15-keto-17-phenyl trinor Prostaglandin F

Cayman Chemical Item Number 16817

15-keto-17-phenyl trinor PGF (CAS 949564-89-0)

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Description

Bimatoprost 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.

1. 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 17 691-704 (1992).

Synonyms
  • 15-keto-17-phenyl trinor PGF
Formal Name 9α,​11α-​dihydroxy-​15-​oxo-​17-​phenyl-​18,​19,​20-​trinor-​prosta-​5Z,​13E-​dien-​1-​oic acid
CAS Number 949564-89-0
Molecular Formula C23H30O5
Formula Weight 386.5
Formulation A solution in methyl acetate
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O[C@@H]​1[C@H]​(C/C=C\CCCC(O)​=O)​[C@@H]​(/C=C/C(CCC2=CC=CC=C2)​=O)​[C@H]​(O)​C1
InCHI Code
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​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
InCHI Key
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HHEYLKRDELKWGI-RKJYIPPQSA-N

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15-keto-17-phenyl trinor Prostaglandin F is available in the following screening library:

Size Price Quantity Subtotal
1 mg $51.00 $0.00
5 mg $230.00 $0.00
10 mg $408.00 $0.00
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Pricing updated 2015-06-30. Prices are subject to change without notice.

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