15-keto-17-phenyl trinor Prostaglandin F2α

• CAT Number: R065361
• CAS Number: 949564-89-0
• Molecular Formula: C23H30O5
• Molecular Weight: 386.488
• Purity: ≥95%
• Synonyms: 15-keto-17-phenyl trinor PGF2α
• Storage: -20°C
• IUPAC Name: (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E)-3-oxo-5-phenylpent-1-enyl]cyclopentyl]hept-5-enoic acid
• InChI: InChI=1S/C23H30O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,14-15,19-22,25-26H,2,7,10-13,16H2,(H,27,28)/b6-1-,15-14+/t19-,20-,21+,22-/m1/s1
• InChIKey: HHEYLKRDELKWGI-RKJYIPPQSA-N
• SMILES: C1C(C(C(C1O)C=CC(=O)CCC2=CC=CC=C2)CC=CCCCC(=O)O)O

Bimatoprost is an F-<wbr></wbr>series prostaglandin (PG) analog which has been approved for use as an ocular hypotensive drug. Oxidation of the C-<wbr></wbr>15 hydroxyl group and amide hydrolysis of Bimatoprost produces 15-<wbr></wbr>keto-<wbr></wbr>17-<wbr></wbr>phenyl trinor PGF2α. 15-<wbr></wbr>keto-<wbr></wbr>17-<wbr></wbr>phenyl trinor PGF2α is a potential metabolite of bimatoprost when administered to animals. 15-<wbr></wbr>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-<wbr></wbr>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. 15-<wbr></wbr>keto Latanoprost (15-<wbr></wbr>keto-<wbr></wbr>17-<wbr></wbr>phenyl-<wbr></wbr>13,14-<wbr></wbr>dihydro trinor PGF2α 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-<wbr></wbr>type PGs; for example, PGF2α will produce this degree of miosis at a dose of less than 1 µg/eye.

Reference

1.Cantor, L.B. Bimatoprost: a member of a new class of agents, the prostamides, for glaucoma management. Expert Opinion on Investigational Drugs 10, 721-731 (2001).