series prostaglandin (PG) analog which has been approved for use as an ocular hypotensive drug.1 Oxidation of the C-15 hydroxyl group and amide hydrolysis of Bimatoprost produces 15-keto-17-phenyl trinor PGF. 15-keto-17-phenyl trinor PGF is a potential metabolite of bimatoprost when administered to animals. 15-keto PG analogs are potential minor impurities in commercial preparations of their corresponding bulk drug compounds. Although much less potent that the parent compound, 15-keto PGs still retain the ability to produce a small but measurable decrease (1 mm Hg) in the intraocular pressure of normal cynomolgus monkeys when administered at a dose of 1 μg/eye.2 15-keto Latanoprost (15-keto-17-phenyl-13,14-dihydro trinor PGF isopropyl ester) is a miotic in the normal cat eye, causing an 8 mm reduction in pupillary diameter at 5 μg/eye. Again, this is not as potent as many other F-type PGs; for example, PGF will produce this degree of miosis at a dose of less than 1 μg/eye.
References1. Cantor, L.B. Bimatoprost: a member of a new class of agents, the prostamides, for glaucoma management Expert Opin. Investig. Drugs 10,721-731(2001).
2. Stjernschantz, J., and Resul, B. Phenyl substituted prostaglandin analogs for glaucoma treatment Drugs Future 17(8),691-704(1992).
15-keto-17-phenyl trinor Prostaglandin F2α Preparation Products And Raw materials
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