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15-keto Latanoprost

Cayman Chemical Item Number 16816

15-keto Latanoprost

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Description

Latanoprost 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 without isopropyl ester hydrolysis produces 15-keto latanoprost. 15-keto Latanoprost is a potential metabolite of latanoprost when administered to animals. 15-keto Latanoprost is also one of the common minor impurities found in commercial preparations of the bulk drug compound. Although much less potent that the parent compound latanoprost, 15-keto latanoprost still retains 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.1 15-keto Latanoprost is also a miotic in the normal cat eye, causing an 8 mm reduction in pupillary diameter at 5 µg/eye.1 Again, this is not as potent as many other F-type PGs; for example, PGF2α will produce this degree of miosis at a dose of less than 1 µg/eye. Products of β-oxidation account for most of the metabolites of latanoprost recovered in plasma and urine. However, 15-keto latanoprost is a minor metabolite, and one which could be enhanced in situations where β-oxidation is reduced.

1 Stjernschantz, J., and Resul, B. Phenyl substituted prostaglandin analogs for glaucoma treatment. Drugs Future 17 691-704 (1992).

Formal Name 9α,​11α-​dihydroxy-​15-​oxo-​17-​phenyl-​18,​19,​20-​trinor-​prost-​5Z-​en-​1-​oic acid,​ isopropyl ester
Molecular Formula C26H38O5
Formula Weight 430.6
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(OC(C)​C)​=O)​[C@@H]​(CCC(CCC2=CC=CC=C2)​=O)​[C@H]​(O)​C1

Background Reading

Stjernschantz, J., and Resul, B. Phenyl substituted prostaglandin analogs for glaucoma treatment. Drugs Future 17 691-704 (1992).

15-keto Latanoprost is available in the following screening library:

Size Price Quantity Subtotal
1 mg $46.00 $0.00
5 mg $207.00 $0.00
10 mg $368.00 $0.00
100 mg $2,760.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-26. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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